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SML1527

Sigma-Aldrich

Abirateronacetat

≥98% (HPLC)

Synonym(e):

17-(Pyridin-3-yl)-androsta-5,16-dien-3β-yl-acetat

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About This Item

Empirische Formel (Hill-System):
C26H33NO2
CAS-Nummer:
154229-18-2
Molekulargewicht:
391.55
MDL-Nummer:
MFCD00934213
UNSPSC-Code:
12352200
PubChem Substanz-ID:
329825944
NACRES:
NA.77

Qualitätsniveau

100

Assay

≥98% (HPLC)

Form

powder

Farbe

white to beige

Löslichkeit

DMSO: 5 mg/mL, clear

Lagertemp.

−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

InChIKey

UVIQSJCZCSLXRZ-UBUQANBQSA-N

Angaben zum Gen

human ... CYP17A1(1586)

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Anwendung

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

Biochem./physiol. Wirkung

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.

Piktogramme

Health hazardEnvironment
GHS08,GHS09

Signalwort

Danger

Gefahreneinstufungen

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

Zielorgane

Endocrine system

Lagerklassenschlüssel

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

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

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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
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)
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
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
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