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

General Information of Drug (ID: DR2400)
Drug Name
Levamisole
Synonyms
Dl-Tetramisol; Dl-Tetramisole; Ergamisol (TN); Ketrax; Ketrax (TN); L(-)-Levamisole; L-Tetramisole; LEVOMYSOL; Lepuron; Levamisol; Levamisol [INN-Spanish]; Levamisole (INN); Levamisole Base;Nilverm base; Levamisole [INN:BAN]; Levamisolum; Levamisolum [INN-Latin]; Levotetramisole; P00039; TCMDC-125847; Tetramisol; Vermisol 150; Wormicid; (-)-Tetramisole; (6S)-6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b][1,3]thiazole; (S)-(-)-Levamisole; L-2,3,5,6-Tetrahyro-6-phenylimidazo(2,1-b)thiazole
Indication Ascariasis [ICD11: 1F62] Discontinued [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 204.29 Topological Polar Surface Area 40.9
Heavy Atom Count 14 Rotatable Bond Count 1
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
26879
PubChem SID
9282 ; 602395 ; 7979761 ; 8169434 ; 10322011 ; 11335842 ; 11361081 ; 11364503 ; 11367065 ; 11369627 ; 11371883 ; 11374574 ; 11377789 ; 11405871 ; 11462053 ; 11466210 ; 11467330 ; 11484645 ; 11485760 ; 11488681 ; 11490777 ; 11492892 ; 11495423 ; 14748767 ; 15171780 ; 34669469 ; 46509052 ; 47440260 ; 47589003 ; 47736487 ; 47736488 ; 48035125 ; 48416165 ; 49761633 ; 49831041 ; 49981671 ; 50111118 ; 53790505 ; 56313649 ; 56313755 ; 57310333 ; 76000434 ; 85789251 ; 85860304 ; 90341409 ; 92309280 ; 92717075 ; 93166530 ; 96024804 ; 103523408
ChEBI ID
CHEBI:6432
CAS Number
14769-73-4
TTD Drug ID
D0CF2Q
Formula
C11H12N2S
Canonical SMILES
C1CSC2=NC(CN21)C3=CC=CC=C3
InChI
1S/C11H12N2S/c1-2-4-9(5-3-1)10-8-13-6-7-14-11(13)12-10/h1-5,10H,6-8H2/t10-/m1/s1
InChIKey
HLFSDGLLUJUHTE-SNVBAGLBSA-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
Aminorex DM006912
16630
Unclear 1 [4]
O.M.P.I. DM006911 N. A. Unclear 1 [4]
p-hydroxylevamisole DM006909
125758
Unclear 1 [4]
Glucuronic acid of p-hydroxylevamisole DM006910 N. A. Unclear 2 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR007520 Levamisole p-hydroxylevamisole Unclear Unclear [4]
MR007522 Levamisole O.M.P.I. Unclear Unclear [4]
MR007523 Levamisole Aminorex Unclear Unclear [4]
MR007521 p-hydroxylevamisole Glucuronic acid of p-hydroxylevamisole Unclear Unclear [4]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Unclear metabolic mechanism (DME-unclear) DME1251 Bacteroides fragilis Not Available Not Available [2]
Unclear metabolic mechanism (DME-unclear) DME1253 Bacteroides oleiciplenus Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1254 Bacteroides thetaiotaomicron Not Available Not Available [2]
Unclear metabolic mechanism (DME-unclear) DME1256 Bacteroides sartorii Not Available Not Available [2]
Unclear metabolic mechanism (DME-unclear) DME1265 Escherichia coli Not Available Not Available [2]
Unclear metabolic mechanism (DME-unclear) DME1358 Anaerococcus hydrogenalis Not Available Not Available [2]
Unclear metabolic mechanism (DME-unclear) DME1361 Anaerotruncus colihominis Not Available Not Available [2]
Unclear metabolic mechanism (DME-unclear) DME1365 Bacteroides dorei Not Available Not Available [2]
Unclear metabolic mechanism (DME-unclear) DME1379 Bacteroides stercoris Not Available Not Available [2]
Unclear metabolic mechanism (DME-unclear) DME1384 Bacteroides vulgatus Not Available Not Available [2]
Unclear metabolic mechanism (DME-unclear) DME1385 Bacteroides xylanisolvens Not Available Not Available [2]
Unclear metabolic mechanism (DME-unclear) DME1398 Clostridioides difficile Not Available Not Available [2]
Unclear metabolic mechanism (DME-unclear) DME1402 Clostridium botulinum Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1404 Clostridium sporogenes Not Available Not Available [2]
Unclear metabolic mechanism (DME-unclear) DME1413 Edwardsiella tarda Not Available Not Available [2]
Unclear metabolic mechanism (DME-unclear) DME1444 Odoribacter splanchnicus Not Available Not Available [2]
Unclear metabolic mechanism (DME-unclear) DME1446 Parabacteroides johnsonii Not Available Not Available [2]
⏷ Show the Full List of 17  DME(s)
References
1 Complications associated with use of levamisole-contaminated cocaine: an emerging public health challenge. Mayo Clin Proc. 2012 Jun;87(6):581-6.
2 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.
3 Metabolism of levamisole, an anti-colon cancer drug, by human intestinal bacteria. Xenobiotica. 1991 Jun;21(6):737-50.
4 Aminorex, a metabolite of the cocaine adulterant levamisole, exerts amphetamine like actions at monoamine transporters

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