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

General Information of Drug (ID: DR1752)
Drug Name
Ethionamide
Synonyms
CHEBI:31536; DRG-0208; FTC-(-); HSDB 7337; UNII-G70B4ETF4S; dOTFC; Emtricitabine; Emtritabine; Emtriva; Ethimide; Ethina; Ethinamide; Ethioniamide; Ethylisothiamide; Ethyonomide; Etimid; Etiocidan; Etionamid; Etioniamid; Etionid; Etionizin; Etionizina; Etionizine; Fatoliamid; Iridocin; Iridozin; Isothin; Isotiamida; Itiocide; Nicotion; Nizotin; Racivir; Rigenicid; Sertinon; Teberus; Thianid; Thianide; Thioamide; Aetina; Aetiva; Amidazin; Amidazine; Coviracil; Thioniden; Tianid; Trecator; Trecator-SC; Trekator; Trescatyl; Trescazide; Tubenamide; Tubermin; Tuberoid; Tuberoson; ethionamide; (-)-2'-Deoxy-5-fluoro-3'-thiacytidine; (-)-FTC; 143491-54-7; 143491-57-0; 2',3',5-FTC; 2'-Deoxy-5-fluoro-3'-oxa-4'-thiocytidine; 2'-Deoxy-5-fluoro-3'-thiacytidine; 2-Ethylthioisonicotinamide; 2-FTC; 2-ethylpyridine-4-carbothioamide; 3'-Thia-2'.3'-dideoxy-5-fluorocytidine; 4-amino-5-fluoro-1-((2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl)pyrimidin-2(1H)-one; 524W91; 536-33-4; Atina; BW 1592; BW 524W91; BW-524W91; BW524W91
Indication Human immunodeficiency virus infection [ICD11: 1C60] Approved []
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 166.25 Topological Polar Surface Area 71
Heavy Atom Count 11 Rotatable Bond Count 2
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
2761171
PubChem SID
9867 ; 138261 ; 602897 ; 3189207 ; 5235093 ; 7847657 ; 7979199 ; 8149340 ; 8815239 ; 10321785 ; 10525861 ; 11112402 ; 11335320 ; 11360559 ; 11363976 ; 11366538 ; 11369100 ; 11371336 ; 11374352 ; 11377262 ; 11461531 ; 11466554 ; 11467674 ; 11484823 ; 11486168 ; 11488810 ; 11490244 ; 11492362 ; 11494896 ; 11532957 ; 15413224 ; 17389895 ; 24894350 ; 26611740 ; 26679347 ; 26747295 ; 26747296 ; 26752898 ; 39176212 ; 46506077 ; 47365040 ; 47515175 ; 47515176 ; 47588853 ; 47959584 ; 48184860 ; 48334345 ; 48413732 ; 48415974 ; 48423391
ChEBI ID
ChEBI:4885
CAS Number
536-33-4
TTD Drug ID
D0P0HB
Formula
C8H10N2S
Canonical SMILES
CCC1=NC=CC(=C1)C(=S)N
InChI
1S/C8H10N2S/c1-2-7-5-6(8(9)11)3-4-10-7/h3-5H,2H2,1H3,(H2,9,11)
InChIKey
AEOCXXJPGCBFJA-UHFFFAOYSA-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
2-ethylisonicotinamide DM000925
76905
Unclear 1 [3]
Ethionamide sulphoxide DM000924
71316501
Reduction - Reduction 1 [4] , [3]
2-ethylisonicotinamide DM000925
76905
Unclear 2 [3]
2-ethylisonicotinic acid DM000926
10125075
Unclear 2 [3]
2-ethylisonicotinic acid DM000926
10125075
Unclear 3 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000970 Ethionamide Ethionamide sulphoxide Reduction - Reduction FMO1 ... [4], [3]
MR000971 Ethionamide 2-ethylisonicotinamide Unclear Unclear [3]
MR000968 Ethionamide sulphoxide 2-ethylisonicotinamide Unclear Unclear [3]
MR000969 2-ethylisonicotinamide 2-ethylisonicotinic acid Unclear Unclear [3]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Dimethylaniline oxidase 2 (FMO2) DME0283 Homo sapiens
FMO2_HUMAN
1.14.13.8
[1]
Dimethylaniline oxidase 3 (FMO3) DME0039 Homo sapiens
FMO3_HUMAN
1.14.13.8
[2]
References
1 Drug metabolism by flavin-containing monooxygenases of human and mouse. Expert Opin Drug Metab Toxicol. 2017 Feb;13(2):167-181.
2 Physiologically based pharmacokinetic modeling approach to predict drug-drug interactions with ethionamide involving impact of genetic polymorphism on FMO3. J Clin Pharmacol. 2019 Jun;59(6):880-889.
3 The metabolism of ethionamide and its sulphoxide J Pharm Pharmacol. 1967 Jan;19(1):1-9. doi: 10.1111/j.2042-7158.1967.tb07986.x.
4 Metabolism and pharmacokinetics of the anti-tuberculosis drug ethionamide in a flavin-containing monooxygenase null mouse Pharmaceuticals (Basel). 2012;5(11):1147-59. doi: 10.3390/ph5111147.

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