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Details

Stereochemistry ABSOLUTE
Molecular Formula C14H18N6O.C4H6O4
Molecular Weight 404.4204
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ABACAVIR SUCCINATE

SMILES

OC(=O)CCC(O)=O.NC1=NC2=C(N=CN2[C@@H]3C[C@H](CO)C=C3)C(NC4CC4)=N1

InChI

InChIKey=BOONDNCXQPMXQT-SCYNACPDSA-N
InChI=1S/C14H18N6O.C4H6O4/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;5-3(6)1-2-4(7)8/h1,4,7-10,21H,2-3,5-6H2,(H3,15,17,18,19);1-2H2,(H,5,6)(H,7,8)/t8-,10+;/m1./s1

HIDE SMILES / InChI

Molecular Formula C4H6O4
Molecular Weight 118.088
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C14H18N6O
Molecular Weight 286.3323
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Abacavir is a nucleoside reverse transcriptase inhibitor used for treatment of HIV infection (either alone or in combination with other antiviral drugs). It was shown that abacavir exerts its antiviral activity through its active metabolite, carbovir triphosphate. Carbovir triphosphate is a guanine analogue and a potent and selective inhibitor of viral reverse transcriptases. Upon administration, abacavir is first converted to abacavir monophosphate by ADK, then the monophosphate is deaminated to carbovir monophosphate, which is then anabolized by cellular kinases to carbovir diphosphate and then finally to carbovir triphosphate. Abacavir causes hypersensitivity reaction in patients with HLA-B*57:01 allele.

CNS Activity

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
21.0 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
ZIAGEN
PubMed

PubMed

TitleDatePubMed
Mutational patterns in the HIV genome and cross-resistance following nucleoside and nucleotide analogue drug exposure.
2001
Antiviral activity of tenofovir (PMPA) against nucleoside-resistant clinical HIV samples.
2001 Apr-Jul
Strategies for treating HIV-related lipodystrophy.
2001 Aug
Editorial comment: the challenge of prescribing abacavir.
2001 Dec
Understanding drug hypersensitivity: what to look for when prescribing abacavir.
2001 Dec
Agranulocytosis and fever seven weeks after starting abacavir.
2001 Dec 7
Prednisolone does not prevent hypersensitivity reactions in antiretroviral drug regimens containing abacavir with or without nevirapine.
2001 Dec 7
Intensification of stable background therapy with abacavir in antiretroviral therapy experienced patients: 48-week data from a randomized, double-blind trial.
2001 Jan
Resistance and cross-resistance to abacavir.
2001 Jul
Resistant to everything.
2001 May
Differential human immunodeficiency virus-suppressive activity of reverse transcription inhibitors in resting and activated peripheral blood lymphocytes: implications for therapy.
2001 May-Jun
The role of NNRTIs in antiretroviral combination therapy: an introduction.
2001 Nov
Anti-human immunodeficiency virus drugs are ineffective against Pneumocystis carinii in vitro and in vivo.
2001 Nov 15
Abacavir sulfate, lamivudine, and zidovudine (Trizivir).
2001 Nov-Dec
Hypersensitivity reactions during therapy with the nucleoside reverse transcriptase inhibitor abacavir.
2001 Oct
Hypersensitivity related to abacavir in two members of a family.
2001 Oct
Methadone blood concentrations are decreased by the administration of abacavir plus amprenavir.
2001 Oct
Comparing different triple-drug combinations.
2001 Oct
Penetration of the nucleoside analogue abacavir into the genital tract of men infected with human immunodeficiency virus type 1.
2001 Oct 15
Prevalence of adverse events associated with potent antiretroviral treatment: Swiss HIV Cohort Study.
2001 Oct 20
High-performance liquid chromatographic assay for abacavir and its two major metabolites in human urine and cerebrospinal fluid.
2001 Oct 25
Improvement of HAART-associated insulin resistance and dyslipidemia after replacement of protease inhibitors with abacavir.
2001 Oct 29
Antiviral activity of cyclosaligenyl prodrugs of acyclovir, carbovir and abacavir.
2001 Sep
Genotypic resistance mutations to antiretroviral drugs in HIV-1 B and non-B subtypes from Cuba.
2001 Sep
HIV protease inhibitor substitution in patients with lipodystrophy: a randomized, controlled, open-label, multicentre study.
2001 Sep 28
[Acceptance of antiretroviral therapy. HIV-infected patients assess convenient triple combination].
2001 Sep 6
Triple nuke therapy--results after one year.
2001 Winter
Tenofovir exhibits low cytotoxicity in various human cell types: comparison with other nucleoside reverse transcriptase inhibitors.
2002 Apr
Broad nucleoside-analogue resistance implications for human immunodeficiency virus type 1 reverse-transcriptase mutations at codons 44 and 118.
2002 Apr 1
Abacavir hypersensitivity reaction.
2002 Apr 15
Efficacy of highly active antiretroviral therapy in HIV-1 infected children.
2002 Feb
Role of sequencing in therapy selection.
2002 Feb 1
HIV-1 genotype and phenotype correlate with virological response to abacavir, amprenavir and efavirenz in treatment-experienced patients.
2002 Feb 15
Abacavir expanded access program for adult patients infected with human immunodeficiency virus type 1.
2002 Feb 15
Response to lamivudine-zidovudine plus abacavir twice daily in antiretroviral-naive, incarcerated patients with HIV infection taking directly observed treatment.
2002 Feb 15
Easier abacavir regimen has promising results.
2002 Jan
Vertigo and abacavir.
2002 Jan
Antiretroviral rounds. A very discordant response.
2002 Jan
Combined effect of zidovudine (ZDV), lamivudine (3TC) and abacavir (ABC) antiretroviral therapy in suppressing in vitro FIV replication.
2002 Jan
Dioxolane guanosine, the active form of the prodrug diaminopurine dioxolane, is a potent inhibitor of drug-resistant HIV-1 isolates from patients for whom standard nucleoside therapy fails.
2002 Jan 1
Kawasaki-like syndrome: abacavir hypersensitivity?
2002 Jan 1
Evidence of immune reconstitution in antiretroviral drug-experienced patients with advanced HIV disease.
2002 Jan 20
Case series assessing the safety of mycophenolate as part of multidrug rescue treatment regimens.
2002 Jan-Feb
Novel use of a guanosine prodrug approach to convert 2',3'-didehydro-2',3'-dideoxyguanosine into a viable antiviral agent.
2002 Mar
Assessment of mitochondrial toxicity in human cells treated with tenofovir: comparison with other nucleoside reverse transcriptase inhibitors.
2002 Mar
Comparison of dual nucleoside-analogue reverse-transcriptase inhibitor regimens with and without nelfinavir in children with HIV-1 who have not previously been treated: the PENTA 5 randomised trial.
2002 Mar 2
Association between presence of HLA-B*5701, HLA-DR7, and HLA-DQ3 and hypersensitivity to HIV-1 reverse-transcriptase inhibitor abacavir.
2002 Mar 2
Individualising HIV treatment--pharmacogenetics and immunogenetics.
2002 Mar 2
[Mutations of resistance of HIV-1 in previously untreated patients at penitentiary centers of the Autonomous Community of Valencia, Spain. REPRICOVA study].
2002 Mar 2
Parallel decline of CD8+/CD38++ T cells and viraemia in response to quadruple highly active antiretroviral therapy in primary HIV infection.
2002 Mar 8
Patents

Sample Use Guides

In Vivo Use Guide
Adults: 600 mg daily, administered as either 300 mg twice daily or 600 mg once daily. Pediatric Patients Aged 3 Months and Older: Administered either once or twice daily. Dose should be calculated on body weight (kg) and should not exceed 600 mg daily.
Route of Administration: Oral
In Vitro Use Guide
In order to study the inhibitory effect of abacavir on HIV strains, MT-2 cell line was infected with HIV-1 strain IIIB and was treated with increasing concentrations of the drug (up to 100 uM).
Substance Class Chemical
Created
by admin
on Tue Oct 22 00:10:14 UTC 2019
Edited
by admin
on Tue Oct 22 00:10:14 UTC 2019
Record UNII
40FH6D8CHK
Record Status Validated (UNII)
Record Version
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Name Type Language
ABACAVIR SUCCINATE
MART.   USAN   WHO-DD  
USAN  
Official Name English
2-CYCLOPENTENE-1-METHANOL, 4-(2-AMINO-6-(CYCLOPROPYLAMINO)-9H-PURIN-9-YL)-, (1S-CIS)-, BUTANEDIOATE (1:1) (SALT)
Common Name English
ABACAVIR SUCCINATE [WHO-DD]
Common Name English
(1S,4R)-4-(2-AMINO-6(CYCLOPROPYLAMINO)-9H-PURIN-9-YL)-2-CYCLOPENTENE-1-METHANOL SUCCINATE(1:1) (SALT)
Common Name English
ABACAVIR SUCCINATE [USAN]
Common Name English
ABACAVIR SUCCINATE [MART.]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C97452
Created by admin on Tue Oct 22 00:10:14 UTC 2019 , Edited by admin on Tue Oct 22 00:10:14 UTC 2019
Code System Code Type Description
PUBCHEM
9822500
Created by admin on Tue Oct 22 00:10:14 UTC 2019 , Edited by admin on Tue Oct 22 00:10:14 UTC 2019
PRIMARY
NCI_THESAURUS
C71608
Created by admin on Tue Oct 22 00:10:14 UTC 2019 , Edited by admin on Tue Oct 22 00:10:14 UTC 2019
PRIMARY
EVMPD
SUB25392
Created by admin on Tue Oct 22 00:10:14 UTC 2019 , Edited by admin on Tue Oct 22 00:10:14 UTC 2019
PRIMARY
CAS
168146-84-7
Created by admin on Tue Oct 22 00:10:14 UTC 2019 , Edited by admin on Tue Oct 22 00:10:14 UTC 2019
PRIMARY
ChEMBL
CHEMBL1380
Created by admin on Tue Oct 22 00:10:14 UTC 2019 , Edited by admin on Tue Oct 22 00:10:14 UTC 2019
PRIMARY
MESH
C106538
Created by admin on Tue Oct 22 00:10:14 UTC 2019 , Edited by admin on Tue Oct 22 00:10:14 UTC 2019
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY