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Details

Stereochemistry ABSOLUTE
Molecular Formula C14H18N6O.ClH
Molecular Weight 322.7937
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ABACAVIR HYDROCHLORIDE

SMILES

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

InChI

InChIKey=QXNOPHSMRJNHHG-SCYNACPDSA-N
InChI=1S/C14H18N6O.ClH/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);1H/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

Molecular Formula ClH
Molecular Weight 36.4609
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
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
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
Editorial comment: the challenge of 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
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
Treatment intensification with abacavir in HIV-infected patients with at least 12 weeks previous lamivudine/zidovudine treatment.
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
Antiretroviral activity and safety of abacavir in combination with selected HIV-1 protease inhibitors in therapy-naive HIV-1-infected adults.
2001 Jun
Differential susceptibility of retroviruses to nucleoside analogues.
2001 Mar
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
Toxicity of antiviral nucleoside analogs and the human mitochondrial DNA polymerase.
2001 Nov 2
Lipodystrophy in HIV-1-positive patients is associated with insulin resistance in multiple metabolic pathways.
2001 Nov 9
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
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
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
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
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
Easier abacavir regimen has promising results.
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
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
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

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 Sat Jun 26 04:33:16 UTC 2021
Edited
by admin
on Sat Jun 26 04:33:16 UTC 2021
Record UNII
RP0T719KX7
Record Status Validated (UNII)
Record Version
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Name Type Language
ABACAVIR HYDROCHLORIDE
Common Name English
ABACAVIR HYDROCHLORIDE [WHO-DD]
Common Name English
2-CYCLOPENTENE-1-METHANOL, 4-(2-AMINO-6-(CYCLOPROPYLAMINO)-9H-PURIN-9-YL)-, HYDROCHLORIDE (1:1), (1S,4R)-
Systematic Name English
Code System Code Type Description
FDA UNII
RP0T719KX7
Created by admin on Sat Jun 26 04:33:16 UTC 2021 , Edited by admin on Sat Jun 26 04:33:16 UTC 2021
PRIMARY
CAS
216698-93-0
Created by admin on Sat Jun 26 04:33:16 UTC 2021 , Edited by admin on Sat Jun 26 04:33:16 UTC 2021
NON-SPECIFIC STOICHIOMETRY
CAS
136777-48-5
Created by admin on Sat Jun 26 04:33:16 UTC 2021 , Edited by admin on Sat Jun 26 04:33:16 UTC 2021
PRIMARY
PUBCHEM
67588134
Created by admin on Sat Jun 26 04:33:16 UTC 2021 , Edited by admin on Sat Jun 26 04:33:16 UTC 2021
PRIMARY
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