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

General Information of Drug (ID: DR0912)
Drug Name
Lamivudine
Synonyms
Lamivudine [USAN:BAN:INN]; Epivir; Epivir-HBV; Hepitec; Heptivir; Heptodin; Heptovir; Zeffix; lamivudine; (-)-2'-Deoxy-3'-thiacytidine; (-)-BCH 189; (-)-BCH-189; (-)NGPB-21; 134678-17-4; 2',3'-Dideoxy-3'-thiacytidine; 3'-Thia-2',3'-dideoxycytidine; 3TC; 4-amino-1-((2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl)pyrimidin-2(1H)-one; BCH-189; GR 109714X; GR-109714X; GR109714X; CIS-LAMIVUDINE; HSDB 7155; UNII-2T8Q726O95; beta-L-2',3'-Dideoxy-3'-thiacytidine; beta-L-3'-Thia-2',3'-dideoxycytidine
Indication Human immunodeficiency virus infection [ICD11: 1C60] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 229.26 Topological Polar Surface Area 113
Heavy Atom Count 15 Rotatable Bond Count 2
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
60825
PubChem SID
9277 ; 596236 ; 601313 ; 643736 ; 811475 ; 3727051 ; 3727058 ; 7847419 ; 7979719 ; 8187080 ; 11528367 ; 12014700 ; 12016245 ; 14798125 ; 15121620 ; 24277302 ; 26719826 ; 29215254 ; 43118163 ; 46386600 ; 46507855 ; 49681736 ; 50140269 ; 57314135 ; 81093205 ; 85279382 ; 87560180 ; 92308311 ; 92712464 ; 92729822 ; 93166191 ; 103195019 ; 103977094 ; 104170203 ; 104253324 ; 104321740 ; 117588081 ; 118048664 ; 121362453 ; 124658974 ; 124757443 ; 124892101 ; 125164247 ; 126584422 ; 126592947 ; 126625491 ; 126656696 ; 126665392 ; 127310181 ; 127310182
ChEBI ID
CHEBI:63577
CAS Number
134678-17-4
TTD Drug ID
D07TQV
Formula
C8H11N3O3S
Canonical SMILES
C1C(OC(S1)CO)N2C=CC(=NC2=O)N
InChI
1S/C8H11N3O3S/c9-5-1-2-11(8(13)10-5)6-4-15-7(3-12)14-6/h1-2,6-7,12H,3-4H2,(H2,9,10,13)/t6-,7+/m0/s1
InChIKey
JTEGQNOMFQHVDC-NKWVEPMBSA-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
Lamivudine monophosphate DM000199
503017
Other reaction - Phosphorylation 1 [4] , [6]
Lamivudine sulfoxide DM000203
3081342
Unclear 1 [5]
Lamivudine diphosphate DM000200
75607483
Other reaction - Phosphorylation 2 [4] , [6]
Lamivudine triphosphate DM000201
454110
Other reaction - Phosphorylation 3 [4] , [6]
Lamivudine metabolite M DM000202
91971784
Unclear 4 [4] , [7]
Lamivudine monophosphate DM000199
503017
Unclear 5 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR001408 Lamivudine Lamivudine monophosphate Other reaction - Phosphorylation Ks [4], [6]
MR001409 Lamivudine Lamivudine sulfoxide Unclear SULT1B1 [5]
MR001404 Lamivudine monophosphate Lamivudine diphosphate Other reaction - Phosphorylation Ks [4], [6]
MR001405 Lamivudine diphosphate Lamivudine triphosphate Other reaction - Phosphorylation PGK2 ... [4], [6]
MR001406 Lamivudine triphosphate Lamivudine metabolite M Unclear Unclear [4], [7]
MR001407 Lamivudine metabolite M Lamivudine monophosphate Unclear Unclear [4]
⏷ 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
Deoxy-5'-nucleotidase 1 (NT5C) DME0150 Homo sapiens
NT5C_HUMAN
3.1.3.5
[2]
Nucleoside diphosphate kinase (NME4) DMEN006 Homo sapiens
NDKM_HUMAN
2.7.4.10
[3]
Phosphoglycerate kinase 2 (PGK2) DMEN005 Homo sapiens
PGK2_HUMAN
2.7.4.6
[3]
Phosphorylcholine transferase A (PCYT1A) DME0151 Homo sapiens
PCY1A_HUMAN
2.7.7.15
[4]
Phosphorylethanolamine transferase (PCYT2) DME0152 Homo sapiens
PCY2_HUMAN
2.7.7.14
[4]
Sulfotransferase 1B1 (SULT1B1) DME0380 Homo sapiens
ST1B1_HUMAN
2.8.2.1
[5]
⏷ Show the Full List of 6  DME(s)
References
1 Lamivudine was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Nucleoside and nucleotide HIV reverse transcriptase inhibitors: 25 years after zidovudine. Antiviral Res. 2010 Jan;85(1):39-58.
3 Model for intracellular Lamivudine metabolism in peripheral blood mononuclear cells ex vivo and in human immunodeficiency virus type 1-infected adolescents Antimicrob Agents Chemother. 2006 Aug;50(8):2686-94. doi: 10.1128/AAC.01637-05.
4 Model for intracellular Lamivudine metabolism in peripheral blood mononuclear cells ex vivo and in human immunodeficiency virus type 1-infected adolescents. Antimicrob Agents Chemother. 2006 Aug;50(8):2686-94.
5 Pharmacogenomics knowledge for personalized medicine Clin Pharmacol Ther. 2012 Oct;92(4):414-7. doi: 10.1038/clpt.2012.96.
6 Antiviral and cellular metabolism interactions between Dexelvucitabine and lamivudine Antimicrob Agents Chemother. 2007 Jun;51(6):2130-5. doi: 10.1128/AAC.01543-06.
7 An open-label, randomized, single intravenous dosing study to investigate the effect of fixed-dose combinations of tenofovir/lamivudine or atazanavir/ritonavir on the pharmacokinetics of remdesivir in Ugandan healthy volunteers (RemTLAR). Trials. 2021 Nov 23;22(1):831. doi: 10.1186/s13063-021-05752-1.

If you find any error in data or bug in web service, please kindly report it to Dr. Yin and Dr. Li.