Hyaluronic acid

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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

Similar Structures

Weight: Average: 776.6486
Monoisotopic: 776.233485724
Chemical Formula: C₂₈H₄₄N₂O₂₃

Synonyms

Hyaluronan
Hyaluronate

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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

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Associated Conditions

Indication Type	Indication	Combined Product Details	Approval Level	Dose Form
Used in combination to treat	Actinic keratosis (ak)	Combination Product in combination with: Diclofenac (DB00586)	••••••••••••	•••
Used in combination to treat	Burns	Combination Product in combination with: Silver sulfadiazine (DB05245)	••••••••••••	•••••
Treatment of	Chronic skin ulcers		••••••••••••	•••••
Treatment of	Conjunctivitis		••••••••••••	•••••••• • •••••
Treatment of	Dehydration		••••••••••••	•••••

Associated Therapies

Contraindications & Blackbox Warnings

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Pharmacodynamics

HA has long-acting lubricant, shock absorbing, joint stabilizing, and water balancing properties.^2,17 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
ALymphatic vessel endothelial hyaluronic acid receptor 1	modulator	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

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

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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

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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
HyGel	Gel	0.25 g/10g	Topical	Gentex Pharma	2015-10-15	2016-07-01
HYLASE Wound	Gel	2.5 g/100g	Topical	ECR Pharmaceuticals Co., Inc.	2012-01-06	2012-01-18
Hylinate	Lotion	1 mg/1mL	Topical	Artesa Labs, Llc	2020-01-13	2020-03-30

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

Over the Counter Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Acnepatch	Patch	0.4298 mg/100mg	Topical	Small Lab Co., Ltd.	2020-04-28	2021-03-26
BELOTERO SOFT	Gel; Injection	20 mg/1ml		บริษัท เมิร์ซ เฮลธ์แคร์ (ประเทศไทย) จำกัด	2016-06-07	Not applicable
C-eye Day	Cream	0.00006 g/30mL	Topical	LCELLS SA DE CV	2019-11-15	Not applicable
C-eye Night	Gel	0.000015 g/15mL	Topical	LCELLS SA DE CV	2019-11-15	Not applicable
Cluederm Aqua Solution Rejuve Plus	Liquid	20 mg/500mL	Topical	Classys Inc.	2018-06-28	2019-03-29

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
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
ACTS38 BoswelliaGel	Sodium hyaluronate (0.01 g/100mL) + Centella asiatica (0.01 g/100mL) + Indian frankincense (1.2 g/100mL) + N-Acetylglucosamine (0.1 g/100mL)	Gel	Topical	A-Lot Biologics Inc	2022-09-07	Not applicable
ACTS38 BoswelliaGel (100ml)	Sodium hyaluronate (0.01 g/100mL) + Centella asiatica (0.01 g/100mL) + Indian frankincense (1.2 g/100mL) + N-Acetylglucosamine (0.1 g/100mL)	Gel	Topical	A-Lot Biologics Inc	2022-10-23	Not applicable
ALTERGEN	Hyaluronic acid (0.05 %) + Silver sulfadiazine (1 %)	Cream	Occlusive dressing technique	Ibsa Farmaceutici Italia S.R.L.	2014-07-08	Not applicable
ALTERGEN	Hyaluronic acid (0.2 %) + Silver sulfadiazine (1 %)	Cream	Topical	Ibsa Farmaceutici Italia S.R.L.	2014-07-08	Not applicable

Unapproved/Other Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
Acnepatch	Sodium hyaluronate (0.4298 mg/100mg)	Patch	Topical	Small Lab Co., Ltd.	2020-04-28	2021-03-26
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
ACTS38 BoswelliaGel	Sodium hyaluronate (0.01 g/100mL) + Centella asiatica (0.01 g/100mL) + Indian frankincense (1.2 g/100mL) + N-Acetylglucosamine (0.1 g/100mL)	Gel	Topical	A-Lot Biologics Inc	2022-09-07	Not applicable
ACTS38 BoswelliaGel (100ml)	Sodium hyaluronate (0.01 g/100mL) + Centella asiatica (0.01 g/100mL) + Indian frankincense (1.2 g/100mL) + N-Acetylglucosamine (0.1 g/100mL)	Gel	Topical	A-Lot Biologics Inc	2022-10-23	Not applicable
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

Chemical Identifiers

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

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
RxNav: 5463
PharmGKB: PA165958431
Wikipedia: Sodium_hyaluronate

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Not Available	Active Not Recruiting	Treatment	Carious Exposure of Pulp	1	somestatus	stop reason	just information to hide
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Not Available	Approved for Marketing	Not Available	Liver Disease	1	somestatus	stop reason	just information to hide
Not Available	Approved for Marketing	Not Available	Total Parenteral Nutrition-Induced Cholestasis	3	somestatus	stop reason	just information to hide
Not Available	Completed	Not Available	Dry Eye Syndrome (DES)	2	somestatus	stop reason	just information to hide

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Packagers

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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
Cream	Topical
Liquid	Topical	20 mg/500mL
Patch	Cutaneous
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
Cream	Cutaneous	0.9 g/3g
Rinse	Cutaneous
Patch	Topical	99.97 mg/100mg
Patch	Topical	94.39 mg/100mg
Soap	Cutaneous
Patch	Topical	6.1 g/100mg
Solution		6 mg/1ml
Solution	Intra-articular	25 mg
Solution / drops	Ophthalmic	0.15 %
Lotion	Topical
Kit; liquid; patch	Topical
Kit	Topical
Emulsion	Cutaneous
Suspension	Ophthalmic	4 mg
Liquid	Cutaneous	4.5 mg/30mg
Gel	Cutaneous
Solution / drops	Ophthalmic	0.15 g/100ml
Solution	Parenteral	20 mg
Lotion / shampoo	Topical	0.05 g/50mL
Lotion / shampoo	Topical	0.23 g/230mL
Gel	Topical	0.3 mg/15g
Granule	Oral
Tablet	Oral
Solution	Parenteral	25 mg
Solution / drops	Ophthalmic	1 MG/ML
Liquid	Ophthalmic	1 mg/1ml
Solution / drops	Ophthalmic	0.1 %
Solution / drops	Ophthalmic	3 mg/1ml
Solution	Ophthalmic	4 mg
Solution	Ophthalmic
Solution / drops	Ophthalmic
Injection
Injection		20 mg/2ml
Injection, solution
Solution	Intra-articular	20 mg
Injection	Parenteral	20 mg
Injection, solution	Intra-articular	20 mg/mL
Injection	Intra-articular	20 mg/2ml
Injection, solution	Parenteral	20 mg
Injection, solution	Parenteral
Solution / drops	Ophthalmic	0.2 %
Liquid	Cutaneous
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
Solution	Topical
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	400000 mg
Emulsion	Topical
Liquid	Dental
Lotion	Cutaneous
Paste	Cutaneous
Spray	Cutaneous
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 g/100mL
Solution	Topical	0.01 mL/100mL
Injection, solution		20 mg/1ml
Oil	Cutaneous
Solution / drops	Ophthalmic
Solution	Conjunctival; Ophthalmic
Injection	Intra-articular	20 mg
Patch	Topical	6.14 g/100g
Gel	Topical	0.01 g/100mL
Powder	Dental
Gel	Topical	1000 g/20mL
Liquid	Topical	100 g/100mL
Gel
Stick	Cutaneous
Gel	Topical	25 mg/1ml
Rinse	Oral	0.1 %
Rinse	Oral	0025 %
Cream	Cutaneous
Patch	Cutaneous	0.42 g/2g
Solution	Intra-articular	25.000 mg
Injection, solution		10 mg/1ml
Injection, solution	Parenteral	8 mg/ml
Liquid	Topical	6 g/100mL
Solution	Conjunctival; Ophthalmic	2 mg
Solution	Ophthalmic	2 mg
Solution	Conjunctival; Ophthalmic	4 mg
Injection		10 mg/ml
Liquid	Topical	0.5 g/100mL
Patch	Topical	0.056 g/100mL
Patch	Topical	99 g/100g
Gel	Topical	0.1 mg/1mL
Solution	Ophthalmic	4.000 mg
Solution	Ophthalmic; Topical	4 mg
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

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	71.14 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	splash10-0a7i-0001010900-9b7debb322295909029e
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-05rr-0000001900-322a49c8419ac444a6bc
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0kcr-0063042900-5e00f06fa5653cca1b4e
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-00w9-0301031900-b297f58d9e3c817537f7
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0fb9-0843204900-27105b3e40a72acc13e9
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-001r-6441569700-d020f61e1ddea7c60ca2

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å²)	Source type	Source
[M-H]-	251.4254994	predicted	DarkChem Lite v0.1.0
[M-H]-	251.18718	predicted	DeepCCS 1.0 (2019)
[M+H]+	256.6512994	predicted	DarkChem Lite v0.1.0
[M+H]+	252.91087	predicted	DeepCCS 1.0 (2019)
[M+Na]+	258.1334994	predicted	DarkChem Lite v0.1.0
[M+Na]+	259.23987	predicted	DeepCCS 1.0 (2019)

Targets

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Details1. CD44 antigen

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Binder

General Function: Cell-surface receptor that plays a role in cell-cell interactions, cell adhesion and migration, helping them to sense and respond to changes in the tissue microenvironment (PubMed:16541107, PubMed:19703720, PubMed:22726066). Participates thereby in a wide variety of cellular functions including the activation, recirculation and homing of T-lymphocytes, hematopoiesis, inflammation and response to bacterial infection (PubMed:7528188). Engages, through its ectodomain, extracellular matrix components such as hyaluronan/HA, collagen, growth factors, cytokines or proteases and serves as a platform for signal transduction by assembling, via its cytoplasmic domain, protein complexes containing receptor kinases and membrane proteases (PubMed:18757307, PubMed:23589287). Such effectors include PKN2, the RhoGTPases RAC1 and RHOA, Rho-kinases and phospholipase C that coordinate signaling pathways promoting calcium mobilization and actin-mediated cytoskeleton reorganization essential for cell migration and adhesion (PubMed:15123640)
Specific Function: collagen binding
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]

Details2. Intercellular adhesion molecule 1

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Inhibitor
Binder

General 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 apical cups through ARHGEF26/SGEF and RHOG activation
Specific Function: integrin binding
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]

Details3. Hyaluronan mediated motility receptor

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Binder

General Function: Receptor for hyaluronic acid (HA) (By similarity). Involved in cell motility (By similarity). 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 formation, and in regulating extracellular-regulated kinase (ERK) activity. May act as a regulator of adipogenisis (By similarity)
Specific Function: cargo receptor activity
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]

Details4. Lymphatic vessel endothelial hyaluronic acid receptor 1

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Modulator

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 (PubMed:10037799). Binds to pericelluar hyaluronan matrices deposited on the surface of leukocytes and facilitates cell adhesion and migration through lymphatic endothelium (PubMed:26823460)
Specific Function: cargo receptor activity
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]
Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]

Details5. Neurocan core protein

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Binder

General 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
Specific Function: calcium ion binding
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]

Details6. Versican core protein

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Binder

General 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
Specific Function: calcium ion binding
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]

Details7. Complement component 1 Q subcomponent-binding protein, mitochondrial

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Binder

General Function: Multifunctional and multicompartmental protein involved in inflammation and infection processes, ribosome biogenesis, protein synthesis in mitochondria, regulation of apoptosis, transcriptional regulation and pre-mRNA splicing (PubMed:10022843, PubMed:10479529, PubMed:10722602, PubMed:11086025, PubMed:11859136, PubMed:15243141, PubMed:16140380, PubMed:16177118, PubMed:17881511, PubMed:18676636, PubMed:19004836, PubMed:19164550, PubMed:20810993, PubMed:21536856, PubMed:21544310, PubMed:22700724, PubMed:28942965, PubMed:8662673, PubMed:8710908, PubMed:9461517). At the cell surface is thought to act as an endothelial receptor for plasma proteins of the complement and kallikrein-kinin cascades (PubMed:10479529, PubMed:11859136, PubMed:8662673, PubMed:8710908). Putative receptor for C1q; specifically binds to the globular 'heads' of C1q thus inhibiting C1; may perform the receptor function through a complex with C1qR/CD93 (PubMed:20810993, PubMed:8195709). In complex with cytokeratin-1/KRT1 is a high affinity receptor for kininogen-1/HMWK (PubMed:21544310). Can also bind other plasma proteins, such as coagulation factor XII leading to its autoactivation. May function to bind initially fluid kininogen-1 to the cell membrane. The secreted form may enhance both extrinsic and intrinsic coagulation pathways. It is postulated that the cell surface form requires docking with transmembrane proteins for downstream signaling which might be specific for a cell-type or response. By acting as C1q receptor is involved in chemotaxis of immature dendritic cells and neutrophils and is proposed to signal through CD209/DC-SIGN on immature dendritic cells, through integrin alpha-4/beta-1 during trophoblast invasion of the decidua, and through integrin beta-1 during endothelial cell adhesion and spreading (PubMed:16140380, PubMed:22700724, PubMed:9461517). Signaling involved in inhibition of innate immune response is implicating the PI3K-AKT/PKB pathway (PubMed:16177118). Required for protein synthesis in mitochondria (PubMed:28942965). In mitochondrial translation may be involved in formation of functional 55S mitoribosomes; the function seems to involve its RNA-binding activity (By similarity). May be involved in the nucleolar ribosome maturation process; the function may involve the exchange of FBL for RRP1 in the association with pre-ribosome particles (By similarity). Involved in regulation of RNA splicing by inhibiting the RNA-binding capacity of SRSF1 and its phosphorylation (PubMed:10022843, PubMed:21536856). Is required for the nuclear translocation of splicing factor U2AF1L4 (By similarity). Involved in regulation of CDKN2A- and HRK-mediated apoptosis. Stabilizes mitochondrial CDKN2A isoform smARF (PubMed:17486078). May be involved in regulation of FOXC1 transcriptional activity and NFY/CCAAT-binding factor complex-mediated transcription (PubMed:15243141, PubMed:18676636). May play a role in antibacterial defense as it can bind to cell surface hyaluronan and inhibit Streptococcus pneumoniae hyaluronate lyase (PubMed:19004836). May be involved in modulation of the immune response; ligation by HCV core protein is resulting in suppression of interleukin-12 production in monocyte-derived dendritic cells (PubMed:11086025, PubMed:17881511). Involved in regulation of antiviral response by inhibiting RIGI- and IFIH1-mediated signaling pathways probably involving its association with MAVS after viral infection (PubMed:19164550). Acts as a regulator of DNA repair via homologous recombination by inhibiting the activity of MRE11: interacts with unphosphorylated MRE11 and RAD50 in absence of DNA damage, preventing formation and activity of the MRN complex. Following DNA damage, dissociates from phosphorylated MRE11, allowing formation of the MRN complex (PubMed:31353207)
Specific Function: adrenergic receptor binding
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]

Details8. Hyaluronan and proteoglycan link protein 1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Binder

General Function: Stabilizes the aggregates of proteoglycan monomers with hyaluronic acid in the extracellular cartilage matrix
Specific Function: hyaluronic acid binding
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]

Details9. Hyaluronan and proteoglycan link protein 3

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Binder

General Function: May function in hyaluronic acid binding
Specific Function: 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]

Details10. Hyaluronan-binding protein 2

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Binder

General 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 does not cause the fibrinolysis directly. It does not cleave (activate) prothrombin and plasminogen but converts the inactive single chain urinary plasminogen activator (pro-urokinase) to the active two chain form. Activates coagulation factor VII (PubMed:10754382, PubMed:11217080, PubMed:8827452). May function as a tumor suppressor negatively regulating cell proliferation and cell migration (PubMed:26222560)
Specific Function: calcium ion binding
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]

Details11. Layilin

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Binder

General Function: Receptor for hyaluronate
Specific Function: carbohydrate binding
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]

Details12. Stabilin-2

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Binder

General 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 a primary systemic scavenger receptor for heparin (Hep), chondroitin sulfate (CS), dermatan sulfate (DS), nonglycosaminoglycan (GAG), acetylated low-density lipoprotein (AcLDL), pro-collagen propeptides and advanced glycation end products (AGE). May serve to maintain tissue integrity by supporting extracellular matrix turnover or it may contribute to maintaining fluidity of bodily liquids by resorption of hyaluronan. Counter receptor which plays an important role in lymphocyte recruitment in the hepatic vasculature. Binds to both Gram-positive and Gram-negative bacteria and may play a role in defense against bacterial infection. The proteolytically processed 190 kDa form also functions as an endocytosis receptor for heparin internalization as well as HA and CS
Specific Function: calcium ion binding
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]

Details13. Tumor necrosis factor-inducible gene 6 protein

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Binder

General Function: Major regulator of extracellular matrix organization during tissue remodeling (PubMed:15917224, PubMed:18042364, PubMed:26823460). Catalyzes the transfer of a heavy chain (HC) from inter-alpha-inhibitor (I-alpha-I) complex to hyaluronan. Cleaves the ester bond between the C-terminus of the HC and GalNAc residue of the chondroitin sulfate chain in I-alpha-I complex followed by transesterification of the HC to hyaluronan. In the process, potentiates the antiprotease function of I-alpha-I complex through release of free bikunin (PubMed:15917224, PubMed:16873769, PubMed:20463016). Acts as a catalyst in the formation of hyaluronan-HC oligomers and hyaluronan-rich matrix surrounding the cumulus cell-oocyte complex, a necessary step for oocyte fertilization (PubMed:26468290). Assembles hyaluronan in pericellular matrices that serve as platforms for receptor clustering and signaling. Enables binding of hyaluronan deposited on the surface of macrophages to LYVE1 on lymphatic endothelium and facilitates macrophage extravasation. Alters hyaluronan binding to functionally latent CD44 on vascular endothelium, switching CD44 into an active state that supports leukocyte rolling (PubMed:15060082, PubMed:26823460). Modulates the interaction of chemokines with extracellular matrix components and proteoglycans on endothelial cell surface, likely preventing chemokine gradient formation (PubMed:27044744). In a negative feedback mechanism, may limit excessive neutrophil recruitment at inflammatory sites by antagonizing the association of CXCL8 with glycosaminoglycans on vascular endothelium (PubMed:24501198). Has a role in osteogenesis and bone remodeling. Inhibits BMP2-dependent differentiation of mesenchymal stem cell to osteoblasts (PubMed:16771708, PubMed:18586671). Protects against bone erosion during inflammation by inhibiting TNFSF11/RANKL-dependent osteoclast activation (PubMed:18586671)
Specific Function: calcium ion binding
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]

Details14. Interphotoreceptor matrix proteoglycan 2

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Binder

General 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 photoreceptor outer segment. Binds heparin
Specific Function: extracellular matrix structural constituent
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]

Details15. Intracellular hyaluronan-binding protein 4

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Binder

General Function: Ribosome-binding protein that promotes ribosome hibernation, a process during which ribosomes are stabilized in an inactive state and preserved from proteasomal degradation (By similarity). Acts via its association with EEF2/eEF2 factor at the A-site of the ribosome, promoting ribosome stabilization in an inactive state compatible with storage (By similarity). Plays a key role in ribosome hibernation in the mature oocyte by promoting ribosome stabilization (By similarity). Ribosomes, which are produced in large quantities during oogenesis, are stored and translationally repressed in the oocyte and early embryo (By similarity). Also binds RNA, regulating transcription and pre-mRNA splicing (PubMed:14699138, PubMed:16455055, PubMed:19523114, PubMed:21771594). Binds (via C-terminus) to poly(U) RNA (PubMed:19523114). Seems to play a role in PML-nuclear bodies formation (PubMed:28695742). Negatively regulates DNA-binding activity of the transcription factor MEF2C in myocardial cells in response to mechanical stress (By similarity)
Specific Function: ribosome binding
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]

Enzymes

Details1. Hyaluronidase enzymes (Protein Group)

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 10-5 kDa fragments (PubMed:37527776). Very specific to hyaluronan; not able to cleave chondroitin sulfate or dermatan sulfate. Has an essential function in systemic hyaluronan catabolism and turnover and regulates cell adhesion and migration via hyaluronan degradation at focal adhesion sites (By similarity). Acts as a regulator of angiogenesis and heart morphogenesis by mediating degradation of extracellular hyaluronan, thereby regulating VEGF signaling (By similarity)
Specific Function: cadherin binding

Components:

Name	UniProt ID
Cell surface hyaluronidase CEMIP2	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

Details1. ATP-binding cassette sub-family C member 5

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: ATP-dependent transporter of the ATP-binding cassette (ABC) family that actively extrudes physiological compounds, and xenobiotics from cells. Mediates ATP-dependent transport of endogenous metabolites such as cAMP and cGMP, folic acid and N-lactoyl-amino acids (in vitro) (PubMed:10893247, PubMed:12637526, PubMed:12695538, PubMed:15899835, PubMed:17229149, PubMed:25964343). Acts also as a general glutamate conjugate and analog transporter that can limit the brain levels of endogenous metabolites, drugs, and toxins (PubMed:26515061). Confers resistance to the antiviral agent PMEA (PubMed:12695538). Able to transport several anticancer drugs including methotrexate, and nucleotide analogs in vitro, however it does with low affinity, thus the exact role of ABCC5 in mediating resistance still needs to be elucidated (PubMed:10840050, PubMed:12435799, PubMed:12695538, PubMed:15899835). Acts as a heme transporter required for the translocation of cytosolic heme to the secretory pathway (PubMed:24836561). May play a role in energy metabolism by regulating the glucagon-like peptide 1 (GLP-1) secretion from enteroendocrine cells (By similarity)
Specific Function: ABC-type xenobiotic transporter activity
Gene Name: ABCC5
Uniprot ID: O15440
Uniprot Name: ATP-binding cassette sub-family C member 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 at February 23, 2012 18:15 / Updated at October 13, 2024 03:40

Hyaluronic acid

Identification

Structure for Hyaluronic acid (DB08818)

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Clinical Trials

Clinical Trial & Rare Diseases Add-on Data Package

Pharmacoeconomics

Properties

Spectra

Collision Cross Sections (CCS)

Targets

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Enzymes

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Transporters

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