Abiraterone acetate

Abiraterone acetate (CB7630) is an oral, potent, selective, and irreversible inhibitor of CYP17A1 with antiandrogen activity. Abiraterone acetate is a prodrug form of Abiraterone (CB7598).

Product information

CAS Number: 154229-18-2

Molecular Weight: 391.55

Formula: C26H33NO2

Synonym:

CB 7630

CB-7630

CB7630

Zytiga

Related CAS Number:

154229-19-3 (Abiraterone)

Chemical Name: (3aS, 3bR, 7S, 9aR, 9bS, 11aS)-9a, 11a-dimethyl-1-(pyridin-3-yl)-3H, 3aH, 3bH, 4H, 6H, 7H, 8H, 9H, 9aH, 9bH, 10H, 11H, 11aH-cyclopenta[a]phenanthren-7-yl acetate

Smiles: CC(=O)O[C@@H]1CC2=CC[C@H]3[C@@H]4CC=C(C5C=CC=NC=5)[C@@]4(C)CC[C@@H]3[C@@]2(C)CC1

InChiKey: UVIQSJCZCSLXRZ-UBUQANBQSA-N

InChi: 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

Technical Data

Appearance: Solid Power

Purity: ≥98% (or refer to the Certificate of Analysis)

Solubility: DMSO : 10 mg/mL (25.54 mM; Need ultrasonic)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥12 months if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined

HS Tariff Code: 382200

How to use

In Vitro:

Abiraterone (Abi) acetate is an ester prodrug of the anticancer agent Abiraterone, which shows IC50 values of 15 nM and 2.5 nM for the 17, 20-lyase and 17α-hydroxylase (CYP17 is a bifunctional enzyme with both 17α-hydroxylase and 17, 20-lyase activity). Abiraterone inhibits human 17, 20-lyase and 17α-hydroxylase with IC50 of 27 and 30 nM respectively. Significant inhibition of proliferation of the AR-positive prostate cancer cell lines LNCaP and VCaP with doses of Abiraterone ≥5 μM is confirmed. Abiraterone inhibits recombinant human 3βHSD1 and 3βHSD2 activity with competitive Ki values of 2.1 and 8.8 μM. 10 μM Abiraterone is sufficient to completely block synthesis of 5α-dione and DHT in both cell lines.Treatment with Abiraterone significantly inhibited CRPC progression in the robustly growing subset, effectively putting a ceiling on tumor growth over 4 weeks of treatment (P<0.00001).

In Vivo:

Abiraterone (Abi) acetate prolongs survival in castration-resistant prostate cancer (CRPC). [3H]-dehydroepiandrosterone (DHEA) depletion and Δ4-androstenedione (AD) accumulation are inhibited by Abiraterone in LNCaP, with an IC50<1 μM. The 0.5 mmol/kg/d Abiraterone treatment dose is previously shown to yield serum concentrations of about 0.5 to 1 μM. Xenograft tumor growth in the control group is widely variable, with some tumors growing slowly and only a subset of tumors exhibiting robust growth.

References:

1. Stein MN, et al. Androgen synthesis inhibitors in the treatment of castration-resistant prostate cancer. Asian J Androl. 2014 May-Jun;16(3):387-400.
2. Richards J, et al. Interactions of abiraterone, eplerenone, and prednisolone with wild-type and mutant androgen receptor: a rationale for increasing abiraterone exposure or combining with MDV3100. Cancer Res. 2012 May 1;72(9):2176-82.
3. Li R, et al. Abiraterone inhibits 3β-hydroxysteroid dehydrogenase: a rationale for increasing drug exposure in castration-resistant prostate cancer. Clin Cancer Res. 2012 Jul 1;18(13):3571-9.
4. Lee GT, et al. Intracrine androgen biosynthesis in renal cell carcinoma. Br J Cancer. 2017 Mar 28;116(7):937-943.
5. A O'Donnell, et al. Hormonal impact of the 17α-hydroxylase/C17,20-lyase inhibitor abiraterone acetate (CB7630) in patients with prostate cancer. British Journal of Cancervolume 90, pages2317–2325 (2004)

Products are for research use only. Not for human use.