Abacavir

Identification

Summary

Abacavir is an antiviral nucleoside reverse transcriptase inhibitor used in combination with other antiretrovirals for the treatment of HIV.

Brand Names
Epzicom, Kivexa, Triumeq, Trizivir, Ziagen
Generic Name
Abacavir
DrugBank Accession Number
DB01048
Background

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.

Type
Small Molecule
Groups
Approved, Investigational
Structure
Weight
Average: 286.3323
Monoisotopic: 286.154209228
Chemical Formula
C14H18N6O
Synonyms
  • {(1S-cis)-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]cyclopent-2-en-1-yl}methanol
  • Abacavir
  • ABC
External IDs
  • 1592U89

Pharmacology

Indication

Abacavir is indicated in combination with other anti-retroviral agents for the treatment of HIV-1 infection.4 It is available in a combination product alongside dolutegravir and lamivudine for the treatment of adult and pediatric patients with HIV-1 who weigh ≥10 kg.3

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Used in combination to manageHiv-1 infectionRegimen in combination with: Zidovudine (DB00495), Lamivudine (DB00709)••••••••••••
Used in combination to treatHuman immunodeficiency virus type 1 (hiv-1) infectionCombination Product in combination with: Dolutegravir (DB08930), Lamivudine (DB00709)•••••••••••••••••• ••••••••••••• •••••• •• •• •• •• ••••••••••• ••••••• ••• ••••••••••
Contraindications & Blackbox Warnings
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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 AvailableHumans
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]
Adverse Effects
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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).

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
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AceclofenacAceclofenac may decrease the excretion rate of Abacavir which could result in a higher serum level.
AcemetacinAcemetacin may decrease the excretion rate of Abacavir which could result in a higher serum level.
AcetaminophenAcetaminophen may decrease the excretion rate of Abacavir which could result in a higher serum level.
AcetazolamideAcetazolamide may increase the excretion rate of Abacavir which could result in a lower serum level and potentially a reduction in efficacy.
Acetylsalicylic acidAcetylsalicylic acid may decrease the excretion rate of Abacavir which could result in a higher serum level.
Food Interactions
  • Avoid alcohol. Alcohol increases the systemic exposure to the drug.
  • Take with or without food. The absorption is unaffected by food.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Abacavir hydrochlorideRP0T719KX7136777-48-5QXNOPHSMRJNHHG-SCYNACPDSA-N
Abacavir hydrochloride monohydrateGZP7A66C3CNot AvailableXYDFTVTUCLYHFD-WAZPLGGWSA-N
Abacavir sulfateJ220T4J9Q2188062-50-2WMHSRBZIJNQHKT-FFKFEZPRSA-N
Product Images
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
EpzicomTablet, film coated600 mg/1OralRemedy Repack2013-03-152014-03-15US flag
ZiagenTablet, film coated300 mg/1OralRemedy Repack2012-02-112013-08-22US flag
ZiagenSolution20 mg/1mLOralGlaxosmithkline Inc1999-01-282012-10-31US flag
ZiagenSolution20 mg/mLOralVii V Healthcare B.V.2020-12-22Not applicableEU flag
ZiagenTablet300 mgOralViiV Healthcare ULC1999-06-09Not applicableCanada flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
AbacavirTablet, film coated300 mg/1OralAvera McKennan Hospital2016-02-292017-05-24US flag
AbacavirTablet, film coated300 mg/1OralREMEDYREPACK INC.2018-06-21Not applicableUS flag
AbacavirTablet300 mg/1OralAvPAK2020-04-10Not applicableUS flag
AbacavirSolution20 mg/1mLOralCamber Pharmaceuticals2016-09-26Not applicableUS flag
AbacavirTablet, film coated300 mg/1OralMajor Pharmaceuticals2012-12-17Not applicableUS flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
ABACAVIR 600 MG + LAMIVUDINA 300 MG TABLETAS RECUBIERTASAbacavir sulfate (600 mg) + Lamivudine (300 mg)Tablet, coatedOralNUTRI MACK S.A.S.2015-03-182020-06-05Colombia flag
Abacavir and LamivudineAbacavir sulfate (600 mg/1) + Lamivudine (300 mg/1)Tablet, film coatedOralBurel Pharmaceuticals, Llc2019-11-15Not applicableUS flag
Abacavir and lamivudineAbacavir sulfate (600 mg/1) + Lamivudine (300 mg/1)Tablet, film coatedOralZydus Pharmaceuticals USA Inc.2019-03-14Not applicableUS flag
Abacavir and LamivudineAbacavir sulfate (600 mg/1) + Lamivudine (300 mg/1)Tablet, film coatedOralLupin Pharmaceuticals, Inc.2017-03-28Not applicableUS flag
Abacavir and LamivudineAbacavir sulfate (600 mg/1) + Lamivudine (300 mg/1)Tablet, film coatedOralTeva Pharmaceuticals USA, Inc.2016-09-292021-11-30US flag

Categories

ATC Codes
J05AR13 — Lamivudine, abacavir and dolutegravirJ05AR02 — Lamivudine and abacavirJ05AR04 — Zidovudine, lamivudine and abacavirJ05AF06 — Abacavir
Drug Categories
Chemical TaxonomyProvided by Classyfire
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 / Alcohol / Amine / Aminopyrimidine / Aromatic heteropolycyclic compound / Azacycle / Azole / Heteroaromatic compound
show 17 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
2,6-diaminopurine (CHEBI:421707)
Affected organisms
  • Human Immunodeficiency Virus

Chemical Identifiers

UNII
WR2TIP26VS
CAS number
136470-78-5
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[C@@H]2C[C@H](CO)C=C2)C(NC2CC2)=N1

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. [Article]
  2. Link [Link]
  3. FDA Approved Drug Products: Triumeq/Triumeq PD (abacavir, dolutegravir, and lamivudine) for oral administration [Link]
  4. FDA Approved Drug Products: ZIAGEN (abacavir) solution or tablets, for oral use (November 2020) [Link]
Human Metabolome Database
HMDB0015182
KEGG Drug
D07057
KEGG Compound
C07624
PubChem Compound
441300
PubChem Substance
46505718
ChemSpider
390063
BindingDB
50366816
RxNav
190521
ChEBI
421707
ChEMBL
CHEMBL1380
ZINC
ZINC000002015928
Therapeutic Targets Database
DAP000704
PharmGKB
PA448004
PDBe Ligand
1KX
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Abacavir
PDB Entries
3upr / 3vri / 3vrj / 5u98
FDA label
Download (118 KB)
MSDS
Download (34.7 KB)

Clinical Trials

Clinical Trials

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • A-S Medication Solutions LLC
  • Dept Health Central Pharmacy
  • GlaxoSmithKline Inc.
  • Lake Erie Medical and Surgical Supply
  • Murfreesboro Pharmaceutical Nursing Supply
  • Physicians Total Care Inc.
  • Remedy Repack
  • Tya Pharmaceuticals
  • ViiV Healthcare ULC
Dosage Forms
FormRouteStrength
Tablet, film coatedOral300.00 mg
TabletOral300 mg/1
SolutionOral2 g
Tablet, coatedOral300 mg
Tablet, film coatedOral
Tablet, coatedOral
SolutionOral
TabletOral
TabletOral351.37 mg
SolutionOral20 mg
Tablet, film coatedOral600.0 mg
Tablet, coatedOral60 mg
TabletOral300.00 mg
Tablet, film coatedOral
Tablet, film coatedOral600 mg/1
TabletOral300.000 mg
TabletOral351.38 mg
TabletOral351.390 mg
Kit; tablet, film coatedOral
TabletOral351.000 mg
SolutionOral20 mg/1mL
SolutionOral20 mg / mL
TabletOral300 mg
Tablet, film coatedOral300 mg/1
SolutionOral300 mg/15mL
SolutionOral20 mg/ml
SolutionOral300 mg
TabletOral
SolutionOral2000 mg
SolutionOral100 mg/5ml
Tablet, film coatedOral300 mg
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)Region
US5089500No1992-02-182009-12-26US flag
CA2289753No2007-01-232018-05-14Canada flag
CA1340589No1999-06-082016-06-08Canada flag
CA2216634No2004-07-202016-03-28Canada flag
US9242986Yes2016-01-262030-06-08US flag
US5905082Yes1999-05-182016-11-18US flag
US6294540Yes2001-09-252018-11-14US flag
US6641843Yes2003-11-042019-08-04US flag
US6417191Yes2002-07-092016-09-28US flag
US8129385Yes2012-03-062028-04-05US flag

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)5.8Chemaxon
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-MSsplash10-004i-4290000000-ff09f3896a50abd46e5c
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0090000000-4dc6311d7b8a16353e41
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0090000000-701d4fe3120cc7c68138
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0890000000-3ee175a900f025a2bee9
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-014l-0890000000-ebbe4b71838fe261ea76
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0940000000-4e7c408ae610ccceaf9b
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-01ot-0980000000-9f447d1dd85c25922db7
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-182.0826554
predicted
DarkChem Lite v0.1.0
[M-H]-162.7835
predicted
DeepCCS 1.0 (2019)
[M+H]+181.3721554
predicted
DarkChem Lite v0.1.0
[M+H]+165.1415
predicted
DeepCCS 1.0 (2019)
[M+Na]+182.1054554
predicted
DarkChem Lite v0.1.0
[M+Na]+171.89769
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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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. [Article]
  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. [Article]
  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. [Article]
2. HLA class I histocompatibility antigen, B-57 alpha chain
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
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. [Article]

Enzymes

Kind
Protein
Organism
Humans
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. [Article]
Kind
Protein
Organism
Humans
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. [Article]
Kind
Protein
Organism
Humans
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. [Article]

Drug created at June 13, 2005 13:24 / Updated at March 18, 2024 16:48