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Details

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

SHOW SMILES / InChI
Structure of ABACAVIR

SMILES

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

InChI

InChIKey=MCGSCOLBFJQGHM-SCZZXKLOSA-N
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

HIDE SMILES / InChI

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
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
Drifting agenda for federal treatment research.
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
New developments in anti-HIV chemotherapy.
2001 Nov
Anti-human immunodeficiency virus drugs are ineffective against Pneumocystis carinii in vitro and in vivo.
2001 Nov 15
Lipodystrophy in HIV-1-positive patients is associated with insulin resistance in multiple metabolic pathways.
2001 Nov 9
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
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
Pharmacokinetics of abacavir in HIV-1-infected patients with impaired renal function.
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
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
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 Mon Oct 21 19:51:30 UTC 2019
Edited
by admin
on Mon Oct 21 19:51:30 UTC 2019
Record UNII
WR2TIP26VS
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ABACAVIR
EMA EPAR   INN   MART.   MI   VANDF   WHO-DD  
INN  
Official Name English
ABACAVIR [INN]
Common Name English
ABACAVIR [MART.]
Common Name English
(-)-CIS-4-(2-AMINO-6-(CYCLOPROPYLAMINO)-9H-PURIN-9-YL)-2-CYCLOPENTENE-1-METHANOL
Systematic Name English
ABACAVIR [VANDF]
Common Name English
ABACAVIR [EMA EPAR]
Common Name English
2-CYCLOPENTENE-1-METHANOL, 4-(2-AMINO-6-(CYCLOPROPYLAMINO)-9H-PURIN-9-YL)-, (1S-CIS)-
Systematic Name English
ABACAVIR [MI]
Common Name English
AVACAVIR [VANDF]
Common Name English
ABACAVIR [WHO-DD]
Common Name English
(1S,4R)-4-(2-AMINO-6-(CYCLOPROPYLAMINO)-9H-PURIN-9-YL)-2-CYCLOPENTENE-1-METHANOL
Systematic Name English
Classification Tree Code System Code
WHO-ATC J05AF06
Created by admin on Mon Oct 21 19:51:30 UTC 2019 , Edited by admin on Mon Oct 21 19:51:30 UTC 2019
NCI_THESAURUS C97452
Created by admin on Mon Oct 21 19:51:30 UTC 2019 , Edited by admin on Mon Oct 21 19:51:30 UTC 2019
WHO-VATC QJ05AF06
Created by admin on Mon Oct 21 19:51:30 UTC 2019 , Edited by admin on Mon Oct 21 19:51:30 UTC 2019
WHO-VATC QJ05AR04
Created by admin on Mon Oct 21 19:51:30 UTC 2019 , Edited by admin on Mon Oct 21 19:51:30 UTC 2019
WHO-VATC QJ05AR02
Created by admin on Mon Oct 21 19:51:30 UTC 2019 , Edited by admin on Mon Oct 21 19:51:30 UTC 2019
WHO-ATC J05AR04
Created by admin on Mon Oct 21 19:51:30 UTC 2019 , Edited by admin on Mon Oct 21 19:51:30 UTC 2019
NDF-RT N0000175459
Created by admin on Mon Oct 21 19:51:30 UTC 2019 , Edited by admin on Mon Oct 21 19:51:30 UTC 2019
EMA ASSESSMENT REPORTS KIVEXA (AUHTORIZED: HIV INFECTIONS)
Created by admin on Mon Oct 21 19:51:30 UTC 2019 , Edited by admin on Mon Oct 21 19:51:30 UTC 2019
NDF-RT N0000175462
Created by admin on Mon Oct 21 19:51:30 UTC 2019 , Edited by admin on Mon Oct 21 19:51:30 UTC 2019
LIVERTOX 1
Created by admin on Mon Oct 21 19:51:30 UTC 2019 , Edited by admin on Mon Oct 21 19:51:30 UTC 2019
WHO-ESSENTIAL MEDICINES LIST 6.4.2.1
Created by admin on Mon Oct 21 19:51:30 UTC 2019 , Edited by admin on Mon Oct 21 19:51:30 UTC 2019
NDF-RT N0000175459
Created by admin on Mon Oct 21 19:51:30 UTC 2019 , Edited by admin on Mon Oct 21 19:51:30 UTC 2019
WHO-ATC J05AR02
Created by admin on Mon Oct 21 19:51:30 UTC 2019 , Edited by admin on Mon Oct 21 19:51:30 UTC 2019
NDF-RT N0000009947
Created by admin on Mon Oct 21 19:51:30 UTC 2019 , Edited by admin on Mon Oct 21 19:51:30 UTC 2019
NDF-RT N0000175459
Created by admin on Mon Oct 21 19:51:30 UTC 2019 , Edited by admin on Mon Oct 21 19:51:30 UTC 2019
WHO-ATC J05AR13
Created by admin on Mon Oct 21 19:51:30 UTC 2019 , Edited by admin on Mon Oct 21 19:51:30 UTC 2019
Code System Code Type Description
ChEMBL
CHEMBL1380
Created by admin on Mon Oct 21 19:51:30 UTC 2019 , Edited by admin on Mon Oct 21 19:51:30 UTC 2019
PRIMARY
DRUG BANK
DB01048
Created by admin on Mon Oct 21 19:51:30 UTC 2019 , Edited by admin on Mon Oct 21 19:51:30 UTC 2019
PRIMARY
INN
7544
Created by admin on Mon Oct 21 19:51:30 UTC 2019 , Edited by admin on Mon Oct 21 19:51:30 UTC 2019
PRIMARY
WIKIPEDIA
ABACAVIR
Created by admin on Mon Oct 21 19:51:30 UTC 2019 , Edited by admin on Mon Oct 21 19:51:30 UTC 2019
PRIMARY
EPA CompTox
136470-78-5
Created by admin on Mon Oct 21 19:51:30 UTC 2019 , Edited by admin on Mon Oct 21 19:51:30 UTC 2019
PRIMARY
EVMPD
SUB07356MIG
Created by admin on Mon Oct 21 19:51:30 UTC 2019 , Edited by admin on Mon Oct 21 19:51:30 UTC 2019
PRIMARY
PUBCHEM
441300
Created by admin on Mon Oct 21 19:51:30 UTC 2019 , Edited by admin on Mon Oct 21 19:51:30 UTC 2019
PRIMARY
RXCUI
190521
Created by admin on Mon Oct 21 19:51:30 UTC 2019 , Edited by admin on Mon Oct 21 19:51:30 UTC 2019
PRIMARY RxNorm
CAS
136470-78-5
Created by admin on Mon Oct 21 19:51:30 UTC 2019 , Edited by admin on Mon Oct 21 19:51:30 UTC 2019
PRIMARY
MERCK INDEX
M1271
Created by admin on Mon Oct 21 19:51:30 UTC 2019 , Edited by admin on Mon Oct 21 19:51:30 UTC 2019
PRIMARY Merck Index
NCI_THESAURUS
C61523
Created by admin on Mon Oct 21 19:51:30 UTC 2019 , Edited by admin on Mon Oct 21 19:51:30 UTC 2019
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
TRANSPORTER -> INHIBITOR
SALT/SOLVATE -> PARENT
BINDER->LIGAND
BINDING
Related Record Type Details
METABOLITE ACTIVE -> PRODRUG
SUBSTRATE
INTRACELLULAR
METABOLITE INACTIVE -> PARENT
MAJOR
URINE
METABOLITE INACTIVE -> PARENT
MAJOR
URINE
METABOLITE INACTIVE -> PARENT
83% of the original dose was eliminated in the urine, and 16% in the feces
MAJOR
FECAL; URINE
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC POPULATION
PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC TYPE
PHARMACOKINETIC
CSF/PLASMA RATIO PHARMACOKINETIC