17-(3-pyridinyl)-androsta-4,16-diene-3-one

Name	17-(3-pyridyl)androsta-5,16-dien-3-one
Synonyms	D4-abiraterone Δ4-Abiraterone Abiraterone (D4A) D4-abiraterone (CB-7627) 7-(3-pyridyl)androsta-5,16-dien-3-one 17-(3-pyridyl)androsta-5,16-dien-3-one 17-(3-pyridinyl)-androsta-4,16-diene-3-one
CAS	154229-21-7

Molecular Formula	C24H29NO
Molar Mass	347.49
Density	1.14±0.1 g/cm3(Predicted)
Boling Point	504.6±50.0 °C(Predicted)
Appearance	powder
Color	white to beige
pKa	5.32±0.12(Predicted)
Storage Condition	2-8°C
In vitro study	D4-abiraterone (D4A ) (10 mM) nearly completely blocks conversion from D4-androstenedione (AD) to 5α-androstanedione and other 5α-reduced androgens. The affinity of D4-abiraterone for mutant (expressed in LNCaP, half-maximum inhibitory concentration (IC 50 =5.3 nM)) and wild type (expressed in LAPC4, IC 50 =7.9 nM) androgen receptor (AR) is greater than that of abiraterone (Abi) (IC 50 =418 and >500 nM, respectively). Compare with Abi, D4-abiraterone clearly better suppresses PSA, TMPRSS2 and FKBP5 expression in LNCAP, LAPC4 and C4-2 cell lines. D4-abiraterone also inhibits AR target gene expression in a dose-dependent manner.
In vivo study	D4-abiraterone (D4A) is tenfold more potent than abiraterone (Abi) in blocking conversion from dehydroepiandrosterone (DHEA) by 3β-hydroxysteroid dehydrogenase (3βHSD) to D4-androstenedione (AD) in LNCaP and VCaP xenografts. 0.1 μM D4-abiraterone is equivalent to 1 μM Abi for blocking AD accumulation at 48 h in both LNCaP and VCaP xenografts. Progression is significantly delayed in the D4-abiraterone group compare with the Abi acetate group (P=0.011). D4-abiraterone treatment increases progression-free survival compare with Abi acetate.

Last Update：2024-01-02 23:10:35

biological activity	D4-abiraterone is the main metabolite of abiraterone. D4-abiraterone is an inhibitor of CYP17A1, 3 β-hydroxysteroid dehydrogenase (3 βhsd) and steroid -5 α-reductase (SRD5A) and is also an antagonist of the androgen receptor.
Target	CYP17A1, 3βhsd, SRD5A, androgen receptor

Last Update：2024-04-09 20:52:54

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17-(3-pyridinyl)-androsta-4,16-diene-3-one

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