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Chemistry

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Also known as: 151-73-5, Bentelan, Betamethasone 21-phosphate disodium salt, Betamethasone 21-phosphate disodium, Betamethasone disodium phosphate, Betamethazone disodium phosphate
Molecular Formula
C22H28FNa2O8P
Molecular Weight
516.4  g/mol
InChI Key
PLCQGRYPOISRTQ-LWCNAHDDSA-L
FDA UNII
7BK02SCL3W

Betamethasone Sodium Phosphate
Betamethasone Sodium Phosphate is the disodium salt of the 21-phosphate ester of betamethasone, a synthetic glucocorticoid with metabolic, immunosuppressive and anti-inflammatory actions. Betamethasone sodium phosphate binds to specific intracellular glucocorticoid receptors and subsequently binds to DNA to modify gene expression. The synthesis of certain anti-inflammatory proteins is induced while the synthesis of certain inflammatory mediators is inhibited. As a result, there is an overall reduction in chronic inflammation and autoimmune reactions.
1 2D Structure

Betamethasone Sodium Phosphate

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
disodium;[2-[(8S,9R,10S,11S,13S,14S,16S,17R)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethyl] phosphate
2.1.2 InChI
InChI=1S/C22H30FO8P.2Na/c1-12-8-16-15-5-4-13-9-14(24)6-7-19(13,2)21(15,23)17(25)10-20(16,3)22(12,27)18(26)11-31-32(28,29)30;;/h6-7,9,12,15-17,25,27H,4-5,8,10-11H2,1-3H3,(H2,28,29,30);;/q;2*+1/p-2/t12-,15-,16-,17-,19-,20-,21-,22-;;/m0../s1
2.1.3 InChI Key
PLCQGRYPOISRTQ-LWCNAHDDSA-L
2.1.4 Canonical SMILES
CC1CC2C3CCC4=CC(=O)C=CC4(C3(C(CC2(C1(C(=O)COP(=O)([O-])[O-])O)C)O)F)C.[Na+].[Na+]
2.1.5 Isomeric SMILES
C[C@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@@]4([C@]3([C@H](C[C@@]2([C@]1(C(=O)COP(=O)([O-])[O-])O)C)O)F)C.[Na+].[Na+]
2.2 Other Identifiers
2.2.1 UNII
7BK02SCL3W
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Bentelan

2. Betamethason Sodium Phosphate

3. Betamethasone 21-phosphate

4. Betamethasone Disodium Phosphate

5. Betamethasone Disodium Phosphate, (11beta)-isomer

6. Betamethasone Phosphate

7. Betamethasone Sodium Phosphate, (11beta,16beta)-isomer

8. Betnesol

9. Celestone Phosphate

10. Rinderone

2.3.2 Depositor-Supplied Synonyms

1. 151-73-5

2. Bentelan

3. Betamethasone 21-phosphate Disodium Salt

4. Betamethasone 21-phosphate Disodium

5. Betamethasone Disodium Phosphate

6. Betamethazone Disodium Phosphate

7. Betamethasone 21-disodium Phosphate

8. Beta-methasone Sodium Phosphate

9. Betamethasone 21-phosphate Sodium Salt

10. 7bk02scl3w

11. Chebi:3078

12. 9-fluoro-11beta,17,21-trihydroxy-16beta-methylpregna-1,4-diene-3,20-dione 21-(disodium Phosphate)

13. Betamethasone Sodium Phosphate, Usp

14. Disodium Betamethasone 21-phosphate

15. Beta-methasone Phosphate

16. Celestone Phosphate Injection

17. Nsc 90616

18. Disodium;[2-[(8s,9r,10s,11s,13s,14s,16s,17r)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethyl] Phosphate

19. Sodium 2-((8s,9r,10s,11s,13s,14s,16s,17r)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3h-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl Phosphate

20. Nsc-90616

21. Beta-methasone, Disodium Phosphate

22. Einecs 205-797-0

23. Unii-7bk02scl3w

24. Beta-methasone Disodium Phosphate

25. Mfcd00200361

26. Betamethasone Sodium Phosphate [usp:jan]

27. Betamethasonesodiumphosphate

28. Schembl8418

29. Dsstox_cid_27137

30. Dsstox_rid_82144

31. Dsstox_gsid_47137

32. Chembl1200762

33. Dtxsid8047137

34. Tox21_302467

35. Akos015896371

36. Ac-2162

37. Ncgc00256717-01

38. As-62442

39. Cas-151-73-5

40. Pregna-1,4-diene-3,20-dione, 9-fluoro-11,17-dihydroxy-16-methyl-21-(phosphonooxy)-, Disodium Salt, (11.beta.,16.beta.)-

41. Pregna-1,4-diene-3,20-dione, 9-fluoro-11,17-dihydroxy-16-methyl-21-(phosphonooxy)-, Disodium Salt, (11beta,16beta)-

42. Pregna-1,4-diene-3,20-dione, 9-fluoro-11-beta,17,21-trihydroxy-16-beta-methyl-, 21-(dihydrogen Phosphate), Disodium Salt

43. Pregna-1,4-diene-3,20-dione, 9-fluoro-11beta,17,21-trihydroxy-16beta-methyl-, 21-(dihydrogen Phosphate), Disodium Salt

44. Betamethasone Sodium Phosphate (jp17/usp)

45. Betamethasone Sodium Phosphate [jan]

46. B4110

47. Betamethasone 21-phosphate Disodium, >=97%

48. Betamethasone Sodium Phosphate [mart.]

49. Betamethasone Sodium Phosphate [vandf]

50. Betamethasone Sodium Phosphate [usp-rs]

51. Betamethasone Sodium Phosphate [who-dd]

52. D00972

53. Betamethasone Sodium Phosphate [green Book]

54. Betamethasone Sodium Phosphate [ep Impurity]

55. Betamethasone Sodium Phosphate [ep Monograph]

56. Betamethasone Sodium Phosphate [orange Book]

57. J-008838

58. Betamethasone Sodium Phosphate [usp Monograph]

59. Q27105936

60. Betamethasone Sodium Phosphate Component Of Celestone Soluspan

61. Celestone Soluspan Component Betamethasone Sodium Phosphate

62. Betamethasone Sodium Phosphate, European Pharmacopoeia (ep) Reference Standard

63. Betamethasone Sodium Phosphate, United States Pharmacopeia (usp) Reference Standard

64. 9-fluoro-11.beta.,17,21-trihydroxy-16.beta.-methylpregna-1,4-diene-3,20-dione 21-(disodium Phosphate)

65. Disodium 9-fluoro-11beta,17-dihydroxy-16beta-methyl-3,20-dioxopregna-1,4-dien-21-yl Phosphate

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 516.4 g/mol
Molecular Formula C22H28FNa2O8P
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count9
Rotatable Bond Count3
Exact Mass516.13012157 g/mol
Monoisotopic Mass516.13012157 g/mol
Topological Polar Surface Area147 Ų
Heavy Atom Count34
Formal Charge0
Complexity962
Isotope Atom Count0
Defined Atom Stereocenter Count8
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count3
4 Pharmacology and Biochemistry
4.1 MeSH Pharmacological Classification

Glucocorticoids

A group of CORTICOSTEROIDS that affect carbohydrate metabolism (GLUCONEOGENESIS, liver glycogen deposition, elevation of BLOOD SUGAR), inhibit ADRENOCORTICOTROPIC HORMONE secretion, and possess pronounced anti-inflammatory activity. They also play a role in fat and protein metabolism, maintenance of arterial blood pressure, alteration of the connective tissue response to injury, reduction in the number of circulating lymphocytes, and functioning of the central nervous system. (See all compounds classified as Glucocorticoids.)


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