Abiraterone Acetate
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MedKoo CAT#: 200030

CAS#: 154229-18-2 (Abiraterone Acetate)

Description: Abiraterone acetate is an FDA approved drug, and is an orally active acetate ester of the steroidal compound abiraterone with antiandrogen activity. Abiraterone acetate was approved by the U.S. Food and Drug Administration (FDA) in April 2011. Abiraterone inhibits the enzymatic activity of steroid 17alpha-monooxygenase (17alpha-hydrolase/C17,20 lyase complex), a member of the cytochrome p450 family that catalyzes the 17alpha-hydroxylation of steroid intermediates involved in testosterone synthesis. Administration of this agent may suppress testosterone production by both the testes and the adrenals to castrate-range levels. FDA Approval this drug in May 2011.


Chemical Structure

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Abiraterone Acetate
CAS# 154229-18-2 (Abiraterone Acetate)

Theoretical Analysis

MedKoo Cat#: 200030
Name: Abiraterone Acetate
CAS#: 154229-18-2 (Abiraterone Acetate)
Chemical Formula: C26H33NO2
Exact Mass: 391.25113
Molecular Weight: 391.54
Elemental Analysis: C, 79.76; H, 8.50; N, 3.58; O, 8.17

Price and Availability

Size Price Availability Quantity
2.0g USD 150.0 Ready to ship
10.0g USD 450.0 Ready to ship
50.0g USD 1250.0 Ready to ship
100.0g USD 2150.0 Ready to ship
200.0g USD 3450.0 Ready to ship
500.0g USD 5650.0 Ready to ship
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Related CAS #: 154229-18-2 (Abiraterone Acetate)   154229-19-3 (Abiraterone)    

Synonym: CB 7630 ; CB-7630; CB7630; Abiraterone Acetate; brand name: Zytiga.

IUPAC/Chemical Name: [(3S,10R,13S)-10,13-dimethyl-17-pyridin-3-yl-2,3,4,7,8,9,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate

InChi Key: UVIQSJCZCSLXRZ-HMMZIKKISA-N

InChi Code: 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

SMILES Code: CC(O[C@H]1CC[C@]2(C)C3CC[C@]4(C)C(C5=CC=CN=C5)=CCC4C3CC=C2C1)=O

Appearance: white 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, not in water

Shelf Life: >10 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

Biological target: Abiraterone acetate is an oral, potent, selective, and irreversible inhibitor of CYP17A1 with antiandrogen activity
In vitro activity: Abiraterone acetate inhibits recombinant 3βHSD activity in vitro and endogenous 3βHSD activity in LNCaP and LAPC4 cells, including conversion of [(3)H]-dehydroepiandrosterone (DHEA) to Δ(4)-androstenedione, androgen receptor nuclear translocation, expression of androgen receptor-responsive genes. Abiraterone acetate inhibits 3βHSD1 and 3βHSD2 enzymatic activity in vitro; blocks conversion from DHEA to androstenedione and DHT with an IC(50) value of less than 1 μmol/L in CRPC cell lines; inhibits androgen receptor nuclear translocation; expression of TMPRSS2, prostate-specific antigen, and FKBP5. Reference: Clin Cancer Res. 2012 Jul 1;18(13):3571-9. https://clincancerres.aacrjournals.org/content/18/13/3571.long
In vivo activity: To mimic DHEA production in the human to test the effect of abi on 3βHSD in CRPC, LAPC4 xenografts were developed in orchiectomized mice that were implanted with 90-day sustained release DHEA pellets. Tumors reaching the threshold volume of 300 mm3 were randomly assigned to vehicle or Abiraterone acetate cohorts, and tumor volume relative to pretreatment values was monitored over 4 weeks of treatment. The 0.5 mmol/kg/d Abiraterone acetate treatment dose was previously shown to yield serum concentrations of about 0.5 to 1 μmol/L (26). Xenograft tumor growth in the control group was widely variable, with some tumors growing slowly and only a subset of tumors exhibiting robust growth. As shown in Fig. 5, treatment with Abiraterone acetate significantly inhibited CRPC progression in the robustly growing subset, effectively putting a ceiling on tumor growth over 4 weeks of treatment (P < 0.00001). Reference: Clin Cancer Res. 2012 Jul 1;18(13):3571-9. https://clincancerres.aacrjournals.org/content/18/13/3571.long

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 14.0 35.76
Ethanol 26.0 66.4

Preparing Stock Solutions

The following data is based on the product molecular weight 391.54 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.

Recalculate based on batch purity %
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
Formulation protocol: 1. Grellety T, Callens C, Richard E, Briaux A, Vélasco V, Pulido M, Gonçalves A, Gestraud P, MacGrogan G, Bonnefoi H, Cardinaud B. Enhancing Abiraterone Acetate Efficacy in Androgen Receptor-positive Triple-negative Breast Cancer: Chk1 as a Potential Target. Clin Cancer Res. 2019 Jan 15;25(2):856-867. doi: 10.1158/1078-0432.CCR-18-1469. Epub 2018 Oct 23. PMID: 30352905. 2. Duc I, Bonnet P, Duranti V, Cardinali S, Rivière A, De Giovanni A, Shields-Botella J, Barcelo G, Adje N, Carniato D, Lafay J, Pascal JC, Delansorne R. In vitro and in vivo models for the evaluation of potent inhibitors of male rat 17alpha-hydroxylase/C17,20-lyase. J Steroid Biochem Mol Biol. 2003 Apr;84(5):537-42. doi: 10.1016/s0960-0760(03)00078-5. PMID: 12767278. 3. Li R, Evaul K, Sharma KK, Chang KH, Yoshimoto J, Liu J, Auchus RJ, Sharifi N. 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. doi: 10.1158/1078-0432.CCR-12-0908. PMID: 22753664. 4. Duc I, Bonnet P, Duranti V, Cardinali S, Rivière A, De Giovanni A, Shields-Botella J, Barcelo G, Adje N, Carniato D, Lafay J, Pascal JC, Delansorne R. In vitro and in vivo models for the evaluation of potent inhibitors of male rat 17alpha-hydroxylase/C17,20-lyase. J Steroid Biochem Mol Biol. 2003 Apr;84(5):537-42. doi: 10.1016/s0960-0760(03)00078-5. PMID: 12767278.
In vitro protocol: 1. Grellety T, Callens C, Richard E, Briaux A, Vélasco V, Pulido M, Gonçalves A, Gestraud P, MacGrogan G, Bonnefoi H, Cardinaud B. Enhancing Abiraterone Acetate Efficacy in Androgen Receptor-positive Triple-negative Breast Cancer: Chk1 as a Potential Target. Clin Cancer Res. 2019 Jan 15;25(2):856-867. doi: 10.1158/1078-0432.CCR-18-1469. Epub 2018 Oct 23. PMID: 30352905. 2. Duc I, Bonnet P, Duranti V, Cardinali S, Rivière A, De Giovanni A, Shields-Botella J, Barcelo G, Adje N, Carniato D, Lafay J, Pascal JC, Delansorne R. In vitro and in vivo models for the evaluation of potent inhibitors of male rat 17alpha-hydroxylase/C17,20-lyase. J Steroid Biochem Mol Biol. 2003 Apr;84(5):537-42. doi: 10.1016/s0960-0760(03)00078-5. PMID: 12767278.
In vivo protocol: 1. Li R, Evaul K, Sharma KK, Chang KH, Yoshimoto J, Liu J, Auchus RJ, Sharifi N. 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. doi: 10.1158/1078-0432.CCR-12-0908. PMID: 22753664. 2. Duc I, Bonnet P, Duranti V, Cardinali S, Rivière A, De Giovanni A, Shields-Botella J, Barcelo G, Adje N, Carniato D, Lafay J, Pascal JC, Delansorne R. In vitro and in vivo models for the evaluation of potent inhibitors of male rat 17alpha-hydroxylase/C17,20-lyase. J Steroid Biochem Mol Biol. 2003 Apr;84(5):537-42. doi: 10.1016/s0960-0760(03)00078-5. PMID: 12767278.

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1. Soylu H, Kırca M, Avcı S, Ozpolat B, Ustunel I. Antiandrogen abiraterone and docetaxel treatments affect Notch1, Jagged1 and Hes1 expressions in metastatic prostate cancer cells. Exp Mol Pathol. 2021 Apr;119:104607. doi: 10.1016/j.yexmp.2021.104607. Epub 2021 Jan 19. PMID: 33482170.

1: Grist E, Attard G. The development of abiraterone acetate for castration-resistant prostate cancer. Urol Oncol. 2015 Jun;33(6):289-294. doi: 10.1016/j.urolonc.2015.03.021. Review. PubMed PMID: 26025264.

2: Petrelli F, Coinu A, Borgonovo K, Cabiddu M, Ghilardi M, Lonati V, Barni S. Enzalutamide After Docetaxel and Abiraterone Acetate Treatment in Prostate Cancer: A Pooled Analysis of 10 Case Series. Clin Genitourin Cancer. 2015 Jun;13(3):193-198. doi: 10.1016/j.clgc.2014.10.006. Epub 2014 Nov 7. Review. PubMed PMID: 25466676.

3: Giacinti S, Bassanelli M, Aschelter AM, Milano A, Roberto M, Marchetti P. Resistance to abiraterone in castration-resistant prostate cancer: a review of the literature. Anticancer Res. 2014 Nov;34(11):6265-9. Review. PubMed PMID: 25368223.

4: Zobniw CM, Causebrook A, Fong MK. Clinical use of abiraterone in the treatment of metastatic castration-resistant prostate cancer. Res Rep Urol. 2014 Aug 5;6:97-105. doi: 10.2147/RRU.S29003. eCollection 2014. Review. PubMed PMID: 25157341; PubMed Central PMCID: PMC4128838.

5: Francini E, Petrioli R, Roviello G. No clear evidence of a clinical benefit of a sequential therapy regimen with abiraterone acetate and enzalutamide. Expert Rev Anticancer Ther. 2014 Oct;14(10):1135-40. doi: 10.1586/14737140.2014.949677. Epub 2014 Aug 19. Review. PubMed PMID: 25135334.

6: Woo HH, Begbie S, Gogna K, Mainwaring PN, Murphy DG, Parnis F, Steer C, Davis ID. Multidisciplinary consensus: a practical guide for the integration of abiraterone into clinical practice. Asia Pac J Clin Oncol. 2014 Sep;10(3):228-36. doi: 10.1111/ajco.12264. Epub 2014 Aug 17. Review. PubMed PMID: 25132163.

7: Nakazawa M, Antonarakis ES, Luo J. Androgen receptor splice variants in the era of enzalutamide and abiraterone. Horm Cancer. 2014 Oct;5(5):265-73. doi: 10.1007/s12672-014-0190-1. Epub 2014 Jul 22. Review. PubMed PMID: 25048254; PubMed Central PMCID: PMC4167475.

8: Boissier E, Loriot Y, Vignot S, Massard C. [Abiraterone acetate (AA): current guidelines of prescription of abiraterone]. Bull Cancer. 2014 Apr;101(4):388-93. doi: 10.1684/bdc.2014.1932. Review. French. PubMed PMID: 24793632.

9: Mostaghel EA, Lin DW. Practical guide to the use of abiraterone in castration resistant prostate cancer. Can J Urol. 2014 Apr;21(2 Supp 1):57-63. Review. PubMed PMID: 24775725; PubMed Central PMCID: PMC4139288.

10: Zhou ZR, Liu SX, Zhang TS, Xia J, Li B. Abiraterone for treatment of metastatic castration-resistant prostate cancer: a systematic review and meta-analysis. Asian Pac J Cancer Prev. 2014;15(3):1313-20. Review. PubMed PMID: 24606458.



Additional Information

ZYTIGA™ (abiraterone acetate) received FDA Approval  in May 2011 for Treatment of Metastatic Prostate Cancer After Priority Review; First Once-Daily, Oral Treatment for Metastatic Prostate Cancer Inhibits Androgen Production. ZYTIGA™ (abiraterone acetate) in combination with prednisone is indicated for the treatment of patients with metastatic castration-resistant prostate cancer (CRPC) who have received prior chemotherapy containing docetaxel.