Abiraterone acetate

Abiraterone acetate
Clinical data
Pronunciationa" bir a' ter one
Trade namesZytiga, Yonsa, others
Other namesCB-7630; JNJ-212082; 17-(3-Pyridinyl)androsta-5,16-dien-3β-ol acetate, abiraterone (BAN UK), abiraterone acetate (JAN JP), abiraterone acetate (USAN US)
AHFS/Drugs.comMonograph
MedlinePlusa611046
License data
Pregnancy
category
Routes of
administration		By mouth[2][3]
Drug classAntineoplastic
ATC code
Legal status
Legal status
Pharmacokinetic data
BioavailabilityUnknown, but may be 50% at most on empty stomach[7]
Protein bindingAbiraterone: ~99.8% (to albumin and α1-AGpTooltip alpha-1 acid glycoprotein)[7][2][8]
MetabolismEsterases, CYP3A4, SULT2A1[8]
MetabolitesAbiraterone, others[2][7]
Elimination half-lifeAbiraterone: 12–24 hours[2][7][3]
ExcretionFeces: 88%[2][8]
Urine: 5%[2][8][3]
Identifiers
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-yl] acetate
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.149.063
Chemical and physical data
FormulaC26H33NO2
Molar mass391.555 g·mol−1
3D model (JSmol)
Melting point144 to 145 °C (291 to 293 °F) [9]
SMILES
  • CC(=O)O[C@H]1CC[C@@]2([C@H]3CC[C@]4([C@H]([C@@H]3CC=C2C1)CC=C4C5=CN=CC=C5)C)C
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 Y
  • Key:UVIQSJCZCSLXRZ-UBUQANBQSA-N Y
  (verify)

Abiraterone acetate, sold under the brand name Zytiga among others, is a medication used to treat prostate cancer.[10] Specifically it is used together with a corticosteroid for metastatic castration-resistant prostate cancer (mCRPC) and metastatic high-risk castration-sensitive prostate cancer (mCSPC).[2][3] It should either be used following removal of the testicles or along with a gonadotropin-releasing hormone (GnRH) analog.[2] It is taken by mouth.[10]

Common side effects include tiredness, vomiting, headache, joint pain, high blood pressure, swelling, low blood potassium, high blood sugar, hot flashes, diarrhea, and cough.[10][2] Other severe side effects may include liver failure and adrenocortical insufficiency.[2] In males whose partners can become pregnant, birth control is recommended.[2] Supplied as abiraterone acetate it is converted in the body to abiraterone.[2] Abiraterone acetate works by suppressing the production of androgens – specifically it inhibits CYP17A1 – and thereby decreases the production of testosterone.[10] In doing so, it prevents the effects of these hormones in prostate cancer.[10]

Abiraterone acetate was described in 1995, and approved for medical use in the United States and the European Union in 2011.[11][2] It is on the World Health Organization's List of Essential Medicines.[12] It is available as a generic medication.[13]

  1. ^ "Abiraterone Use During Pregnancy". Drugs.com. 13 March 2020. Archived from the original on 25 November 2020. Retrieved 8 June 2020.
  2. ^ a b c d e f g h i j k l m n "Zytiga- abiraterone acetate tablet, film coated". DailyMed. 13 June 2019. Archived from the original on 13 November 2014. Retrieved 15 November 2019.
  3. ^ a b c d e "Yonsa- abiraterone acetate tablet". DailyMed. 5 June 2018. Archived from the original on 13 August 2020. Retrieved 15 November 2019.
  4. ^ Cite error: The named reference TGA was invoked but never defined (see the help page).
  5. ^ Cite error: The named reference EMC was invoked but never defined (see the help page).
  6. ^ Cite error: The named reference Zytiga EPAR was invoked but never defined (see the help page).
  7. ^ a b c d Benoist GE, Hendriks RJ, Mulders PF, Gerritsen WR, Somford DM, Schalken JA, et al. (November 2016). "Pharmacokinetic Aspects of the Two Novel Oral Drugs Used for Metastatic Castration-Resistant Prostate Cancer: Abiraterone Acetate and Enzalutamide". Clin Pharmacokinet. 55 (11): 1369–1380. doi:10.1007/s40262-016-0403-6. PMC 5069300. PMID 27106175.
  8. ^ a b c d Sternberg CN, Petrylak DP, Madan RA, Parker C (May 2014). "Progress in the treatment of advanced prostate cancer". American Society of Clinical Oncology Educational Book. American Society of Clinical Oncology. Annual Meeting (34): 117–131. doi:10.14694/EdBook_AM.2014.34.117. PMID 24857068. Archived from the original on 20 September 2016. Retrieved 9 September 2016.
  9. ^ Potter GA, Barrie SE, Jarman M, Rowlands MG (June 1995). "Novel steroidal inhibitors of human cytochrome P45017 alpha (17 alpha-hydroxylase-C17,20-lyase): potential agents for the treatment of prostatic cancer". Journal of Medicinal Chemistry. 38 (13): 2463–2471. doi:10.1021/jm00013a022. PMID 7608911.
  10. ^ a b c d e "Abiraterone Acetate Monograph for Professionals". Drugs.com. Archived from the original on 6 May 2012. Retrieved 15 November 2019.
  11. ^ Scowcroft H (21 September 2011). "Where did abiraterone come from?". Journal of Medicinal Chemistry. 38 (13). Cancer Research UK: 2463–2471. Archived from the original on 25 September 2011. Retrieved 28 September 2011.
  12. ^ World Health Organization (2023). The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). Geneva: World Health Organization. hdl:10665/371090. WHO/MHP/HPS/EML/2023.02.
  13. ^ "First Generic Drug Approvals". U.S. Food and Drug Administration. 17 October 2022. Retrieved 28 November 2022.
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