Details
Stereochemistry | ABSOLUTE |
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 | H2O4S |
Molecular Weight | 98.078 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
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 |
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 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24625462 |
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 |
---|---|---|
Four new antiretroviral medications will soon offer more options to HIV patients. | 1998 Jul-Aug |
|
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 |
|
Mutational patterns in the HIV genome and cross-resistance following nucleoside and nucleotide analogue drug exposure. | 2001 |
|
A near-fatal hypersensitivity reaction to abacavir: case report and literature review. | 2001 Apr |
|
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 |
|
Simultaneous determination of Ziagen and its phosphorylated metabolites by ion-pairing high-performance liquid chromatography-tandem mass spectrometry. | 2001 Apr 25 |
|
Antiviral activity of tenofovir (PMPA) against nucleoside-resistant clinical HIV samples. | 2001 Apr-Jul |
|
Antiviral drugs: current state of the art. | 2001 Aug |
|
Editorial comment: the challenge of prescribing abacavir. | 2001 Dec |
|
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 |
|
Trizivir on the market. | 2001 Jan |
|
Triple-drug tablet approved for HIV infection. | 2001 Jan 1 |
|
Patterns of resistance mutations to antiretroviral drugs in extensively treated HIV-1-infected patients with failure of highly active antiretroviral therapy. | 2001 Jan 1 |
|
Abacavir and diabetes. | 2001 Jan 11 |
|
Liquid chromatographic assay for simultaneous determination of abacavir and mycophenolic acid in human plasma using dual spectrophotometric detection. | 2001 Jan 5 |
|
New developments in anti-HIV chemotherapy. | 2001 Jan-Feb |
|
Resistance and cross-resistance to abacavir. | 2001 Jul |
|
Differential susceptibility of retroviruses to nucleoside analogues. | 2001 Mar |
|
Phase III trials for new PI. | 2001 Mar |
|
Increased turnover of CCR5+ and redistribution of CCR5- CD4 T lymphocytes during primary human immunodeficiency virus type 1 infection. | 2001 Mar 1 |
|
Mutations in the non-nucleoside binding-pocket interfere with the multi-nucleoside resistance phenotype. | 2001 Mar 30 |
|
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 |
|
Lipodystrophy in HIV-1-positive patients is associated with insulin resistance in multiple metabolic pathways. | 2001 Nov 9 |
|
Methadone blood concentrations are decreased by the administration of abacavir plus amprenavir. | 2001 Oct |
|
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 |
|
Abacavir hypersensitivity reaction. | 2002 Apr 15 |
|
Vertigo and abacavir. | 2002 Jan |
|
Kawasaki-like syndrome: abacavir hypersensitivity? | 2002 Jan 1 |
|
Case series assessing the safety of mycophenolate as part of multidrug rescue treatment regimens. | 2002 Jan-Feb |
|
Association between presence of HLA-B*5701, HLA-DR7, and HLA-DQ3 and hypersensitivity to HIV-1 reverse-transcriptase inhibitor abacavir. | 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 Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11796359
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
Edited
Fri Dec 15 15:47:38 UTC 2023
by
admin
on
Fri Dec 15 15:47:38 UTC 2023
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Record UNII |
J220T4J9Q2
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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EMA ASSESSMENT REPORTS |
TRIZIVIR (AUTHORIZED: HIV INFECTIONS)
Created by
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EMA ASSESSMENT REPORTS |
TRIUMEQ (AUTHORIZED: HIV INFECTIONS)
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EMA ASSESSMENT REPORTS |
ZIAGEN (AUTHORIZED: HIV INFECTIONS)
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EMA ASSESSMENT REPORTS |
KIVEXA (AUTHORIZED: HIV INFECTIONS)
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NCI_THESAURUS |
C97452
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C28804
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441384
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DBSALT000871
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CHEMBL1380
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J220T4J9Q2
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7154
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221052
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m1271
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JJ-59
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SUB00231MIG
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1000408
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760063
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100000090705
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ABACAVIR SULFATE
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PRIMARY | Description: White to almost white powder. Solubility: Soluble in water. Category: Antiretroviral (Nucleoside Reverse Transcriptase Inhibitor). Storage: Abacavir sulfate should be kept in a well-closed container. Definition: Abacavir sulfate contains not less than 99.0% and not more than 101.0% of (C14H18N6O)2,H2SO4 calculated with reference to the anhydrous substance. Manufacture: The production method is validated to demonstrate that the substance, if tested, would comply with a limit of not more than 0.5% for (1R, 4S)-abacavir enantiomer using a suitable chiral chromatographic method. | ||
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188062-50-2
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Related Record | Type | Details | ||
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ENANTIOMER -> ENANTIOMER |
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PARENT -> SALT/SOLVATE |
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (HPLC)
USP
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RACEMATE -> ENANTIOMER |
Related Record | Type | Details | ||
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IMPURITY -> PARENT |
ABACAVIR SULFATE Impurity C
In the chromatogram obtained with solution (3) the impurity peaks are eluted at the following relative retention with reference to abacavir (retention time about 19 minutes): impurity C about 0.6. The test is not valid unless the resolution between the peaks corresponding to abacavir and impurity D is at least 1.5.In the chromatogram obtained with solution (1) the area of any individual peak corresponding to impurity C is not greater than 0.3 times the area of the principal peak obtained with solution (2) (0.3%).
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IMPURITY -> PARENT | |||
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
ABACAVIR SULFATE Impurity F
In the chromatogram obtained with solution (3) the impurity peaks are eluted at the following relative retention with reference to abacavir (retention time about 19 minutes): impurity F about 1.7. The test is not valid unless the resolution between the peaks corresponding to abacavir and impurity D is at least 1.5. In the chromatogram obtained with solution (1) the area of any individual peak corresponding to impurity F is not greater than 0.3 times the area of the principal peak obtained with solution (2) (0.3%).
CHROMATOGRAPHIC PURITY (HPLC/UV)
INTERNATIONAL PHARMACOPEIA
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IMPURITY -> PARENT | |||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
ABACAVIR SULFATE Impurity A
Amount not specified.
CHROMATOGRAPHIC PURITY (HPLC/UV)
INTERNATIONAL PHARMACOPEIA
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
Abacavir sulfate Impurity D
In the chromatogram obtained with solution (3) the impurity peaks are eluted at the following relative retention with reference to abacavir (retention time about 19 minutes): impurity D about 1.05. The test is not valid unless the resolution between the peaks corresponding to abacavir and impurity D is at least 1.5. In the chromatogram obtained with solution (1) the area of any individual peak corresponding to impurity D is not greater than 0.3 times the area of the principal peak obtained with solution (2) (0.3%).
CHROMATOGRAPHIC PURITY (HPLC/UV)
INTERNATIONAL PHARMACOPEIA
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IMPURITY -> PARENT |
ABACAVIR SULFATE Impurity B
In the chromatogram obtained with solution (3) the impurity peaks are eluted at the following relative retention with reference to abacavir (retention time about 19 minutes): impurity B about 1.3. The test is not valid unless the resolution between the peaks corresponding to abacavir and impurity D is at least 1.5.In the chromatogram obtained with solution (1) the area of any individual peak corresponding to impurity B is not greater than 0.3 times the area of the principal peak obtained with solution (2) (0.3%).
CHROMATOGRAPHIC PURITY (HPLC/UV)
INTERNATIONAL PHARMACOPEIA
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
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