Δ4-Abiraterone | CAS# 154229-21-7 | Active metabolite

MedKoo Cat#: 574210 | Name: Δ4-Abiraterone

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Δ4-Abiraterone is an active metabolite of the CYP17A1 inhibitor Abiraterone. D4A is an androgen receptor antagonist that reduces expression of the androgen receptor target genes PSA, TMPRSS2, and FKBP5 in LNCaP, LAPC4, and C4-2 cell lines. It inhibits the cytochrome P450 (CYP) isoform CYP17A1 and blocks SRD5A conversion of Δ4-androstenedione to 5α-androstanedione in LAPC4 cells. In vivo, D4A delays tumor progression in a VCaP mouse xenograft model and increases progression-free survival in a C4-2 mouse xenograft model.

Chemical Structure

Δ4-Abiraterone

CAS#154229-21-7

Theoretical Analysis

MedKoo Cat#: 574210

Name: Δ4-Abiraterone

CAS#: 154229-21-7

Chemical Formula: C24H29NO

Exact Mass: 347.2249

Molecular Weight: 347.50

Elemental Analysis: C, 82.95; H, 8.41; N, 4.03; O, 4.60

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 350.00	2 Weeks

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Related CAS #

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Synonym

Δ4-Abiraterone, CB 7627, D4A

IUPAC/Chemical Name

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

InChi Key

GYJZZAJJENTSTP-NHFPKVKZSA-N

InChi Code

InChI=1S/C24H29NO/c1-23-11-9-18(26)14-17(23)5-6-19-21-8-7-20(16-4-3-13-25-15-16)24(21,2)12-10-22(19)23/h3-4,7,13-15,19,21-22H,5-6,8-12H2,1-2H3/t19-,21-,22-,23-,24+/m0/s1

SMILES Code

O=C1CC[C@@]2(C)C(CC[C@]3([H])[C@]2([H])CC[C@@]4(C)[C@@]3([H])CC=C4C5=CN=CC=C5)=C1

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 347.50 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Shiota M, Inoue R, Tashiro K, Kobayashi K, Horiyama S, Kanji H, Eto M, Egawa S, Haginaka J, Matsuyama H. A Phase II Trial of Abiraterone With Dutasteride for Second-Generation Antiandrogen- and Chemotherapy-Naïve Patients With Castration- Resistant Prostate Cancer. J Clin Pharmacol. 2023 Apr;63(4):445-454. doi: 10.1002/jcph.2191. Epub 2023 Jan 17. PMID: 36484758. 2: Takahashi Y, Narita S, Shiota M, Miura M, Kagaya H, Kashima S, Yamamoto R, Nara T, Huang M, Numakura K, Saito M, Eto M, Habuchi T. Impact of trough abiraterone level on adverse events in patients with prostate cancer treated with abiraterone acetate. Eur J Clin Pharmacol. 2023 Jan;79(1):89-98. doi: 10.1007/s00228-022-03420-0. Epub 2022 Nov 15. PMID: 36378297. 3: Weiss TLD, Furtado CM, Antunes MV, Gössling G, Schwartsmann G, Linden R, Verza SG. A quick UPLC-MS/MS method for therapeutic drug monitoring of abiraterone and delta(4)-abiraterone in human plasma. Biomed Chromatogr. 2020 Nov;34(11):e4947. doi: 10.1002/bmc.4947. Epub 2020 Aug 7. PMID: 32652651. 4: Masamrekh R, Filippova T, Haurychenka Y, Shcherbakov K, Veselovsky A, Strushkevich N, Shkel T, Gilep A, Usanov S, Shumyantseva V, Kuzikov A. Estimation of the inhibiting impact of abiraterone D4A metabolite on human steroid 21-monooxygenase (CYP21A2). Steroids. 2020 Feb;154:108528. doi: 10.1016/j.steroids.2019.108528. Epub 2019 Oct 31. Erratum in: Steroids. 2020 Sep;161:108674. doi: 10.1016/j.steroids.2020.108674. PMID: 31678135. 5: Bhatnagar A, McKay MJ, Thaysen-Andersen M, Arasaratnam M, Crumbaker M, Gurney H, Molloy MP. Bioanalytical evaluation of dried plasma spots for monitoring of abiraterone and ∆(4)-abiraterone from cancer patients. J Chromatogr B Analyt Technol Biomed Life Sci. 2019 Sep 15;1126-1127:121741. doi: 10.1016/j.jchromb.2019.121741. Epub 2019 Jul 31. PMID: 31421381. 6: Blanchet B, Carton E, Alyamani M, Golmard L, Huillard O, Thomas-Scheomann A, Vidal M, Goldwasser F, Sharifi N, Alexandre J. A PK/PD study of Delta-4 abiraterone metabolite in metastatic castration-resistant prostate cancer patients. Pharmacol Res. 2018 Oct;136:56-61. doi: 10.1016/j.phrs.2018.08.016. Epub 2018 Aug 22. PMID: 30142421. 7: Hahn AW, Gill DM, Nussenzveig RH, Poole A, Farnham J, Cannon-Albright L, Agarwal N. Germline Variant in HSD3B1 (1245 A > C) and Response to Abiraterone Acetate Plus Prednisone in Men With New-Onset Metastatic Castration-Resistant Prostate Cancer. Clin Genitourin Cancer. 2018 Aug;16(4):288-292. doi: 10.1016/j.clgc.2018.03.006. Epub 2018 Mar 27. PMID: 29674118. 8: Bhatnagar A, McKay MJ, Crumbaker M, Ahire K, Karuso P, Gurney H, Molloy MP. Quantitation of the anticancer drug abiraterone and its metabolite Δ(4)-abiraterone in human plasma using high-resolution mass spectrometry. J Pharm Biomed Anal. 2018 May 30;154:66-74. doi: 10.1016/j.jpba.2018.03.012. Epub 2018 Mar 6. PMID: 29533860. 9: Li Z, Bishop AC, Alyamani M, Garcia JA, Dreicer R, Bunch D, Liu J, Upadhyay SK, Auchus RJ, Sharifi N. Conversion of abiraterone to D4A drives anti-tumour activity in prostate cancer. Nature. 2015 Jul 16;523(7560):347-51. doi: 10.1038/nature14406. Epub 2015 Jun 1. PMID: 26030522; PMCID: PMC4506215.