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

General Information of Drug (ID: DR0141)
Drug Name
Artemisinin
Synonyms
Arteannuin; Artemisinin, 98%; Artemisinin, analytical standard; Artemisinine; Artemisnini; Coartem, 63968-64-9; MCULE-9877817795; Prestwick_818; Qing Hau Sau; SDCCGMLS-0066721.P001; SPECTRUM1503042; UPCMLD-DP074; UPCMLD-DP074:001; artemisinin; (+)-Arteannuin; 3,12-Epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin-10(3H)-one, octahydro-3,6,9-trimethyl-, (3R,5aS,6R,8aS,9R,12S,12aR)-; 63968-64-9; AC-2064; AC1L9Q59; AKOS004119830; BCP9000320; BCPP000391; CA0142; CCG-38886; HMS1569D17; HMS1923O03; HMS502A18; NSC369397; SCHEMBL13428542
Indication Malaria [ICD11: 1F40] Phase 4 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 282.33 Topological Polar Surface Area 54
Heavy Atom Count 20 Rotatable Bond Count 0
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
452191
PubChem SID
11729 ; 597201 ; 3154164 ; 8149879 ; 10321764 ; 11537742 ; 11538015 ; 14873071 ; 17396660 ; 22391483 ; 24263048 ; 24862236 ; 25621962 ; 26612376 ; 26679989 ; 26755288 ; 29203860 ; 46488006 ; 49681218 ; 49698524 ; 49834379 ; 50110885 ; 50110886 ; 57405324 ; 57649481 ; 79908771 ; 87560451 ; 92124957 ; 92125361 ; 92710903 ; 99301744 ; 99437070 ; 103914249 ; 104179191 ; 104644865 ; 108667034 ; 124636730 ; 124757138 ; 125163942 ; 126631402 ; 131480746 ; 135692091 ; 136367381 ; 136368092 ; 140607255 ; 144115625 ; 162249932 ; 163614422 ; 166223153 ; 176484289
CAS Number
63968-64-9
TTD Drug ID
D0S3WH
Formula
C15H22O5
Canonical SMILES
CC1CCC2C(C(=O)OC3C24C1CCC(O3)(OO4)C)C
InChI
1S/C15H22O5/c1-8-4-5-11-9(2)12(16)17-13-15(11)10(8)6-7-14(3,18-13)19-20-15/h8-11,13H,4-7H2,1-3H3/t8-,9-,10+,11+,13-,14?,15-/m1/s1
InChIKey
BLUAFEHZUWYNDE-DCJAHCNHSA-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
9beta-hydroxyartemisinin DM001588 N. A. Unclear 1 [6] , [6]
Artemisinin Metobolite M1-M13 DM001584 N. A. Reduction - Reduction 1 [7]
Artemisinin Metobolite M14-M22 DM001587 N. A. Oxidation - Dihydroxylation 1 [7]
Artemisinin Metobolite M23 DM001581 N. A. Reduction - Reduction 1 [7]
Artemisinin Metobolite M32 DM001578 N. A. Other reaction - Hydrogenation 1 [7]
Artemisinin Metobolite 5 DM001585 N. A. Unclear 2 [6]
Artemisinin Metobolite M24-M31 DM001582 N. A. Reduction - Reduction 2 [7]
Artemisinin Metobolite M33-M37 DM001579 N. A. Other reaction - Hydrogenation 2 [7]
Artemisinin Metobolite M33-M37 DM001579 N. A. Reduction - Reduction 2 [7]
Artemisinin Metobolite M38 DM001583 N. A. Other reaction - Hydrogenation 2 [7]
1alpha-hydroxydeoxyartemisinin DM001586
21602077
Unclear 3 [6]
Artemisinin Metobolite M39 DM001580 N. A. Reduction - Reduction 3 [7]
Artemisinin Metobolite M39 DM001580 N. A. Other reaction - Hydrogenation 3 [7]
⏷ Show the Full List of 13  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR003023 Artemisinin Artemisinin Metobolite M32 Other reaction - Hydrogenation Unclear [7]
MR003028 Artemisinin Artemisinin Metobolite M23 Reduction - Reduction Unclear [7]
MR003033 Artemisinin Artemisinin Metobolite M1-M13 Reduction - Reduction Unclear [7]
MR003035 Artemisinin 9beta-hydroxyartemisinin Unclear Unclear [6], [6]
MR003036 Artemisinin Artemisinin Metobolite M14-M22 Oxidation - Dihydroxylation Unclear [7]
MR003034 Artemisinin Metobolite M1-M13 Artemisinin Metobolite M33-M37 Other reaction - Hydrogenation Unclear [7]
MR003029 Artemisinin Metobolite M23 Artemisinin Metobolite M24-M31 Reduction - Reduction Unclear [7]
MR003031 Artemisinin Metobolite M23 Artemisinin Metobolite M38 Other reaction - Hydrogenation Unclear [7]
MR003024 Artemisinin Metobolite M32 Artemisinin Metobolite M33-M37 Reduction - Reduction Unclear [7]
MR003026 Artemisinin Metobolite M32 Artemisinin Metobolite 5 Unclear Unclear [6]
MR003027 Artemisinin Metobolite 5 1alpha-hydroxydeoxyartemisinin Unclear Unclear [6]
MR003030 Artemisinin Metobolite M24-M31 Artemisinin Metobolite M39 Other reaction - Hydrogenation Unclear [7]
MR003025 Artemisinin Metobolite M33-M37 Artemisinin Metobolite M39 Reduction - Reduction Unclear [7]
MR003032 Artemisinin Metobolite M38 Artemisinin Metobolite M39 Other reaction - Hydrogenation Unclear [7]
⏷ Show the Full List of 14 MR(s)
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]
Cytochrome P450 2B6 (CYP2B6) DME0020 Homo sapiens
CP2B6_HUMAN
1.14.14.1
[3]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[3]
Glutathione S-transferase alpha-1 (GSTA1) DME0011 Homo sapiens
GSTA1_HUMAN
2.5.1.18
[4]
Unclear metabolic mechanism (DME-unclear) DME1251 Bacteroides fragilis Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1254 Bacteroides thetaiotaomicron Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1256 Bacteroides sartorii Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1257 Bifidobacterium longum Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1265 Escherichia coli Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1267 Anaerobutyricum hallii Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1355 Akkermansia muciniphila Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1357 Alistipes indistinctus Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1358 Anaerococcus hydrogenalis Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1360 Anaerostipes hadrus Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1361 Anaerotruncus colihominis Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1363 Bacteroides cellulosilyticus Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1365 Bacteroides dorei Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1366 Bacteroides eggerthii Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1367 Bacteroides finegoldii Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1375 Bacteroides intestinalis Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1376 Bacteroides ovatus Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1377 Bacteroides pectinophilus Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1378 Bacteroides uniformis Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1379 Bacteroides stercoris Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1384 Bacteroides vulgatus Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1385 Bacteroides xylanisolvens Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1386 Bifidobacterium adolescentis Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1388 Bifidobacterium breve Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1391 Bifidobacterium ruminatum Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1393 Blautia hansenii Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1394 Blautia luti Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1398 Clostridioides difficile Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1399 Enterocloster asparagiformis Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1400 Enterocloster bolteae Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1401 Clostridium scindens Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1402 Clostridium botulinum Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1403 Clostridium spiroforme Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1404 Clostridium sporogenes Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1405 Clostridium symbiosum Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1407 Collinsella intestinalis Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1408 Coprococcus comes Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1412 Dorea formicigenerans Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1413 Edwardsiella tarda Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1415 Eggerthella lenta Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1416 Enterobacter cancerogenus Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1418 Enterococcus faecalis Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1420 Erysipelatoclostridium ramosum Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1425 Eubacterium rectale Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1427 Eubacterium ventriosum Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1431 Holdemanella biformis Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1432 Hungatella hathewayi Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1435 Lactobacillus reuteri Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1439 Marvinbryantia formatexigens Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1444 Odoribacter splanchnicus Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1445 Parabacteroides distasonis Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1446 Parabacteroides johnsonii Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1447 Parabacteroides merdae Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1449 Prevotella copri Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1451 Proteus penneri Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1452 Providencia alcalifaciens Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1453 Providencia rettgeri Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1454 Providencia stuartii Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1456 Roseburia intestinalis Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1458 Ruminococcus gnavus Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1459 Ruminococcus lactaris Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1460 Ruminococcus torques Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1462 Salmonella enterica Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1467 Subdoligranulum variabile Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1470 Victivallis vadensis Not Available Not Available [5]
⏷ Show the Full List of 69  DME(s)
References
1 ClinicalTrials.gov (NCT01190371) Have Malaria Infections in Kenya Become Less Responsive to Artemisinin Treatment?.
2 Identification of the human cytochrome P450 enzymes involved in the in vitro metabolism of artemisinin. Br J Clin Pharmacol. 1999 Oct;48(4):528-35.
3 Antimalarial artemisinin drugs induce cytochrome P450 and MDR1 expression by activation of xenosensors pregnane X receptor and constitutive androstane receptor. Mol Pharmacol. 2005 Jun;67(6):1954-65.
4 Inhibition of glutathione S-transferases by antimalarial drugs possible implications for circumventing anticancer drug resistance. Int J Cancer. 2002 Feb 10;97(5):700-5.
5 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.
6 Microbial metabolism of artemisinin by Mucor polymorphosporus and Aspergillus niger J Nat Prod. 2002 Nov;65(11):1693-5. doi: 10.1021/np020113r.
7 A Microbial Transformation Model for Simulating Mammal Metabolism of Artemisinin Molecules. 2019 Jan 16;24(2):315. doi: 10.3390/molecules24020315.

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