Abacavir

Abacavir
Clinical data

Chemical structure of abacavir
Pronunciation	ⁱ/ʌ.bæk.ʌ.vɪər/
Trade names	Ziagen, others
AHFS/Drugs.com	Monograph
MedlinePlus	a699012
Pregnancy category	AU: B3 US: C (Risk not ruled out)
Routes of administration	By mouth (solution or tablets)
ATC code	J05AF06 (WHO)
Legal status
Legal status	UK: POM (Prescription only) US: ℞-only
Pharmacokinetic data
Bioavailability	83%
Metabolism	Liver
Biological 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^Y
PubChem (CID)	441300
DrugBank	DB01048^Y
ChemSpider	390063^Y
UNII	WR2TIP26VS^Y
KEGG	D07057^Y
ChEBI	CHEBI:421707^Y
ChEMBL	CHEMBL1380^Y
NIAID ChemDB	028596
ECHA InfoCard	100.149.341
Chemical and physical data
Formula	C₁₄H₁₈N₆O
Molar mass	286.332 g/mol
3D model (Jmol)	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^Y Key:MCGSCOLBFJQGHM-SCZZXKLOSA-N^Y

Abacavir (ABC) is a medication used to prevent and treat HIV/AIDS. Similar to other nucleoside 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, trouble sleeping, fever, and feeling tired. 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 duplication. 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, the most effective and safe medicines needed in a health system. It is available as a generic medication. The wholesale cost in the developing world as of 2014 is between 0.36 and 0.83 USD per day. As of 2016 the wholesale cost for a typical month of medication in the United States is 70.50 USD. Commonly, abacavir is sold together with other HIV medications, such as abacavir/lamivudine/zidovudine, abacavir/dolutegravir/lamivudine, and abacavir/lamivudine.

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