Hyaluronic acid

Summary

Hyaluronic acid is a glycosaminoglycan used for the relief of joint pain, wound healing, ophthalmologic treatment, cosmetic treatment, and various other applications.

Generic Name
Hyaluronic acid
DrugBank Accession Number
DB08818
Background

Hyaluronic acid (HA) is an anionic, nonsulfated glycosaminoglycan found in connective, epithelial, and neural tissues; it was first isolated in 1934. Karl Meyer and John Palmer obtained glycosaminoglycan (GAG) from the bovine eye, giving it the name "hyaluronic acid". HA is involved in many important physiological processes, including but not limited to wound healing, tissue regeneration, and joint lubrication. It demonstrates unique viscoelasticity, moisturizing, anti-inflammatory qualities, and other important properties that prove beneficial in various clinical applications.2

HA is used in drug delivery systems for the treatment of cancer, ophthalmological conditions, joint conditions, and aesthetic imperfections.3 Several preparations of hyaluronic acid have been approved by the FDA and are available in oral, topical, and injectable forms. A popular use of hyaluronic acid in recent years is cosmetic injection due to its ability to minimize the appearance of wrinkles and aging-related skin imperfections.17

Type
Small Molecule
Groups
Approved, Vet approved
Structure

Thumb

Image

Weight
Average: 776.6486
Monoisotopic: 776.233485724
Chemical Formula
C28H44N2O23
Synonyms
  • Hyaluronan
  • Hyaluronate
Indication

The intra-articular preparations of hyaluronic acid are indicated for knee pain associated with osteoarthritis.23 Hyaluronic acid is used in cosmetic applications to prevent and reduce the appearance of wrinkles on the face, and as a dermal filler to correct facial imperfections or other imperfections on other parts of the body.20,22 It is frequently an ingredient in topical applications for wound healing and symptomatic treatment of skin irritation from various causes.18 Hyaluronic acid may also be indicated in ophthalmological preparations or oral capsules to treat discomfort caused by dry eyes or conjunctivitis and for its protective qualities during and before eye surgery.2,21 Finally, hyaluronic acid can be used off-label to coat the bladder for relief of interstitial cystitis symptoms.6

Pharmacology

Reduce drug development failure rates

Build, train, & validate machine-learning models
with evidence-based and structured datasets.

Build, train, & validate predictive machine-learning models with structured datasets.

Associated Conditions
  • Actinic Keratosis (AK)
  • Burns
  • Burns of the Skin
  • Chronic Skin Ulcers
  • Conjunctivitis
  • Dehydration (Physiology)
  • Dermabrasion
  • Dermatosis
  • Dry Eyes
  • Facial Defect
  • Interstitial Cystitis
  • Keratoconjunctivitis
  • Ocular Irritation
  • Osteoarthritis (OA)
  • Pain of the knee
  • Seasonal Allergic Conjunctivitis
  • Skin Irritation
  • Skin fissures
  • Tissue Adhesions
  • Varicose Ulcers
  • Eye discomfort
  • Facial fine wrinkling
  • Sensation of burning in the eyes
  • Superficial Wounds
  • Wound site
Associated Therapies
  • Dermal Filler
  • Synovial Fluid Lubrication
  • Wound Healing
Contraindications & Blackbox Warnings

Contraindications

Avoid life-threatening adverse drug events

Improve clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.

Avoid life-threatening adverse drug events & improve clinical decision support.

Pharmacodynamics

HA has long-acting lubricant, shock absorbing, joint stabilizing, and water balancing properties.2 It is similar to the naturally occurring glycosaminoglycan (GAG) in joints. Hyaluronic acid works by acting as a lubricant and shock absorber, facilitating joint mobility and thereby reducing osteoarthritic pain. Hyaluronic acid has antioxidative, anti-inflammatory, and analgesic effects.2 The water-balancing properties and viscoelasticity of hyaluronic acid are beneficial in cosmetic injections, imparting volume and reducing the appearance of imperfections and wrinkles.17 Due to the abovementioned properties, HA has a protective effect on the eyes and cornea.3

Mechanism of action

General principles and hyaluronic acid receptor binding

Hyaluronic acid works by two basic mechanisms: serving as a passive structural molecule or serving as signaling molecule, depending on the molecule size. The physicochemical properties of high molecular weight HA contribute to passive structural effects, demonstrating hygroscopicity and viscoelasticity and improving hydration, water balance, and structural integrity. As a signalling molecule interacting with proteins, HA causes several opposing effects based on molecular weight: pro- or anti-inflammatory effects, promotion or inhibition of cell migration, and activating or inhibiting cell division.3

Hyaluronic acid exerts its therapeutic effects through binding to three primary types of cell surface receptors: CD44 (a membrane glycoprotein), the receptor for hyaluronate-mediated motility (RHAMM), and the Intercellular Adhesion Molecule 1 (ICAM-1). CD44 is considered the most widely distributed receptor for hyaluronic acid, demonstrating cellular interactions with osteopontin, collagen, and matrix metalloproteinases (MMPs). High and low molecular weight hyaluronic acids demonstrate differing molecular and cellular mechanisms in their interaction with CD44 receptors. Some examples of these effects include modification of chondrocyte survival pathways in addition to alteration of apoptosis pathways. Lymphatic vessel endothelial hyaluronan receptor (LYVE-1), and hyaluronic acid receptor for endocytosis (HARE), (also known as Stabilin-2) also bind to hyaluronic acid.2

Hyaluronic acid for skin conditions and cosmetics

Hyaluronic acid's anionic proprieties cause it to attract water and induce swelling, increasing tissue volume and skin structural integrity. The aging process is associated with reduced production of skin hyaluronic acid and collagen, causing the appearance of wrinkles and the loss of facial volume. Dermal fillers of hyaluronic acid replace lost tissue volume, imparting a full and youthful appearance to skin that has lost its elasticity. Hyaluronic acid fillers contain cross-linked hyaluronic acid particles, rendering a concentrated substance with resistance to various forms of physical and chemical breakdown. The cosmetic benefits of hyaluronic acid filler may last up to 6 months, depending on the brand and technique used for injection.17 Additionally, dermal hyaluronic acid fillers are known to increase the production of fibroblasts17, supporting wound healing and offering relief from irritating and inflammatory skin conditions.1

Hyaluronic acid for joint pain

Most cells in the human body are capable of synthesizing HA. It is a primary component of the extracellular matrix (ECM) and can be found in bone marrow, cartilage, and synovial fluid in joints.2 In osteoarthritis, the concentration of naturally occurring hyaluronic acid gradually decreases, lowering the viscosity of synovial fluid that protects joints from excess friction. Administration of intra-articular hyaluronic acid increases viscosity of synovial joint fluid, reducing friction and subsequently relieving painful arthritic symptoms.17

Hyaluronic acid for ophthalmic conditions and ophthalmological procedures

Solutions of hyaluronic acid with a concentration greater than 0.1% moisturize the surface of the eyes to treat symptoms of dry eye while improving the stabilization of tear film, replenishing deficiencies of HA, reducing friction, and preventing binding of foreign substances to the ocular tissue.2,17 Hyaluronic acid is frequently used during and after ophthalmological surgeries and plays important roles by virtue of its moisturizing, viscoelastic, and protective properties. It promotes tissue healing of the corneal epithelium and other parts of the eye following ophthalmological surgery, minimizing the risk of adhesions and free radical formation.2

Target Actions Organism
ACD44 antigen

binder

 Humans
AIntercellular adhesion molecule 1

inhibitor

binder

 Humans
AHyaluronan mediated motility receptor

binder

 Humans
UNeurocan core protein

binder

 Humans
UVersican core protein

binder

 Humans
UComplement component 1 Q subcomponent-binding protein, mitochondrial

binder

 Humans
UHyaluronan and proteoglycan link protein 1

binder

 Humans
UHyaluronan and proteoglycan link protein 3

binder

 Humans
UHyaluronan-binding protein 2

binder

 Humans
ULayilin

binder

 Humans
UStabilin-2

binder

 Humans
UTumor necrosis factor-inducible gene 6 protein

binder

 Humans
UInterphotoreceptor matrix proteoglycan 2

binder

 Humans
UIntracellular hyaluronan-binding protein 4

binder

 Humans
ULymphatic vessel endothelial hyaluronic acid receptor 1 Not Available Humans
Absorption

There is limited information in the literature regarding the human absorption and pharmacokinetics of hyaluronic acid.2 When administered to rats in the oral form, hyaluronic acid is broken down to oligosaccharides by intestinal bacteria and absorbed in the colon.8 In pharmacokinetic studies of beagle dogs, HA was readily absorbed and rapidly excreted.2 When applied topically, HA with low molecular weight ranging from 20-300 kDa is absorbed through the stratum corneum, and HA with high molecular weight (1000-1400 kDa) does not penetrate the stratum corneum.7 The bioavailability of hyaluronic acid depends on its molecular weight.9

Volume of distribution

There is limited information in the literature regarding the human pharmacokinetics of hyaluronic acid.2 After a dermal filler injection, HA distributes rapidly into the superficial and deep dermis.11 Hyaluronic acid is distributed to skin of rats after intestinal metabolism into oligosaccharides.8 In rats and beagle dogs receiving oral hyaluronic acid, HA accumulated in the thyroid gland, kidneys, bladder, and stomach. HA was found to be concentrated in the vertebrae, joints, and salivary glands within 4 hours after a single dose. It is suggested by pharmacokinetic studies in animals that HA distributes into the lymphatic system.2,10

Protein binding

There is limited information in the literature regarding the human pharmacokinetics of hyaluronic acid.2 In vitro studies determined that serum albumin and hyaluronic acid bind to form a soluble complex.14

Metabolism

Hyaluronic acid is degraded by a family of enzymes called hyaluronidases.4 In animals, it is metabolized into oligosaccharides by intestinal bacteria and subsequently reabsorbed in the large intestine.8

Route of elimination

There is limited information in the literature regarding the human pharmacokinetics of hyaluronic acid.2 Studies in rats and dogs administered a radio-labeled oral dose of HA showed 87-96% excretion the feces. Excretion of hyaluronic acid is primarily extra-renal, with some contribution from the spleen.10,2

Half-life

When injected by the intra-articular route hyaluronic acid has a half-life ranging from 17 hours to 1.5 days. The half-life of hyaluronic acid is longer for purified or formulations or preparations with high molecular weight.17 It can vary according to the molecular weight of the administered HA, according to studies in animals. The metabolic half-life of hyaluronic acid in sheep was determined to be approximately 27 hours in pharmacokinetic studies. In sheep, HA is believed to undergo rapid elimination via the blood and liver.2

Clearance

There is limited information in the literature regarding the human pharmacokinetics of hyaluronic acid.2 In a pharmacokinetic study of rabbits, maximum clearance capacity of intravenously administered hyaluronic acid was about 30 mg/day/kg.12

Adverse Effects

Adverseeffects

Improve decision support & research outcomes

With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.

Improve decision support & research outcomes with our structured adverse effects data.

Toxicity

The oral LD50 of the sodium salt of hyaluronic acid is >800 mg/kg in the rat.24 Overdose information is not readily available in the literature. The safety profile for hyaluronic acid favourable, however, single case reports of death following vaginal injection of hyaluronic acid are published; the deaths likely occurred due to poor procedure regulation.16

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available
Drug Interactions

This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

Not Available
Food Interactions
No interactions found.

Products2

Drug product information from 10+ global regions

Our datasets provide approved product information including:
dosage, form, labeller, route of administration, and marketing period.

Access drug product information from over 10 global regions.

Product Ingredients
Ingredient UNII CAS InChI Key
Hyaluronate sodium Not Available Not Available Not applicable
Potassium hyaluronate Not Available 31799-91-4 Not applicable
Sodium hyaluronate YSE9PPT4TH 9067-32-7 Not applicable
International/Other Brands
AMO Vitrax / AMVISIC Plus / Cystistar / Euflexxa (Ferring) / Hyalart / Hyalgan (Fidia) / Hylo-Comod / Legend / Monovisc (Anika Therapeutics, Inc.) / Recosyn / Synvisc / Viscure / Yardel
Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image
HyGel Gel 0.25 g/10g Topical Gentex Pharma, Llc 2015-10-15 2016-07-01 US flag
HYLASE Wound Gel 2.5 g/100g Topical ECR Pharmaceuticals Co., Inc. 2012-01-06 2012-01-18 US flag
Hylinate Lotion 1 mg/1mL Topical Artesa Labs, Llc 2020-01-13 2020-03-30 US flag
Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image
Hyaluronic Acid Injection 2.5 g/1 Intraepidermal Quimfa S.A 2002-12-06 Not applicable US flag
Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image
Acnepatch Patch 0.4298 mg/100mg Topical Small Lab Co., Ltd. 2020-04-28 2021-03-26 US flag
BELOTERO SOFT Gel; Injection 20 mg/1ml บริษัท เมิร์ซ เฮลธ์แคร์ (ประเทศไทย) จำกัด 2016-06-07 Not applicable Thailand flag
C-eye Day Cream 0.00006 g/30mL Topical LCELLS SA DE CV 2019-11-15 Not applicable US flag
C-eye Night Gel 0.000015 g/15mL Topical LCELLS SA DE CV 2019-11-15 Not applicable US flag
Cluederm Aqua Solution Rejuve Plus Liquid 20 mg/500mL Topical Classys Inc. 2018-06-28 2019-03-29 US flag
Curestin Patch 99.97 mg/100mg Topical J World 2019-07-21 Not applicable US flag
Curithys Patch 94.39 mg/100mg Topical J World 2019-07-21 Not applicable US flag
Deepair Micro Intensive Magic Patch 6.1 g/100mg Topical Acosmetic. co.ltd 2016-08-01 Not applicable US flag
E- Repair Cream 0.00006 g/30mL Topical LCELLS SA DE CV 2019-11-15 Not applicable US flag
Elcosys Patch 99.97 mg/100mg Topical DS TECH CO., LTD 2019-07-21 Not applicable US flag
Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image
Acropass Trouble Cure Hyaluronic acid (0.53 mg/0.58mg) + Nicotinamide (0.03 mg/0.58mg) Patch Topical Raphas Co.,ltd 2016-11-01 2018-10-01 US flag
bdr Bio cell mask Hyaluronic acid (0.14 g/28g) + Honey (0.56 g/28g) Patch Topical Goldeneye Permanent System GmbH Germany 2016-11-21 Not applicable US flag
bdr Laser Effect Peptide Complex Face Mask Hyaluronic acid (0.51 g/30g) + Tocopherol (0.105 g/30g) Patch Topical Hanaim International Llc 2016-11-22 Not applicable US flag
bdr Stretch lift mask Hyaluronic acid (0.14 1/28g) + Calendula officinalis whole (0.28 g/28g) Patch Topical Hanaim International Llc 2016-11-21 Not applicable US flag
BELOTERO BALANCE LIDOCAINE Hyaluronic acid (22.5 MG/1ML) + Lidocaine hydrochloride (3 MG/1ML) Gel; Injection บริษัท เมิร์ซ เฮลธ์แคร์ (ประเทศไทย) จำกัด 2017-11-24 2020-05-14 Thailand flag
BELOTERO INTENSE LIDOCAINE Hyaluronic acid (25.5 MG/1ML) + Lidocaine hydrochloride (3 MG/1ML) Gel; Injection บริษัท เมิร์ซ เฮลธ์แคร์ (ประเทศไทย) จำกัด 2017-11-24 2020-05-14 Thailand flag
BELOTERO SOFT LIDOCAINE Hyaluronic acid (20 MG/1ML) + Lidocaine hydrochloride (3 ML/1ML) Gel; Injection บริษัท เมิร์ซ เฮลธ์แคร์ (ประเทศไทย) จำกัด 2017-11-24 2020-05-14 Thailand flag
BELOTERO VOLUME LIDOCAINE Hyaluronic acid (26 MG/1ML) + Lidocaine hydrochloride (3 ML/1ML) Gel; Injection บริษัท เมิร์ซ เฮลธ์แคร์ (ประเทศไทย) จำกัด 2017-11-24 2020-05-14 Thailand flag
Clapiel Hyalon Serum Sodium hyaluronate (10.5 mg/30mL) + Nicotinamide (0.6 mg/30mL) Cream Topical Aus Korea Co., Ltd. 2015-05-01 Not applicable US flag
Cotta Sodium hyaluronate (.3 g/100g) + Garden snail mucin (.1 g/100g) + Morus alba root bark (.1 g/100g) Film, extended release Topical Eco Industry Co., Ltd 2013-07-01 Not applicable US flag
Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image
Acnepatch Sodium hyaluronate (0.4298 mg/100mg) Patch Topical Small Lab Co., Ltd. 2020-04-28 2021-03-26 US flag
Acropass Trouble Cure Hyaluronic acid (0.53 mg/0.58mg) + Nicotinamide (0.03 mg/0.58mg) Patch Topical Raphas Co.,ltd 2016-11-01 2018-10-01 US flag
Ascorbyl Palmitate 2% / Hyaluronic Acid Sodium Salt 0.2% / Niacinamide 5% / Tretinoin 0.025% Sodium hyaluronate (0.2 g/100g) + Nicotinamide (5 g/100g) + Tretinoin (0.025 g/100g) Gel Topical Sincerus Florida, LLC 2019-05-17 Not applicable US flag
bdr Bio cell mask Hyaluronic acid (0.14 g/28g) + Honey (0.56 g/28g) Patch Topical Goldeneye Permanent System GmbH Germany 2016-11-21 Not applicable US flag
bdr Laser Effect Peptide Complex Face Mask Hyaluronic acid (0.51 g/30g) + Tocopherol (0.105 g/30g) Patch Topical Hanaim International Llc 2016-11-22 Not applicable US flag
bdr Stretch lift mask Hyaluronic acid (0.14 1/28g) + Calendula officinalis whole (0.28 g/28g) Patch Topical Hanaim International Llc 2016-11-21 Not applicable US flag
C-eye Day Hyaluronic acid (0.00006 g/30mL) Cream Topical LCELLS SA DE CV 2019-11-15 Not applicable US flag
C-eye Night Hyaluronic acid (0.000015 g/15mL) Gel Topical LCELLS SA DE CV 2019-11-15 Not applicable US flag
Calcipotriene 0.005% / Diclofenac Sodium 3% / Hyaluronic Acid Sodium Salt 2% / Niacinamide 2% Sodium hyaluronate (2 g/100g) + Calcipotriol (0.005 g/100g) + Diclofenac sodium (3 g/100g) + Nicotinamide (2 g/100g) Cream Topical Sincerus Florida, LLC 2019-05-07 Not applicable US flag
Clapiel Hyalon Serum Sodium hyaluronate (10.5 mg/30mL) + Nicotinamide (0.6 mg/30mL) Cream Topical Aus Korea Co., Ltd. 2015-05-01 Not applicable US flag
ATC Codes
S01KA51 — Hyaluronic acid, combinations
  • S01KA — Viscoelastic substances
  • S01K — SURGICAL AIDS
  • S01 — OPHTHALMOLOGICALS
  • S — SENSORY ORGANS
S01KA01 — Hyaluronic acid
  • S01KA — Viscoelastic substances
  • S01K — SURGICAL AIDS
  • S01 — OPHTHALMOLOGICALS
  • S — SENSORY ORGANS
D03AX05 — Hyaluronic acid
  • D03AX — Other cicatrizants
  • D03A — CICATRIZANTS
  • D03 — PREPARATIONS FOR TREATMENT OF WOUNDS AND ULCERS
  • D — DERMATOLOGICALS
M09AX01 — Hyaluronic acid
  • M09AX — Other drugs for disorders of the musculo-skeletal system
  • M09A — OTHER DRUGS FOR DISORDERS OF THE MUSCULO-SKELETAL SYSTEM
  • M09 — OTHER DRUGS FOR DISORDERS OF THE MUSCULO-SKELETAL SYSTEM
  • M — MUSCULO-SKELETAL SYSTEM
R01AX09 — Hyaluronic acid
  • R01AX — Other nasal preparations
  • R01A — DECONGESTANTS AND OTHER NASAL PREPARATIONS FOR TOPICAL USE
  • R01 — NASAL PREPARATIONS
  • R — RESPIRATORY SYSTEM
Drug Categories
  • Adjuvants, Immunologic
  • Biocompatible Materials
  • Carbohydrates
  • Cicatrizants
  • Compounds used in a research, industrial, or household setting
  • Dermatologicals
  • Glycosaminoglycans
  • Immunologic Factors
  • Lubricants
  • Musculo-Skeletal System
  • Nasal Preparations
  • Ophthalmologicals
  • Polysaccharides
  • Preparations for Treatment of Wounds and Ulcers
  • Protective Agents
  • Sensory Organs
  • Surgical Aids
  • Viscoelastic Substances
  • Viscosupplements
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Carbohydrates and carbohydrate conjugates
Direct Parent
Acylaminosugars
Alternative Parents
Oligosaccharides / Fatty acyl glycosides / N-acyl-alpha-hexosamines / O-glucuronides / O-glycosyl compounds / Beta hydroxy acids and derivatives / Dicarboxylic acids and derivatives / Pyrans / Oxanes / Acetamides / Secondary carboxylic acid amides / Hemiacetals / Secondary alcohols / Polyols / Acetals / Carboxylic acids / Oxacyclic compounds / Organic oxides / Primary alcohols / Hydrocarbon derivatives / Carbonyl compounds / Organonitrogen compounds / Organopnictogen compounds show 13 more
Substituents
1-o-glucuronide / Acetal / Acetamide / Acylaminosugar / Alcohol / Aliphatic heteromonocyclic compound / Beta-hydroxy acid / Carbonyl group / Carboxamide group / Carboxylic acid / Carboxylic acid derivative / Dicarboxylic acid or derivatives / Fatty acyl / Fatty acyl glycoside / Glucuronic acid or derivatives / Glycosyl compound / Hemiacetal / Hydrocarbon derivative / Hydroxy acid / N-acyl-alpha-hexosamine / O-glucuronide / O-glycosyl compound / Oligosaccharide / Organic nitrogen compound / Organic oxide / Organoheterocyclic compound / Organonitrogen compound / Organopnictogen compound / Oxacycle / Oxane / Polyol / Primary alcohol / Pyran / Secondary alcohol / Secondary carboxylic acid amide show 25 more
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
  • Humans and other mammals
UNII
S270N0TRQY
CAS number
9004-61-9
InChI Key
KIUKXJAPPMFGSW-MNSSHETKSA-N
InChI

InChI=1S/C28H44N2O23/c1-5(33)29-9-18(11(35)7(3-31)47-25(9)46)49-28-17(41)15(39)20(22(53-28)24(44)45)51-26-10(30-6(2)34)19(12(36)8(4-32)48-26)50-27-16(40)13(37)14(38)21(52-27)23(42)43/h7-22,25-28,31-32,35-41,46H,3-4H2,1-2H3,(H,29,33)(H,30,34)(H,42,43)(H,44,45)/t7-,8-,9-,10-,11-,12-,13+,14+,15-,16-,17-,18?,19?,20+,21+,22+,25-,26+,27-,28-/m1/s1

IUPAC Name

(2S,3S,4R,5R,6R)-3-{[(2S,3R,5S,6R)-4-{[(2R,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}-3-acetamido-5-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-{[(2R,3R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-4,5-dihydroxyoxane-2-carboxylic acid

SMILES

CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)C1O[C@@H]1O[C@@H]([C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)C(O[C@@H]3O[C@@H]([C@@H](O)[C@H](O)[C@H]3O)C(O)=O)[C@H]2NC(C)=O)[C@H](O)[C@H]1O)C(O)=O

Synthesis Reference

Susan Hockfield, Diane M. Jaworski, "DNA encoding BEHAB, a brain hyaluronan-binding protein, and recombinant expression systems for production of BEHAB polypeptides." U.S. Patent US5635370, issued June 03, 1997.

US5635370
General References
  1. Bukhari SNA, Roswandi NL, Waqas M, Habib H, Hussain F, Khan S, Sohail M, Ramli NA, Thu HE, Hussain Z: Hyaluronic acid, a promising skin rejuvenating biomedicine: A review of recent updates and pre-clinical and clinical investigations on cosmetic and nutricosmetic effects. Int J Biol Macromol. 2018 Dec;120(Pt B):1682-1695. doi: 10.1016/j.ijbiomac.2018.09.188. Epub 2018 Oct 1. [Article]
  2. Gupta RC, Lall R, Srivastava A, Sinha A: Hyaluronic Acid: Molecular Mechanisms and Therapeutic Trajectory. Front Vet Sci. 2019 Jun 25;6:192. doi: 10.3389/fvets.2019.00192. eCollection 2019. [Article]
  3. Fallacara A, Baldini E, Manfredini S, Vertuani S: Hyaluronic Acid in the Third Millennium. Polymers (Basel). 2018 Jun 25;10(7). pii: polym10070701. doi: 10.3390/polym10070701. [Article]
  4. How KN, Yap WH, Lim CLH, Goh BH, Lai ZW: Hyaluronic Acid-Mediated Drug Delivery System Targeting for Inflammatory Skin Diseases: A Mini Review. Front Pharmacol. 2020 Jul 24;11:1105. doi: 10.3389/fphar.2020.01105. eCollection 2020. [Article]
  5. Witting M, Boreham A, Brodwolf R, Vavrova K, Alexiev U, Friess W, Hedtrich S: Interactions of hyaluronic Acid with the skin and implications for the dermal delivery of biomacromolecules. Mol Pharm. 2015 May 4;12(5):1391-401. doi: 10.1021/mp500676e. Epub 2015 Apr 22. [Article]
  6. Pyo JS, Cho WJ: Systematic Review and Meta-Analysis of Intravesical Hyaluronic Acid and Hyaluronic Acid/Chondroitin Sulfate Instillation for Interstitial Cystitis/Painful Bladder Syndrome. Cell Physiol Biochem. 2016;39(4):1618-25. doi: 10.1159/000447863. Epub 2016 Sep 15. [Article]
  7. Essendoubi M, Gobinet C, Reynaud R, Angiboust JF, Manfait M, Piot O: Human skin penetration of hyaluronic acid of different molecular weights as probed by Raman spectroscopy. Skin Res Technol. 2016 Feb;22(1):55-62. doi: 10.1111/srt.12228. Epub 2015 Apr 16. [Article]
  8. Kimura M, Maeshima T, Kubota T, Kurihara H, Masuda Y, Nomura Y: Absorption of Orally Administered Hyaluronan. J Med Food. 2016 Dec;19(12):1172-1179. doi: 10.1089/jmf.2016.3725. [Article]
  9. Oe M, Sakai S, Yoshida H, Okado N, Kaneda H, Masuda Y, Urushibata O: Oral hyaluronan relieves wrinkles: a double-blinded, placebo-controlled study over a 12-week period. Clin Cosmet Investig Dermatol. 2017 Jul 18;10:267-273. doi: 10.2147/CCID.S141845. eCollection 2017. [Article]
  10. Balogh L, Polyak A, Mathe D, Kiraly R, Thuroczy J, Terez M, Janoki G, Ting Y, Bucci LR, Schauss AG: Absorption, uptake and tissue affinity of high-molecular-weight hyaluronan after oral administration in rats and dogs. J Agric Food Chem. 2008 Nov 26;56(22):10582-93. doi: 10.1021/jf8017029. [Article]
  11. Ho D, Jagdeo J: Biological properties of a new volumizing hyaluronic acid filler: a systematic review. J Drugs Dermatol. 2015 Jan;14(1):50-4. [Article]
  12. Fraser JR, Laurent TC, Pertoft H, Baxter E: Plasma clearance, tissue distribution and metabolism of hyaluronic acid injected intravenously in the rabbit. Biochem J. 1981 Nov 15;200(2):415-24. doi: 10.1042/bj2000415. [Article]
  13. J. Necas, L. Bartosikova, P. Brauner, J. Kolar: Hyaluronic acid (hyaluronan): a review Veterinarni Medicina. 2008 Aug 12;53(8):397–411. [Article]
  14. Grymonpre KR, Staggemeier BA, Dubin PL, Mattison KW: Identification by integrated computer modeling and light scattering studies of an electrostatic serum albumin-hyaluronic acid binding site. Biomacromolecules. 2001 Summer;2(2):422-9. doi: 10.1021/bm005656z. [Article]
  15. Serro AP, Degiampietro K, Colaco R, Saramago B: Adsorption of albumin and sodium hyaluronate on UHMWPE: a QCM-D and AFM study. Colloids Surf B Biointerfaces. 2010 Jun 15;78(1):1-7. doi: 10.1016/j.colsurfb.2010.01.022. Epub 2010 Feb 17. [Article]
  16. Yang Y, Sheng H, Gu Q, Su L, Tong H, Chen J, Qi X: Death Caused by Vaginal Injection of Hyaluronic Acid and Collagen: A Case Report. Aesthet Surg J. 2020 Apr 14;40(5):NP263-NP268. doi: 10.1093/asj/sjz275. [Article]
  17. NIH StatPearls: Hyaluronic acid [Link]
  18. DailyMed: HALUCORT gel dressing with hyaluronic acid [Link]
  19. NIH DailyMed: Hyaluronic acid injection [Link]
  20. DailyMed: PRO PH (hyaluronic acid gel) for injection [Link]
  21. DailyMed: Vista advanced dry eye capsule [Link]
  22. DailyMed: Hyaluronic acid gel [Link]
  23. FDA Approved Drug Products: SYNOJOYNT (sodium hyaluronate) intra-articular injection [Link]
  24. Fischer Scientific MSDS: Sodium hyaluronate [Link]
Human Metabolome Database
HMDB0010366
KEGG Drug
D08043
KEGG Compound
C00518
PubChem Compound
24759
PubChem Substance
310264899
ChemSpider
23145
RxNav
5463
PharmGKB
PA165958431
Wikipedia
Sodium_hyaluronate
MSDS
Clinical Trials
Phase Status Purpose Conditions Count
4 Active Not Recruiting Treatment Rhizarthrosis 1
4 Completed Not Available Dry Eyes 1
4 Completed Basic Science Actinic Keratosis (AK) 1
4 Completed Basic Science Osteoarthritis of the Knee 1
4 Completed Other Osteoarthritis of the Knee 1
4 Completed Prevention Recurrent Cystitis 1
4 Completed Treatment Antiseptic Gel / Bacterial Growth / Bioadhesive Gel / Chistosan / Clorhexidine Gel Bacteria / Clorhexidine-chitosan / Surgery, Oral / Suture Bacteria / Third Molar Surgery / Wisdom Teeth 1
4 Completed Treatment Arthrocentesis / Pain / Temporomandibular Joint Dysfunction 1
4 Completed Treatment Chronic Periodontitis, Hyaluronic Acid 1
4 Completed Treatment Complete Tear, Knee, Anterior Cruciate Ligament 1
Manufacturers

Not Available

Packagers

Not Available

Dosage Forms
Form Route Strength
Patch Topical 0.4298 mg/100mg
Solution Conjunctival; Ophthalmic 14 mg
Injection, solution Intra-articular
Gel Topical
Injection, solution 25 mg/2.5ml
Patch Topical
Gel; injection 22.5 mg/1ml
Gel; injection 25.5 mg/1ml
Gel; injection 20 mg/1ml
Gel; injection 52 mg/2ml
Solution Intraocular 16 mg
Cream Topical 0.00006 g/30mL
Gel Topical 0.000015 g/15mL
Solution / drops Ophthalmic
Cream Topical
Liquid Topical 20 mg/500mL
Solution / drops Conjunctival 0.4 %
Solution, gel forming / drops Intraocular 10 mg
Aerosol, foam 0.2 %
Cloth Topical 12 MG
Cloth Topical 2 MG
Cloth Topical 4 MG
Cream Topical 0.2 %
Gel Topical 0.2 %
Ointment 10 G
Spray Cutaneous 200 MG/100ML
Cream Occlusive dressing technique
Film, extended release Topical
Patch Topical 99.97 mg/100mg
Patch Topical 94.39 mg/100mg
Patch Topical 6.1 g/100mg
Solution 6 mg/1ml
Solution Intra-articular 25 mg
Lotion Topical
Kit Topical
Suspension Ophthalmic 4 mg
Solution Parenteral 20 mg
Lotion / shampoo Topical 0.05 g/50mL
Lotion / shampoo Topical 0.23 g/230mL
Granule Oral
Tablet Oral
Solution Parenteral 25 mg
Liquid Ophthalmic 1 mg/1ml
Solution / drops Ophthalmic 3 mg/1ml
Solution Ophthalmic 4 mg
Solution Conjunctival; Ophthalmic 4 mg
Injection, solution
Injection Parenteral
Injection, solution Intra-articular 20 mg/mL
Injection Intra-articular 20 mg/2ml
Injection, solution Parenteral
Solution / drops Ophthalmic 0.2 %
Cream Topical 0.15 g/50mL
Injection Intraepidermal 2.5 g/1
Injection, solution Intra-articular
Gel Topical 3.5 mg/1mL
Patch Topical 1.14 g/41
Gel Topical 0.25 g/10g
Gel Topical 2.5 g/100g
Lotion Topical 1 mg/1mL
Solution 10 mg/1ml
Patch Topical 99.97 g/100g
Solution
Injection, suspension, extended release
Gel; injection
Solution / drops Ophthalmic 1.8 mg/1ml
Solution Ophthalmic; Topical 4 mg
Emulsion Topical
Patch Topical 67.9 mg/70mg
Liquid Ophthalmic 2 mg/1ml
Solution Conjunctival; Ophthalmic 10 mg
Gel Topical 0.005 g/100g
Cream Topical 0.0014 g/28g
Solution Topical 0.01 mL/100mL
Solution Topical 0.01 g/100mL
Injection, solution 20 mg/1ml
Solution Ophthalmic
Solution Conjunctival; Ophthalmic
Solution / drops Ophthalmic
Injection Intra-articular
Patch Topical 6.14 g/100g
Gel Topical 0.01 g/100mL
Gel Topical 1000 g/20mL
Liquid Topical 100 g/100mL
Gel
Gel Topical 25 mg/1ml
Rinse Oral
Solution Intra-articular 20 mg
Injection, solution 10 mg/1ml
Liquid Topical 6 g/100mL
Solution Conjunctival; Ophthalmic 2 mg
Injection
Liquid Topical 0.5 g/100mL
Patch Topical 0.056 g/100mL
Patch Topical 99 g/100g
Gel Topical 0.1 mg/1mL
Injection Intra-articular 8 mg/1ml
Injection, solution, concentrate 8 mg/1ml
Solution 20 mg/2ml
Injection, solution 20 mg/2ml
Liquid Ophthalmic 1.8 mg/1ml
Solution 25 mg/2.5ml
Solution 20 mg/1ml
Gel Topical 20 mg/1ml
Gel Topical 12 mg/1ml
Injection, solution 27 mg/1ml
Gel Topical 3 g/3ml
Solution / drops Ophthalmic 2 mg/1ml
Prices
Not Available
Patents
Not Available
State
Solid
Experimental Properties
Property Value Source
melting point (°C) 241-247 https://aksci.com/item_detail.php?cat=H926
boiling point (°C) 1274.4 ± 65.0 http://www.chemspider.com/Chemical-Structure.2341173.html
water solubility 5 mg/mL https://aksci.com/item_detail.php?cat=H926
logP -6.62 http://www.chemspider.com/Chemical-Structure.2341173.html
pKa 3-4 https://www.google.com/url?sa=t&rct=j&q=&esrc=s&source=web&cd=&cad=rja&uact=8&ved=2ahUKEwilp7XI1ZTvAhVHnJ4KHdzWCcYQFjABegQIDhAD&url=https%3A%2F%2Fwww.mdpi.com%2F2073-4360%2F6%2F2%2F346%2Fpdf-vor&usg=AOvVaw0TAENuKz4FHSiyy8MR2405
Predicted Properties
Property Value Source
Water Solubility 46.6 mg/mL ALOGPS
logP -1.8 ALOGPS
logP -8.2 ChemAxon
logS -1.2 ALOGPS
pKa (Strongest Acidic) 2.87 ChemAxon
pKa (Strongest Basic) -3.9 ChemAxon
Physiological Charge -2 ChemAxon
Hydrogen Acceptor Count 23 ChemAxon
Hydrogen Donor Count 14 ChemAxon
Polar Surface Area 399.71 Å2 ChemAxon
Rotatable Bond Count 12 ChemAxon
Refractivity 155.1 m3·mol-1 ChemAxon
Polarizability 70.56 Å3 ChemAxon
Number of Rings 4 ChemAxon
Bioavailability 0 ChemAxon
Rule of Five No ChemAxon
Ghose Filter No ChemAxon
Veber's Rule No ChemAxon
MDDR-like Rule Yes ChemAxon
Predicted ADMET Features
Not Available
Mass Spec (NIST)
Not Available
Spectra
Spectrum Spectrum Type Splash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available

Targets

Drugtargets2

Build, predict & validate machine-learning models

Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.

Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.

Kind
Protein
Organism
Humans
Pharmacological action

Yes

Actions

Binder

General Function
Hyalurononglucosaminidase activity
Specific Function
Receptor for hyaluronic acid (HA). Mediates cell-cell and cell-matrix interactions through its affinity for HA, and possibly also through its affinity for other ligands such as osteopontin, collage...
Gene Name
CD44
Uniprot ID
P16070
Uniprot Name
CD44 antigen
Molecular Weight
81537.025 Da
References
  1. Higa K, Shimmura S, Shimazaki J, Tsubota K: Hyaluronic acid-CD44 interaction mediates the adhesion of lymphocytes by amniotic membrane stroma. Cornea. 2005 Mar;24(2):206-12. doi: 10.1097/01.ico.0000133999.45262.83. [Article]
  2. Uff CR, Neame SJ, Isacke CM: Hyaluronan binding by CD44 is regulated by a phosphorylation-independent mechanism. Eur J Immunol. 1995 Jul;25(7):1883-7. doi: 10.1002/eji.1830250714. [Article]
  3. Lesley J, Hascall VC, Tammi M, Hyman R: Hyaluronan binding by cell surface CD44. J Biol Chem. 2000 Sep 1;275(35):26967-75. doi: 10.1074/jbc.M002527200. [Article]
  4. Gupta RC, Lall R, Srivastava A, Sinha A: Hyaluronic Acid: Molecular Mechanisms and Therapeutic Trajectory. Front Vet Sci. 2019 Jun 25;6:192. doi: 10.3389/fvets.2019.00192. eCollection 2019. [Article]
Kind
Protein
Organism
Humans
Pharmacological action

Yes

Actions

Inhibitor

Binder

General Function
Virus receptor activity
Specific Function
ICAM proteins are ligands for the leukocyte adhesion protein LFA-1 (integrin alpha-L/beta-2). During leukocyte trans-endothelial migration, ICAM1 engagement promotes the assembly of endothelial api...
Gene Name
ICAM1
Uniprot ID
P05362
Uniprot Name
Intercellular adhesion molecule 1
Molecular Weight
57824.785 Da
References
  1. Gupta RC, Lall R, Srivastava A, Sinha A: Hyaluronic Acid: Molecular Mechanisms and Therapeutic Trajectory. Front Vet Sci. 2019 Jun 25;6:192. doi: 10.3389/fvets.2019.00192. eCollection 2019. [Article]
  2. Zhang X, He H, Lu G, Xu T, Qin L, Wang X, Jin X, Liu B, Zhao Z, Shen Z, Shao Y: Specific inhibition of ICAM-1 effectively reduces bladder inflammation in a rat model of severe non-bacterial cystitis. Sci Rep. 2016 Oct 26;6:35672. doi: 10.1038/srep35672. [Article]
Kind
Protein
Organism
Humans
Pharmacological action

Yes

Actions

Binder

General Function
Hyaluronic acid binding
Specific Function
Involved in cell motility. When hyaluronan binds to HMMR, the phosphorylation of a number of proteins, including PTK2/FAK1 occurs. May also be involved in cellular transformation and metastasis for...
Gene Name
HMMR
Uniprot ID
O75330
Uniprot Name
Hyaluronan mediated motility receptor
Molecular Weight
84099.845 Da
References
  1. Hatano H, Shigeishi H, Kudo Y, Higashikawa K, Tobiume K, Takata T, Kamata N: Overexpression of receptor for hyaluronan-mediated motility (RHAMM) in MC3T3-E1 cells induces proliferation and differentiation through phosphorylation of ERK1/2. J Bone Miner Metab. 2012 May;30(3):293-303. doi: 10.1007/s00774-011-0318-0. Epub 2011 Sep 27. [Article]
  2. Gupta RC, Lall R, Srivastava A, Sinha A: Hyaluronic Acid: Molecular Mechanisms and Therapeutic Trajectory. Front Vet Sci. 2019 Jun 25;6:192. doi: 10.3389/fvets.2019.00192. eCollection 2019. [Article]
  3. Kouvidi K, Berdiaki A, Nikitovic D, Katonis P, Afratis N, Hascall VC, Karamanos NK, Tzanakakis GN: Role of receptor for hyaluronic acid-mediated motility (RHAMM) in low molecular weight hyaluronan (LMWHA)-mediated fibrosarcoma cell adhesion. J Biol Chem. 2011 Nov 4;286(44):38509-20. doi: 10.1074/jbc.M111.275875. Epub 2011 Sep 13. [Article]
Kind
Protein
Organism
Humans
Pharmacological action

Unknown

Actions

Binder

General Function
Hyaluronic acid binding
Specific Function
May modulate neuronal adhesion and neurite growth during development by binding to neural cell adhesion molecules (NG-CAM and N-CAM). Chondroitin sulfate proteoglycan; binds to hyaluronic acid.
Gene Name
NCAN
Uniprot ID
O14594
Uniprot Name
Neurocan core protein
Molecular Weight
143092.14 Da
References
  1. Meyer-Puttlitz B, Milev P, Junker E, Zimmer I, Margolis RU, Margolis RK: Chondroitin sulfate and chondroitin/keratan sulfate proteoglycans of nervous tissue: developmental changes of neurocan and phosphacan. J Neurochem. 1995 Nov;65(5):2327-37. doi: 10.1046/j.1471-4159.1995.65052327.x. [Article]
  2. Zhou XH, Brakebusch C, Matthies H, Oohashi T, Hirsch E, Moser M, Krug M, Seidenbecher CI, Boeckers TM, Rauch U, Buettner R, Gundelfinger ED, Fassler R: Neurocan is dispensable for brain development. Mol Cell Biol. 2001 Sep;21(17):5970-8. doi: 10.1128/mcb.21.17.5970-5978.2001. [Article]
Kind
Protein
Organism
Humans
Pharmacological action

Unknown

Actions

Binder

General Function
Hyaluronic acid binding
Specific Function
May play a role in intercellular signaling and in connecting cells with the extracellular matrix. May take part in the regulation of cell motility, growth and differentiation. Binds hyaluronic acid.
Gene Name
VCAN
Uniprot ID
P13611
Uniprot Name
Versican core protein
Molecular Weight
372816.875 Da
References
  1. Wu YJ, La Pierre DP, Wu J, Yee AJ, Yang BB: The interaction of versican with its binding partners. Cell Res. 2005 Jul;15(7):483-94. doi: 10.1038/sj.cr.7290318. [Article]
  2. Hasegawa K, Yoneda M, Kuwabara H, Miyaishi O, Itano N, Ohno A, Zako M, Isogai Z: Versican, a major hyaluronan-binding component in the dermis, loses its hyaluronan-binding ability in solar elastosis. J Invest Dermatol. 2007 Jul;127(7):1657-63. doi: 10.1038/sj.jid.5700754. Epub 2007 Mar 15. [Article]
Kind
Protein
Organism
Humans
Pharmacological action

Unknown

Actions

Binder

General Function
Transcription factor binding
Specific Function
Is believed to be a multifunctional and multicompartmental protein involved in inflammation and infection processes, ribosome biogenesis, regulation of apoptosis, transcriptional regulation and pre...
Gene Name
C1QBP
Uniprot ID
Q07021
Uniprot Name
Complement component 1 Q subcomponent-binding protein, mitochondrial
Molecular Weight
31361.935 Da
References
  1. Yadav G, Prasad RL, Jha BK, Rai V, Bhakuni V, Datta K: Evidence for inhibitory interaction of hyaluronan-binding protein 1 (HABP1/p32/gC1qR) with Streptococcus pneumoniae hyaluronidase. J Biol Chem. 2009 Feb 6;284(6):3897-905. doi: 10.1074/jbc.M804246200. Epub 2008 Nov 11. [Article]
  2. Agostinis C, Vidergar R, Belmonte B, Mangogna A, Amadio L, Geri P, Borelli V, Zanconati F, Tedesco F, Confalonieri M, Tripodo C, Kishore U, Bulla R: Complement Protein C1q Binds to Hyaluronic Acid in the Malignant Pleural Mesothelioma Microenvironment and Promotes Tumor Growth. Front Immunol. 2017 Nov 20;8:1559. doi: 10.3389/fimmu.2017.01559. eCollection 2017. [Article]
Kind
Protein
Organism
Humans
Pharmacological action

Unknown

Actions

Binder

General Function
Hyaluronic acid binding
Specific Function
Stabilizes the aggregates of proteoglycan monomers with hyaluronic acid in the extracellular cartilage matrix.
Gene Name
HAPLN1
Uniprot ID
P10915
Uniprot Name
Hyaluronan and proteoglycan link protein 1
Molecular Weight
40165.215 Da
References
  1. Spicer AP, Joo A, Bowling RA Jr: A hyaluronan binding link protein gene family whose members are physically linked adjacent to chondroitin sulfate proteoglycan core protein genes: the missing links. J Biol Chem. 2003 Jun 6;278(23):21083-91. Epub 2003 Mar 27. [Article]
  2. Arming S, Strobl B, Wechselberger C, Kreil G: In vitro mutagenesis of PH-20 hyaluronidase from human sperm. Eur J Biochem. 1997 Aug 1;247(3):810-4. [Article]
Kind
Protein
Organism
Humans
Pharmacological action

Unknown

Actions

Binder

General Function
Hyaluronic acid binding
Specific Function
May function in hyaluronic acid binding.
Gene Name
HAPLN3
Uniprot ID
Q96S86
Uniprot Name
Hyaluronan and proteoglycan link protein 3
Molecular Weight
40893.995 Da
References
  1. Spicer AP, Joo A, Bowling RA Jr: A hyaluronan binding link protein gene family whose members are physically linked adjacent to chondroitin sulfate proteoglycan core protein genes: the missing links. J Biol Chem. 2003 Jun 6;278(23):21083-91. Epub 2003 Mar 27. [Article]
  2. Buckwalter JA, Rosenberg LC, Tang LH: The effect of link protein on proteoglycan aggregate structure. An electron microscopic study of the molecular architecture and dimensions of proteoglycan aggregates reassembled from the proteoglycan monomers and link proteins of bovine fetal epiphyseal cartilage. J Biol Chem. 1984 May 10;259(9):5361-3. [Article]
Kind
Protein
Organism
Humans
Pharmacological action

Unknown

Actions

Binder

General Function
Serine-type endopeptidase activity
Specific Function
Cleaves the alpha-chain at multiple sites and the beta-chain between 'Lys-53' and 'Lys-54' but not the gamma-chain of fibrinogen and therefore does not initiate the formation of the fibrin clot and...
Gene Name
HABP2
Uniprot ID
Q14520
Uniprot Name
Hyaluronan-binding protein 2
Molecular Weight
62671.255 Da
References
  1. Choi-Miura NH, Tobe T, Sumiya J, Nakano Y, Sano Y, Mazda T, Tomita M: Purification and characterization of a novel hyaluronan-binding protein (PHBP) from human plasma: it has three EGF, a kringle and a serine protease domain, similar to hepatocyte growth factor activator. J Biochem. 1996 Jun;119(6):1157-65. [Article]
  2. Choi-Miura NH, Yoda M, Saito K, Takahashi K, Tomita M: Identification of the substrates for plasma hyaluronan binding protein. Biol Pharm Bull. 2001 Feb;24(2):140-3. [Article]
  3. Lennon FE, Singleton PA: Role of hyaluronan and hyaluronan-binding proteins in lung pathobiology. Am J Physiol Lung Cell Mol Physiol. 2011 Aug;301(2):L137-47. doi: 10.1152/ajplung.00071.2010. Epub 2011 May 13. [Article]
Kind
Protein
Organism
Humans
Pharmacological action

Unknown

Actions

Binder

General Function
Hyaluronic acid binding
Specific Function
Receptor for hyaluronate.
Gene Name
LAYN
Uniprot ID
Q6UX15
Uniprot Name
Layilin
Molecular Weight
43108.055 Da
References
  1. Bono P, Rubin K, Higgins JM, Hynes RO: Layilin, a novel integral membrane protein, is a hyaluronan receptor. Mol Biol Cell. 2001 Apr;12(4):891-900. [Article]
  2. Murata M, Yudoh K, Shimizu H, Beppu M, Nakamura H, Kato T, Masuko K: Layilin, a talin-binding hyaluronan receptor, is expressed in human articular chondrocytes and synoviocytes and is down-regulated by interleukin-1beta. Mod Rheumatol. 2013 May;23(3):478-88. doi: 10.1007/s10165-012-0686-x. Epub 2012 Jun 22. [Article]
Kind
Protein
Organism
Humans
Pharmacological action

Unknown

Actions

Binder

General Function
Scavenger receptor activity
Specific Function
Phosphatidylserine receptor that enhances the engulfment of apoptotic cells. Hyaluronan receptor that binds to and mediates endocytosis of hyaluronic acid (HA). Acts also, in different species, as ...
Gene Name
STAB2
Uniprot ID
Q8WWQ8
Uniprot Name
Stabilin-2
Molecular Weight
276985.63 Da
References
  1. Politz O, Gratchev A, McCourt PA, Schledzewski K, Guillot P, Johansson S, Svineng G, Franke P, Kannicht C, Kzhyshkowska J, Longati P, Velten FW, Johansson S, Goerdt S: Stabilin-1 and -2 constitute a novel family of fasciclin-like hyaluronan receptor homologues. Biochem J. 2002 Feb 15;362(Pt 1):155-64. [Article]
  2. Zhou B, McGary CT, Weigel JA, Saxena A, Weigel PH: Purification and molecular identification of the human hyaluronan receptor for endocytosis. Glycobiology. 2003 May;13(5):339-49. Epub 2002 Dec 17. [Article]
  3. Harris EN, Kyosseva SV, Weigel JA, Weigel PH: Expression, processing, and glycosaminoglycan binding activity of the recombinant human 315-kDa hyaluronic acid receptor for endocytosis (HARE). J Biol Chem. 2007 Feb 2;282(5):2785-97. Epub 2006 Dec 4. [Article]
  4. Harris EN, Weigel JA, Weigel PH: The human hyaluronan receptor for endocytosis (HARE/Stabilin-2) is a systemic clearance receptor for heparin. J Biol Chem. 2008 Jun 20;283(25):17341-50. doi: 10.1074/jbc.M710360200. Epub 2008 Apr 22. [Article]
Kind
Protein
Organism
Humans
Pharmacological action

Unknown

Actions

Binder

General Function
Hyaluronic acid binding
Specific Function
Possibly involved in cell-cell and cell-matrix interactions during inflammation and tumorigenesis.
Gene Name
TNFAIP6
Uniprot ID
P98066
Uniprot Name
Tumor necrosis factor-inducible gene 6 protein
Molecular Weight
31203.09 Da
References
  1. Wisniewski HG, Burgess WH, Oppenheim JD, Vilcek J: TSG-6, an arthritis-associated hyaluronan binding protein, forms a stable complex with the serum protein inter-alpha-inhibitor. Biochemistry. 1994 Jun 14;33(23):7423-9. [Article]
  2. Lee TH, Wisniewski HG, Vilcek J: A novel secretory tumor necrosis factor-inducible protein (TSG-6) is a member of the family of hyaluronate binding proteins, closely related to the adhesion receptor CD44. J Cell Biol. 1992 Jan;116(2):545-57. [Article]
  3. Kohda D, Morton CJ, Parkar AA, Hatanaka H, Inagaki FM, Campbell ID, Day AJ: Solution structure of the link module: a hyaluronan-binding domain involved in extracellular matrix stability and cell migration. Cell. 1996 Sep 6;86(5):767-75. [Article]
Kind
Protein
Organism
Humans
Pharmacological action

Unknown

Actions

Binder

General Function
Hyaluronic acid binding
Specific Function
Chondroitin sulfate- and hyaluronan-binding proteoglycan involved in the organization of interphotoreceptor matrix; may participate in the maturation and maintenance of the light-sensitive photorec...
Gene Name
IMPG2
Uniprot ID
Q9BZV3
Uniprot Name
Interphotoreceptor matrix proteoglycan 2
Molecular Weight
138619.39 Da
References
  1. Acharya S, Foletta VC, Lee JW, Rayborn ME, Rodriguez IR, Young WS 3rd, Hollyfield JG: SPACRCAN, a novel human interphotoreceptor matrix hyaluronan-binding proteoglycan synthesized by photoreceptors and pinealocytes. J Biol Chem. 2000 Mar 10;275(10):6945-55. [Article]
  2. Interpro entry: Interphotoreceptor matrix proteoglycan 2 ( IPR032975) [Link]
Kind
Protein
Organism
Humans
Pharmacological action

Unknown

Actions

Binder

General Function
Not Available
Specific Function
May be involved in nuclear functions such as the remodeling of chromatin and the regulation of transcription.
Gene Name
HABP4
Uniprot ID
Q5JVS0
Uniprot Name
Intracellular hyaluronan-binding protein 4
Molecular Weight
45785.09 Da
References
  1. Huang L, Grammatikakis N, Yoneda M, Banerjee SD, Toole BP: Molecular characterization of a novel intracellular hyaluronan-binding protein. J Biol Chem. 2000 Sep 22;275(38):29829-39. [Article]
Kind
Protein
Organism
Humans
Pharmacological action

Unknown

General Function
Ligand-specific transporter trafficking between intracellular organelles (TGN) and the plasma membrane. Plays a role in autocrine regulation of cell growth mediated by growth regulators containing cell surface retention sequence binding (CRS). May act as a hyaluronan (HA) transporter, either mediating its uptake for catabolism within lymphatic endothelial cells themselves, or its transport into the lumen of afferent lymphatic vessels for subsequent re-uptake and degradation in lymph nodes.
Specific Function
Hyaluronic acid binding
Gene Name
LYVE1
Uniprot ID
Q9Y5Y7
Uniprot Name
Lymphatic vessel endothelial hyaluronic acid receptor 1
Molecular Weight
35213.105 Da
References
  1. Gupta RC, Lall R, Srivastava A, Sinha A: Hyaluronic Acid: Molecular Mechanisms and Therapeutic Trajectory. Front Vet Sci. 2019 Jun 25;6:192. doi: 10.3389/fvets.2019.00192. eCollection 2019. [Article]
  2. Lawrance W, Banerji S, Day AJ, Bhattacharjee S, Jackson DG: Binding of Hyaluronan to the Native Lymphatic Vessel Endothelial Receptor LYVE-1 Is Critically Dependent on Receptor Clustering and Hyaluronan Organization. J Biol Chem. 2016 Apr 8;291(15):8014-30. doi: 10.1074/jbc.M115.708305. Epub 2016 Jan 28. [Article]

Enzymes

Kind
Protein group
Organism
Humans
Pharmacological action

Unknown

Actions

Substrate

General Function
Cell surface hyaluronidase that mediates the initial cleavage of extracellular high-molecular-weight hyaluronan into intermediate-size hyaluronan of approximately 5 kDa fragments (PubMed:28246172). Acts as a regulator of angiogenesis and heart morphogenesis by mediating degradation of extracellular hyaluronan, thereby regulating VEGF signaling (By similarity). Is very specific to hyaluronan; not able to cleave chondroitin sulfate or dermatan sulfate (PubMed:28246172).
Specific Function
Cadherin binding
Components:
References
  1. Gupta RC, Lall R, Srivastava A, Sinha A: Hyaluronic Acid: Molecular Mechanisms and Therapeutic Trajectory. Front Vet Sci. 2019 Jun 25;6:192. doi: 10.3389/fvets.2019.00192. eCollection 2019. [Article]
  2. Fallacara A, Baldini E, Manfredini S, Vertuani S: Hyaluronic Acid in the Third Millennium. Polymers (Basel). 2018 Jun 25;10(7). pii: polym10070701. doi: 10.3390/polym10070701. [Article]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action

Unknown

Actions

Substrate

General Function
Organic anion transmembrane transporter activity
Specific Function
Acts as a multispecific organic anion pump which can transport nucleotide analogs.
Gene Name
ABCC5
Uniprot ID
O15440
Uniprot Name
Multidrug resistance-associated protein 5
Molecular Weight
160658.8 Da
References
  1. Schulz T, Schumacher U, Prehm P: Hyaluronan export by the ABC transporter MRP5 and its modulation by intracellular cGMP. J Biol Chem. 2007 Jul 20;282(29):20999-1004. doi: 10.1074/jbc.M700915200. Epub 2007 May 31. [Article]
  2. Thomas NK, Brown TJ: ABC transporters do not contribute to extracellular translocation of hyaluronan in human breast cancer in vitro. Exp Cell Res. 2010 Apr 15;316(7):1241-53. doi: 10.1016/j.yexcr.2010.01.004. Epub 2010 Jan 11. [Article]
  3. Stracke D, Schulz T, Prehm P: Inhibitors of hyaluronan export from hops prevent osteoarthritic reactions. Mol Nutr Food Res. 2011 Mar;55(3):485-94. doi: 10.1002/mnfr.201000210. Epub 2010 Sep 16. [Article]

Drug created at February 23, 2012 18:15 / Updated at December 04, 2021 10:28