Drug

D0002 | Abacavir

Molecular Formula C14H18N6O
Molecular Weight 286.33
Structure
State solid
Clearance * 0.80 ± 0.24 L/hr/kg [asymptomatic, HIV-1-infected adult patients receiving single (IV dose of 150 mg]
Volume of distribution * 0.86 ± 0.15 L/kg [IV administration]
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.
Protein binding Moderate (approximately 50%). Binding of abacavir to plasma protein was independent of concentration.
Half life 1.54 ± 0.63 hours
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.
Trade names Ziagen
Description nucleoside analog reverse transcriptase inhibitor (NRTI) to treat HIV and AIDS; a synthetic carbocyclic nucleoside; guanine analogue

J

J05AR13 Lamivudine, abacavir and dolutegravir


[J05AR] Antivirals for treatment of HIV infections, combinations


[J05A] DIRECT ACTING ANTIVIRALS


[J05] ANTIVIRALS FOR SYSTEMIC USE


[J] Antiinfectives for systemic use


J05AR04 Zidovudine, lamivudine and abacavir


[J05AR] Antivirals for treatment of HIV infections, combinations


[J05A] DIRECT ACTING ANTIVIRALS


[J05] ANTIVIRALS FOR SYSTEMIC USE


[J] Antiinfectives for systemic use


J05AR02 Lamivudine and abacavir


[J05AR] Antivirals for treatment of HIV infections, combinations


[J05A] DIRECT ACTING ANTIVIRALS


[J05] ANTIVIRALS FOR SYSTEMIC USE


[J] Antiinfectives for systemic use


J05AF06 Abacavir


[J05AF] Nucleoside and nucleotide reverse transcriptase inhibitors


[J05A] DIRECT ACTING ANTIVIRALS


[J05] ANTIVIRALS FOR SYSTEMIC USE


[J] Antiinfectives for systemic use


Toxicity Dose Time Species Model Method Action Positive criterion Reference
MITOCHONDRIAL DNA METABOLIC PROCESS 185
MITOCHONDRIAL DNA METABOLIC PROCESS 194

Target Dose Time Species Model Method Action Positive criterion Reference
DNA polymerase gamma 194

Pictogram Signal Statements Precautionary Statement Codes
Warning

Aggregated GHS information provided by 39 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.


H302 (89.74%): Harmful if swallowed [Warning Acute toxicity, oral]


H319 (89.74%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]


H341 (94.87%): Suspected of causing genetic defects [Warning Germ cell mutagenicity]


H351 (92.31%): Suspected of causing cancer [Warning Carcinogenicity]


H361 (94.87%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]


Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.


P201, P202, P264, P270, P280, P281, P301+P312, P305+P351+P338, P308+P313, P330, P337+P313, P405, and P501; (The corresponding statement to each P-code can be found at the GHS Classification page.)

  • Disease progression

  • Drug interaction

  • Epilepsy

  • Hypersensitivity

  • Immunodeficiency

  • Infection

  • Pathogen resistance

  • Chills (0.12)

  • Pruritus (0.17)

  • Abdominal discomfort

  • Abnormal dreams

  • Anxiety

  • Asthenia

  • Body temperature increased

  • Cough

  • Depression

  • Dermatitis

  • Diarrhoea

  • Discomfort

  • Dizziness

  • Drug hypersensitivity

  • Fatigue

  • Feeling abnormal

  • Headache

  • Ill-defined disorder

  • Infection

  • Insomnia

  • Malaise

  • Musculoskeletal pain

  • Nausea

  • Neuropathy peripheral

  • Pain

  • Rash

  • Sleep disorder

  • Vomiting

  • ((1s,4r)-4-(2-amino-6-(cyclopropylamino)-9h-purin-9-yl)cyclopent-2-enyl)methanol (+/-)-4-[2-Amino-6-(cyclopropylamino)-9H-purin-9-yl]-2-cyclopentene-1-methanol (+/-)-Abacavir
    (+/-)-cis-4-[2-Amino-6-(cyclopropylamino)-9H-purin-9-yl]-2-cyclopentene-1-methanol (1S,4R)-4-[2-Amino-6-(cyclopropylamino)-9H-purin-9-yl]-2-cyclopentene-1-methanol 136470-78-5
    1592U89 2-Cyclopentene-1-methanol, 4-(2-amino-6-(cyclopropylamino)-9H-purin-9-yl)-, (1S,4R)- 2-Cyclopentene-1-methanol, 4-(2-amino-6-(cyclopropylamino)-9H-purin-9-yl)-, (1S-cis)-
    2-Cyclopentene-1-methanol, 4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]-, (1S,4R)- 470A785 A807079
    AB01566826_01 AC-1299 ACT03218
    AK163479 AKOS024464970 Abacavir (INN)
    Abacavir [INN:BAN] Abacavir sulfate BCP07728
    BDBM50366816 C-18039 C07624
    CC-23613 CHEBI:421707 CHEMBL1380
    CS-1354 D07057 DB01048
    EN300-258000 Epitope ID:137341 FT-0631153
    HY-17423 J-700136 KS-00000XJM
    MCGSCOLBFJQGHM-SCZZXKLOSA-N MFCD00903850 MLS006010117
    NCGC00164560-01 NCGC00164560-02 NSC742406
    Q304330 SC-16996 SC-20023
    SCHEMBL38632 SMR004701251 ST24045890
    UNII-WR2TIP26VS W-5205 WR2TIP26VS
    ZINC2015928 Ziagen Ziagen (TM)(*Succinate salt*)
    [(1S,4R)-4-[2-amino-6-(cyclopropylamino)-9-purinyl]-1-cyclopent-2-enyl]methanol [(1S,4R)-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]cyclopent-2-en-1-yl]methanol [(1S,4R)-4-[2-amino-6-(cyclopropylamino)purin-9-yl]cyclopent-2-en-1-yl]methanol
    [(1S,4R)-4-[2-azanyl-6-(cyclopropylamino)purin-9-yl]cyclopent-2-en-1-yl]methanol [(1s,4r)-4-[2-amino-6-(cyclopropylamino)purin-9-yl]-1-cyclopent-2-enyl]methanol abacavir
    {(1S,4R)-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]cyclopent-2-en-1-yl}methanol {(1S-cis)-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]cyclopent-2-en-1-yl}methanol

    DrugBank Name Abacavir
    DrugBank DB01048
    CAS Number 136470-78-5, 188062-50-2
    PubChem Compound 441300
    KEGG Compound ID C07624
    KEGG Drug D07057
    PubChem.Substance 46505718
    ChEBI 421707
    PharmGKB PA448004
    ChemSpider 390063
    BindingDB 50366816.0
    TTD DAP000704
    Wikipedia Abacavir
    HET 1KX
    DPD 11893

    1. Chan et al. (2005)
    2. Dykens et al. (2007)