ABACAVIR

Details

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

SHOW SMILES / InChI

Structure Search

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	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24625462 | https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020977s032,020978s035lbl.pdf

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

Primary Target	Pharmacology	Condition	Potency
Human immunodeficiency virus type 1 reverse transcriptase 70 Target ID: CHEMBL247 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24625462	Inhibitor 8504		21.0 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
HIV-1 infection 156 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020977s032,020978s035lbl.pdf	Primary		Approved 8583	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 1998

C_max

Value	Dose	Co-administered	Analyte	Population
3 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020977s033s034,020978s036s037lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020977s033s034,020978s036s037lbl.pdf	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

Value	Dose	Co-administered	Analyte	Population
6.02 μg × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020977s033s034,020978s036s037lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020977s033s034,020978s036s037lbl.pdf	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
1.54 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020977s033s034,020978s036s037lbl.pdf	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

F_unbound

Value	Dose	Co-administered	Analyte	Population
50% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020977s033s034,020978s036s037lbl.pdf	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

Dose	Population	Adverse events
150 mg single, intravenous Dose: 150 mg Route: intravenous Route: single Dose: 150 mg Sources: https://pubmed.ncbi.nlm.nih.gov/10453964	unhealthy, 27–39 years Health Status: unhealthy Age Group: 27–39 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/10453964	Sources: https://pubmed.ncbi.nlm.nih.gov/10453964
1200 mg single, oral Highest studied dose Dose: 1200 mg Route: oral Route: single Dose: 1200 mg Sources: https://pubmed.ncbi.nlm.nih.gov/10049274	unhealthy, 38 years (range: 24–48 years) Health Status: unhealthy Age Group: 38 years (range: 24–48 years) Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/10049274	Other AEs: Asthenia, Abdominal pain... Other AEs: Asthenia (33%) Abdominal pain (33%) Headache (25%) Diarrhea (17%) Dyspepsia (17%) Sources: https://pubmed.ncbi.nlm.nih.gov/10049274
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: https://pubmed.ncbi.nlm.nih.gov/10898676	unhealthy, > 13 years Health Status: unhealthy Age Group: > 13 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/10898676	Sources: https://pubmed.ncbi.nlm.nih.gov/10898676
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/201107Orig1s000lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/201107Orig1s000lbl.pdf	Other AEs: Hypersensitivity reaction... Other AEs: Hypersensitivity reaction (serious\|grade 5, 8%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/201107Orig1s000lbl.pdf

AEs

AE	Significance	Dose	Population
Diarrhea	17%	1200 mg single, oral Highest studied dose Dose: 1200 mg Route: oral Route: single Dose: 1200 mg Sources: https://pubmed.ncbi.nlm.nih.gov/10049274	unhealthy, 38 years (range: 24–48 years) Health Status: unhealthy Age Group: 38 years (range: 24–48 years) Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/10049274
Dyspepsia	17%	1200 mg single, oral Highest studied dose Dose: 1200 mg Route: oral Route: single Dose: 1200 mg Sources: https://pubmed.ncbi.nlm.nih.gov/10049274	unhealthy, 38 years (range: 24–48 years) Health Status: unhealthy Age Group: 38 years (range: 24–48 years) Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/10049274
Headache	25%	1200 mg single, oral Highest studied dose Dose: 1200 mg Route: oral Route: single Dose: 1200 mg Sources: https://pubmed.ncbi.nlm.nih.gov/10049274	unhealthy, 38 years (range: 24–48 years) Health Status: unhealthy Age Group: 38 years (range: 24–48 years) Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/10049274
Abdominal pain	33%	1200 mg single, oral Highest studied dose Dose: 1200 mg Route: oral Route: single Dose: 1200 mg Sources: https://pubmed.ncbi.nlm.nih.gov/10049274	unhealthy, 38 years (range: 24–48 years) Health Status: unhealthy Age Group: 38 years (range: 24–48 years) Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/10049274
Asthenia	33%	1200 mg single, oral Highest studied dose Dose: 1200 mg Route: oral Route: single Dose: 1200 mg Sources: https://pubmed.ncbi.nlm.nih.gov/10049274	unhealthy, 38 years (range: 24–48 years) Health Status: unhealthy Age Group: 38 years (range: 24–48 years) Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/10049274
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/201107Orig1s000lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/201107Orig1s000lbl.pdf

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252	inhibitor 2438	inhibitor 2507

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
P-gp 1741 MRP1 116 MRP2 499 MRP3 246 BCRP 910 OCT1 620	ADH 7 UGT 219 P-gp 2052 BCRP 697

Drug as perpetrator

Target	Modality	Activity
P-gp 1932	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/24273637/	no [IC50 >500 uM]
CYP2C9 2497	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/20-977_ZIAGEN_biopharmr.pdf#page=5 Page: 5.0	no
CYP2D6 2546	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/20-977_ZIAGEN_biopharmr.pdf#page=5 Page: 5.0	no
CYP3A4 2633	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/20-977_ZIAGEN_biopharmr.pdf#page=5 Page: 5.0	no
MRP3 326	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/17172311/	no
BCRP 985	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/17202245/	weak [IC50 385 uM]
MRP1 232	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/17172311/	yes
MRP2 625	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/17172311/	yes
OCT1 656	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/27445813/	yes

Drug as victim

Target	Modality	Activity
ADH 7	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/20-977_ZIAGEN_pharmr_P1.pdf#page=3 Page: 3.0	yes
BCRP 697	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/28696229/	yes
P-gp 2052	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/24273637/	yes
UGT 219	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/20-977_ZIAGEN_pharmr_P1.pdf#page=3 Page: 3.0	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:421707	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:421707
ChemicalBook	CB5698138	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB5698138
eMolecules	30512521	https://www.emolecules.com/cgi-bin/more?vid=30512521
MolPort	MolPort-006-069-118	https://www.molport.com/shop/molecule-link/MolPort-006-069-118
ZINC	ZINC000002015928	http://zinc15.docking.org/substances/ZINC000002015928

PubMed

Title	Date	PubMed
Abacavir hypersensitivity reaction.	2002-04-15	11915004
Broad nucleoside-analogue resistance implications for human immunodeficiency virus type 1 reverse-transcriptase mutations at codons 44 and 118.	2002-04-01	11920313
Tenofovir exhibits low cytotoxicity in various human cell types: comparison with other nucleoside reverse transcriptase inhibitors.	2002-04	11888656
Parallel decline of CD8+/CD38++ T cells and viraemia in response to quadruple highly active antiretroviral therapy in primary HIV infection.	2002-03-08	11873002
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.	2002-03-02	11888583
Association between presence of HLA-B*5701, HLA-DR7, and HLA-DQ3 and hypersensitivity to HIV-1 reverse-transcriptase inhibitor abacavir.	2002-03-02	11888582
Individualising HIV treatment--pharmacogenetics and immunogenetics.	2002-03-02	11888578
[Mutations of resistance of HIV-1 in previously untreated patients at penitentiary centers of the Autonomous Community of Valencia, Spain. REPRICOVA study].	2002-03-02	11882275
Novel use of a guanosine prodrug approach to convert 2',3'-didehydro-2',3'-dideoxyguanosine into a viable antiviral agent.	2002-03	11850281
Assessment of mitochondrial toxicity in human cells treated with tenofovir: comparison with other nucleoside reverse transcriptase inhibitors.	2002-03	11850253
HIV-1 genotype and phenotype correlate with virological response to abacavir, amprenavir and efavirenz in treatment-experienced patients.	2002-02-15	11834950
Abacavir expanded access program for adult patients infected with human immunodeficiency virus type 1.	2002-02-15	11797183
Response to lamivudine-zidovudine plus abacavir twice daily in antiretroviral-naive, incarcerated patients with HIV infection taking directly observed treatment.	2002-02-15	11797179
Role of sequencing in therapy selection.	2002-02-01	11832698
Efficacy of highly active antiretroviral therapy in HIV-1 infected children.	2002-02	11901656
Case series assessing the safety of mycophenolate as part of multidrug rescue treatment regimens.	2002-01-31	11819181
Evidence of immune reconstitution in antiretroviral drug-experienced patients with advanced HIV disease.	2002-01-20	11839142
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.	2002-01-01	11782585
Kawasaki-like syndrome: abacavir hypersensitivity?	2002-01-01	11731962
Easier abacavir regimen has promising results.	2002-01	11862734
Vertigo and abacavir.	2002-01	11839213
Antiretroviral rounds. A very discordant response.	2002-01	11802628
Combined effect of zidovudine (ZDV), lamivudine (3TC) and abacavir (ABC) antiretroviral therapy in suppressing in vitro FIV replication.	2002-01	11684314
Agranulocytosis and fever seven weeks after starting abacavir.	2001-12-07	11774836
Prednisolone does not prevent hypersensitivity reactions in antiretroviral drug regimens containing abacavir with or without nevirapine.	2001-12-07	11740193
Editorial comment: the challenge of prescribing abacavir.	2001-12	11806177
Understanding drug hypersensitivity: what to look for when prescribing abacavir.	2001-12	11806176
Abacavir sulfate, lamivudine, and zidovudine (Trizivir).	2001-11-29	11723917
Anti-human immunodeficiency virus drugs are ineffective against Pneumocystis carinii in vitro and in vivo.	2001-11-15	11679930
Lipodystrophy in HIV-1-positive patients is associated with insulin resistance in multiple metabolic pathways.	2001-11-09	11684928
The role of NNRTIs in antiretroviral combination therapy: an introduction.	2001-11	11589821
Improvement of HAART-associated insulin resistance and dyslipidemia after replacement of protease inhibitors with abacavir.	2001-10-29	11698228
High-performance liquid chromatographic assay for abacavir and its two major metabolites in human urine and cerebrospinal fluid.	2001-10-25	11678376
Prevalence of adverse events associated with potent antiretroviral treatment: Swiss HIV Cohort Study.	2001-10-20	11684213
Penetration of the nucleoside analogue abacavir into the genital tract of men infected with human immunodeficiency virus type 1.	2001-10-15	11565093
Hypersensitivity reactions during therapy with the nucleoside reverse transcriptase inhibitor abacavir.	2001-10	11726000
Hypersensitivity related to abacavir in two members of a family.	2001-10	11675863
Methadone blood concentrations are decreased by the administration of abacavir plus amprenavir.	2001-10	11591903
Comparing different triple-drug combinations.	2001-10	11590925
HIV protease inhibitor substitution in patients with lipodystrophy: a randomized, controlled, open-label, multicentre study.	2001-09-28	11579243
Differential human immunodeficiency virus-suppressive activity of reverse transcription inhibitors in resting and activated peripheral blood lymphocytes: implications for therapy.	2001-09-27	11572234
[Acceptance of antiretroviral therapy. HIV-infected patients assess convenient triple combination].	2001-09-06	11584535
Antiviral activity of cyclosaligenyl prodrugs of acyclovir, carbovir and abacavir.	2001-09	11900349
Genotypic resistance mutations to antiretroviral drugs in HIV-1 B and non-B subtypes from Cuba.	2001-09	11702373
Strategies for treating HIV-related lipodystrophy.	2001-08	11772261
Resistance and cross-resistance to abacavir.	2001-07	11737395
Resistant to everything.	2001-05	11682786
Intensification of stable background therapy with abacavir in antiretroviral therapy experienced patients: 48-week data from a randomized, double-blind trial.	2001-01	11737373
Mutational patterns in the HIV genome and cross-resistance following nucleoside and nucleotide analogue drug exposure.	2001	11678471
Triple nuke therapy--results after one year.	2001	11570063

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 `Wed Apr 02 09:27:32 GMT 2025` Edited by `admin` on `Wed Apr 02 09:27:32 GMT 2025`
Record UNII	WR2TIP26VS
Record Status	`Validated (UNII)`
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Name

Type

Language

1592U89

Preferred Name

English

ABACAVIR

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

NSC-742406

Code

English

(1S,4R)-4-(2-AMINO-6-(CYCLOPROPYLAMINO)-9H-PURIN-9-YL)-2-CYCLOPENTENE-1-METHANOL

Systematic Name

English

Abacavir [WHO-DD]

Common Name

English

Classification Tree Code System Code

WHO-ATC

J05AF06