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SML1527

Abiraterone acetate

Name: Abiraterone acetate
Brand: SIGMA

≥98% (HPLC), CYP17A1 inhibitor, powder

Synonym(s):

CB 7598, 17-(Pyridin-3-yl)androsta-5,16-dien-3β-yl acetate

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About This Item

Empirical Formula (Hill Notation):

C₂₆H₃₃NO₂

CAS Number:

154229-18-2

Molecular Weight:

391.55

UNSPSC Code:

12352200

PubChem Substance ID:

329825944

NACRES:

NA.77

MDL number:

MFCD00934213

Assay:

≥98% (HPLC)

Form:

powder

Quality level:

100

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Properties

Product Name

Abiraterone acetate, ≥98% (HPLC)

Quality Level

100

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 5 mg/mL, clear

storage temp.

−20°C

SMILES string

C[C@]12C(C[C@@H](OC(C)=O)CC2)=CC[C@]3([H])[C@]1([H])CC[C@@]4(C)[C@@]3([H])CC=C4C5=CC=CN=C5

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

InChI key

UVIQSJCZCSLXRZ-UBUQANBQSA-N

Gene Information

human ... CYP17A1(1586)

Description

Application

Abiraterone acetate has been used to study its antitumor action in 3D micro-tumour platform.

Biochem/physiol Actions

Abiraterone acetate is a prodrug of abiraterone, which is a potent, selective, and orally bioavailable inhibitor of CYP17A1 (CYP450c17), an enzyme that catalyzes two key serial reactions (17α hydroxylase and 17,20 lyase) in androgen and estrogen biosynthesis resulting in the formation of DHEA and androstenedione, which may ultimately be metabolized into testosterone. CYP17 is the key enzyme for androgen biosynthesis in both the testes and adrenals, so its inhibition should stop the production of androgens in both places. Abiraterone acetate is used for the treatment of metastatic castration-resistant prostate cancer. Abiraterone acetate possesses significant antitumor activity in post-docetaxel patients with CRPC (castration-resistant prostate cancer). It is highly essential for androgen biosynthesis in the testes, adrenal glands, and prostate tissue.

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pictograms

GHS08,GHS09

signalword

Danger

hcodes

H360F,H373,H410

pcodes

P202 - P260 - P273 - P280 - P308 + P313 - P391

Hazard Classifications

Aquatic Chronic 1 - Repr. 1B - STOT RE 2

target_organs

Endocrine system

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Phase I clinical trial of the CYP17 inhibitor abiraterone acetate demonstrating clinical activity in patients with castration-resistant prostate cancer who received prior ketoconazole therapy.

Charles J Ryan et al.

Journal of clinical oncology : official journal of the American Society of Clinical Oncology, 28(9), 1481-1488 (2010-02-18)

Abiraterone acetate is a prodrug of abiraterone, a selective inhibitor of CYP17, the enzyme catalyst for two essential steps in androgen biosynthesis. In castration-resistant prostate cancers (CRPCs), extragonadal androgen sources may sustain tumor growth despite a castrate environment. This phase

Selective inhibition of CYP17 with abiraterone acetate is highly active in the treatment of castration-resistant prostate cancer.

Gerhardt Attard et al.

Journal of clinical oncology : official journal of the American Society of Clinical Oncology, 27(23), 3742-3748 (2009-05-28)

It has been postulated that castration-resistant prostate cancer (CRPC) commonly remains hormone dependent. Abiraterone acetate is a potent, selective, and orally available inhibitor of CYP17, the key enzyme in androgen and estrogen biosynthesis. This was a phase I/II study of

The Microwell-mesh: A high-throughput 3D prostate cancer spheroid and drug-testing platform.

E. O. Mosaad, et al.

Scientific Reports, 8(1) (2018)

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Global Trade Item Number

SKU	GTIN
SML1527-25MG	04061832868653
SML1527-5MG	04061832868660