Abiraterone acetate

Abiraterone acetate
Clinical data
Pronunciation	a" bir a' ter one
Trade names	Zytiga, Yonsa, others
Other names	CB-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.com	Monograph
MedlinePlus	a611046
License data	US DailyMed: Abiraterone_acetate;
Pregnancy; category	AU: D;
Routes of; administration	By mouth
Drug class	Antineoplastic
ATC code	L02BX03 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); CA: ℞-only; UK: POM (Prescription only); US: ℞-only; EU: Rx-only; In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	Unknown, but may be 50% at most on empty stomach
Protein binding	Abiraterone: ~99.8% (to albumin and α1-AGpTooltip alpha-1 acid glycoprotein)
Metabolism	Esterases, CYP3A4, SULT2A1
Metabolites	Abiraterone, others
Elimination half-life	Abiraterone: 12–24 hours
Excretion	Feces: 88%; Urine: 5%
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	154229-18-2 ; 154229-19-3 (abiraterone);
PubChem CID	9821849;
IUPHAR/BPS	9288;
DrugBank	DBSALT001173 ;
ChemSpider	7997598 ;
UNII	EM5OCB9YJ6;
KEGG	D09701;
ChEBI	CHEBI:68639;
ChEMBL	ChEMBL271227 ;
CompTox Dashboard (EPA)	DTXSID3049043 ;
ECHA InfoCard	100.149.063
Chemical and physical data
Formula	C26H33NO2
Molar mass	391.555 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	144 to 145 °C (291 to 293 °F)
	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 ; Key:UVIQSJCZCSLXRZ-UBUQANBQSA-N ;
	(verify)

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

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

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

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