Details
| Stereochemistry | RACEMIC |
| Molecular Formula | 2C14H18N6O.H2O4S |
| Molecular Weight | 670.743 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OS(O)(=O)=O.NC1=NC2=C(N=CN2[C@@H]3C[C@H](CO)C=C3)C(NC4CC4)=N1.NC5=NC6=C(N=CN6[C@@H]7C[C@H](CO)C=C7)C(NC8CC8)=N5
InChI
InChIKey=WMHSRBZIJNQHKT-FFKFEZPRSA-N
InChI=1S/2C14H18N6O.H2O4S/c2*15-14-18-12(17-9-2-3-9)11-13(19-14)20(7-16-11)10-4-1-8(5-10)6-21;1-5(2,3)4/h2*1,4,7-10,21H,2-3,5-6H2,(H3,15,17,18,19);(H2,1,2,3,4)/t2*8-,10+;/m11./s1
| Molecular Formula | C14H18N6O |
| Molecular Weight | 286.3323 |
| Charge | 0 |
| Count |
|
| Stereochemistry | RACEMIC |
| Additional Stereochemistry | No |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
| Molecular Formula | H2O4S |
| Molecular Weight | 98.078 |
| 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.
CNS Activity
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL247 |
21.0 nM [Ki] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | ZIAGEN Approved UseZIAGEN, 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 Date9.1385279E11 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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
| Dose | Population | Adverse 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 |
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%) Sources: Abdominal pain (33%) Headache (25%) Diarrhea (17%) Dyspepsia (17%) |
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
| AE | Significance | Dose | Population |
|---|---|---|---|
| Diarrhea | 17% | 1200 mg single, oral Highest studied dose |
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 |
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 |
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 |
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 |
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
| Title | Date | PubMed |
|---|---|---|
| Mutational patterns in the HIV genome and cross-resistance following nucleoside and nucleotide analogue drug exposure. | 2001 |
|
| 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 |
|
| Prednisolone does not prevent hypersensitivity reactions in antiretroviral drug regimens containing abacavir with or without nevirapine. | 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 |
|
| 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 |
|
| 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 |
|
| 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 |
|
| 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 |
|
| 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 |
|
| HIV-1 genotype and phenotype correlate with virological response to abacavir, amprenavir and efavirenz in treatment-experienced patients. | 2002 Feb 15 |
|
| 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 |
|
| 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
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
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 09:42:45 UTC 2023
by
admin
on
Sat Dec 16 09:42:45 UTC 2023
|
| Record UNII |
1PPL256S5A
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
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| Name | Type | Language | ||
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| Code System | Code | Type | Description | ||
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441384
Created by
admin on Sat Dec 16 09:42:45 UTC 2023 , Edited by admin on Sat Dec 16 09:42:45 UTC 2023
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PRIMARY | |||
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1000419
Created by
admin on Sat Dec 16 09:42:45 UTC 2023 , Edited by admin on Sat Dec 16 09:42:45 UTC 2023
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1423331-68-3
Created by
admin on Sat Dec 16 09:42:45 UTC 2023 , Edited by admin on Sat Dec 16 09:42:45 UTC 2023
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NON-SPECIFIC STEREOCHEMISTRY | |||
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2736655-48-2
Created by
admin on Sat Dec 16 09:42:45 UTC 2023 , Edited by admin on Sat Dec 16 09:42:45 UTC 2023
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1PPL256S5A
Created by
admin on Sat Dec 16 09:42:45 UTC 2023 , Edited by admin on Sat Dec 16 09:42:45 UTC 2023
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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ENANTIOMER -> RACEMATE |
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ENANTIOMER -> RACEMATE |
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