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Anecortave Acetate

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Chemistry

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Also known as: 7753-60-8, Retaane, Al 3789, Al-3789, Anecortave acetate [usan], Nsc 15475

Molecular Formula

C₂₃H₃₀O₅

Molecular Weight

386.5 g/mol

InChI Key

YUWPMEXLKGOSBF-GACAOOTBSA-N

FDA UNII

Y0PC411K4T

Anecortave acetate (Retaane) is an analog of cortisol acetate; among the modifications to the steroid are the removal of the 11 hydroxyl OH group and an addition of a 21-acetate group. As a result of these modifications, anecortave acetate lacks the typical antiinflammatory and immunosuppressive properties of glucocorticoids.Alcon Inc. is developing and marketing Retaane.

1 2D Structure

Anecortave Acetate

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

[2-[(8S,10S,13S,14S,17R)-17-hydroxy-10,13-dimethyl-3-oxo-2,6,7,8,12,14,15,16-octahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl] acetate

2.1.2 InChI

InChI=1S/C23H30O5/c1-14(24)28-13-20(26)23(27)11-8-19-17-5-4-15-12-16(25)6-9-21(15,2)18(17)7-10-22(19,23)3/h7,12,17,19,27H,4-6,8-11,13H2,1-3H3/t17-,19+,21+,22+,23+/m1/s1

2.1.3 InChI Key

YUWPMEXLKGOSBF-GACAOOTBSA-N

2.1.4 Canonical SMILES

CC(=O)OCC(=O)C1(CCC2C1(CC=C3C2CCC4=CC(=O)CCC43C)C)O

2.1.5 Isomeric SMILES

CC(=O)OCC(=O)[C@]1(CC[C@@H]2[C@@]1(CC=C3[C@H]2CCC4=CC(=O)CC[C@@]43C)C)O

2.2 Other Identifiers

2.2.1 UNII

Y0PC411K4T

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 4,9(11)-pregnadien-17alpha,21-diol-3,20-dione-21-acetate

2.3.2 Depositor-Supplied Synonyms

1. 7753-60-8

2. Retaane

3. Al 3789

4. Al-3789

5. Anecortave Acetate [usan]

6. Nsc 15475

7. Nsc 24345

8. Anecortave [inn]

9. Nsc-15475

10. Nsc-24345

11. 17,21-dihydroxypregna-4,9(11)-diene-3,20-dione 21-acetate

12. Y0pc411k4t

13. 21-(acetyloxy)-17-hydroxypregna-4,9(11)-diene-3,20-dione

14. [2-[(8s,10s,13s,14s,17r)-17-hydroxy-10,13-dimethyl-3-oxo-2,6,7,8,12,14,15,16-octahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl] Acetate

15. 17-hydroxy-3,20-dioxopregna-4,9(11)-dien-21-yl Acetate

16. Anecortave Acetate (200 Mg)f0e2980.997mg/mg(ai)

17. Retaane Suspension

18. Unii-y0pc411k4t

19. Anecortave-acetate

20. Ncgc00181018-01

21. Einecs 231-812-5

22. Anecortave [mart.]

23. Dsstox_cid_26805

24. Dsstox_rid_81919

25. Dsstox_gsid_46805

26. Schembl94110

27. 17-hydroxy-3,20-dioxopregna-4,9(11)-dien-21-yl Acetate #

28. Anecortave Acetate [mi]

29. Anecortave Acetate (jan/usan)

30. Anecortave Acetate [jan]

31. Chembl2106613

32. Dtxsid5046805

33. Chebi:31215

34. Ex-a5253

35. Nsc15475

36. Nsc24345

37. Zinc3931050

38. Tox21_112668

39. 17-alpha,21-dihydroxypregna-4,9(11)-diene-3,20-dione 21-acetate

40. Akos015917580

41. Db05288

42. Cas-7753-60-8

43. Hy-116868

44. Cs-0066714

45. D01733

46. Q4761567

47. Hydrocortisone Acetate Impurity E [ep Impurity]

48. 21-acetoxy-17-hydroxy-4,9(11)-pregnadiene-3,20-dione

49. 17alpha-hydroxy-21-acetoxypregna-4,9(11)-diene-3,20-dione

50. 4,9(11)-pregnadien-17alpha,21-diol-3,20-dione-21-acetate

51. Pregn-4,9(11)-dien-17,21-diol-3,20-dione, Acetate(ester)

52. 17alpha-hydroxy-21 -acetoxy-pregna-4,9(11)-diene-3,20-dione

53. Pregna-4,9(11)-diene-3,20-dione, 21-(acetyloxy)-17-hydroxy-

2.4 Create Date

2005-03-26

3 Chemical and Physical Properties

Molecular Formula	C₂₃H₃₀O₅
Molecular Weight	386.5 g/mol
XLogP3	2.1
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	4
Exact Mass	386.20932405 g/mol
Monoisotopic Mass	386.20932405 g/mol
Topological Polar Surface Area	80.7 Å²
Heavy Atom Count	28
Formal Charge	0
Complexity	808
Isotope Atom Count	0
Defined Atom Stereocenter Count	5
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Investigated for use/treatment in glaucoma and macular degeneration.

5 Pharmacology and Biochemistry

5.1 Mechanism of Action

Anecortave acetate functions as an antiangiogenic agent, inhibiting blood vessel growth by decreasing extracellular protease expression and inhibiting endothelial cell migration. Its angiostatic activity does not seem to be mediated through any of the commonly known pharmacological receptors. (Ophthalmology 2004;111:2316-7) RETAANE blocks signals from multiple growth factors because it acts downstream and independent of the initiating angiogenic stimuli and inhibits angiogenesis subsequent to the angiogenic stimulation.

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