U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C14H18N6O
Molecular Weight 286.3329
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ABACAVIR

SMILES

C1=C[C@@]([H])(C[C@]1([H])CO)n2cnc3c(NC4CC4)[nH]c(=N)nc32

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 286.3329
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
21.0 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
ZIAGEN

Approved Use

ZIAGEN, a nucleoside analogue human immunodeficiency virus (HIV-1) reverse transcriptase inhibitor, is indicated in combination with other antiretroviral agents for the treatment of HIV-1 infection.

Launch Date

9.1385279E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
3 μg/mL
300 mg 2 times / day steady-state, oral
dose: 300 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
ABACAVIR SULFATE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
4.26 μg/mL
600 mg single, oral
dose: 600 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ABACAVIR SULFATE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
6.02 μg × h/mL
300 mg 2 times / day steady-state, oral
dose: 300 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
ABACAVIR SULFATE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
11.95 μg × h/mL
600 mg single, oral
dose: 600 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ABACAVIR SULFATE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
1.54 h
600 mg single, oral
dose: 600 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ABACAVIR SULFATE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
50%
300 mg 2 times / day steady-state, oral
dose: 300 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
ABACAVIR SULFATE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
150 mg single, intravenous
Dose: 150 mg
Route: intravenous
Route: single
Dose: 150 mg
Sources:
unhealthy, 27–39 years
n = 6
Health Status: unhealthy
Condition: HIV-1-infection
Age Group: 27–39 years
Sex: M
Population Size: 6
Sources:
1200 mg single, oral
Highest studied dose
Dose: 1200 mg
Route: oral
Route: single
Dose: 1200 mg
Sources:
unhealthy, 38 years (range: 24–48 years)
n = 12
Health Status: unhealthy
Condition: HIV-1-infection
Age Group: 38 years (range: 24–48 years)
Sex: M+F
Population Size: 12
Sources:
Other AEs: Asthenia, Abdominal pain...
Other AEs:
Asthenia (33%)
Abdominal pain (33%)
Headache (25%)
Diarrhea (17%)
Dyspepsia (17%)
Sources:
600 mg 3 times / day steady, oral
Highest studied dose
Dose: 600 mg, 3 times / day
Route: oral
Route: steady
Dose: 600 mg, 3 times / day
Sources:
unhealthy, > 13 years
n = 20
Health Status: unhealthy
Condition: HIV-1-infection
Age Group: > 13 years
Sex: M+F
Population Size: 20
Sources:
600 mg 1 times / day steady, oral
Recommended
Dose: 600 mg, 1 times / day
Route: oral
Route: steady
Dose: 600 mg, 1 times / day
Sources:
unhealthy
n = 2670
Health Status: unhealthy
Condition: HIV infection
Population Size: 2670
Sources:
Other AEs: Hypersensitivity reaction...
Other AEs:
Hypersensitivity reaction (serious|grade 5, 8%)
Sources:
AEs

AEs

AESignificanceDosePopulation
Diarrhea 17%
1200 mg single, oral
Highest studied dose
Dose: 1200 mg
Route: oral
Route: single
Dose: 1200 mg
Sources:
unhealthy, 38 years (range: 24–48 years)
n = 12
Health Status: unhealthy
Condition: HIV-1-infection
Age Group: 38 years (range: 24–48 years)
Sex: M+F
Population Size: 12
Sources:
Dyspepsia 17%
1200 mg single, oral
Highest studied dose
Dose: 1200 mg
Route: oral
Route: single
Dose: 1200 mg
Sources:
unhealthy, 38 years (range: 24–48 years)
n = 12
Health Status: unhealthy
Condition: HIV-1-infection
Age Group: 38 years (range: 24–48 years)
Sex: M+F
Population Size: 12
Sources:
Headache 25%
1200 mg single, oral
Highest studied dose
Dose: 1200 mg
Route: oral
Route: single
Dose: 1200 mg
Sources:
unhealthy, 38 years (range: 24–48 years)
n = 12
Health Status: unhealthy
Condition: HIV-1-infection
Age Group: 38 years (range: 24–48 years)
Sex: M+F
Population Size: 12
Sources:
Abdominal pain 33%
1200 mg single, oral
Highest studied dose
Dose: 1200 mg
Route: oral
Route: single
Dose: 1200 mg
Sources:
unhealthy, 38 years (range: 24–48 years)
n = 12
Health Status: unhealthy
Condition: HIV-1-infection
Age Group: 38 years (range: 24–48 years)
Sex: M+F
Population Size: 12
Sources:
Asthenia 33%
1200 mg single, oral
Highest studied dose
Dose: 1200 mg
Route: oral
Route: single
Dose: 1200 mg
Sources:
unhealthy, 38 years (range: 24–48 years)
n = 12
Health Status: unhealthy
Condition: HIV-1-infection
Age Group: 38 years (range: 24–48 years)
Sex: M+F
Population Size: 12
Sources:
Hypersensitivity reaction serious|grade 5, 8%
600 mg 1 times / day steady, oral
Recommended
Dose: 600 mg, 1 times / day
Route: oral
Route: steady
Dose: 600 mg, 1 times / day
Sources:
unhealthy
n = 2670
Health Status: unhealthy
Condition: HIV infection
Population Size: 2670
Sources:
PubMed

PubMed

TitleDatePubMed
Hydroxyurea-induced neurotoxicity in HIV disease.
1999 Aug 20
A novel genotype encoding a single amino acid insertion and five other substitutions between residues 64 and 74 of the HIV-1 reverse transcriptase confers high-level cross-resistance to nucleoside reverse transcriptase inhibitors. Abacavir CNA2007 International Study Group.
1999 Oct 1
Prevalence and characteristics of multinucleoside-resistant human immunodeficiency virus type 1 among European patients receiving combinations of nucleoside analogues.
2000 Aug
Mutational patterns in the HIV genome and cross-resistance following nucleoside and nucleotide analogue drug exposure.
2001
A comparison of the steady-state pharmacokinetics and safety of abacavir, lamivudine, and zidovudine taken as a triple combination tablet and as abacavir plus a lamivudine-zidovudine double combination tablet by HIV-1-infected adults.
2001 Apr
An open-label randomized trial to evaluate different therapeutic strategies of combination therapy in HIV-1 infection: design, rationale, and methods of the initio trial.
2001 Apr
HIV-1 reverse transcriptase sequence in plasma and cerebrospinal fluid of patients with AIDS dementia complex treated with Abacavir.
2001 Apr 13
A pilot study of the use of mycophenolate mofetil as a component of therapy for multidrug-resistant HIV-1 infection.
2001 Apr 15
[Observational study with abacavir. Decreased viral load and quality of life improves].
2001 Apr 2
Simultaneous determination of Ziagen and its phosphorylated metabolites by ion-pairing high-performance liquid chromatography-tandem mass spectrometry.
2001 Apr 25
Antiviral drugs: current state of the art.
2001 Aug
Tenofovir, adefovir, and zidovudine susceptibilities of primary human immunodeficiency virus type 1 isolates with non-B subtypes or nucleoside resistance.
2001 Aug 10
Simplification with abacavir-based triple nucleoside therapy versus continued protease inhibitor-based highly active antiretroviral therapy in HIV-1-infected patients with undetectable plasma HIV-1 RNA.
2001 Aug 17
Prednisolone does not prevent hypersensitivity reactions in antiretroviral drug regimens containing abacavir with or without nevirapine.
2001 Dec 7
Twice-daily triple nucleoside intensification treatment with lamivudine-zidovudine plus abacavir sustains suppression of human immunodeficiency virus type 1: results of the TARGET Study.
2001 Feb 15
Intensification of stable background therapy with abacavir in antiretroviral therapy experienced patients: 48-week data from a randomized, double-blind trial.
2001 Jan
A randomized, double-blind study of triple nucleoside therapy of abacavir, lamivudine, and zidovudine versus lamivudine and zidovudine in previously treated human immunodeficiency virus type 1-infected children. The CNAA3006 Study Team.
2001 Jan
Patterns of resistance mutations to antiretroviral drugs in extensively treated HIV-1-infected patients with failure of highly active antiretroviral therapy.
2001 Jan 1
Severe anaphylactic shock after rechallenge with abacavir without preceding hypersensitivity.
2001 Jan 26
Resistance and cross-resistance to abacavir.
2001 Jul
A dose-ranging study to evaluate the antiretroviral activity and safety of amprenavir alone and in combination with abacavir in HIV-infected adults with limited antiretroviral experience.
2001 Jun
Increased drug susceptibility of HIV-1 reverse transcriptase mutants containing M184V and zidovudine-associated mutations: analysis of enzyme processivity, chain-terminator removal and viral replication.
2001 Jun
Resistant to everything.
2001 May
Choosing which nuke to use first.
2001 May
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
Lipodystrophy in HIV-1-positive patients is associated with insulin resistance in multiple metabolic pathways.
2001 Nov 9
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
Transport characteristics of the anti-human immunodeficiency virus nucleoside analog, abacavir, into brain and cerebrospinal fluid.
2001 Sep
Comparison of genotypic and phenotypic resistance patterns of human immunodeficiency virus type 1 isolates from patients treated with stavudine and didanosine or zidovudine and lamivudine.
2001 Sep 15
[Acceptance of antiretroviral therapy. HIV-infected patients assess convenient triple combination].
2001 Sep 6
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
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
Combined effect of zidovudine (ZDV), lamivudine (3TC) and abacavir (ABC) antiretroviral therapy in suppressing in vitro FIV replication.
2002 Jan
Kawasaki-like syndrome: abacavir hypersensitivity?
2002 Jan 1
Evidence of immune reconstitution in antiretroviral drug-experienced patients with advanced HIV disease.
2002 Jan 20
Patents

Sample Use Guides

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 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 Fri Jun 25 21:54:11 UTC 2021
Edited
by admin
on Fri Jun 25 21:54:11 UTC 2021
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
NSC-742406
Code 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 Fri Jun 25 21:54:11 UTC 2021 , Edited by admin on Fri Jun 25 21:54:11 UTC 2021
NCI_THESAURUS C97452
Created by admin on Fri Jun 25 21:54:11 UTC 2021 , Edited by admin on Fri Jun 25 21:54:11 UTC 2021
WHO-VATC QJ05AF06
Created by admin on Fri Jun 25 21:54:11 UTC 2021 , Edited by admin on Fri Jun 25 21:54:11 UTC 2021
WHO-VATC QJ05AR04
Created by admin on Fri Jun 25 21:54:11 UTC 2021 , Edited by admin on Fri Jun 25 21:54:11 UTC 2021
WHO-VATC QJ05AR02
Created by admin on Fri Jun 25 21:54:11 UTC 2021 , Edited by admin on Fri Jun 25 21:54:11 UTC 2021
WHO-ATC J05AR04
Created by admin on Fri Jun 25 21:54:11 UTC 2021 , Edited by admin on Fri Jun 25 21:54:11 UTC 2021
NDF-RT N0000175459
Created by admin on Fri Jun 25 21:54:11 UTC 2021 , Edited by admin on Fri Jun 25 21:54:11 UTC 2021
EMA ASSESSMENT REPORTS KIVEXA (AUHTORIZED: HIV INFECTIONS)
Created by admin on Fri Jun 25 21:54:11 UTC 2021 , Edited by admin on Fri Jun 25 21:54:11 UTC 2021
NDF-RT N0000175462
Created by admin on Fri Jun 25 21:54:11 UTC 2021 , Edited by admin on Fri Jun 25 21:54:11 UTC 2021
LIVERTOX NBK548225
Created by admin on Fri Jun 25 21:54:11 UTC 2021 , Edited by admin on Fri Jun 25 21:54:11 UTC 2021
WHO-ESSENTIAL MEDICINES LIST 6.4.2.1
Created by admin on Fri Jun 25 21:54:11 UTC 2021 , Edited by admin on Fri Jun 25 21:54:11 UTC 2021
NDF-RT N0000175459
Created by admin on Fri Jun 25 21:54:11 UTC 2021 , Edited by admin on Fri Jun 25 21:54:11 UTC 2021
WHO-ATC J05AR02
Created by admin on Fri Jun 25 21:54:11 UTC 2021 , Edited by admin on Fri Jun 25 21:54:11 UTC 2021
NDF-RT N0000009947
Created by admin on Fri Jun 25 21:54:11 UTC 2021 , Edited by admin on Fri Jun 25 21:54:11 UTC 2021
NDF-RT N0000175459
Created by admin on Fri Jun 25 21:54:11 UTC 2021 , Edited by admin on Fri Jun 25 21:54:11 UTC 2021
WHO-ATC J05AR13
Created by admin on Fri Jun 25 21:54:11 UTC 2021 , Edited by admin on Fri Jun 25 21:54:11 UTC 2021
Code System Code Type Description
ChEMBL
CHEMBL1380
Created by admin on Fri Jun 25 21:54:11 UTC 2021 , Edited by admin on Fri Jun 25 21:54:11 UTC 2021
PRIMARY
DRUG BANK
DB01048
Created by admin on Fri Jun 25 21:54:11 UTC 2021 , Edited by admin on Fri Jun 25 21:54:11 UTC 2021
PRIMARY
FDA UNII
WR2TIP26VS
Created by admin on Fri Jun 25 21:54:11 UTC 2021 , Edited by admin on Fri Jun 25 21:54:11 UTC 2021
PRIMARY
DRUG CENTRAL
34
Created by admin on Fri Jun 25 21:54:11 UTC 2021 , Edited by admin on Fri Jun 25 21:54:11 UTC 2021
PRIMARY
LACTMED
Abacavir
Created by admin on Fri Jun 25 21:54:11 UTC 2021 , Edited by admin on Fri Jun 25 21:54:11 UTC 2021
PRIMARY
INN
7544
Created by admin on Fri Jun 25 21:54:11 UTC 2021 , Edited by admin on Fri Jun 25 21:54:11 UTC 2021
PRIMARY
WIKIPEDIA
ABACAVIR
Created by admin on Fri Jun 25 21:54:11 UTC 2021 , Edited by admin on Fri Jun 25 21:54:11 UTC 2021
PRIMARY
EPA CompTox
136470-78-5
Created by admin on Fri Jun 25 21:54:11 UTC 2021 , Edited by admin on Fri Jun 25 21:54:11 UTC 2021
PRIMARY
EVMPD
SUB07356MIG
Created by admin on Fri Jun 25 21:54:11 UTC 2021 , Edited by admin on Fri Jun 25 21:54:11 UTC 2021
PRIMARY
PUBCHEM
441300
Created by admin on Fri Jun 25 21:54:11 UTC 2021 , Edited by admin on Fri Jun 25 21:54:11 UTC 2021
PRIMARY
RXCUI
190521
Created by admin on Fri Jun 25 21:54:11 UTC 2021 , Edited by admin on Fri Jun 25 21:54:11 UTC 2021
PRIMARY RxNorm
CAS
136470-78-5
Created by admin on Fri Jun 25 21:54:11 UTC 2021 , Edited by admin on Fri Jun 25 21:54:11 UTC 2021
PRIMARY
MERCK INDEX
M1271
Created by admin on Fri Jun 25 21:54:11 UTC 2021 , Edited by admin on Fri Jun 25 21:54:11 UTC 2021
PRIMARY Merck Index
NCI_THESAURUS
C61523
Created by admin on Fri Jun 25 21:54:11 UTC 2021 , Edited by admin on Fri Jun 25 21:54:11 UTC 2021
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
BREAST MILK/PLASMA RATIO PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC POPULATION
PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC TYPE
PHARMACOKINETIC
CSF/PLASMA RATIO PHARMACOKINETIC