Hyaluronic acid
Identification
- 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
Structure for Hyaluronic acid (DB08818)
- Weight
- Average: 776.6486
Monoisotopic: 776.233485724 - Chemical Formula
- C28H44N2O23
- Synonyms
- Hyaluronan
- Hyaluronate
Pharmacology
- 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
Accelerate your drug discovery research with the industry’s only fully connected ADMET dataset, ideal for:Accelerate your drug discovery research with our fully connected ADMET dataset- Associated Conditions
- Actinic Keratosis (AK)
- Burns
- Chronic Skin Ulcers
- Conjunctivitis
- Dehydration
- Dermabrasion
- Dermatosis
- Dry Eyes
- Facial Defect
- Interstitial Cystitis
- Keratoconjunctivitis
- Ocular Irritation
- Osteoarthritis (OA)
- Pain of the knee
- Seasonal Allergic Conjunctivitis
- Skin Burn
- Skin Irritation
- Skin fissures
- Tissue Adhesions
- Varicose Ulcers
- Wounds
- Eye discomfort
- Facial fine wrinkling
- Sensation of burning in the eyes
- Superficial Wounds
- Associated Therapies
- Contraindications & Blackbox Warnings
Contraindications & Blackbox WarningsWith our commercial data, access important information on dangerous risks, contraindications, and adverse effects.Our Blackbox Warnings cover Risks, Contraindications, and Adverse Effects- 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 binderHumans AIntercellular adhesion molecule 1 inhibitorbinderHumans AHyaluronan mediated motility receptor binderHumans UNeurocan core protein binderHumans UVersican core protein binderHumans UComplement component 1 Q subcomponent-binding protein, mitochondrial binderHumans UHyaluronan and proteoglycan link protein 1 binderHumans UHyaluronan and proteoglycan link protein 3 binderHumans UHyaluronan-binding protein 2 binderHumans ULayilin binderHumans UStabilin-2 binderHumans UTumor necrosis factor-inducible gene 6 protein binderHumans UInterphotoreceptor matrix proteoglycan 2 binderHumans UIntracellular hyaluronan-binding protein 4 binderHumans 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
Reduce medical errorsand improve treatment outcomes with our comprehensive & structured data on drug adverse effects.Reduce medical errors & improve treatment outcomes with our 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
Interactions
- 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.
Products
Comprehensive & structured drug product infoFrom application numbers to product codes, connect different identifiers through our commercial datasets.Easily connect various identifiers back to our datasets- 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 
HYLASE Wound Gel 2.5 g/100g Topical ECR Pharmaceuticals Co., Inc. 2012-01-06 2012-01-18 US Hylinate Lotion 1 mg/1mL Topical Artesa Labs, Llc 2020-01-13 2020-03-30 US - 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 - 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 BELOTERO SOFT Gel; Injection บริษัท เมิร์ซ เฮลธ์แคร์ (ประเทศไทย) จำกัด 2016-06-07 Not applicable Thailand 
C-eye Day Cream 0.00006 g/30mL Topical LCELLS SA DE CV 2019-11-15 Not applicable US C-eye Night Gel 0.000015 g/15mL Topical LCELLS SA DE CV 2019-11-15 Not applicable US Cluederm Aqua Solution Rejuve Plus Liquid 20 mg/500mL Topical Classys Inc. 2018-06-28 2019-03-29 US Curestin Patch 99.97 mg/100mg Topical J World 2019-07-21 Not applicable US Curithys Patch 94.39 mg/100mg Topical J World 2019-07-21 Not applicable US Deepair Micro Intensive Magic Patch 6.1 g/100mg Topical Acosmetic. co.ltd 2016-08-01 Not applicable US E- Repair Cream 0.00006 g/30mL Topical LCELLS SA DE CV 2019-11-15 Not applicable US Elcosys Patch 99.97 mg/100mg Topical DS TECH CO., LTD 2019-07-21 Not applicable US - 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 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 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 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 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 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 Elcure Ato Sodium hyaluronate (65 g/100mL) + Jojoba oil (5 g/100mL) + Morus alba root bark (10 g/100mL) + Platycodon grandiflorus leaf (7 g/100mL) Lotion Topical Elcure Co., Ltd. 2011-02-11 2017-04-20 US Eldeen Age Twenty One Micro Therapy Program Sodium hyaluronate (0.4298 g/100mL) + Sodium hyaluronate (6.14 g/100mg) Kit Topical Small Lab Co., Ltd. 2020-01-01 Not applicable US Eldeen Age Twenty One Micro Therapy Program Sodium hyaluronate (0.4298 g/100mL) + Sodium hyaluronate (6.14 g/100mg) Kit Topical Small Lab Co., Ltd. 2020-01-01 Not applicable US ELDEEN AGE TWENTY ONE MifitPatch and Serum Sodium hyaluronate (0.4298 g/100g) + Sodium hyaluronate (6.14 g/100mg) Kit Topical Small Lab Co., Ltd. 2018-10-01 Not applicable US - 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 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 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 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 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 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 C-eye Day Hyaluronic acid (0.00006 g/30mL) Cream Topical LCELLS SA DE CV 2019-11-15 Not applicable US C-eye Night Hyaluronic acid (0.000015 g/15mL) Gel Topical LCELLS SA DE CV 2019-11-15 Not applicable US 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 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
Categories
- ATC Codes
- S01KA51 — Hyaluronic acid, combinationsS01KA01 — Hyaluronic acidD03AX05 — Hyaluronic acid
- D03AX — Other cicatrizants
- D03A — CICATRIZANTS
- D03 — PREPARATIONS FOR TREATMENT OF WOUNDS AND ULCERS
- D — DERMATOLOGICALS
- 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
- 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 show 13 more
- Substituents
- 1-o-glucuronide / Acetal / Acetamide / Acylaminosugar / Alcohol / Aliphatic heteromonocyclic compound / Beta-hydroxy acid / Carbonyl group / Carboxamide group / Carboxylic acid show 25 more
- Molecular Framework
- Aliphatic heteromonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 01OUW6MA4L
- 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
References
- 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
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- J. Necas, L. Bartosikova, P. Brauner, J. Kolar: Hyaluronic acid (hyaluronan): a review Veterinarni Medicina. 2008 Aug 12;53(8):397–411. [Article]
- 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]
- 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]
- 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]
- NIH StatPearls: Hyaluronic acid [Link]
- DailyMed: HALUCORT gel dressing with hyaluronic acid [Link]
- NIH DailyMed: Hyaluronic acid injection [Link]
- DailyMed: PRO PH (hyaluronic acid gel) for injection [Link]
- DailyMed: Vista advanced dry eye capsule [Link]
- DailyMed: Hyaluronic acid gel [Link]
- FDA Approved Drug Products: SYNOJOYNT (sodium hyaluronate) intra-articular injection [Link]
- Fischer Scientific MSDS: Sodium hyaluronate [Link]
- External Links
- Human Metabolome Database
- HMDB0010366
- KEGG Drug
- D08043
- KEGG Compound
- C00518
- PubChem Compound
- 24759
- PubChem Substance
- 310264899
- ChemSpider
- 23145
- 5463
- PharmGKB
- PA165958431
- Wikipedia
- Sodium_hyaluronate
- MSDS
- Download (19.5 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Active Not Recruiting Treatment Dry Eye Syndromes / Meibomian Gland Dysfunction (MGD) 1 4 Active Not Recruiting Treatment Immediate Dental Implant 1 4 Active Not Recruiting Treatment Osteoarthritis of the Knee 1 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
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Patch Topical 0.4298 mg/100mg Injection, solution Intra-articular Gel Topical Patch Topical Gel; injection Solution Intraocular Cream Topical 0.00006 g/30mL Gel Topical 0.000015 g/15mL Cream Topical Liquid Topical 20 mg/500mL Solution / drops Conjunctival Solution, gel forming / drops Intraocular Aerosol, foam Cloth Topical Cream Topical Gel Topical Ointment 10 G Spray Cutaneous 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 Lotion Topical Kit Topical Suspension Ophthalmic Lotion / shampoo Topical 0.05 g/50mL Lotion / shampoo Topical 0.23 g/230mL Granule Oral Tablet Oral Solution Parenteral Liquid Ophthalmic Solution / drops Ophthalmic Solution Conjunctival; Ophthalmic Solution Ophthalmic Solution Ophthalmic Solution Intra-articular Injection Parenteral Injection, solution Parenteral 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 Patch Topical 99.97 g/100g Solution Injection, suspension, extended release Gel; injection Solution Ophthalmic; Topical Emulsion Topical Patch Topical 67.9 mg/70mg Gel Topical 0.005 g/100g Cream Topical 0.0014 g/28g Solution Topical 0.01 mL/100mL Solution Topical 0.01 g/100mL Solution Conjunctival; Ophthalmic Solution / drops Ophthalmic 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 Injection, solution Liquid Topical 6 g/100mL Injection Patch Topical 0.056 g/100mL Patch Topical 99 g/100g Gel Topical 0.1 mg/1mL Injection Intra-articular Injection, solution, concentrate Gel Topical 20 mg/1ml Gel Topical 12 mg/1ml Gel Topical 3 g/3ml - Prices
- Not Available
- Patents
- Not Available
Properties
- 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
Spectra
- 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
- 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
- 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]
- 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]
- 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]
- 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
- InhibitorBinder
- 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
- 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]
- 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
- 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]
- 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]
- 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
- 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]
- 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
- 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]
- 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
- 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]
- 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
- 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]
- 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
- 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]
- 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
- 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]
- 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]
- 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
- 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]
- 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
- 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]
- 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]
- 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]
- 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
- 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]
- 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]
- 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
- 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]
- 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
- 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
- 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]
- 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:
| Name | UniProt ID |
|---|---|
| Cell surface hyaluronidase | Q9UHN6 |
| Hyaluronidase PH-20 | P38567 |
| Hyaluronidase-1 | Q12794 |
| Hyaluronidase-2 | Q12891 |
| Hyaluronidase-3 | O43820 |
| Hyaluronidase-4 | Q2M3T9 |
References
- 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]
- 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
- 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]
- 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]
- 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 on February 23, 2012 18:15 / Updated on May 07, 2021 21:39