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2D Structure
Also known as: Oxabolone cypionate, 1254-35-9, Oxabolone cipioncate, Fi 5852, Oxabolone cipionate [inn], 5rxy50q01n
Molecular Formula
C26H38O4
Molecular Weight
414.6  g/mol
InChI Key
KHKDIUPVDIEHAH-KXLSUQFWSA-N
FDA UNII
5RXY50Q01N

Oxabolone cipionate is the C17 cypionate ester and a prodrug of [DB01500]. A synthetic anabolic-androgenic (AAS) steroid, it is a derivative of 19-nortestosterone (nandrolone). It is considered as a performance enhancing drug thus is prohibited from use in sports.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
[(8R,9S,10R,13S,14S,17S)-4-hydroxy-13-methyl-3-oxo-2,6,7,8,9,10,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl] 3-cyclopentylpropanoate
2.1.2 InChI
InChI=1S/C26H38O4/c1-26-15-14-18-17-9-11-22(27)25(29)20(17)8-7-19(18)21(26)10-12-23(26)30-24(28)13-6-16-4-2-3-5-16/h16-19,21,23,29H,2-15H2,1H3/t17-,18-,19-,21+,23+,26+/m1/s1
2.1.3 InChI Key
KHKDIUPVDIEHAH-KXLSUQFWSA-N
2.1.4 Canonical SMILES
CC12CCC3C(C1CCC2OC(=O)CCC4CCCC4)CCC5=C(C(=O)CCC35)O
2.1.5 Isomeric SMILES
C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2OC(=O)CCC4CCCC4)CCC5=C(C(=O)CC[C@H]35)O
2.2 Other Identifiers
2.2.1 UNII
5RXY50Q01N
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 4,17beta-dihydroxy-estr-4-en-3-one 17-cyclopentylpropionate

2. Oxabolone Cypionate

2.3.2 Depositor-Supplied Synonyms

1. Oxabolone Cypionate

2. 1254-35-9

3. Oxabolone Cipioncate

4. Fi 5852

5. Oxabolone Cipionate [inn]

6. 5rxy50q01n

7. Oxabolone 17-cyclopentanepropionate

8. Nsc-522767

9. Fi-5852

10. Oxaboloni Cipionas

11. Esterbol Depo

12. Oxaboloni Cypionas

13. Ossabolone Cipionato

14. Cipionate D'oxabolone

15. Cipionato De Oxabolona

16. Unii-5rxy50q01n

17. Ossabolone Cipionato [dcit]

18. Oxaboloni Cipionas [inn-latin]

19. Ncgc00181156-01

20. Cipionate D'oxabolone [inn-french]

21. Einecs 215-011-8

22. Cipionato De Oxabolona [inn-spanish]

23. Dsstox_cid_26879

24. Dsstox_rid_81983

25. Dsstox_gsid_46879

26. [(8r,9s,10r,13s,14s,17s)-4-hydroxy-13-methyl-3-oxo-2,6,7,8,9,10,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-17-yl] 3-cyclopentylpropanoate

27. Schembl4821339

28. Oxabolone Cipionate (jan/inn)

29. Chembl2105318

30. Dtxsid3046879

31. Chebi:31940

32. Oxabolone Cipionate [jan]

33. 4,17beta-dihydroxy-estr-4-en-3-one 17-cyclopentylpropionate

34. Oxabolone Cipionate [mart.]

35. Tox21_112760

36. Oxabolone Cipionate [who-dd]

37. Zinc26892649

38. Db13185

39. Nsc 522767

40. Cas-1254-35-9

41. 4-hydroxy-19-nortestosterone 17beta-cypionate

42. D01149

43. Oxabolone 17-cyclopentanepropionate [mi]

44. Q7115043

45. 4,17beta-dihydroxyestr-4-en-3-one 17-cyclopentanepropionate

46. 4,17.beta.-dihydroxyestr-4-en-3-one 17-cyclopentanepropionate

47. (8r,9s,13s,14s,17s)-4-hydroxy-13-methyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl 3-cyclopentylpropanoate

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 414.6 g/mol
Molecular Formula C26H38O4
XLogP35.7
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count4
Rotatable Bond Count5
Exact Mass414.27700969 g/mol
Monoisotopic Mass414.27700969 g/mol
Topological Polar Surface Area63.6 Ų
Heavy Atom Count30
Formal Charge0
Complexity733
Isotope Atom Count0
Defined Atom Stereocenter Count6
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Indication

Used as a performance enhancing drug illicitly in athletes.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Androgenic effects include enhanced secondary sexual characteristics.


5.2 ATC Code

A - Alimentary tract and metabolism

A14 - Anabolic agents for systemic use

A14A - Anabolic steroids

A14AB - Estren derivatives

A14AB03 - Oxabolone cipionate


5.3 Absorption, Distribution and Excretion

Route of Elimination

The metabolites and unchanged form of oxabolone can be detected in the urine.


Clearance

The elimination on the first day following intravenous injection of oxabolone cipionate is slow and reaches a rapid excretion phase with the maximum urinary level in the fifth day of administration.


5.4 Metabolism/Metabolites

The prodrug oxabolone cipionate is converted to oxabolone. Oxabolone is then metabolized into 4-Hydroxyestr-4-en-3,17-dione (M2) which is the most abundant metabolite via oxidation of the 17-hydroxyl group. 4-Hydroxyestran-3,17-dione (M1) is formed by reduction of the A ring double bond along with the oxidation of the 17-hydroxyl group. Three isomeric compounds exist as another metabolite, as the 3,4-dihydroxy-5-estran-17-one, 3,4-dihydroxy-5-estran-17-one, and 3,4-dihydroxy-5-estran-17-one.