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Chemistry

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Also known as: 851983-85-2, Tok-001, Vn/124-1, Galaterone, Tok 001, Vn/124
Molecular Formula
C26H32N2O
Molecular Weight
388.5  g/mol
InChI Key
PAFKTGFSEFKSQG-PAASFTFBSA-N
FDA UNII
WA33E149SW

Galeterone
Galeterone is an orally bioavailable small-molecule androgen receptor modulator and CYP17 lyase inhibitor with potential antiandrogen activity. Galeterone exhibits three distinct mechanisms of action: 1) as an androgen receptor antagonist, 2) as a CYP17 lyase inhibitor and 3) by decreasing overall androgen receptor levels in prostate cancer tumors, all of which may result in a decrease in androgen-dependent growth signaling. Localized to the endoplasmic reticulum (ER), the cytochrome P450 enzyme CYP17 (P450C17 or CYP17A1) exhibits both 17alpha-hydroxylase and 17,20-lyase activities, and plays a key role in the steroidogenic pathway that produces progestins, mineralocorticoids, glucocorticoids, androgens, and estrogens.
1 2D Structure

Galeterone

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(3S,8R,9S,10R,13S,14S)-17-(benzimidazol-1-yl)-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthren-3-ol
2.1.2 InChI
InChI=1S/C26H32N2O/c1-25-13-11-18(29)15-17(25)7-8-19-20-9-10-24(26(20,2)14-12-21(19)25)28-16-27-22-5-3-4-6-23(22)28/h3-7,10,16,18-21,29H,8-9,11-15H2,1-2H3/t18-,19-,20-,21-,25-,26-/m0/s1
2.1.3 InChI Key
PAFKTGFSEFKSQG-PAASFTFBSA-N
2.1.4 Canonical SMILES
CC12CCC(CC1=CCC3C2CCC4(C3CC=C4N5C=NC6=CC=CC=C65)C)O
2.1.5 Isomeric SMILES
C[C@]12CC[C@@H](CC1=CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CC=C4N5C=NC6=CC=CC=C65)C)O
2.2 Other Identifiers
2.2.1 UNII
WA33E149SW
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 17-(1h-benzimidazol-1-yl)androsta-5,16-dien-3beta-ol

2. 3-hydroxy-17-(1h-benzimidazole-1-yl)androsta-5,16-diene

3. Vn-124-1

2.3.2 Depositor-Supplied Synonyms

1. 851983-85-2

2. Tok-001

3. Vn/124-1

4. Galaterone

5. Tok 001

6. Vn/124

7. Galeterone [usan]

8. Tok-001 (galeterone)

9. Vn 124

10. Vn-124-1

11. Wa33e149sw

12. (3s,8r,9s,10r,13s,14s)-17-(benzimidazol-1-yl)-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15-decahydro-1h-cyclopenta[a]phenanthren-3-ol

13. Galeterone (usan)

14. Vn-124

15. 3-hydroxy-17-(1h-benzimidazole-1-yl)androsta-5,16-diene

16. (3s,8r,9s,10r,13s,14s)-17-(1h-benzo[d]imidazol-1-yl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1h-cyclopenta[a]phenanthren-3-ol

17. Galeterone [usan:inn]

18. Unii-wa33e149sw

19. (3beta)-17-(1h-benzimidazol-1-yl)androsta-5,16-dien-3-ol

20. Tok-001(galeterone)

21. Tok-001; Galeterone

22. Galeterone [inn]

23. Galeterone [who-dd]

24. Schembl939234

25. Gtpl8638

26. 17-(1h-benzimidazol-1-yl)androsta-5,16-dien-3beta-ol

27. Chembl2105738

28. Galeterone, >=98% (hplc)

29. Chebi:177536

30. (3?)-17-(1h-benzimidazol-1-yl)androsta-5,16-dien-3-ol

31. 3beta-hydroxy-17-(1h-benzimidazole-1-yl)androsta-5,16-diene

32. Bcpp000040

33. Dtxsid101025602

34. Amy27882

35. Bcp02827

36. Ex-a1025

37. Zinc6718442

38. Bdbm50435990

39. Mfcd16660907

40. Akos005146524

41. Cs-0334

42. Db12415

43. Ac-26549

44. As-56204

45. Hy-70006

46. D10125

47. J-501178

48. Q5518498

49. Vn/124-1;tok-001;vn 124;tok001;tok 001

50. 3beta-hydroxy-17-(1h-benzimidazol-1-yl)-androsta-5,16-diene

51. 3beta-hydroxy-17-(1h-benzimidazol-1-yl)androsta-5,16-diene

52. Androsta-5,16-dien-3-ol, 17-(1h-benzimidazol-1-yl)-, (3beta)-

53. Androsta-5,16-dien-3-ol, 17-(1h-benzimidazol-1-yl)-, (3.beta.)-

2.4 Create Date
2006-10-26
3 Chemical and Physical Properties
Molecular Weight 388.5 g/mol
Molecular Formula C26H32N2O
XLogP35.2
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count1
Exact Mass388.251463648 g/mol
Monoisotopic Mass388.251463648 g/mol
Topological Polar Surface Area38 Ų
Heavy Atom Count29
Formal Charge0
Complexity743
Isotope Atom Count0
Defined Atom Stereocenter Count6
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Pharmacology and Biochemistry
4.1 MeSH Pharmacological Classification

Enzyme Inhibitors

Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. (See all compounds classified as Enzyme Inhibitors.)


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