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154229-18-2

154229-18-2 Structure

154229-18-2 Structure
IdentificationBack Directory
[Name]

17-(3-pyridyl)-5,16-androstadien-3beta-acetate
[CAS]

154229-18-2
[EINECS(EC#)]

620-314-7
[Molecular Formula]

C26H33NO2
[MDL Number]

MFCD00934213
[MOL File]

154229-18-2.mol
[Molecular Weight]

391.55
Chemical PropertiesBack Directory
[Melting point ]

127-130°C
[Boiling point ]

506.7±50.0 °C(Predicted)
[density ]

1.14±0.1 g/cm3(Predicted)
[storage temp. ]

-20°C Freezer
[pka]

5.31±0.12(Predicted)
[form ]

powder
[color ]

white to beige
Safety DataBack Directory
[WGK Germany ]

3
[RTECS ]

BV7992100
[HS Code ]

2937290000
Hazard InformationBack Directory
[Description]

In April 2011, the United States FDA approved abiraterone acetate (CB7630) in combination with the steroid prednisone for the treatment of metastatic castration-resistant prostate cancer (mCRPC) for patients who were previously treated with a docetaxel containing regimen for late-stage disease. Abiraterone acetate affects prostate, testicular, and adrenal androgens by irreversibly inhibiting both the lyase and hydroxylase activity of cytochrome P450 17A (CYP17) signaling pathways (IC50's of 2.9 and 4 nM, respectively) thereby decreasing testosterone levels.Most common serious adverse events for abiraterone acetate versus placebo included fluid retention (30.5% vs. 22.3%), hypokalemia (17.1% vs. 8.4%), hypertension (9.7% vs. 7.9%), hepatic transaminase abnormalities (10.4% vs. 8.1%), and cardiac abnormalities (13.3% vs. 10.4%).
[Chemical Properties]

Off-White Solid
[Originator]

Institute of Cancer Research, London (United Kingdom)
[Uses]

A novel steroidal inhibitor of human Cytochrome P450(17a-Hydroxylase-C17,20-lyase): potential agent for the treatment of prostatic cancer.
[Uses]

A steroidal inhibitor of CYP17A1 in androgen biosynthesis
[Uses]

Abiraterone acetate is a novel steroidal inhibitor of human Cytochrome P450 (17α-Hydroxylase-C17,20-lyase): potential agent for the treatment of prostatic cancer.
[Definition]

ChEBI: A sterol ester obtained by formal condensation of the 3-hydroxy group of abiraterone with the carboxy group of acetic acid. A prodrug that is converted in vivo to abiraterone. Used for treatment of metastatic castrate-resistant prostate cance .
[Brand name]

Zytiga
[Enzyme inhibitor]

This steroid-based antineoplastic pro-drug (FW = 391.55 g/mol; CAS 154229-18-2), also known as Zytiga?, CB-7630, and systematically as (3β) -17- (pyridin-3-yl) androsta-5,16-dien-3-ol, is converted in vivo to abiraterone (FW = 349.51 g/mol; CAS 154229-19-3), an androgen biosynthesis inhibitor that targets 17-a-hydroxylase/C17,20-lyase, or CYP17 (Ki = 2 nM), an enzyme expressed in testicular, adrenal, and prostatic tumor tissues and required for androgen biosynthesis . CYP17A1 catalyzes the conversion of pregnenolone (and progesterone) to 17-α-hydroxy derivatives via its 17 α-hydroxylase activity, as well as the subsequent formation of dehydroepiandrosterone, or DHEA, (and androstenedione) via its C17,20 lyase activity. Zytiga is effective for the treatment of castration-resistant prostate cancer (previously known as hormone-resistant prostate cancer). A sensitive and selective LC-MS/MS method is available for the quantification of abiraterone acetate and abiraterone. The major circulating metabolites of abiraterone in humans are abiraterone sulfate and the N-oxide of abiraterone sulfate. Each of these metabolites occur at >100 times the respective concentration of abiraterone. The sulfate metabolite is approximately 7x more potent than abiraterone against rat testicular microsomal CYP17.
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