Abiraterone - CAS 154229-19-3
Not Intended for Therapeutic Use. For research use only.
Category:
Inhibitor
Product Name:
Abiraterone
Catalog Number:
B0084-059670
Synonyms:
(3beta)-17-(3-pyridinyl)-androsta-5,16-dien-3-ol; 17-(3-Pyridyl)androsta-5,16-dien-3beta-ol; CB 7598; CB-7598
CAS Number:
154229-19-3
Description:
Abiraterone blocks the synthesis of androgens by inhibiting CYP17A1. It is used to treat metastatic, castration-resistant prostate cancer.
Molecular Weight:
349.51
Molecular Formula:
C24H31NO
COA:
Inquire
MSDS:
Inquire
Canonical SMILES:
CC12CCC(CC1=CCC3C2CCC4(C3CC=C4C5=CN=CC=C5)C)O
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
InChIKey:
GZOSMCIZMLWJML-VJLLXTKPSA-N
Targets:
Cytochrome P450
Catalog Number Size Price Stock Quantity
B0084-059670 5 g $198 In stock
Bulk Inquiry
Chemical Structure
CAS 154229-19-3 Abiraterone

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Reference Reading


1. Inhibitors of enzymes of androgen biosynthesis: cytochrome P45017α and 5α-steroid reductase
Michael Jarman, H. John Smith, Paul J. Nicholls and Claire Simons. Natural Product Reports, 1998
In fact, the 3-pyridyl steroid 95 (abiraterone), was substantially more potent (Table 14) than its 2-pyridyl counterpart 96 whereas the 4-pyridyl derivative 97 was as predicted the least potent. Structural variations in rings A–C of the steroid skeleton were widely tolerated e.g. compounds 98–102. However, reduction of the △-bond led to ca. 10-fold lower inhibition, cf. 95 and 103.
2. Highly sensitive ultra-performance liquid chromatography–tandem mass spectrometry method for the determination of abiraterone in human plasma
Tanveer A. Wani*. Anal. Methods, 2013, 5, 3693–3699
Few liquid chromatography–mass spectrometry (LC–MS) methods have been reported for the analysis of ABR. These methods include a stability indicating assay to monitor ABR, and its potential degradation products besides this, two reports were found describing the determination of the ABR in biological samples (plasma). The first one employed LC–MS using single ion monitoring with a limit of quantitation of 5 nM. This method had a disadvantage of high separation time and low sensitivity. The second method included the determination of ABR by high-performance liquid chromatography–tandem mass spectrometry (HPLC–MS/MS) with a limit of quantitation of 0.20 ng mL-1.
3. Recent discoveries and developments of androgen receptor based therapy for prostate cancer
R. Elancheran, V. L. Maruthanila, M. Ramanathan, S. Kabilan, R. Devi, A. Kunnumakarae and Jibon Kotoky*. Med. Chem. Commun.,2015, 6,746–768
Abiraterone (4a), an inhibitor of CYP17 (17α-hydroxylase/C17,20-lyase), is a drug used in combination with prednisone in metastatic castration-resistant prostate cancer. It is formulated as the prodrug, abiraterone acetate. Abiraterone acetate (4b) is the active ingredient of ZYTIGA, which is the acetyl ester of abiraterone. It blocks androgen production at three sources; the testes, the adrenal glands, as well as from the tumor itself. This medication is classified as an “adrenal inhibitor”. TAK 700 (3p) is a potent, orally bioavailable and highly selective androgen synthesis inhibitor of 17, 20-lyase (CYP17A1) with IC50 values of 19 nM and 48 nM for humans and rats, respectively. It was selected for evaluation in patients in phase III clinical trials for the potential treatment of prostate cancer.
4. Anticancer steroids: linking natural and semi-synthetic compounds
Jorge A. R. Salvador,* M. Luisa Sa e Melo*. Nat. Prod. Rep., 2013, 30, 324–374
The Schneider group prepared a series of 17b-dihydrooxazinyl, oxazolidonyl and oxazolinyl steroids as presumed inhibitors of 17a-hydroxylase-C17, 20-lyase. In this group of compounds, 17β-dihydrooxazinyl derivatives did not display efficient rat testicular C17,20-lyase inhibition, however, several steroids in the oxazolidonyl and oxazolinyl series (e.g. compounds 58–60, Fig. 11) have IC50 values close to that of ketoconazole 42 and abiraterone 49.