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SML1527

Abiraterone acetate

≥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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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)

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

Health hazardEnvironment
GHS08,GHS09

signalword

Danger

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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Certificates of Analysis (COA)

Lot/Batch Number
0000474873
0000474873
0000335765
0000353757
0000353757

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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
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
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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