1. 17-(3-pyridyl)androsta-5,16-dien-3beta-ol
2. Cb 7598
3. Cb-7598
4. Cb7598
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
Molecular Weight | 349.5 g/mol |
---|---|
Molecular Formula | C24H31NO |
XLogP3 | 4.6 |
Hydrogen Bond Donor Count | 1 |
Hydrogen Bond Acceptor Count | 2 |
Rotatable Bond Count | 1 |
Exact Mass | Da |
Monoisotopic Mass | Da |
Topological Polar Surface Area | 33.1 |
Heavy Atom Count | 26 |
Formal Charge | 0 |
Complexity | 636 |
Isotope Atom Count | 0 |
Defined Atom Stereocenter Count | 6 |
Undefined Atom Stereocenter Count | 0 |
Defined Bond Stereocenter Count | 0 |
Undefined Bond Stereocenter Count | 0 |
Covalently Bonded Unit Count | 1 |
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.
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
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.
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
In patients with mCRPC, the mean ( SD) terminal half-life of abiraterone in plasma is 12 ( 5) hours.
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.
BUILDING BLOCK