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 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

913852800000
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
Health Status: unhealthy
Age Group: 27–39 years
Sex: M
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)
Health Status: unhealthy
Age Group: 38 years (range: 24–48 years)
Sex: M+F
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
Health Status: unhealthy
Age Group: > 13 years
Sex: M+F
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
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)
Health Status: unhealthy
Age Group: 38 years (range: 24–48 years)
Sex: M+F
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)
Health Status: unhealthy
Age Group: 38 years (range: 24–48 years)
Sex: M+F
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)
Health Status: unhealthy
Age Group: 38 years (range: 24–48 years)
Sex: M+F
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)
Health Status: unhealthy
Age Group: 38 years (range: 24–48 years)
Sex: M+F
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)
Health Status: unhealthy
Age Group: 38 years (range: 24–48 years)
Sex: M+F
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
PubMed

PubMed

TitleDatePubMed
Abacavir and mycophenolic acid, an inhibitor of inosine monophosphate dehydrogenase, have profound and synergistic anti-HIV activity.
1999 Aug 15
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
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
Amino acid deletion at codon 67 and Thr-to-Gly change at codon 69 of human immunodeficiency virus type 1 reverse transcriptase confer novel drug resistance profiles.
2001 Apr
[Determining resistance in HIV therapy. Careful interpretation only].
2001 Apr 2
[Observational study with abacavir. Decreased viral load and quality of life improves].
2001 Apr 2
Antiviral activity of tenofovir (PMPA) against nucleoside-resistant clinical HIV samples.
2001 Apr-Jul
Tenofovir, adefovir, and zidovudine susceptibilities of primary human immunodeficiency virus type 1 isolates with non-B subtypes or nucleoside resistance.
2001 Aug 10
Editorial comment: the challenge of prescribing abacavir.
2001 Dec
Understanding drug hypersensitivity: what to look for when prescribing abacavir.
2001 Dec
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
New developments in anti-HIV chemotherapy.
2001 Jan-Feb
The abacavir hypersensitivity reaction and interruptions in therapy.
2001 Jul 6
Phase III trials for new PI.
2001 Mar
Abacavir/lamivudine/zidovudine as a combined formulation tablet: bioequivalence compared with each component administered concurrently and the effect of food on absorption.
2001 Mar
Abacavir-lamivudine-zidovudine vs indinavir-lamivudine-zidovudine in antiretroviral-naive HIV-infected adults: A randomized equivalence trial.
2001 Mar 7
Influenza and human immunodeficiency virus infection: absence of HIV progression after acute influenza infection.
2001 May 1
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
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
Comparing different triple-drug combinations.
2001 Oct
Antiviral activity of cyclosaligenyl prodrugs of acyclovir, carbovir and abacavir.
2001 Sep
Transport characteristics of the anti-human immunodeficiency virus nucleoside analog, abacavir, into brain and cerebrospinal fluid.
2001 Sep
Mismatched double-stranded RNA (polyI-polyC(12)U) is synergistic with multiple anti-HIV drugs and is active against drug-sensitive and drug-resistant HIV-1 in vitro.
2001 Sep
[Acceptance of antiretroviral therapy. HIV-infected patients assess convenient triple combination].
2001 Sep 6
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
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
Kawasaki-like syndrome: abacavir hypersensitivity?
2002 Jan 1
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
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
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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