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Also known as: 154229-19-3, Cb 7598, Cb-7598, 17-(3-pyridyl)androsta-5,16-dien-3beta-ol, Abiraterona, Unii-g819a456d0
Molecular Formula
C24H31NO
Molecular Weight
349.5  g/mol
InChI Key
GZOSMCIZMLWJML-VJLLXTKPSA-N
FDA UNII
G819A456D0

CAS 154229-19-3
ABIRATERONE is a small molecule drug with a maximum clinical trial phase of IV (across all indications) and is indicated for cancer and neoplasm and has 4 investigational indications.
Abiraterone is a Cytochrome P450 17A1 Inhibitor. The mechanism of action of abiraterone is as a Cytochrome P450 17A1 Inhibitor.
1 2D Structure

CAS 154229-19-3

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-ol
2.1.2 InChI
InChI=1S/C24H31NO/c1-23-11-9-18(26)14-17(23)5-6-19-21-8-7-20(16-4-3-13-25-15-16)24(21,2)12-10-22(19)23/h3-5,7,13,15,18-19,21-22,26H,6,8-12,14H2,1-2H3/t18-,19-,21-,22-,23-,24+/m0/s1
2.1.3 InChI Key
GZOSMCIZMLWJML-VJLLXTKPSA-N
2.2 Other Identifiers
2.2.1 UNII
G819A456D0
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 17-(3-pyridyl)androsta-5,16-dien-3beta-ol

2. Cb 7598

3. Cb-7598

4. Cb7598

2.3.2 Depositor-Supplied Synonyms

1. 154229-19-3

2. Cb 7598

3. Cb-7598

4. 17-(3-pyridyl)androsta-5,16-dien-3beta-ol

5. Abiraterona

6. Unii-g819a456d0

7. Chebi:68642

8. G819a456d0

9. Nsc-741232

10. (3beta)-17-(pyridin-3-yl)androsta-5,16-dien-3-ol

11. Androsta-5,16-dien-3-ol, 17-(3-pyridinyl)-, (3beta)-

12. Dtxsid80879993

13. 17-(pyridin-3-yl)androsta-5,16-dien-3beta-ol

14. Nsc 741232

15. Abiraterone (usp Impurity)

16. Abiraterone [usp Impurity]

17. Abirateronum

18. L02bx03

19. Dtxcid501021626

20. Androsta-5,16-dien-3-ol, 17-(3-pyridinyl)-(3beta)-

21. (3beta)-17-(3-pyridinyl)-androsta-5,16-dien-3-ol

22. Abiraterone (cb-7598)

23. Cb7598

24. Mfcd00924100

25. Chembl254328

26. (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-ol

27. 154229-19-3 (abiraterone)

28. (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-ol

29. 17-(3-pyridyl)androsta-5,16-dien-3.beta.-ol

30. (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-ol

31. (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-ol.

32. Abiraterone [inn:ban]

33. Abiraterone; Cb 7598; (3beta)-17-(3-pyridinyl)androsta-5,16-dien-3-ol; 17-(3-pyridinyl)-androsta-5,16-dien-3beta-ol

34. Androsta-5,16-dien-3-ol, 17-(3-pyridinyl)-, (3b)-

35. Abiraterone (standard)

36. Abiraterone [mi]

37. Abiraterone [inn]

38. Abiraterone [vandf]

39. Cb 7630 [as Acetate]

40. Schembl61108

41. Abiraterone [who-dd]

42. Mls006010235

43. Us9487554, Abiraterone

44. Gtpl6745

45. Abiraterone - Bio-x Trade Mark

46. Bdbm25458

47. Ex-a106

48. Gzosmcizmlwjml-vjllxtkpsa-n

49. Hy-70013r

50. Nsc749226

51. S1123

52. Akos005146525

53. Cs-0156

54. Db05812

55. Es-0045

56. Fa16899

57. Nsc-749226

58. Us9611270, Example 5, Abiraterone

59. Ac-25764

60. Ba164060

61. Hy-70013

62. Smr002530050

63. A2868

64. 17-(3-pyridyl)androsta-5.16-dien-3beta-ol

65. En300-311691

66. Ab01274738-01

67. Ab01274738_02

68. Q321431

69. Sr-01000941584

70. (3b)-17-(3-pyridinyl)androsta-5,16-dien-3-ol

71. Sr-01000941584-1

72. Brd-k50071428-001-01-7

73. Brd-k50071428-001-03-3

74. Z2301684603

75. 17-(pyridin-3-yl)androsta-5,16-dien-3.beta.-ol

76. (3b)-17-(3-pyridinyl)androsta-5,16-dien-3-ol;cb 7598

77. Cb 7598;(3b)-17-(3-pyridinyl)androsta-5,16-dien-3-ol

78. Androsta-5,16-dien-3-ol, 17-(3-pyridinyl)-(3.beta.)-

79. (3as,3br,7s,9ar,9bs,11as)-9a,11a-dimethyl-1-(pyridin-3-yl)-3h,3ah,3bh,4h,6h,7h,8h,9h,9ah,9bh,10h,11h,11ah-cyclopenta[a]phenanthren-7-ol

2.4 Create Date
2005-08-08
3 Chemical and Physical Properties
Molecular Weight 349.5 g/mol
Molecular Formula C24H31NO
XLogP34.6
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count1
Exact Mass Da
Monoisotopic Mass Da
Topological Polar Surface Area33.1
Heavy Atom Count26
Formal Charge0
Complexity636
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

Abiraterone is indicated for the treatment of **metastatic castration-resistant prostate cancer (mCRPC)** in combination with [methylprednisolone] or [prednisone]. In Europe and Canada, it is also used in patients with mCRPC who are asymptomatic or mildly symptomatic after the failure of androgen deprivation therapy for whom chemotherapy is not yet clinically indicated. In Europe, it is used in patients whose disease has progressed on or after a docetaxel-based chemotherapy regimen. In Canada, it is used in patients who have received prior chemotherapy containing [docetaxel] after the failure of androgen deprivation therapy. Abiraterone is indicated in combination with [prednisone] for the treatment of **metastatic high-risk castration-sensitive prostate cancer (CSPC)**. In Europe and Canada, it may also be used in combination with [prednisolone] and androgen deprivation therapy in newly diagnosed patients. In Canada and the US, abiraterone is also available in a combination product with [niraparib], which is indicated with [prednisone] for the treatment of adults with deleterious or suspected deleterious BRCA-mutated (BRCAm) mCRPC. In Canada, this combination product is also used with [prednisolone] and is reserved for patients who are asymptomatic or mildly symptomatic, and in whom chemotherapy is not clinically indicated.



5 Pharmacology and Biochemistry
5.1 FDA Pharmacological Classification
5.1.1 Active Moiety
ABIRATERONE
5.1.2 FDA UNII
G819A456D0
5.1.3 Pharmacological Classes
Cytochrome P450 17A1 Inhibitors [MoA]; Cytochrome P450 17A1 Inhibitor [EPC]; Cytochrome P450 2C8 Inhibitors [MoA]; Cytochrome P450 2D6 Inhibitors [MoA]
5.2 ATC Code

L02BX03

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355


L - Antineoplastic and immunomodulating agents

L02 - Endocrine therapy

L02B - Hormone antagonists and related agents

L02BX - Other hormone antagonists and related agents

L02BX03 - Abiraterone


L02BX03


5.3 Absorption, Distribution and Excretion

Absorption

Geometric mean ( SD) Cmax was 73 ( 44) ng/mL and AUC0- was 373 ( 249) ng x hr/mL following a single dose of 500 mg abiraterone acetate in overnight-fasted healthy subjects. Dose proportionality was observed in single doses of abiraterone acetate ranging from 125 mg to 625 mg. A group of patients with mCRPC received a daily dose of 1,000 mg: at steady-state, the mean ( SD) Cmax was 226 ( 178) ng/mL and AUC was 993 ( 639) ng x hr/mL. Following oral administration of abiraterone acetate to patients with metastatic castration-resistant prostate cancer, the median Tmax was two hours. _In vivo_, abiraterone acetate is converted to abiraterone. In clinical studies of other abiraterone acetate formulations, abiraterone acetate plasma concentrations were below detectable levels (< 0.2 ng/mL) in > 99% of the analyzed samples. Systemic exposure to abiraterone is increased when abiraterone acetate is administered with food. Abiraterone Cmax was approximately 6.5-fold higher, and AUC0- was 4.4-fold higher when a single dose of abiraterone acetate 500 mg was administered with a high-fat meal (56-60% fat, 900-1,000 calories) compared to overnight fasting in healthy subjects. Given the normal variation in the content and composition of meals, taking abiraterone with meals has the potential to result in increased and highly variable exposures.


Route of Elimination

Following oral administration of 14C-abiraterone acetate, approximately 88% of the radioactive dose is recovered in feces: the major compounds present in feces are unchanged abiraterone acetate and abiraterone, accounting for approximately 55% and 22% of the administered dose, respectively. Approximately 5% of the dose is recovered in urine.


Volume of Distribution

The mean ( SD) apparent steady-state volume of distribution is 19,669 ( 13,358) L.


5.4 Metabolism/Metabolites

The conversion of abiraterone acetate to abiraterone, the active metabolite, is likely to be mediated by esterases, although specific esterases have not been identified. In human plasma, the two main circulating metabolites are abiraterone sulfate, which is formed by CYP3A4 and SULT2A1, and N-oxide abiraterone sulfate, which is formed by SULT2A1. These metabolites each account for about 43% of abiraterone exposure and are pharmacologically inactive.


Abiraterone has known human metabolites that include abiraterone sulfate.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560


5.5 Biological Half-Life

In patients with mCRPC, the mean ( SD) terminal half-life of abiraterone in plasma is 12 ( 5) hours.


5.6 Mechanism of Action

17-hydroxylase/C17,20-lyase (CYP17) is a key enzyme in androgen biosynthesis. It is primarily expressed in testicular, adrenal, and prostatic tumours. CYP17 catalyzes the 17-hydroxylation of pregnenolone and progesterone to their 17-hydroxy derivative, followed by subsequent cleavage of the C 20,21-acetyl group to yield dehydroepiandrosterone (DHEA) and androstenedione. DHEA and androstenedione are precursors of testosterone. Aberrant androgen levels and unregulated androgen receptor signalling have been implicated in the development and progression of various prostate cancers. Androgen-sensitive prostatic carcinoma responds to treatment that decreases androgen levels. Androgen deprivation therapies, such as treatment with GnRH agonists or orchiectomy, decrease androgen production in the testes but do not affect androgen production by the adrenals or in the tumour. Abiraterone inhibits CYP17 to block androgen production. Inhibition of CYP17 can also result in increased mineralocorticoid production by the adrenals.


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