Abacavir

Abacavir
	Chemical structure of abacavir
Clinical data
Pronunciation	/əˈbækəvɪər/ ⓘ
Trade names	Ziagen
Other names	Abacavir sulfate (USAN US)
AHFS/Drugs.com	Monograph
MedlinePlus	a699012
License data	EU EMA: by INN; US DailyMed: Abacavir;
Pregnancy; category	AU: B3;
Routes of; administration	By mouth
ATC code	J05AF06 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); UK: POM (Prescription only); US: WARNINGRx-only; EU: Rx-only;
Pharmacokinetic data
Bioavailability	83%
Metabolism	Liver
Elimination half-life	1.54 ± 0.63 h
Excretion	Kidney (1.2% abacavir, 30% 5'-carboxylic acid metabolite, 36% 5'-glucuronide metabolite, 15% unidentified minor metabolites). Fecal (16%)
Identifiers
	IUPAC name {(1S,4R)-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]cyclopent-2-en-1-yl}methanol;
CAS Number	136470-78-5 ;
PubChem CID	441300;
DrugBank	DB01048 ;
ChemSpider	390063 ;
UNII	WR2TIP26VS;
KEGG	D07057 ;
ChEBI	CHEBI:421707 ;
ChEMBL	ChEMBL1380 ;
NIAID ChemDB	028596;
CompTox Dashboard (EPA)	DTXSID4046444 ;
ECHA InfoCard	100.149.341
Chemical and physical data
Formula	C14H18N6O
Molar mass	286.339 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	165 °C (329 °F)
	SMILES n3c1c(ncn1[C@H]2/C=C\[C@@H](CO)C2)c(nc3N)NC4CC4;
	InChI InChI=1S/C14H18N6O/c15-14-18-12(17-9-2-3-9)11-13(19-14)20(7-16-11)10-4-1-8(5-10)6-21/h1,4,7-10,21H,2-3,5-6H2,(H3,15,17,18,19)/t8-,10+/m1/s1 ; Key:MCGSCOLBFJQGHM-SCZZXKLOSA-N ;
	(verify)

Abacavir, sold under the brand name Ziagen among others, is a medication used to treat HIV/AIDS. Similar to other nucleoside analog reverse-transcriptase inhibitors (NRTIs), abacavir is used together with other HIV medications, and is not recommended by itself. It is taken by mouth as a tablet or solution and may be used in children over the age of three months.

Abacavir is generally well tolerated. Common side effects include vomiting, insomnia (trouble sleeping), fever, and feeling tired. Other common side effects include loss of appetite, headache, nausea (feeling sick), diarrhea, rash, and lethargy (lack of energy). More severe side effects include hypersensitivity, liver damage, and lactic acidosis. Genetic testing can indicate whether a person is at higher risk of developing hypersensitivity. Symptoms of hypersensitivity include rash, vomiting, and shortness of breath. Abacavir is in the NRTI class of medications, which work by blocking reverse transcriptase, an enzyme needed for HIV virus replication. Within the NRTI class, abacavir is a carbocyclic nucleoside.

Abacavir was patented in 1988, and approved for use in the United States in 1998. It is on the World Health Organization's List of Essential Medicines. It is available as a generic medication. Abacavir is used together with other HIV medications, such as abacavir/lamivudine/zidovudine, abacavir/dolutegravir/lamivudine, and abacavir/lamivudine. The combination abacavir/lamivudine is an essential medicine.

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