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SML1527

Sigma-Aldrich

Abiraterone acetate

≥98% (HPLC)

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C26H33NO2
Numéro CAS:
Poids moléculaire :
391.55
Numéro MDL:
Code UNSPSC :
12352200
ID de substance PubChem :
Nomenclature NACRES :
NA.77

Niveau de qualité

Pureté

≥98% (HPLC)

Forme

powder

Couleur

white to beige

Solubilité

DMSO: 5 mg/mL, clear

Température de stockage

−20°C

Chaîne SMILES 

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

Clé InChI

UVIQSJCZCSLXRZ-UBUQANBQSA-N

Informations sur le gène

human ... CYP17A1(1586)

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Application

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

Actions biochimiques/physiologiques

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.

Pictogrammes

Health hazardEnvironment

Mention d'avertissement

Danger

Mentions de danger

Classification des risques

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

Organes cibles

Endocrine system

Code de la classe de stockage

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

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable


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Consulter la Bibliothèque de documents

Gerhardt Attard et al.
Cancer research, 69(12), 4937-4940 (2009-06-11)
Abiraterone acetate is a potent, selective, and orally bioavailable small molecule inhibitor of CYP17, an enzyme that catalyzes two key serial reactions (17 alpha hydroxylase and 17,20 lyase) in androgen and estrogen biosynthesis. Clinical trials have confirmed that specific inhibition
Daniel C Danila et al.
Journal of clinical oncology : official journal of the American Society of Clinical Oncology, 28(9), 1496-1501 (2010-02-18)
Persistence of ligand-mediated androgen receptor signaling has been documented in castration-resistant prostate cancers (CRPCs). Abiraterone acetate (AA) is a potent and selective inhibitor of CYP17, which is required for androgen biosynthesis in the testes, adrenal glands, and prostate tissue. This
Alison H M Reid et al.
Journal of clinical oncology : official journal of the American Society of Clinical Oncology, 28(9), 1489-1495 (2010-02-18)
The principal objective of this trial was to evaluate the antitumor activity of abiraterone acetate, an oral, specific, irreversible inhibitor of CYP17 in docetaxel-treated patients with castration-resistant prostate cancer (CRPC). In this multicenter, two-stage, phase II study, abiraterone acetate 1,000
E David Crawford et al.
The Journal of urology, 194(6), 1537-1547 (2015-07-22)
The availability of newly approved treatment options for metastatic castration resistant prostate cancer is not matched with conclusive data on optimal sequencing strategies and resistance patterns. A comprehensive review of efficacy and safety data for new agents and current knowledge
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

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