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Home > Encyclopedia > Hyaluronate Sodium

Hyaluronate Sodium

Hyaluronate Sodium structure

Hyaluronate Sodium 

structure
  • CAS No:

    125935-84-4

  • Formula:

    C28H44N2O23

  • Chemical Name:

    Hyaluronate Sodium

  • Synonyms:

    Acid, Hyaluronic;Amo Vitrax;Amvisc;Biolon;Etamucine;Healon;Hyaluronan;Hyaluronate Sodium;Hyaluronate, Sodium;Hyaluronic Acid;Hyvisc;Luronit;Sodium Hyaluronate;Vitrax, Amo;Hyaluronan;(2S,3S,4S,5R,6R)-6-[(2S,3R,5S,6R)-3-acetamido-2-[(2S,3S,4R,5R,6R)-6-[(2R,3R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid;Hyaluronic acid from Cockscomb;DTXSID90925319;EBD21970;DB08818;(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;125935-84-4;Hexopyranuronosyl-(1->3)-2-deoxy-2-[(1-hydroxyethylidene)amino]hexopyranosyl-(1->4)hexopyranuronosyl-(1->3)-2-deoxy-2-[(1-hydroxyethylidene)amino]hexopyranose

Description

Hyaluronic acid (HA) is an anionic, nonsulfated glycosaminoglycan distributed widely throughout connective, epithelial, and neural tissues. It is unique among glycosaminoglycans in that it is nonsulfated, forms in the plasma membrane instead of the Golgi, and can be very large, with its molecular weight often reaching the millions. One of the chief components of the extracellular matrix, hyaluronic acid contributes significantly to cell proliferation and migration, and may also be involved in the progression of some malignant tumors.|A natural high-viscosity mucopolysaccharide with alternating beta (1-3) glucuronide and beta (1-4) glucosaminidic bonds. It is found in the UMBILICAL CORD, in VITREOUS BODY and in SYNOVIAL FLUID. A high urinary level is found in PROGERIA.

Hyaluronate Sodium Basic Attributes

776.6 g/mol

776.23348565 g/mol

Characteristics

400 Ų

Easily soluble in cold water. Insoluble in organic solvents.

Toxicity

>2400 mg/kg (mouse, oral, sodium salt) >4000 mg/kg (mouse, subcutaneous, sodium salt) 1500 mg/kg (mouse, intraperitoneal, sodium salt)

Drug Information

Used to treat knee pain in patients with joint inflammation (osteoarthritis). It is usually used in patients who have not responded to other treatments such as acetaminophen, exercise, or physical therapy. Hyaluronic acid may also be used in plastic surgery to reduce wrinkles on the face or as a filler in other parts of the body. May be used in ophthalmology to assist in the extraction of cataracts, the implantation of intraocular lenses, corneal transplants, glaucoma filtration, retinal attachment and in the treatment of dry eyes. Finally, hyaluronic acid is also used to coat the bladder lining in treating interstitial cystitis.

Hyaluronic acid is similar to a substance that occurs naturally in the joints. It may work by acting as a lubricant and shock absorber in the joint, helping the knee to move smoothly, thereby lessening pain.

Substances that augment, stimulate, activate, potentiate, or modulate the immune response at either the cellular or humoral level. The classical agents (Freund's adjuvant, BCG, Corynebacterium parvum, et al.) contain bacterial antigens. Some are endogenous (e.g., histamine, interferon, transfer factor, tuftsin, interleukin-1). Their mode of action is either non-specific, resulting in increased immune responsiveness to a wide variety of antigens, or antigen-specific, i.e., affecting a restricted type of immune response to a narrow group of antigens. The therapeutic efficacy of many biological response modifiers is related to their antigen-specific immunoadjuvanticity. (See all compounds classified as Adjuvants, Immunologic.)|Viscoelastic solutions that are injected into JOINTS in order to alleviate symptoms of joint-related disorders such as OSTEOARTHRITIS. (See all compounds classified as Viscosupplements.)

Hyaluronic acid is absorbed and diffuses slowly out of the injection site.|Hyaluronic acid is eliminated via the canal of Schlemm.

Hyaluronic acid is degraded by a family of enzymes called hyaluronidases.

Hyaluronic acid performs its activities as a tissue lubricant and hence, it is thought to be key in the modulation of interactions between adjacent tissues. Hyaluronic acid is a polysaccharide which is distributed widely in the extracellular matrix of connective tissue in man. It forms a viscoelastic solution in water which makes it suitable for aqueous and vitreous humor in ophthalmic surgery. It is suggested to provide mechanical protection for ocular tissues and cell layers due to its high viscosity. The elasticity of the solutions of hyaluronic acid can assist in the absorption of mechanical stress and the generation of a protective buffer for the tissues. This viscoelasticity enables maintenance of a deep chamber during surgical manipulation since the solution does not flow out of the open anterior chamber. In the area of wound healing, hyaluronic acid acts as a protective vehicle that allows the transport of peptide growth factors and other structural proteins to the site of action. After promoting the transport of key molecules, it is enzymatically degraded and the transported proteins are released to promote tissue repair. Hyaluronic acid is being used intra-articularly to treat osteoarthritis. Cell receptors that have been identified for hyaluronic acid fall into three main groups: CD44, Receptor for Hyaluronan-mediated motility (RHAMM) and intracellular adhesion molecule-1 (ICAM-1). CD44 mediates cell interaction with hyaluronic acid and the binding of the two functions as an important part in various physiologic events, such as cell aggregation, migration, proliferation and activation; cell-cell and cell-substrate adhesion; endocytosis of hyaluronic acid, which leads to hyaluronic acid catabolism in macrophages; and assembly of petircellular matrices from HA and proteoglycan. CD44 has two important roles in skin, regulation of keratinocyte proliferation in response to extracellular stimuli and the maintenance of local hyaluronic acid homeostasis. ICAM-1 is known mainly as a metabolic cell surface receptor for hyaluronic acid, and this protein may be responsible mainly for the clearance of hyaluronic acid from lymph and blood plasma, which accounts for perhaps most of its whole-body turnover. Ligand binding of this receptor, thus, triggers a highly coordinated cascade of events that includes the formation of an endocytotic vesicle, its fusion with primary lysosomes, enzymatic digestion to monosaccharides, active transmembrane transport of these sugars to cell sap, phosphorylation of GlcNAc and enzymatic deacetylation. ICAM-1 may also serve as a cell adhesion molecule, and the binding of hyaluronic acid to ICAM-1 may contribute to the control of ICAM-1-mediated inflammatory activation.

Acid, Hyaluronic

Computed Properties

Molecular Weight:776.6
XLogP3:-7.4
Hydrogen Bond Donor Count:14
Hydrogen Bond Acceptor Count:23
Rotatable Bond Count:12
Exact Mass:776.23348565
Monoisotopic Mass:776.23348565
Topological Polar Surface Area:400
Heavy Atom Count:53
Complexity:1300
Defined Atom Stereocenter Count:18
Undefined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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