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CHEMISTRY

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Also known as: Estr-4-ene-3,17-dione, 19-norandrost-4-ene-3,17-dione, 734-32-7, 19-nor-4-androstene-3,17-dione, Nordione, Delta4-estrene-3,17-dione

Molecular Formula

C₁₈H₂₄O₂

Molecular Weight

272.4 g/mol

InChI Key

JRIZOGLBRPZBLQ-QXUSFIETSA-N

FDA UNII

U90987PVU5

19-Norandrostenedione refers to two steroid isomers that were once marketed as dietary supplements and mainly used by body builders. After 2005, 19-Norandrostenedione was regulated in the United States as a schedule III controlled substance, as well as banned from use in competitive sports by the World Anti-Doping Agency. In the body 19-norandrostenedione is rapidly metabolized into [nandrolone], also known as nortestosterone.

1 2D Structure

CAS 734-32-7

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(8R,9S,10R,13S,14S)-13-methyl-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene-3,17-dione

2.1.2 InChI

InChI=1S/C18H24O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h10,13-16H,2-9H2,1H3/t13-,14+,15+,16-,18-/m0/s1

2.1.3 InChI Key

JRIZOGLBRPZBLQ-QXUSFIETSA-N

2.1.4 Canonical SMILES

CC12CCC3C(C1CCC2=O)CCC4=CC(=O)CCC34

2.1.5 Isomeric SMILES

C[C@]12CC[C@H]3[C@H]([C@@H]1CCC2=O)CCC4=CC(=O)CC[C@H]34

2.2 Other Identifiers

2.2.1 UNII

U90987PVU5

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 19-nor-4-androstene-3,17-dione

2. 19-nor-a-dione

3. 19-norandrost-4-ene-3,17-dione

2.3.2 Depositor-Supplied Synonyms

1. Estr-4-ene-3,17-dione

2. 19-norandrost-4-ene-3,17-dione

3. 734-32-7

4. 19-nor-4-androstene-3,17-dione

5. Nordione

6. Delta4-estrene-3,17-dione

7. Norandrostenedione

8. Delta,4-estrene-3,17-dione

9. 19-nor-4-androstenedione

10. (+)-19-norandrost-4-ene-3,17-dione

11. .delta.4-estrene-3,17-dione

12. U90987pvu5

13. Nsc-12164

14. (8r,9s,10r,13s,14s)-13-methyl-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene-3,17-dione

15. Unii-u90987pvu5

16. (+)-estr-4-ene-3,17-dione

17. 3,17-dioxo-19-norandrost-4-ene

18. Einecs 211-995-8

19. Nsc 12164

20. D-19-norandrost-4-ene-3,17-dione

21. 4-oestrendione

22. 4-norendione

23. 4-norendion

24. Estra4-ene-3,17-dione

25. Estra-4-ene-3,17-dione

26. Schembl868884

27. Chebi:34187

28. 4-oestren-3,17-dione

29. Dtxsid50862392

30. 19-norandrost-4-en-3,17-dione

31. Nsc12164

32. Zinc4428372

33. Akos015896166

34. Db01434

35. 19-nor-androstene-4-ene-3,17-dione

36. Estra-4-en-3,17-dione(19-nor Ad)

37. 19-nor-4-androstene-3,17-dion

38. Norethisterone Impurity B [ep Impurity]

39. (+)-19-norandrost-4-en-3,17-dione

40. 734n327

41. Norethindrone Related Compound B [usp-rs]

42. Q-102802

43. Q4557695

44. Norandrostenedione (19-norandrost-4-ene-3,17-dione)

45. Norethisterone Acetate Impurity J [ep Impurity]

46. 19-norandrost-4-ene-3,17-dione 100 Microg/ml In Methanol

47. 19-norandrost-4-en-3,17-dione (8.beta.,9.alpha.,10.beta.)

48. 19-norandrost-4-ene-3,17-dione 100 Microg/ml In Acetonitrile

49. Norandrostenedione (19-norandrost-4-ene-3,17-dione) 1.0 Mg/ml In Acetonitrile

50. (3as,3br,9ar,9bs,11as)-11a-methyl-1h,2h,3h,3ah,3bh,4h,5h,7h,8h,9h,9ah,9bh,10h,11h,11ah-cyclopenta[a]phenanthrene-1,7-dione

2.4 Create Date

2005-03-26

3 Chemical and Physical Properties

Molecular Formula	C₁₈H₂₄O₂
Molecular Weight	272.4 g/mol
XLogP3	2.5
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	0
Exact Mass	272.177630004 g/mol
Monoisotopic Mass	272.177630004 g/mol
Topological Polar Surface Area	34.1 Å²
Heavy Atom Count	20
Formal Charge	0
Complexity	504
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

The claim that supplemental 19-norandrostenedione has anabolic effects is unsubstantiated.

5 Pharmacology and Biochemistry

5.1 Absorption, Distribution and Excretion

Absorption

Absorption appears variable, but some absorption does occur.

5.2 Metabolism/Metabolites

Specific metabolites of 19-nor-5-androstene-3, 17-dione are 19-nordehydroandrosterone and 19-nordehydroepiandrosterone.

5.3 Mechanism of Action

19-Norandrostenedione may be metabolized to 19-nortestosterone in both men and women. 19-Norandrostenedione, also known as nandrolone, is the basic substance of some very popular injectable anabolic steroids, however 19-norandrostenedione is not metabolized to testosterone. Whether or not increases in 19-nortestosterone levels would be sustained long enough by taking 19-norandrostenedione to show an increase in nitrogen retention and muscle strength and mass is unknown. 19-Norandrostenedione has also been shown to bind to androgen receptors with high selectivity. Transactivation of androgen receptor dependent reporter gene expression was 10 times lower than that produced by dihydrotestosterone. [1]

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