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

General Information of Drug (ID: DR5926)
Drug Name
Artesunate
Synonyms
Artesunate|Artesunic acid|Arsumax|88495-63-0|Plasmotrin|Qinghaozhi|Saphnate|Dihydroqinghasu hemsuccinate|Artesunatum|Zysunate|Arinate|Arsuamoon|Artesunato|Asumax|Gsunate Forte|cosunate|Artesunata|Plasmotrim|Cosinate|Artesunate [INN]|CHEBI:63918|.alpha.-artesunic acid|Armax 200|Dihydroqinghaosu hemisuccinate|Artesunate [USAN:INN:BAN]|artesunate amivas|Succinyl dihydroartemisinin|UNII-60W3249T9M|HSDB 7458|LJPC-0118|Dihydroartemisinine-12alpha-succinate|60W3249T9M|NSC-712571|Butanedioic acid, 1-[(3R,5aS,6R,8aS,9R,10S,12R,12aR)-decahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin-10-yl] ester|WR-256283|Artesunatum [INN-Latin]|SM 804|Artesunato [INN-Spanish]|Artsuna|Nuartez|Quinghaosu reduced succinate ester|Artesunate [USAN]|4-oxo-4-(((3R,5aS,6R,8aS,9R,10S,12R,12aR)-3,6,9-trimethyldecahydro-3H-3,12-epoxy[1,2]dioxepino[4,3-i]isochromen-10-yl)oxy)butanoic acid|4-oxo-4-{[(3R,5aS,6R,8aS,9R,10S,12R,12aR)-3,6,9-trimethyldecahydro-3,12-epoxypyrano[4,3-j][1,2]benzodioxepin-10-yl]oxy}butanoic acid|Butanedioic acid, mono((3R,5aS,6R,8aS,9R,10S,12R,12aR)-decahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano(4,3-j)-1,2-benzodioxepin-10-yl) ester|WR 256283|Artesunate [USAN:INN]|DTXSID3042681|C19-H28-O8|(3R,5aS,6R,8aS,9R,10S,12R,12aR)-Decahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano(4,3-j)-1,2-benzodioxepin-10-ol, hydrogen succinate|D95|ARTESUNATE [MI]|ARTESUNATE [HSDB]|ARTESUNATE [VANDF]|ARTESUNATE [MART.]|ARTESUNATE [USP-RS]|ARTESUNATE [WHO-DD]|ARTESUNATE [WHO-IP]|MLS006011590|CHEMBL361497|GTPL9956|ARTESUNATE [ORANGE BOOK]|SCHEMBL14552891|FIHJKUPKCHIPAT-AHIGJZGOSA-N|ARTESUNATUM [WHO-IP LATIN]|4-Oxo-4-(((3R,5aS,6R,8aS,9R,10S,12R,12aR)-3,6,9-trimethyldecahydro-3,12-epoxypyrano(4,3-j)-1,2-benzodioxepin-10-yl hydrogen butanedioate|4-oxo-4-[[(1R,4S,5R,8S,9R,10S,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-yl]oxy]butanoic acid|HY-N0193|STR09744|BDBM50248021|AKOS037515734|CS-8151|DB09274|NCGC00164600-10|NCGC00164600-15|SMR002499399|DIHYDROARTEMISININE-12.ALPHA.-SUCCINATE|EN300-6482026|Q707939|BRD-K54634444-001-05-9|WR-256283;ART;Armax 200;SM-804;HSDB-7458|3R,5AS,6R,8AS,9R,10S,12R,12AR)-3,6,9-TRIMETHYLDECAHYDRO-3,12-EPOXY-12H-PYRANO(4,3-J)-1,2-BENZODIOXEPIN-10-YL HYDROGEN BUTANEDIOATE|4-OXO-4-(3R,5AS,6R,8AS,9R,10S,12R,12AR)-3,6,9-TRIMETHYLDECAHYDRO-3,12-EPOXYPYRANO(4,3-J)-1,2-BENZODIOXEPIN-10-YL HYDROGEN BUTANEDIOATE|4-oxo-4-{[(1R,4S,5R,8S,9R,10S,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0?,(1)(3).0?,(1)(3)]hexadecan-10-yl]oxy}butanoic acid|4-oxo-4-{[(1R,4S,5R,8S,9R,10S,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0^{4,13}.0^{8,13}]hexadecan-10-yl]oxy}butanoic acid|BUTANEDIOIC ACID, MONO(DECAHYDRO-3,6,9-TRIMETHYL-3,12-EPOXY-12H-PYRANO(4,3-J)-1,2-BENZODIOXEPIN-10-YL) ESTER, (3R-(3.ALPHA.,5A.BETA.,6.BETA.,8A.BETA.,9.ALPHA.,10.BETA.,12.BETA.,12AR*))-
Indication Malaria [ICD11: 1F40-1F45] Approved [1]
Pharmaceutical Properties Molecular Weight 384.4 Topological Polar Surface Area 101
Heavy Atom Count 27 Rotatable Bond Count 5
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 8
Cross-matching ID
PubChem CID
6917864
Formula
C19H28O8
Canonical SMILES
CC1CCC2C(C(OC3C24C1CCC(O3)(OO4)C)OC(=O)CCC(=O)O)C
InChI
InChI=1S/C19H28O8/c1-10-4-5-13-11(2)16(23-15(22)7-6-14(20)21)24-17-19(13)12(10)8-9-18(3,25-17)26-27-19/h10-13,16-17H,4-9H2,1-3H3,(H,20,21)/t10-,11-,12+,13+,16-,17-,18-,19-/m1/s1
InChIKey
FIHJKUPKCHIPAT-AHIGJZGOSA-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
Dihydroartemisinin DM001753
131770024
Unclear 1 [6] , [7]
Dihydroartemisinin Glucuronide DM004991 N. A. Unclear 2 [4] , [5]
Furano Acetate of Dihydroartemisinin DM004992 N. A. Unclear 3 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR005413 Artesunate Dihydroartemisinin Unclear Unclear [6], [7]
MR005414 Dihydroartemisinin Dihydroartemisinin Glucuronide Unclear UGT1A9 ... [4], [5]
MR005415 Dihydroartemisinin Glucuronide Furano Acetate of Dihydroartemisinin Unclear Unclear [4]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2A6 (CYP2A6) DME0005 Homo sapiens
CP2A6_HUMAN
1.14.14.1
[2]
Exported protein 1 (EXP1) DMEN829 Bacteroides fragilis Not Available Not Available [3]
UDP-glucuronosyltransferase 1A9 (UGT1A9) DME0042 Homo sapiens
UD19_HUMAN
2.4.1.17
[4] , [5]
UDP-glucuronosyltransferase 1A9 (UGT1A9) DME0042 Homo sapiens
UD19_HUMAN
2.4.1.17
[4]
UDP-glucuronosyltransferase 2B7 (UGT2B7) DME0040 Homo sapiens
UD2B7_HUMAN
2.4.1.17
[4] , [5]
UDP-glucuronosyltransferase 2B7 (UGT2B7) DME0040 Homo sapiens
UD2B7_HUMAN
2.4.1.17
[4]
⏷ Show the Full List of 6  DME(s)
References
1 The fight against drug-resistant malaria: novel plasmodial targets and antimalarial drugs. Curr Med Chem. 2008;15(2):161-71.
2 High prevalence of CYP2A6*4 and CYP2A6*9 alleles detected among a Malaysian population
3 Supergenomic network compression and the discovery of EXP1 as a glutathione transferase inhibited by artesunate
4 Glucuronidation of dihydroartemisinin in vivo and by human liver microsomes and expressed UDP-glucuronosyltransferases
5 LC-MS/MS method for the simultaneous quantification of artesunate and its metabolites dihydroartemisinin and dihydroartemisinin glucuronide in human plasma
6 Predicting the Disposition of the Antimalarial Drug Artesunate and Its Active Metabolite Dihydroartemisinin Using Physiologically Based Pharmacokinetic Modeling
7 Review of the clinical pharmacokinetics of artesunate and its active metabolite dihydroartemisinin following intravenous, intramuscular, oral or rectal administration

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