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Chemistry

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Also known as: 154229-18-2, Zytiga, Cb7630, Cb-7630, Yonsa, Cb 7630
Molecular Formula
C26H33NO2
Molecular Weight
391.5  g/mol
InChI Key
UVIQSJCZCSLXRZ-UBUQANBQSA-N
FDA UNII
EM5OCB9YJ6

Abiraterone Acetate
An androstene derivative that inhibits STEROID 17-ALPHA-HYDROXYLASE and is used as an ANTINEOPLASTIC AGENT in the treatment of metastatic castration-resistant PROSTATE CANCER.
1 2D Structure

Abiraterone Acetate

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
[(3S,8R,9S,10R,13S,14S)-10,13-dimethyl-17-pyridin-3-yl-2,3,4,7,8,9,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
2.1.2 InChI
InChI=1S/C26H33NO2/c1-17(28)29-20-10-12-25(2)19(15-20)6-7-21-23-9-8-22(18-5-4-14-27-16-18)26(23,3)13-11-24(21)25/h4-6,8,14,16,20-21,23-24H,7,9-13,15H2,1-3H3/t20-,21-,23-,24-,25-,26+/m0/s1
2.1.3 InChI Key
UVIQSJCZCSLXRZ-UBUQANBQSA-N
2.1.4 Canonical SMILES
CC(=O)OC1CCC2(C3CCC4(C(C3CC=C2C1)CC=C4C5=CN=CC=C5)C)C
2.1.5 Isomeric SMILES
CC(=O)O[C@H]1CC[C@@]2([C@H]3CC[C@]4([C@H]([C@@H]3CC=C2C1)CC=C4C5=CN=CC=C5)C)C
2.2 Other Identifiers
2.2.1 UNII
EM5OCB9YJ6
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 17-(3-pyridyl)-5,16-androstadien-3beta-acetate

2. Cb 7630

3. Cb-7630

4. Cb7630

5. Zytiga

2.3.2 Depositor-Supplied Synonyms

1. 154229-18-2

2. Zytiga

3. Cb7630

4. Cb-7630

5. Yonsa

6. Cb 7630

7. Abiraterone Acetate [usan]

8. 17-(3-pyridyl)-5,16-androstadien-3beta-acetate

9. Em5ocb9yj6

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

11. Nsc-748121

12. Nsc-749227

13. Chebi:68639

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

15. 17-(pyridin-3-yl)androsta-5,16-dien-3beta-yl Acetate

16. (3beta)-17-(pyridin-3-yl)androsta-5,16-dien-3-yl Acetate

17. Abiraterone Acotate

18. 17-(3-pyridyl)androsta-5, Acetate

19. Androsta-5, 17-(3-pyridinyl)-, 3-acetate,

20. Unii-em5ocb9yj6

21. Abiraterone-acetate

22. Ncgc00186462-01

23. 3s,9s,10r,13s,14s)-10,13-dimethyl-17-pyridin-3-yl-2,3,4,7,8,9,11,12,14,15-decahydro-1h-cyclopenta[a]phenanthren-3-ol, 3-acetate

24. Abiraterone Acetate

25. Mfcd00934213

26. Zytiga (tn)

27. Abiraterone (acetate)

28. Jnj-212082

29. Abiraterone Acetate- Bio-x

30. Dsstox_cid_28969

31. Dsstox_rid_83234

32. Dsstox_gsid_49043

33. Schembl93715

34. Mls006010090

35. Chembl271227

36. Gtpl9288

37. Abiraterone Acetate (jan/usp)

38. 3beta-17-(3-pyridyl)androsta-5,16-dien-3-ol Acetate

39. Abiraterone (as Acetate)

40. Abiraterone Acetate [mi]

41. Dtxsid3049043

42. Abiraterone Acetate [jan]

43. Ex-a107

44. Abiraterone Acetate [vandf]

45. Abiraterone Acetate [mart.]

46. Bcp02949

47. Zinc3809191

48. Tox21_113589

49. Abiraterone Acetate [usp-rs]

50. Abiraterone Acetate [who-dd]

51. Bdbm50407398

52. Nsc748121

53. Nsc749227

54. S2246

55. Abiraterone Acetate, >=98% (hplc)

56. Akos015896502

57. Cs-0544

58. Ds-2007

59. Jnj 212082

60. Nsc 748121

61. Nsc 749227

62. Jnj-2012082

63. Abiraterone Acetate [orange Book]

64. Ncgc00379022-06

65. Ac-25760

66. Ba164133

67. Hy-75054

68. Smr004701235

69. Abiraterone Acetate [usp Monograph]

70. Cas-154229-18-2

71. D09701

72. 3b-acetoxy-17-(3-pyridyl)androsta-5,16-diene

73. A809510

74. 3beta-acetoxy-17-(3-pyridyl)androsta-5,16-diene

75. W-201385

76. Brd-k24048528-001-02-5

77. Q27888393

78. (3s)-3-acetoxy-17-(pyridin-3-yl)androsta-5,16-diene

79. (3?)-17-(3-pyridinyl)androsta-5,16-dien-3-yl Acetate

80. (3beta)-17-(3-pyridinyl)androsta-5,16-dien-3-ol Acetate

81. 17-(pyridin-3-yl)androsta-5,16-dien-3.beta.-yl Acetate

82. Abiraterone Acetate, United States Pharmacopeia (usp) Reference Standard

83. Androsta-5,16-dien-3-ol, 17-(3-pyridinyl)-, Acetate (ester), (3beta)-

84. Androsta-5,16-dien-3-ol, 17-(3-pyridinyl)-, Acetate (ester), (3.beta.)-

85. (1s,2r,5s,10r,11s,15s)-2,15-dimethyl-14-(pyridin-3-yl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-7,13-dien-5-yl Acetate

86. [(3s,8r,9s,10r,13s,14s)-10,13-dimethyl-17-pyridin-3-yl-2,3,4,7,8,9,11,12,14,15-decahydro-1h-cyclopenta[a]phenanthren-3-yl] Ethanoate

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

2.4 Create Date
2006-10-25
3 Chemical and Physical Properties
Molecular Weight 391.5 g/mol
Molecular Formula C26H33NO2
XLogP35.2
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count3
Rotatable Bond Count3
Exact Mass391.251129295 g/mol
Monoisotopic Mass391.251129295 g/mol
Topological Polar Surface Area39.2 Ų
Heavy Atom Count29
Formal Charge0
Complexity739
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

Zytiga is indicated with prednisone or prednisolone for:

- the treatment of metastatic castration resistant prostate cancer in adult men who are asymptomatic or mildly symptomatic after failure of androgen deprivation therapy in whom chemotherapy is not yet clinically indicated

- the treatment of metastatic castration resistant prostate cancer in adult men whose disease has progressed on or after a docetaxel based chemotherapy regimen.


Abiraterone Mylan is indicated with prednisone or prednisolone for:

- the treatment of newly diagnosed high risk metastatic hormone sensitive prostate cancer (mHSPC) in adult men in combination with androgen deprivation therapy (ADT).

- the treatment of metastatic castration resistant prostate cancer (mCRPC) in adult men who are asymptomatic or mildly symptomatic after failure of androgen deprivation therapy in whom chemotherapy is not yet clinically indicated.

- the treatment of mCRPC in adult men whose disease has progressed on or after a docetaxel based chemotherapy regimen.


Abiraterone Krka is indicated with prednisone or prednisolone for:

- the treatment of newly diagnosed high risk metastatic hormone sensitive prostate cancer (mHSPC) in adult men in combination with androgen deprivation therapy (ADT) (see section 5. 1)

- the treatment of metastatic castration resistant prostate cancer (mCRPC) in adult men who are asymptomatic or mildly symptomatic after failure of androgen deprivation therapy in whom chemotherapy is not yet clinically indicated (see section 5. 1)

- the treatment of mCRPC in adult men whose disease has progressed on or after a docetaxel-based chemotherapy regimen.


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Antineoplastic Agents

Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)


Cytochrome P-450 Enzyme Inhibitors

Drugs and compounds which inhibit or antagonize the biosynthesis or actions of CYTOCHROME P-450 ENZYMES. (See all compounds classified as Cytochrome P-450 Enzyme Inhibitors.)


Steroid Synthesis Inhibitors

Compounds that bind to and inhibit enzymes involved in the synthesis of STEROIDS. (See all compounds classified as Steroid Synthesis Inhibitors.)


5.2 FDA Pharmacological Classification
5.2.1 Pharmacological Classes
Cytochrome P450 17A1 Inhibitors [MoA]; Cytochrome P450 2C8 Inhibitors [MoA]; Cytochrome P450 2D6 Inhibitors [MoA]; Cytochrome P450 17A1 Inhibitor [EPC]
5.3 ATC Code

L02BX03


L02BX03


L02BX03


API Reference Price

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06-Jan-2021
29-Oct-2024
KGS
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DOSAGE - TABLET;ORAL - 250MG

USFDA APPLICATION NUMBER - 202379

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DOSAGE - TABLET;ORAL - 500MG

USFDA APPLICATION NUMBER - 202379

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