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Sodium Hyaluronate

Synopsis, Chemistry

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Also known as: Hyaluronic acid, sodium salt, Hyaluronic acid sodium, Kopuron, Healon, Hyalgan, Hyalurone sodium

Molecular Formula

C₂₈H₄₄N₂NaO₂₃+

Molecular Weight

799.6 g/mol

InChI Key

YWIVKILSMZOHHF-QJZPQSOGSA-N

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.

1 2D Structure

Sodium Hyaluronate

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

sodium;(2S,3S,4S,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-acetamido-2-[(2S,3S,4R,5R,6R)-6-[(2R,3R,4R,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

2.1.2 InChI

InChI=1S/C28H44N2O23.Na/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);/q;+1/t7-,8-,9-,10-,11-,12-,13+,14+,15-,16-,17-,18-,19-,20+,21+,22+,25-,26+,27-,28-;/m1./s1

2.1.3 InChI Key

YWIVKILSMZOHHF-QJZPQSOGSA-N

2.1.4 Canonical SMILES

CC(=O)NC1C(C(C(OC1O)CO)O)OC2C(C(C(C(O2)C(=O)O)OC3C(C(C(C(O3)CO)O)OC4C(C(C(C(O4)C(=O)O)O)O)O)NC(=O)C)O)O.[Na+]

2.1.5 Isomeric SMILES

CC(=O)N[C@@H]1[C@H]([C@@H]([C@H](O[C@H]1O)CO)O)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)C(=O)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)C(=O)O)O)O)O)NC(=O)C)O)O.[Na+]

2.2 Synonyms

2.2.1 MeSH Synonyms

1. Acid, Hyaluronic

2. Amo Vitrax

3. Amvisc

4. Biolon

5. Etamucine

6. Healon

7. Hyaluronate Sodium

8. Hyaluronate, Sodium

9. Hyaluronic Acid

10. Hyvisc

11. Luronit

12. Vitrax, Amo

2.2.2 Depositor-Supplied Synonyms

1. Hyaluronic Acid, Sodium Salt

2. Hyaluronic Acid Sodium

3. Kopuron

4. Healon

5. Hyalgan

6. Hyalurone Sodium

7. 6-[3-acetamido-2-[6-[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

8. Sodium;(2s,3s,4s,5r,6r)-6-[(2s,3r,4r,5s,6r)-3-acetamido-2-[(2s,3s,4r,5r,6r)-6-[(2r,3r,4r,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

9. Equron (veterinary)

10. Synacid (veterinary)

11. Arthrease

12. Cystistat

13. Hyalart

14. Hyalein

15. Hyalovet

16. Hyladerm

17. Khionat

18. Monovisc

19. Nidelon

20. Orthovisc

21. Ostenil

22. Provisc

23. Sinovial

24. Supartz

25. Suvenyl

26. Hyasol

27. Hyladerm Khionat

28. Nrd101

29. Ha

30. Hyaluronsan Ha-lq

31. Bio Hyaluro 12

32. Euflexxa Injection

33. Euflexxa

34. Ccris 4127

35. Hyaluronate Sodium [usan:jan]

36. Sodium Hyaluronate Hmw

37. Unii-yse9ppt4th

38. Si-4402

39. Sl-1010

40. Synacid

41. Equron

42. Chlamyhyaluronic Acid Sodium Salt

43. Sl 1010

44. Hyalauronic Acid 99%

45. Yse9ppt4th

46. Gtpl4954

47. Sodium Hyaluronate (food Grade)

48. Sodium Hyaluronate (cosmetic Grade)

49. Akos015896610

50. Sodium Hyaluronate, Low Molecular Weight

51. Sodium Hyaluronate, High Molecular Weight

52. Q27078001

53. (3s,4r,5r,6r)-3-[(2s,3r,5s,6r)-3-acetamido-4-[(2s,3r,4s,6s)-6-carboxy-3,4,5-trihydroxy-tetrahydropyran-2-yl]oxy-5-hydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-6-[(3r,4r,5s,6r)-3-acetamido-2,5-dih

54. Sodium (2s,3s,4r,5r,6r)-3-{[(2s,3r,4r,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,4r,5s,6r)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-4,5-dihydroxyoxane-2-carboxylic Acid

2.3 Create Date

2005-08-09

3 Chemical and Physical Properties

Molecular Formula	C₂₈H₄₄N₂NaO₂₃+
Molecular Weight	799.6 g/mol
Hydrogen Bond Donor Count	14
Hydrogen Bond Acceptor Count	23
Rotatable Bond Count	12
Exact Mass	799.22325494 g/mol
Monoisotopic Mass	799.22325494 g/mol
Topological Polar Surface Area	400 Å²
Heavy Atom Count	54
Formal Charge	1
Complexity	1300
Isotope Atom Count	0
Defined Atom Stereocenter Count	20
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Adjuvants, Immunologic

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.)

Viscosupplements

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.)

4.2 FDA Pharmacological Classification

4.2.1 Pharmacological Classes

Vitamin B 6 [Chemical/Ingredient]; Vitamin B6 Analog [EPC]; Analogs/Derivatives [Chemical/Ingredient]