Abacavir

Abacavir
Chemical structure of abacavir
Clinical data
Pronunciation/əˈbækəvɪər/ ⓘ
Trade namesZiagen
Other namesAbacavir sulfate (USAN US)
AHFS/Drugs.comMonograph
MedlinePlusa699012
License data
Pregnancy
category
  • AU: B3
Routes of
administration		By mouth
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability83%
MetabolismLiver
Elimination half-life1.54 ± 0.63 h
ExcretionKidney (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
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
NIAID ChemDB
CompTox Dashboard (EPA)
ECHA InfoCard100.149.341
Chemical and physical data
FormulaC14H18N6O
Molar mass286.339 g·mol−1
3D model (JSmol)
Melting point165 °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
  (verify)

Abacavir, sold under the brand name Ziagen among others, is a medication used to treat HIV/AIDS.[2][3][4][5] Similar to other nucleoside analog reverse-transcriptase inhibitors (NRTIs), abacavir is used together with other HIV medications, and is not recommended by itself.[6] It is taken by mouth as a tablet or solution and may be used in children over the age of three months.[4][7]

Abacavir is generally well tolerated.[7] Common side effects include vomiting, insomnia (trouble sleeping), fever, and feeling tired.[4] Other common side effects include loss of appetite, headache, nausea (feeling sick), diarrhea, rash, and lethargy (lack of energy).[3] More severe side effects include hypersensitivity, liver damage, and lactic acidosis.[4] Genetic testing can indicate whether a person is at higher risk of developing hypersensitivity.[4] Symptoms of hypersensitivity include rash, vomiting, and shortness of breath.[7] Abacavir is in the NRTI class of medications, which work by blocking reverse transcriptase, an enzyme needed for HIV virus replication.[8] Within the NRTI class, abacavir is a carbocyclic nucleoside.[4]

Abacavir was patented in 1988, and approved for use in the United States in 1998.[9][10] It is on the World Health Organization's List of Essential Medicines.[11] It is available as a generic medication.[4] Abacavir is used together with other HIV medications, such as abacavir/lamivudine/zidovudine, abacavir/dolutegravir/lamivudine, and abacavir/lamivudine.[7][8] The combination abacavir/lamivudine is an essential medicine.[11]

  1. ^ "TGA eBS - Product and Consumer Medicine Information Licence". Archived from the original on 24 March 2022. Retrieved 23 August 2022.
  2. ^ a b Cite error: The named reference Ziagen FDA label was invoked but never defined (see the help page).
  3. ^ a b c "Ziagen EPAR". European Medicines Agency. 17 September 2018. Archived from the original on 30 July 2022. Retrieved 22 August 2022. Text was copied from this source which is copyright European Medicines Agency. Reproduction is authorized provided the source is acknowledged.
  4. ^ a b c d e f g "Abacavir Sulfate". The American Society of Health-System Pharmacists. Archived from the original on 21 August 2017. Retrieved 31 July 2015.
  5. ^ "Drug Name Abbreviations Adult and Adolescent ARV Guidelines". AIDSinfo. Archived from the original on 9 November 2016. Retrieved 8 November 2016.
  6. ^ "What Not to Use Adult and Adolescent ARV Guidelines". AIDSinfo. Archived from the original on 9 November 2016. Retrieved 8 November 2016.
  7. ^ a b c d Yuen GJ, Weller S, Pakes GE (2008). "A review of the pharmacokinetics of abacavir". Clinical Pharmacokinetics. 47 (6): 351–371. doi:10.2165/00003088-200847060-00001. PMID 18479171. S2CID 31107341.
  8. ^ a b "Nucleoside reverse transcriptase inhibitors (NRTIs or 'nukes') - HIV/AIDS". www.hiv.va.gov. Archived from the original on 9 November 2016. Retrieved 8 November 2016.
  9. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 505. ISBN 9783527607495. Archived from the original on 8 September 2017.
  10. ^ Kane BM (2008). HIV/AIDS Treatment Drugs. Infobase Publishing. p. 56. ISBN 9781438102078. Archived from the original on 8 September 2017.
  11. ^ a b 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.
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