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

General Information of Drug (ID: DR1593)
Drug Name
Tienilic acid
Synonyms
Thienylic acid; Ticrex; Ticrynafen; Ticrynafen [USAN]; Tienilic acid; Tienilico acido; Tienilico acido [Spanish]; ANP 3624; Acide tienilique; Acide tienilique [INN-French]; Acido tienilico; Acido tienilico [INN-Spanish]; Acidum tienilicum; Acidum tienilicum [INN-Latin]; Diflurex; SKF 62698; Selacryn; (2,3-Dichloro-4-(2-thenoyl)phenoxy)acetic acid; 2-(2,3-dichloro-4-(thiophene-2-carbonyl)phenoxy)acetic acid; 4-(2-Thienylketo)-2,3-dichlorophenoxyacetic acid; 40180-04-9; C13H8Cl2O4S; CCRIS 5489; UNII-HC95205SY4
Indication Congestive heart failure [ICD11: BD10] Phase 4 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 331.2 Topological Polar Surface Area 91.8
Heavy Atom Count 20 Rotatable Bond Count 5
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
38409
ChEBI ID
CHEBI:9590
CAS Number
40180-04-9
TTD Drug ID
D0T0TZ
Formula
C13H8Cl2O4S
Canonical SMILES
C1=CSC(=C1)C(=O)C2=C(C(=C(C=C2)OCC(=O)O)Cl)Cl
InChI
1S/C13H8Cl2O4S/c14-11-7(13(18)9-2-1-5-20-9)3-4-8(12(11)15)19-6-10(16)17/h1-5H,6H2,(H,16,17)
InChIKey
AGHANLSBXUWXTB-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
5-Hydroxy-tienilic Acid DM005796
146269
Oxidation - Hydrolyzationn 1 [4] , [5]
Thiophene-4,5-epoxide DM000398 N. A. Oxidation - Epoxidation 1 [2]
Ticrynafen S-oxide DM005794 N. A. Oxidation - Oxidationn 1 [2]
Tienilic acid-s-oxide DM005795
154699897
Oxidation - S-oxidation 1 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR006190 Tienilic acid Ticrynafen S-oxide Oxidation - Oxidationn CYP2C8 ... [2]
MR006191 Tienilic acid Tienilic acid-s-oxide Oxidation - S-oxidation CYP2C8 ... [2]
MR006192 Tienilic acid Thiophene-4,5-epoxide Oxidation - Epoxidation CYP2C8 ... [2]
MR006193 Tienilic acid 5-Hydroxy-tienilic Acid Oxidation - Hydrolyzationn CYP2C9 [4], [5]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2C18 (CYP2C18) DME0017 Homo sapiens
CP2CI_HUMAN
1.14.14.1
[2]
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[2]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[3]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[2]
References
1 National Center for Advancing Translational Science-Inxight: drug (HC95205SY4)
2 Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675.
3 Cytochrome P450 enzymes and UDP-glucuronosyltransferases as hepatocellular autoantigens. Mol Biol Rep. 1996;23(3-4):235-42.
4 Hydroxylation and formation of electrophilic metabolites of tienilic acid and its isomer by human liver microsomes. Catalysis by a cytochrome P450 IIC different from that responsible for mephenytoin hydroxylation
5 Human-liver cytochromes P-450 expressed in yeast as tools for reactive-metabolite formation studies. Oxidative activation of tienilic acid by cytochromes P-450 2C9 and 2C10

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