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136470-78-5-Abacavir Abacavir

Abacavir

For research use only. Not for therapeutic Use.

  • CAT Number: I001404
  • CAS Number: 136470-78-5
  • Molecular Formula: C14H18N6O
  • Molecular Weight: 286.33
  • Purity: ≥95%
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Related Small Molecules: DSLET     2-Phenylglycine-d5     4-(Hydroxymethyl)piperidin-4-ol    
Research Areas: Antiviral     Infection Disease Research     Viral Entry    

Abacavir（Cat No.:I001404）is a nucleoside reverse transcriptase inhibitor (NRTI) used in combination antiretroviral therapy for the treatment of HIV-1 infections. It works by incorporating into viral DNA during reverse transcription, causing chain termination and inhibiting viral replication. Abacavir is known for its high efficacy and is commonly used in fixed-dose regimens. However, it requires genetic screening for HLA-B*5701 to minimize the risk of hypersensitivity reactions. Abacavir is extensively studied in HIV research for its pharmacokinetics, resistance mechanisms, and role in optimizing combination therapies to improve long-term patient outcomes.


Catalog Number I001404
CAS Number 136470-78-5
Synonyms

[(1S,4R)-4-[2-amino-6-(cyclopropylamino)purin-9-yl]cyclopent-2-en-1-yl]methanol

Molecular Formula C14H18N6O
Purity ≥95%
Target Cell Cycle/DNA Damage
Solubility DMSO: ≥ 3 mg/mL
Storage Store at -20°C
Overview of Clinical Research

Abacavir is a nucleoside reverse transcriptase inhibitor developed by GlaxoSmithKline. It is intended to treat HIV infection. 

IUPAC Name [(1S,4R)-4-[2-amino-6-(cyclopropylamino)purin-9-yl]cyclopent-2-en-1-yl]methanol
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
InChIKey MCGSCOLBFJQGHM-SCZZXKLOSA-N
SMILES C1CC1NC2=C3C(=NC(=N2)N)N(C=N3)[C@@H]4C[C@@H](C=C4)CO
Reference

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1:Abacavir Therapy and <i>HLA-B*57:01</i> Genotype. Dean L.In: Pratt V, McLeod H, Dean L, Malheiro A, Rubinstein W, editors. Medical Genetics Summaries [Internet]. Bethesda (MD): National Center for Biotechnology Information (US); 2012-.2015 Sep 1. PMID: 28520363 Free Books &amp; Documents<br />
2:Factors associated with pre-treatment HIV RNA: application for the use of abacavir and rilpivirine as the first-line regimen for HIV-infected patients in resource-limited settings. Kiertiburanakul S, Boettiger D, Ng OT, Van Kinh N, Merati TP, Avihingsanon A, Wong WW, Lee MP, Chaiwarith R, Kamarulzaman A, Kantipong P, Zhang F, Choi JY, Kumarasamy N, Ditangco R, Cuong DD, Oka S, Sim BLH, Ratanasuwan W, Ly PS, Yunihastuti E, Pujari S, Ross JL, Law M, Sungkanuparph S; TREAT Asia HIV Observational Databases (TAHOD)..AIDS Res Ther. 2017 May 5;14:27. doi: 10.1186/s12981-017-0151-1. eCollection 2017. PMID: 28484509 Free PMC Article<br />
3:Plasma and saliva concentrations of abacavir, tenofovir, darunavir, and raltegravir in HIV-1-infected patients
. Yamada E, Takagi R, Tanabe Y, Fujiwara H, Hasegawa N, Kato S.Int J Clin Pharmacol Ther. 2017 Apr 21. doi: 10.5414/CP202789. [Epub ahead of print] PMID: 28427498<br />
4:Response by gender of HIV-1-infected subjects treated with abacavir/lamivudine plus atazanavir, with or without ritonavir, for 144 weeks. Squires KE, Young B, Santiago L, Dretler RH, Walmsley SL, Zhao HH, Pakes GE, Ross LL, Shaefer MS.HIV AIDS (Auckl). 2017 Mar 3;9:51-61. doi: 10.2147/HIV.S108756. eCollection 2017. PMID: 28424561 Free PMC Article<br />
5:Bone density, microarchitecture and tissue quality following long-term treatment with tenofovir/emtricitabine or abacavir/lamivudine. G&uuml;erri-Fern&aacute;ndez R, Molina-Morant D, Villar-Garc&iacute;a J, Herrera S, Gonz&aacute;lez-Mena A, Guelar A, Trenchs-Rodr&iacute;guez M, D&iacute;ez-P&eacute;rez A, Knobel H.J Acquir Immune Defic Syndr. 2017 Apr 7. doi: 10.1097/QAI.0000000000001396. [Epub ahead of print] PMID: 28418990<br />
6:Dolutegravir/abacavir/lamivudine versus current ART in virally suppressed patients (STRIIVING): a 48-week, randomized, non-inferiority, open-label, Phase IIIb study. Trottier B, Lake JE, Logue K, Brinson C, Santiago L, Brennan C, Koteff JA, Wynne B, Hopking J, Granier C, Aboud M.Antivir Ther. 2017 Apr 12. doi: 10.3851/IMP3166. [Epub ahead of print] PMID: 28401876<br />
7:HLA-B*57:01 allele prevalence in HIV-infected North American subjects and the impact of allele testing on the incidence of abacavir-associated hypersensitivity reaction in HLA-B*57:01-negative subjects. Small CB, Margolis DA, Shaefer MS, Ross LL.BMC Infect Dis. 2017 Apr 11;17(1):256. doi: 10.1186/s12879-017-2331-y. PMID: 28399804 Free PMC Article<br />
8:High Prevalence of Abacavir-Associated L74V/I Mutations in Kenyan Children Failing Antiretroviral Therapy. Dziuban EJ, DeVos J, Ngeno B, Ngugi E, Zhang G, Sabatier J, Wagar N, Diallo K, Nganga L, Katana A, Yang C, Rivadeneira ED, Mukui I, Odhiambo F, Redfield R, Raizes E.Pediatr Infect Dis J. 2017 Apr 5. doi: 10.1097/INF.0000000000001597. [Epub ahead of print] PMID: 28383390<br />
9:[Biliary and kidney lithiasis during treatment with daclatasvir/sofosbuvir/ribavirin and atazanavir/ritonavir + abacavir/lamivudine in an HIV/HCV genotype 4-infected patient: a case report.] Vavassori A, Lanza P, Izzo I, Casari S, Odolini S, Zaltron S, Festa E, Castelli F.Recenti Prog Med. 2017 Feb;108(2):98-100. doi: 10.1701/2636.27101. Italian. PMID: 28287204<br />
10:Abacavir induces platelet-endothelium interactions by interfering with purinergic signalling: A step from inflammation to thrombosis. Alvarez A, Rios-Navarro C, Blanch-Ruiz MA, Collado-Diaz V, Andujar I, Martinez-Cuesta MA, Orden S, Esplugues JV.Antiviral Res. 2017 May;141:179-185. doi: 10.1016/j.antiviral.2017.03.001. Epub 2017 Mar 2. PMID: 28263802

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