User:Mr. Ibrahem/Abacavir

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Mr. Ibrahem/Abacavir
Chemical structure of abacavir
Clinical data
Pronunciation/əˈbækəvɪər/ ⓘ
Trade namesZiagen, others[1]
AHFS/Drugs.comMonograph
MedlinePlusa699012
License data
Pregnancy
category
  • AU: B3
Routes of
administration		By mouth (solution or tablets)
Drug classNucleoside analog reverse-transcriptase inhibitors (NRTIs)[1]
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
  • {(1S,4R)-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]cyclopent-2-en-1-yl}methanol
Chemical and physical data
FormulaC14H18N6O
Molar mass286.339 g·mol−1
3D model (JSmol)
Melting point165 °C (329 °F)
  • n3c1c(ncn1[C@H]2/C=C\[C@@H](CO)C2)c(nc3N)NC4CC4
  • 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 checkY
  • Key:MCGSCOLBFJQGHM-SCZZXKLOSA-N checkY
  (verify)

Abacavir, sold under the brand name Ziagen, is a medication used to prevent and treat HIV/AIDS.[1][4] Similar to other nucleoside analog reverse-transcriptase inhibitors (NRTIs), abacavir is used together with other HIV medications, and is not recommended by itself.[5] It is taken by mouth as a tablet or solution and may be used in children over the age of three months.[1][6]

Abacavir is generally well tolerated.[6] Common side effects include vomiting, trouble sleeping, fever, and feeling tired.[1] More severe side effects include hypersensitivity, liver damage, and lactic acidosis.[1] Genetic testing can indicate whether a person is at higher risk of developing hypersensitivity.[1] Symptoms of hypersensitivity include rash, vomiting, and shortness of breath.[6] Abacavir is in the NRTI class of medications, which work by blocking reverse transcriptase, an enzyme needed for HIV virus replication.[7] Within the NRTI class, abacavir is a carbocyclic nucleoside.[1]

Abacavir was patented in 1988, and approved for use in the United States in 1998.[8][9] It is on the World Health Organization's List of Essential Medicines.[10] It is available as a generic medication.[1] The wholesale cost in the developing world as of 2014 is between US$0.36 and US$0.83 per day.[11] As of 2016 the wholesale cost for a typical month of medication in the United States is US$70.50.[12] Commonly, abacavir is sold together with other HIV medications, such as abacavir/lamivudine/zidovudine, abacavir/dolutegravir/lamivudine, and abacavir/lamivudine.[6][7] The combination abacavir/lamivudine is also an essential medicine.[10]

References[edit]

  1. ^ a b c d e f g h i j "Abacavir Sulfate". The American Society of Health-System Pharmacists. Archived from the original on 21 August 2017. Retrieved 31 July 2015.
  2. ^ "ABACAVIR = ABC oral - Essential drugs". medicalguidelines.msf.org. Archived from the original on 27 August 2021. Retrieved 25 August 2020.
  3. ^ "WHOCC - ATC/DDD Index". www.whocc.no. Archived from the original on 7 August 2020. Retrieved 21 September 2020.
  4. ^ "Drug Name Abbreviations Adult and Adolescent ARV Guidelines". AIDSinfo. Archived from the original on 9 November 2016. Retrieved 8 November 2016.
  5. ^ "What Not to Use Adult and Adolescent ARV Guidelines". AIDSinfo. Archived from the original on 9 November 2016. Retrieved 8 November 2016.
  6. ^ a b c d Yuen GJ, Weller S, Pakes GE (2008). "A review of the pharmacokinetics of abacavir". Clinical Pharmacokinetics. 47 (6): 351–71. doi:10.2165/00003088-200847060-00001. PMID 18479171. S2CID 31107341.
  7. ^ 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.
  8. ^ Fischer, Janos; Ganellin, C. Robin (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 505. ISBN 9783527607495. Archived from the original on 8 September 2017.
  9. ^ Kane, Brigid M. (2008). HIV/AIDS Treatment Drugs. Infobase Publishing. p. 56. ISBN 9781438102078. Archived from the original on 8 September 2017.
  10. ^ a b World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  11. ^ "International Drug Price Indicator Guide". ERC. Archived from the original on 29 March 2019. Retrieved 20 November 2016.
  12. ^ "NADAC as of 2016-12-07 | Data.Medicaid.gov". Centers for Medicare and Medicaid Services. Archived from the original on 21 December 2016. Retrieved 12 December 2016.
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