Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR0027)
Drug Name
Abacavir
Synonyms
Abacavir (INN); Abacavir [INN:BAN]; Abacavir sulfate; CHEBI:421707; MFCD00903850; NSC742406; UNII-WR2TIP26VS; [(1S,4R)-4-[2-amino-6-(cyclopropylamino)purin-9-yl]cyclopent-2-en-1-yl]methanol; abacavir; {(1S-cis)-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]cyclopent-2-en-1-yl}methanol; Ziagen; (+/-)-Abacavir; (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)-; WR2TIP26VS
Indication Human immunodeficiency virus infection [ICD11: 1C60] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 286.33 Topological Polar Surface Area 102
Heavy Atom Count 21 Rotatable Bond Count 4
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 6
Cross-matching ID
PubChem CID
441300
PubChem SID
9826 ; 603460 ; 612310 ; 7978623 ; 10298786 ; 14775540 ; 14799909 ; 26757979 ; 26757980 ; 36885172 ; 46505718 ; 51091399 ; 57403623 ; 70504220 ; 76364492 ; 81092778 ; 85612588 ; 92729708 ; 103463308 ; 104052305 ; 104625144 ; 126654052 ; 128575040 ; 131298145 ; 135025044 ; 136345668 ; 137006087 ; 142178555 ; 160845918 ; 160964383 ; 162011475 ; 162176802 ; 163621096 ; 163686421 ; 163883088 ; 164814948 ; 165235811 ; 175267614 ; 175442679 ; 179149865 ; 184545024 ; 186014779 ; 196109919 ; 223516662 ; 223703089 ; 223704757 ; 223900945 ; 226424139 ; 241033176 ; 241383802
ChEBI ID
ChEBI:2360
CAS Number
136470-78-5
TTD Drug ID
D0A4IJ
Formula
C14H18N6O
Canonical SMILES
C1CC1NC2=NC(=NC3=C2N=CN3C4CC(C=C4)CO)N
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
InChIKey
MCGSCOLBFJQGHM-SCZZXKLOSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
1144U88 DM000581
10582871
Unclear 1 [6]
2269W93(Carboxylate) DM000579
56927907
Oxidation - Oxidation 1 [3]
361W94(glucuronide) DM000580
29969962
Conjugation - Glucuronidation 1 [7]
Abacavir monophosphate DM000576
469588
Other reaction - Phosphorylation 1 [4]
Carbovir monophosphate DM000577
135457337
Oxidation - Deamination 2 [4]
Carbovir triphosphate DM000578
135499583
Other reaction - Phosphorylation 3 [4] , [8]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000003 Abacavir Abacavir monophosphate Other reaction - Phosphorylation ADK [4]
MR000004 Abacavir 2269W93(Carboxylate) Oxidation - Oxidation ADH [3]
MR000005 Abacavir 361W94(glucuronide) Conjugation - Glucuronidation UGT2B7 [7]
MR000006 Abacavir 1144U88 Unclear Unclear [6]
MR000001 Abacavir monophosphate Carbovir monophosphate Oxidation - Deamination Unclear [4]
MR000002 Carbovir monophosphate Carbovir triphosphate Other reaction - Phosphorylation Unclear [4], [8]
⏷ Show the Full List of 6 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Adenosine kinase (ADK) DME0448 Homo sapiens
ADK_HUMAN
2.7.1.20
[2]
Alcohol dehydrogenase (ADH) DME1317 Lactobacillus reuteri
A4L2V0_LACRE
1.1.1.1
[3]
Alcohol dehydrogenase class-V (ADH6) DME0073 Homo sapiens
ADH6_HUMAN
1.1.1.1
[4]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[5]
UDP-glucuronosyltransferase 2B7 (UGT2B7) DME0040 Homo sapiens
UD2B7_HUMAN
2.4.1.17
[5]
References
1 Abacavir was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 A review of the pharmacokinetics of abacavir Clin Pharmacokinet. 2008;47(6):351-71. doi: 10.2165/00003088-200847060-00001.
3 The metabolic activation of abacavir by human liver cytosol and expressed human alcohol dehydrogenase isozymes Chem Biol Interact. 2002 Nov 10;142(1-2):135-54. doi: 10.1016/s0009-2797(02)00059-5.
4 A review of the pharmacokinetics of abacavir. Clin Pharmacokinet. 2008;47(6):351-71.
5 Product characteristics of Triumeq.
6 Pharmacokinetics of [(14)C]abacavir, a human immunodeficiency virus type 1 (HIV-1) reverse transcriptase inhibitor, administered in a single oral dose to HIV-1-infected adults: a mass balance study Antimicrob Agents Chemother. 1999 Dec;43(12):2855-61. doi: 10.1128/AAC.43.12.2855.
7 Product characteristics of Triumeq
8 Abacavir Increases Purinergic P2X7 Receptor Activation by ATP: Does a Pro-inflammatory Synergism Underlie Its Cardiovascular Toxicity?. Front Pharmacol. 2021 Mar 31;12:613449. doi: 10.3389/fphar.2021.613449.

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