Identification

Name
Abacavir
Accession Number
DB01048  (APRD00216)
Type
Small Molecule
Groups
Approved, Investigational
Description

Abacavir (ABC) is a powerful nucleoside analog reverse transcriptase inhibitor (NRTI) used to treat HIV and AIDS. Chemically, it is a synthetic carbocyclic nucleoside and is the enantiomer with 1S, 4R absolute configuration on the cyclopentene ring. In vivo, abacavir sulfate dissociates to its free base, abacavir.

Structure
Thumb
Synonyms
  • {(1S-cis)-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]cyclopent-2-en-1-yl}methanol
  • ABC
External IDs
1592U89
Product Ingredients
IngredientUNIICASInChI Key
Abacavir SulfateJ220T4J9Q2188062-50-2WMHSRBZIJNQHKT-FFKFEZPRSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
ZiagenTablet, film coated300 mg/1OralRemedy Repack2013-04-082016-10-20Us
ZiagenSolution20 mgOralViiV Healthcare ULC1999-06-15Not applicableCanada
ZiagenTablet, film coated300 mg/1OralA S Medication Solutions1998-12-292017-06-20Us
ZiagenTablet, film coated300 mg/1OralState of Florida DOH Central Pharmacy2009-07-01Not applicableUs
ZiagenTablet, film coated300 mg/1OralViiV Healthcare ULC1998-12-29Not applicableUs49702 0221 18 nlmimage10 5f192fc9
ZiagenTablet300 mgOralViiV Healthcare ULC1999-06-09Not applicableCanada
ZiagenSolution20 mg/mLOralViiV Healthcare ULC1999-01-28Not applicableUs
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AbacavirTablet, film coated300 mg/1OralAurobindo Pharma2012-12-17Not applicableUs
AbacavirTablet300 1/1OralStrides Shasun Limited2016-10-28Not applicableUs
AbacavirTablet300 mg/1OralCamber Pharmaceuticals2013-09-18Not applicableUs
AbacavirTablet, film coated300 mg/1OralAmerincan Health Packaging2013-02-07Not applicableUs
AbacavirTablet, film coated300 mg/1OralRemedy Repack2017-05-30Not applicableUs
AbacavirTablet, film coated300 mg/1OralAvera Mc Kennan Hospital2016-02-29Not applicableUs
AbacavirSolution20 mg/mLOralCamber Pharmaceuticals2016-09-26Not applicableUs
AbacavirTablet300 mg/1OralRemedy Repack2014-05-29Not applicableUs
Abacavir SulfateTablet, film coated300 mg/1OralMylan Pharmaceuticals2012-06-19Not applicableUs
Abacavir SulfateTablet, film coated300 mg/1OralMylan Institutional2012-08-01Not applicableUs
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Abacavir and LamivudineAbacavir Sulfate (600 mg/1) + Lamivudine (300 mg/1)Tablet, film coatedOralRemedy Repack2017-08-28Not applicableUs
Abacavir and LamivudineAbacavir Sulfate (600 mg/1) + Lamivudine (300 mg/1)Tablet, film coatedOralCipla Limited2017-03-28Not applicableUs
Abacavir and LamivudineAbacavir Sulfate (600 mg/1) + Lamivudine (300 mg/1)Tablet, film coatedOralPrasco, Laboratories2016-09-29Not applicableUs
Abacavir and LamivudineAbacavir Sulfate (600 mg/1) + Lamivudine (300 mg/1)Tablet, film coatedOralAurobindo Pharma2017-03-28Not applicableUs
Abacavir and LamivudineAbacavir Sulfate (600 mg/1) + Lamivudine (300 mg/1)Tablet, film coatedOralTeva2016-09-29Not applicableUs
Abacavir and LamivudineAbacavir Sulfate (600 mg/1) + Lamivudine (300 mg/1)Tablet, film coatedOralLupin Pharmaceuticals2017-03-28Not applicableUs
Abacavir Sulfate, Lamivudine and ZidovudineAbacavir Sulfate (300 mg/1) + Lamivudine (150 mg/1) + Zidovudine (300 mg/1)TabletOralLupin Pharmaceuticals2013-12-17Not applicableUs
Abacavir, Lamivudine and ZidovudineAbacavir Sulfate (300 mg/1) + Lamivudine (150 mg/1) + Zidovudine (300 mg/1)TabletOralLupin Pharmaceuticals2013-12-17Not applicableUs
Apo-abacavir-lamivudineAbacavir (600 mg) + Lamivudine (300 mg)TabletOralApotex Corporation2016-03-15Not applicableCanada
Apo-abacavir-lamivudine-zidovudineAbacavir (300 mg) + Lamivudine (150 mg) + Zidovudine (300 mg)TabletOralApotex Corporation2015-12-28Not applicableCanada
Categories
UNII
WR2TIP26VS
CAS number
136470-78-5
Weight
Average: 286.3323
Monoisotopic: 286.154209228
Chemical Formula
C14H18N6O
InChI Key
MCGSCOLBFJQGHM-SCZZXKLOSA-N
InChI
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
IUPAC Name
[(1S,4R)-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]cyclopent-2-en-1-yl]methanol
SMILES
NC1=NC2=C(N=CN2[[email protected]@H]2C[[email protected]](CO)C=C2)C(NC2CC2)=N1

Pharmacology

Indication

For the treatment of HIV-1 infection, in combination with other antiretroviral agents.

Structured Indications
Pharmacodynamics

Abacavir is a nucleoside reverse transcriptase inhibitor (NRTI) with activity against Human Immunodeficiency Virus Type 1 (HIV-1). Abacavir is phosphorylated to active metabolites that compete for incorporation into viral DNA. They inhibit the HIV reverse transcriptase enzyme competitively and act as a chain terminator of DNA synthesis. The concentration of drug necessary to effect viral replication by 50 percent (EC50) ranged from 3.7 to 5.8 μM (1 μM = 0.28 mcg/mL) and 0.07 to 1.0 μM against HIV-1IIIB and HIV-1BaL, respectively, and was 0.26 ± 0.18 μM against 8 clinical isolates. Abacavir had synergistic activity in cell culture in combination with the nucleoside reverse transcriptase inhibitor (NRTI) zidovudine, the non-nucleoside reverse transcriptase inhibitor (NNRTI) nevirapine, and the protease inhibitor (PI) amprenavir; and additive activity in combination with the NRTIs didanosine, emtricitabine, lamivudine, stavudine, tenofovir, and zalcitabine.

Mechanism of action

Abacavir is a carbocyclic synthetic nucleoside analogue and an antiviral agent. Intracellularly, abacavir is converted by cellular enzymes to the active metabolite carbovir triphosphate, an analogue of deoxyguanosine-5'-triphosphate (dGTP). Carbovir triphosphate inhibits the activity of HIV-1 reverse transcriptase (RT) both by competing with the natural substrate dGTP and by its incorporation into viral DNA. Viral DNA growth is terminated because the incorporated nucleotide lacks a 3'-OH group, which is needed to form the 5′ to 3′ phosphodiester linkage essential for DNA chain elongation.

TargetActionsOrganism
AReverse transcriptase/RNaseH
inhibitor
Human immunodeficiency virus 1
UHLA class I histocompatibility antigen, B-57 alpha chainNot AvailableHuman
Absorption

Rapid and extensive after oral administration (83% bioavailability, tablet). When a 300 mg tablet is given twice daily to subjects, the peak plasma concentration (Cmax) was 3.0 ± 0.89 mcg/mL and the area under the curve (AUC 0-12 hours) was 6.02 ± 1.73 mcg•hr/mL.

Volume of distribution
  • 0.86 ± 0.15 L/kg [IV administration]
Protein binding

Moderate (approximately 50%). Binding of abacavir to plasma protein was independent of concentration.

Metabolism

Hepatic, by alcohol dehydrogenase and glucuronosyltransferase to a 5′-carboxylic acid metabolite and 5′-glucuronide metabolite, respectively. These metabolites have no antiviral activity. Abacavir is not significantly metabolized by cytochrome P450 enzymes.

Route of elimination

Elimination of abacavir was quantified in a mass balance study following administration of a 600-mg dose of 14C-abacavir: 99% of the radioactivity was recovered, 1.2% was excreted in the urine as abacavir, 30% as the 5′-carboxylic acid metabolite, 36% as the 5′-glucuronide metabolite, and 15% as unidentified minor metabolites in the urine. Fecal elimination accounted for 16% of the dose. Renal excretion of unchanged abacavir is a minor route of elimination in humans.

Half life

1.54 ± 0.63 hours

Clearance
  • 0.80 ± 0.24 L/hr/kg [asymptomatic, HIV-1-infected adult patients receiving single (IV dose of 150 mg]
Toxicity

Some myocardial degeneration has been noticed in rats and mice. The most commonly reported adverse reactions of at least moderate intensity (incidence ≥10%) in adult HIV-1 clinical trials were nausea, headache, malaise and fatigue, nausea and vomiting, and dreams/sleep disorders. Serious hypersensitivity reactions have been associated with abacavir which has been strongly linked to the presence of the HLA-B*57:01 allele. This reaction manifests itself in patients within the first 6 weeks of treatment. Patients should be tested for the presence of this allele as recommended by the U.S Food and Drug Administration (FDA).

Affected organisms
  • Human Immunodeficiency Virus
Pathways
PathwayCategory
Abacavir Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetails
HLA class I histocompatibility antigen protein P5HLA-B*5701(G;G)G alleleADR Directly StudiedPatients who carry this SNP are at a higher risk of experiencing a hypersensitivity reaction to abacavir.Details

Interactions

Drug Interactions
DrugInteractionDrug group
1,10-PhenanthrolineThe serum concentration of Abacavir can be decreased when it is combined with 1,10-Phenanthroline.Experimental
3,4-DichloroisocoumarinThe serum concentration of Abacavir can be decreased when it is combined with 3,4-Dichloroisocoumarin.Experimental
4-(2-Aminoethyl)Benzenesulfonyl FluorideThe serum concentration of Abacavir can be decreased when it is combined with 4-(2-Aminoethyl)Benzenesulfonyl Fluoride.Experimental
AlogliptinThe serum concentration of Abacavir can be decreased when it is combined with Alogliptin.Approved
Alpha-1-proteinase inhibitorThe serum concentration of Abacavir can be decreased when it is combined with Alpha-1-proteinase inhibitor.Approved
AmprenavirThe serum concentration of Abacavir can be decreased when it is combined with Amprenavir.Approved
Antithrombin III humanThe serum concentration of Abacavir can be decreased when it is combined with Antithrombin III human.Approved
ApixabanThe serum concentration of Abacavir can be decreased when it is combined with Apixaban.Approved
AprotininThe serum concentration of Abacavir can be decreased when it is combined with Aprotinin.Approved, Withdrawn
ArgatrobanThe serum concentration of Abacavir can be decreased when it is combined with Argatroban.Approved, Investigational
AsunaprevirThe serum concentration of Abacavir can be decreased when it is combined with Asunaprevir.Approved, Investigational
AtazanavirThe serum concentration of Abacavir can be decreased when it is combined with Atazanavir.Approved, Investigational
BatimastatThe serum concentration of Abacavir can be decreased when it is combined with Batimastat.Experimental
BenazeprilThe serum concentration of Abacavir can be decreased when it is combined with Benazepril.Approved, Investigational
BenzamidineThe serum concentration of Abacavir can be decreased when it is combined with Benzamidine.Experimental
BivalirudinThe serum concentration of Abacavir can be decreased when it is combined with Bivalirudin.Approved, Investigational
BoceprevirThe serum concentration of Abacavir can be decreased when it is combined with Boceprevir.Approved, Withdrawn
CamostatThe serum concentration of Abacavir can be decreased when it is combined with Camostat.Experimental
CandoxatrilThe serum concentration of Abacavir can be decreased when it is combined with Candoxatril.Experimental
CandoxatrilatThe serum concentration of Abacavir can be decreased when it is combined with Candoxatrilat.Experimental
CaptoprilThe serum concentration of Abacavir can be decreased when it is combined with Captopril.Approved
CholesterolThe serum concentration of Abacavir can be decreased when it is combined with Cholesterol.Experimental, Investigational
ChymostatinThe serum concentration of Abacavir can be decreased when it is combined with Chymostatin.Experimental
CilastatinThe serum concentration of Abacavir can be decreased when it is combined with Cilastatin.Approved
CilazaprilThe serum concentration of Abacavir can be decreased when it is combined with Cilazapril.Approved
Dabigatran etexilateThe serum concentration of Abacavir can be decreased when it is combined with Dabigatran etexilate.Approved
DarexabanThe serum concentration of Abacavir can be decreased when it is combined with Darexaban.Investigational
DarunavirThe serum concentration of Abacavir can be decreased when it is combined with Darunavir.Approved
DelanzomibThe serum concentration of Abacavir can be decreased when it is combined with Delanzomib.Investigational
DelaprilThe serum concentration of Abacavir can be decreased when it is combined with Delapril.Experimental
EcabetThe serum concentration of Abacavir can be decreased when it is combined with Ecabet.Approved, Investigational
EdoxabanThe serum concentration of Abacavir can be decreased when it is combined with Edoxaban.Approved
ElafinThe serum concentration of Abacavir can be decreased when it is combined with Elafin.Investigational
EnalaprilThe serum concentration of Abacavir can be decreased when it is combined with Enalapril.Approved, Vet Approved
EnalaprilatThe serum concentration of Abacavir can be decreased when it is combined with Enalaprilat.Approved
EnalkirenThe serum concentration of Abacavir can be decreased when it is combined with Enalkiren.Experimental
Epigallocatechin GallateThe serum concentration of Abacavir can be decreased when it is combined with Epigallocatechin Gallate.Investigational
FaldaprevirThe serum concentration of Abacavir can be decreased when it is combined with Faldaprevir.Investigational
FosamprenavirThe serum concentration of Abacavir can be decreased when it is combined with Fosamprenavir.Approved
FosinoprilThe serum concentration of Abacavir can be decreased when it is combined with Fosinopril.Approved
GabexateThe serum concentration of Abacavir can be decreased when it is combined with Gabexate.Investigational
GanciclovirThe risk or severity of adverse effects can be increased when Ganciclovir is combined with Abacavir.Approved, Investigational
GeldanamycinThe serum concentration of Abacavir can be decreased when it is combined with Geldanamycin.Experimental, Investigational
GM6001The serum concentration of Abacavir can be decreased when it is combined with GM6001.Experimental
IdraparinuxThe serum concentration of Abacavir can be decreased when it is combined with Idraparinux.Investigational
ImidaprilThe serum concentration of Abacavir can be decreased when it is combined with Imidapril.Investigational
IndinavirThe serum concentration of Abacavir can be decreased when it is combined with Indinavir.Approved
IsoflurophateThe serum concentration of Abacavir can be decreased when it is combined with Isoflurophate.Approved, Investigational, Withdrawn
IxazomibThe serum concentration of Abacavir can be decreased when it is combined with Ixazomib.Approved
LepirudinThe serum concentration of Abacavir can be decreased when it is combined with Lepirudin.Approved
LetaxabanThe serum concentration of Abacavir can be decreased when it is combined with Letaxaban.Investigational
LinagliptinThe serum concentration of Abacavir can be decreased when it is combined with Linagliptin.Approved
LisinoprilThe serum concentration of Abacavir can be decreased when it is combined with Lisinopril.Approved, Investigational
LopinavirThe serum concentration of Abacavir can be decreased when it is combined with Lopinavir.Approved
MelagatranThe serum concentration of Abacavir can be decreased when it is combined with Melagatran.Experimental
MethadoneThe therapeutic efficacy of Abacavir can be decreased when used in combination with Methadone.Approved
MoexiprilThe serum concentration of Abacavir can be decreased when it is combined with Moexipril.Approved
N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-ProlineThe serum concentration of Abacavir can be decreased when it is combined with N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-Proline.Experimental
NafamostatThe serum concentration of Abacavir can be decreased when it is combined with Nafamostat.Approved, Investigational
NelfinavirThe serum concentration of Abacavir can be decreased when it is combined with Nelfinavir.Approved
NitroaspirinThe serum concentration of Abacavir can be decreased when it is combined with Nitroaspirin.Investigational
OmapatrilatThe serum concentration of Abacavir can be decreased when it is combined with Omapatrilat.Investigational
OtamixabanThe serum concentration of Abacavir can be decreased when it is combined with Otamixaban.Investigational
PerindoprilThe serum concentration of Abacavir can be decreased when it is combined with Perindopril.Approved
PhosphoramidonThe serum concentration of Abacavir can be decreased when it is combined with Phosphoramidon.Experimental
PrinomastatThe serum concentration of Abacavir can be decreased when it is combined with Prinomastat.Investigational
QuinaprilThe serum concentration of Abacavir can be decreased when it is combined with Quinapril.Approved, Investigational
RacecadotrilThe serum concentration of Abacavir can be decreased when it is combined with Racecadotril.Investigational
RamiprilThe serum concentration of Abacavir can be decreased when it is combined with Ramipril.Approved
RemikirenThe serum concentration of Abacavir can be decreased when it is combined with Remikiren.Approved
RibavirinRibavirin may increase the hepatotoxic activities of Abacavir.Approved
RitonavirThe serum concentration of Abacavir can be decreased when it is combined with Ritonavir.Approved, Investigational
RivaroxabanThe serum concentration of Abacavir can be decreased when it is combined with Rivaroxaban.Approved
S-3304The serum concentration of Abacavir can be decreased when it is combined with S-3304.Investigational
SaquinavirThe serum concentration of Abacavir can be decreased when it is combined with Saquinavir.Approved, Investigational
SaxagliptinThe serum concentration of Abacavir can be decreased when it is combined with Saxagliptin.Approved
SimeprevirThe serum concentration of Abacavir can be decreased when it is combined with Simeprevir.Approved
SitagliptinThe serum concentration of Abacavir can be decreased when it is combined with Sitagliptin.Approved, Investigational
SivelestatThe serum concentration of Abacavir can be decreased when it is combined with Sivelestat.Investigational
SpiraprilThe serum concentration of Abacavir can be decreased when it is combined with Spirapril.Approved
TelaprevirThe serum concentration of Abacavir can be decreased when it is combined with Telaprevir.Approved, Withdrawn
TemocaprilThe serum concentration of Abacavir can be decreased when it is combined with Temocapril.Experimental, Investigational
ThiorphanThe serum concentration of Abacavir can be decreased when it is combined with Thiorphan.Experimental
TipranavirThe serum concentration of Abacavir can be decreased when it is combined with Tipranavir.Approved, Investigational
TrandolaprilThe serum concentration of Abacavir can be decreased when it is combined with Trandolapril.Approved
UbenimexThe serum concentration of Abacavir can be decreased when it is combined with Ubenimex.Experimental, Investigational
UlinastatinThe serum concentration of Abacavir can be decreased when it is combined with Ulinastatin.Investigational
ValganciclovirThe risk or severity of adverse effects can be increased when Valganciclovir is combined with Abacavir.Approved, Investigational
VildagliptinThe serum concentration of Abacavir can be decreased when it is combined with Vildagliptin.Approved, Investigational
XimelagatranThe serum concentration of Abacavir can be decreased when it is combined with Ximelagatran.Approved, Investigational, Withdrawn
Z-Val-Ala-Asp fluoromethyl ketoneThe serum concentration of Abacavir can be decreased when it is combined with Z-Val-Ala-Asp fluoromethyl ketone.Experimental
ZofenoprilThe serum concentration of Abacavir can be decreased when it is combined with Zofenopril.Experimental
Food Interactions
  • Abacavir is partly metabolised through the alcohol-dehydrogenase enzyme system.
  • Alcohol significantly increases abacavir's area under the curve (about 41%).
  • Avoid alcohol.
  • Take without regard to meals.

References

Synthesis Reference
US5034394
General References
  1. Zucman D, Truchis Pd, Majerholc C, Stegman S, Caillat-Zucman S: Prospective screening for human leukocyte antigen-B*5701 avoids abacavir hypersensitivity reaction in the ethnically mixed French HIV population. J Acquir Immune Defic Syndr. 2007 May 1;45(1):1-3. [PubMed:17356469]
  2. Link [Link]
External Links
Human Metabolome Database
HMDB15182
KEGG Drug
D07057
KEGG Compound
C07624
PubChem Compound
441300
PubChem Substance
46505718
ChemSpider
390063
BindingDB
50366816
ChEBI
421707
ChEMBL
CHEMBL1380
Therapeutic Targets Database
DAP000704
PharmGKB
PA448004
HET
1KX
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Abacavir
ATC Codes
J05AR02 — Lamivudine and abacavirJ05AR13 — Lamivudine, abacavir and dolutegravirJ05AR04 — Zidovudine, lamivudine and abacavirJ05AF06 — Abacavir
AHFS Codes
  • 08:18.08.20 — Nucleoside and Nucleotide Reverse Transcriptase Inhibitors
PDB Entries
3upr / 3vri / 3vrj / 5u98
FDA label
Download (118 KB)
MSDS
Download (34.7 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedNot AvailableHuman Immunodeficiency Virus (HIV)1
1CompletedNot AvailablePsoriasis1
1CompletedOtherHIV-DDI1
1CompletedTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) Infections1
1CompletedTreatmentHealthy Volunteers1
1CompletedTreatmentHuman Immunodeficiency Virus (HIV)1
1CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections11
1TerminatedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
1, 2RecruitingTreatmentAmyotrophic Lateral Sclerosis (ALS)1
2CompletedNot AvailableHuman Immunodeficiency Virus (HIV)1
2CompletedPreventionHuman Immunodeficiency Virus (HIV) Infections1
2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections20
2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Lipodystrophies1
2CompletedTreatmentInfection, Human Immunodeficiency Virus I2
2RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections1
2WithdrawnTreatmentHuman Immunodeficiency Virus (HIV) Infections1
2, 3CompletedTreatmentAcidosis, Respiratory1
2, 3CompletedTreatmentHuman Immunodeficiency Virus (HIV)1
2, 3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
2, 3CompletedTreatmentKaposi's Sarcoma AIDS Related1
3Active Not RecruitingTreatmentInfection, Human Immunodeficiency Virus I3
3CompletedTreatmentAIDS-Related Dementia Complex / Human Immunodeficiency Virus (HIV) Infections1
3CompletedTreatmentHIV / AIDS / Human Immunodeficiency Virus (HIV) Infections1
3CompletedTreatmentHuman Immunodeficiency Virus (HIV)1
3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections18
3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Infection, Human Immunodeficiency Virus I2
3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Tuberculosis1
3CompletedTreatmentHuman Immunodeficiency Virus (HIV) / Human Immunodeficiency Virus (HIV) Infections1
3CompletedTreatmentInfection, Human Immunodeficiency Virus I3
3RecruitingTreatmentAcute HIV Infection1
3RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections2
3SuspendedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
3TerminatedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
3Unknown StatusTreatmentHuman Immunodeficiency Virus (HIV) Infections3
4Active Not RecruitingOtherHuman Immunodeficiency Virus (HIV)1
4Active Not RecruitingTreatmentHuman Immunodeficiency Virus (HIV)1
4CompletedNot AvailableHuman Immunodeficiency Virus (HIV) Infections1
4CompletedNot AvailableHuman Immunodeficiency Virus (HIV) / Proteinuria1
4CompletedDiagnosticCardiovascular Disease (CVD) / HIV-Associated Lipodystrophy Syndrome1
4CompletedPreventionHuman Immunodeficiency Virus (HIV) Infections1
4CompletedTreatmentCardiovascular Disease (CVD) / Human Immunodeficiency Virus (HIV)1
4CompletedTreatmentHiV1- Positive1
4CompletedTreatmentHuman Immunodeficiency Virus (HIV)2
4CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections11
4CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Infection, Human Immunodeficiency Virus I2
4CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Lipodystrophies1
4CompletedTreatmentHuman Immunodeficiency Virus (HIV) / Tuberculosis1
4CompletedTreatmentHuman Immunodeficiency Virus Type 1 (HIV-1)1
4CompletedTreatmentInfection, Human Immunodeficiency Virus I1
4Not Yet RecruitingTreatmentHuman Immunodeficiency Virus (HIV)1
4RecruitingTreatmentAntiretroviral Therapy Intolerance / Patients Compliance1
4RecruitingTreatmentHuman Immunodeficiency Virus (HIV) / Renal Insufficiency,Chronic / Therapeutic Agent Toxicity1
4TerminatedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
4Unknown StatusTreatmentHuman Immunodeficiency Virus (HIV) Infections3
4Unknown StatusTreatmentHuman Immunodeficiency Virus (HIV) Infections / Tuberculosis1
Not AvailableActive Not RecruitingNot AvailableHuman Immunodeficiency Virus (HIV) Infections1
Not AvailableCompletedNot AvailableInfection, Human Immunodeficiency Virus I2
Not AvailableCompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections11
Not AvailableCompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Lipodystrophies / Wasting Disease1
Not AvailableRecruitingBasic ScienceHuman Immunodeficiency Virus (HIV)1
Not AvailableRecruitingTreatmentAcute HIV Infection / Human Immunodeficiency Virus (HIV)1
Not AvailableRecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections2
Not AvailableWithdrawnTreatmentHuman Immunodeficiency Virus (HIV) Infections1
Not AvailableWithdrawnTreatmentHuman Immunodeficiency Virus (HIV) Infections / Viral Hepatitis B1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Dosage forms
FormRouteStrength
TabletOral300 mg/1
TabletOral300 1/1
Tablet, film coatedOral
TabletOral
SolutionOral20 mg/mL
SolutionOral20 mg
TabletOral300 mg
Tablet, film coatedOral300 mg/1
Prices
Unit descriptionCostUnit
Epzicom tablet35.78USD tablet
Ziagen 300 mg tablet10.46USD tablet
Ziagen 20 mg/ml Solution0.7USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5089500No1992-12-262009-12-26Us
CA2289753No2007-01-232018-05-14Canada
CA1340589No1999-06-082016-06-08Canada
CA2216634No2004-07-202016-03-28Canada
US9242986No2009-10-082029-10-08Us
US5905082Yes1996-11-182016-11-18Us
US6294540Yes1998-11-142018-11-14Us
US6641843Yes1999-08-042019-08-04Us
US6417191Yes1996-09-282016-09-28Us
US8129385No2007-10-052027-10-05Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)165 °CNot Available
water solubility77 mg/mL (sulfate salt)FDA label
logP1.20 FDA label
Predicted Properties
PropertyValueSource
Water Solubility1.21 mg/mLALOGPS
logP0.61ALOGPS
logP0.39ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)15.41ChemAxon
pKa (Strongest Basic)5.77ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area101.88 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity82.62 m3·mol-1ChemAxon
Polarizability30.43 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9383
Caco-2 permeable-0.5808
P-glycoprotein substrateNon-substrate0.5551
P-glycoprotein inhibitor INon-inhibitor0.9155
P-glycoprotein inhibitor IINon-inhibitor0.6573
Renal organic cation transporterNon-inhibitor0.7734
CYP450 2C9 substrateNon-substrate0.8595
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.7376
CYP450 1A2 substrateNon-inhibitor0.538
CYP450 2C9 inhibitorNon-inhibitor0.8707
CYP450 2D6 inhibitorNon-inhibitor0.7852
CYP450 2C19 inhibitorNon-inhibitor0.8667
CYP450 3A4 inhibitorNon-inhibitor0.559
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8683
Ames testNon AMES toxic0.6662
CarcinogenicityNon-carcinogens0.8649
BiodegradationNot ready biodegradable0.9806
Rat acute toxicity2.4758 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8918
hERG inhibition (predictor II)Non-inhibitor0.8734
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as 1,3-substituted cyclopentyl purine nucleosides. These are nucleoside analogues with a structure that consists of a cyclobutane that is substituted a the 1-position with a hydroxyl group and at the 3-position with either a purine base.
Kingdom
Organic compounds
Super Class
Nucleosides, nucleotides, and analogues
Class
Nucleoside and nucleotide analogues
Sub Class
Cyclopentyl nucleosides
Direct Parent
1,3-substituted cyclopentyl purine nucleosides
Alternative Parents
6-alkylaminopurines / Secondary alkylarylamines / Aminopyrimidines and derivatives / N-substituted imidazoles / Imidolactams / Heteroaromatic compounds / Azacyclic compounds / Primary amines / Primary alcohols / Organopnictogen compounds
show 1 more
Substituents
1,3-substituted cyclopentyl purine nucleoside / 6-alkylaminopurine / 6-aminopurine / Imidazopyrimidine / Purine / Aminopyrimidine / Secondary aliphatic/aromatic amine / N-substituted imidazole / Pyrimidine / Imidolactam
show 17 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
2,6-diaminopurine (CHEBI:421707)

Targets

Kind
Protein
Organism
Human immunodeficiency virus 1
Pharmacological action
Yes
Actions
Inhibitor
General Function
Rna-dna hybrid ribonuclease activity
Specific Function
Not Available
Gene Name
pol
Uniprot ID
Q72547
Uniprot Name
Reverse transcriptase/RNaseH
Molecular Weight
65223.615 Da
References
  1. De Clercq E: New anti-HIV agents and targets. Med Res Rev. 2002 Nov;22(6):531-65. [PubMed:12369088]
  2. Faletto MB, Miller WH, Garvey EP, St Clair MH, Daluge SM, Good SS: Unique intracellular activation of the potent anti-human immunodeficiency virus agent 1592U89. Antimicrob Agents Chemother. 1997 May;41(5):1099-107. [PubMed:9145876]
  3. Crimmins MT, King BW: An Efficient Asymmetric Approach to Carbocyclic Nucleosides: Asymmetric Synthesis of 1592U89, a Potent Inhibitor of HIV Reverse Transcriptase. J Org Chem. 1996 Jun 26;61(13):4192-4193. [PubMed:11667311]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Involved in the presentation of foreign antigens to the immune system.
Specific Function
Peptide antigen binding
Gene Name
HLA-B
Uniprot ID
P18465
Uniprot Name
HLA class I histocompatibility antigen, B-57 alpha chain
Molecular Weight
40223.825 Da
References
  1. Yang L, Chen J, He L: Harvesting candidate genes responsible for serious adverse drug reactions from a chemical-protein interactome. PLoS Comput Biol. 2009 Jul;5(7):e1000441. doi: 10.1371/journal.pcbi.1000441. Epub 2009 Jul 24. [PubMed:19629158]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Zinc ion binding
Specific Function
Not Available
Gene Name
ADH6
Uniprot ID
P28332
Uniprot Name
Alcohol dehydrogenase 6
Molecular Weight
39088.335 Da
References
  1. Yuen GJ, Weller S, Pakes GE: A review of the pharmacokinetics of abacavir. Clin Pharmacokinet. 2008;47(6):351-71. [PubMed:18479171]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid binding
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the...
Gene Name
UGT1A1
Uniprot ID
P22309
Uniprot Name
UDP-glucuronosyltransferase 1-1
Molecular Weight
59590.91 Da
References
  1. Yuen GJ, Weller S, Pakes GE: A review of the pharmacokinetics of abacavir. Clin Pharmacokinet. 2008;47(6):351-71. [PubMed:18479171]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Poly(a) rna binding
Specific Function
ATP dependent phosphorylation of adenosine and other related nucleoside analogs to monophosphate derivatives. Serves as a potential regulator of concentrations of extracellular adenosine and intrac...
Gene Name
ADK
Uniprot ID
P55263
Uniprot Name
Adenosine kinase
Molecular Weight
40545.075 Da
References
  1. Faletto MB, Miller WH, Garvey EP, St Clair MH, Daluge SM, Good SS: Unique intracellular activation of the potent anti-human immunodeficiency virus agent 1592U89. Antimicrob Agents Chemother. 1997 May;41(5):1099-107. [PubMed:9145876]

Drug created on June 13, 2005 07:24 / Updated on November 19, 2017 20:33