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

General Information of Drug (ID: DR0140)
Drug Name
Artemether
Synonyms
Artemetero; Artemetero [INN-Spanish]; Artemether; Artemether Labeled d3; Artemether [INN]; Artemetherum; Artemetherum [INN-Latin]; Artemisininelactol methyl ether; Artemos; Artenam; Artesaph; Dihydroartemisinin methyl ether; Dihydroqinghaosu methyl ether; Dihydroquinghaosu methyl ether; Falcidol; Malartem; Methyl-dihydroartemisinine; SM 224; SM-224; beta-Artemether; methoxy(trimethyl)[?]; 71963-77-4; C16H26O5; CHEBI:195280; CPD000469218; Gvither; HSDB 7456; NSC 665970; beta-Dihydroartemisinin methyl ether
Indication Malaria [ICD11: 1F40] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 298.37 Topological Polar Surface Area 46.2
Heavy Atom Count 21 Rotatable Bond Count 1
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
68911
ChEBI ID
CHEBI:195280
CAS Number
71963-77-4
TTD Drug ID
D0M9BW
Formula
C16H26O5
Canonical SMILES
CC1CCC2C(C(OC3C24C1CCC(O3)(OO4)C)OC)C
InChI
1S/C16H26O5/c1-9-5-6-12-10(2)13(17-4)18-14-16(12)11(9)7-8-15(3,19-14)20-21-16/h9-14H,5-8H2,1-4H3/t9-,10-,11+,12+,13+,14-,15-,16-/m1/s1
InChIKey
SXYIRMFQILZOAM-HVNFFKDJSA-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
9,10-dihydrodeoxy-artemsinin DM001754 N. A. Unclear 1 [7]
Alpha-dihydroartemisinin DM001755
456410
Unclear 1 [7]
Deoxyartemsinin DM001756
156094
Unclear 1 [7]
Deoxydihydro-artemisinin DM001757
496630
Unclear 1 [7]
Dihydroartemisinin DM001753
131770024
Oxidation - Oxidation 1 [8]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000298 Artemether Dihydroartemisinin Oxidation - Oxidation CYP2B6 ... [8]
MR000299 Artemether 9,10-dihydrodeoxy-artemsinin Unclear Unclear [7]
MR000300 Artemether Alpha-dihydroartemisinin Unclear CYP2B6 [7]
MR000301 Artemether Deoxyartemsinin Unclear CYP2B6 [7]
MR000302 Artemether Deoxydihydro-artemisinin Unclear CYP2B6 [7]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2B6 (CYP2B6) DME0020 Homo sapiens
CP2B6_HUMAN
1.14.14.1
[2]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[3]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[4]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[5]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[6]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[4]
⏷ Show the Full List of 6  DME(s)
References
1 Artemether was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Insights into CYP2B6-mediated drug-drug interactions. Acta Pharm Sin B. 2016 Sep;6(5):413-425.
3 Pharmacokinetic interaction between etravirine or darunavir/ritonavir and artemether/lumefantrine in healthy volunteers: a two-panel, two-way, two-period, randomized trial. HIV Med. 2013 Aug;14(7):421-9.
4 The contribution of the enzymes CYP2D6 and CYP2C19 in the demethylation of artemether in healthy subjects. Eur J Drug Metab Pharmacokinet. 1998 Jul-Sep;23(3):429-36.
5 The effect of grapefruit juice on the time-dependent decline of artemether plasma levels in healthy subjects. Clin Pharmacol Ther. 1999 Oct;66(4):408-14.
6 Effect of pharmacogenetics on plasma lumefantrine pharmacokinetics and malaria treatment outcome in pregnant women. Malar J. 2017 Jul 3;16(1):267.
7 DrugBank(Pharmacology-Metabolism)Artemether
8 Use of a physiologically-based pharmacokinetic model to simulate artemether dose adjustment for overcoming the drug-drug interaction with efavirenz In Silico Pharmacol. 2013 Mar 1;1:4. doi: 10.1186/2193-9616-1-4.

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