Abiraterone

  • CAT Number: A000733
  • CAS Number: 154229-19-3
  • Molecular Formula: C24H31NO
  • Molecular Weight: 349.5
  • Purity: ≥95%
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Abiraterone  (CAS 154229-19-3), also known as CB7598, is the active metabolite of abiraterone acetate, which 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.

Catalog Number A000733
CAS Number 154229-19-3
Molecular Formula

C24H31NO

Purity 95%
Target P450
Solubility Limited solubility
Storage -20°C
Overview of Clinical Research

Abiraterone is a CYP17A1 protein inhibitor. The Phase I clinical trials in Prostate cancer starts in 2020.

IUPAC Name (3S,8R,9S,10R,13S,14S)-10,13-dimethyl-17-pyridin-3-yl-2,3,4,7,8,9,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthren-3-ol
InChI InChI=1S/C24H31NO/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/h3-5,7,13,15,18-19,21-22,26H,6,8-12,14H2,1-2H3/t18-,19-,21-,22-,23-,24+/m0/s1
InChIKey GZOSMCIZMLWJML-VJLLXTKPSA-N
SMILES CC12CCC(CC1=CCC3C2CCC4(C3CC=C4C5=CN=CC=C5)C)O
Reference

1: Bir&oacute; K, Budai B, Szőnyi M, K&uuml;ronya Z, Gyergyay F, Nagyiv&aacute;nyi K, G&eacute;czi L. Abiraterone acetate + prednisolone treatment beyond prostate specific antigen and radiographic progression in metastatic castration-resistant prostate cancer patients. Urol Oncol. 2017 Nov 15. pii: S1078-1439(17)30552-5. doi: 10.1016/j.urolonc.2017.10.015. [Epub ahead of print] PubMed PMID: 29153623.<br />
2: Fan L, Chi C, Guo S, Wang Y, Cai W, Shao X, Xu F, Pan J, Zhu Y, Shangguan X, Xin Z, Hu J, Qian H, Xie S, Wang R, Zhou L, Dong B, Xue W. Serum Pre-Albumin Predicts the Clinical Outcome in Metastatic Castration-Resistant Prostate Cancer Patients Treated With Abiraterone. J Cancer. 2017 Sep 20;8(17):3448-3455. doi: 10.7150/jca.21134. eCollection 2017. PubMed PMID: 29151928; PubMed Central PMCID: PMC5687158.<br />
3: Stein CA, Levin R, Given R, Higano CS, Nemeth P, Bosch B, Chapas-Reed J, Dreicer R. Randomized phase 2 therapeutic equivalence study of abiraterone acetate fine particle formulation vs. originator abiraterone acetate in patients with metastatic castration-resistant prostate cancer: The STAAR study. Urol Oncol. 2017 Nov 14. pii: S1078-1439(17)30555-0. doi: 10.1016/j.urolonc.2017.10.018. [Epub ahead of print] PubMed PMID: 29150328.<br />
4: Moreira RB, Debiasi M, Francini E, Nuzzo PV, Velasco G, Maluf FC, Fay AP, Bellmunt J, Choueiri TK, Schutz FA. Differential side effects profile in patients with mCRPC treated with abiraterone or enzalutamide: a meta-analysis of randomized controlled trials. Oncotarget. 2017 Aug 8;8(48):84572-84578. doi: 10.18632/oncotarget.20028. eCollection 2017 Oct 13. Review. PubMed PMID: 29137449; PubMed Central PMCID: PMC5663621.<br />
5: Aggarwal R. Abiraterone or Docetaxel Plus Androgen Deprivation in Hormone-Sensitive Prostate Cancer: More Questions Than Answers. Eur Urol. 2017 Nov 8. pii: S0302-2838(17)30967-3. doi: 10.1016/j.eururo.2017.10.028. [Epub ahead of print] PubMed PMID: 29128209.<br />
6: Cindolo L, Natoli C, De Nunzio C, De Tursi M, Valeriani M, Giacinti S, Micali S, Rizzo M, Bianchi G, Martorana E, Scarcia M, Ludovico GM, Bove P, Laudisi A, Selvaggio O, Carrieri G, Bada M, Castellan P, Boccasile S, Ditonno P, Chiodini P, Verze P, Mirone V, Schips L. Safety and efficacy of abiraterone acetate in chemotherapy-naive patients with metastatic castration-resistant prostate cancer: an Italian multicenter /real life/ study. BMC Cancer. 2017 Nov 10;17(1):753. doi: 10.1186/s12885-017-3755-x. PubMed PMID: 29126389; PubMed Central PMCID: PMC5681753.<br />
7: Tatsuzawa M, Ogawa R, Kinjo N, Kim S, Shimizu F, Sakamoto Y, Shimojima K, Echizen H, Miyazaki A. Consequences of Different Corticosteroids on Serum Potassium and Prostate-Specific Antigen in Patients Receiving Abiraterone for Castration-Resistant Prostate Cancer: A Retrospective Observational Study. Clin Med Insights Oncol. 2017 Oct 30;11:1179554917737736. doi: 10.1177/1179554917737736. eCollection 2017. PubMed PMID: 29118587; PubMed Central PMCID: PMC5666518.<br />
8: Yang YJ, Lin GW, Li GX, Dai B, Ye DW, Wu JL, Xie HY, Zhu Y. External validation and newly development of a nomogram to predict overall survival of abiraterone-treated, castration-resistant patients with metastatic prostate cancer. Asian J Androl. 2017 Nov 7. doi: 10.4103/aja.aja_39_17. [Epub ahead of print] PubMed PMID: 29111539.<br />
9: Rizzo S, Galvano A, Pantano F, Iuliani M, Vincenzi B, Passiglia F, Spoto S, Tonini G, Bazan V, Russo A, Santini D. The effects of enzalutamide and abiraterone on skeletal related events and bone radiological progression free survival in castration resistant prostate cancer patients: An indirect comparison of randomized controlled trials. Crit Rev Oncol Hematol. 2017 Oct 16. pii: S1040-8428(17)30225-1. doi: 10.1016/j.critrevonc.2017.09.008. [Epub ahead of print] Review. PubMed PMID: 29110971.<br />
10: Caroli P, De Giorgi U, Scarpi E, Fantini L, Moretti A, Galassi R, Celli M, Conteduca V, Rossi L, Bianchi E, Paganelli G, Matteucci F. Prognostic value of 18F-choline PET/CT metabolic parameters in patients with metastatic castration-resistant prostate cancer treated with abiraterone or enzalutamide. Eur J Nucl Med Mol Imaging. 2017 Nov 6. doi: 10.1007/s00259-017-3866-2. [Epub ahead of print] PubMed PMID: 29110067.

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