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

General Information of Drug (ID: DR0036)
Drug Name
G-23350
Synonyms
Acitrom; Ascumar; Neositron; Nicoumalone; Nicumalon; Nitrovarfarian; Nitrowarfarin; Sincoumar; Sinkumar; Sinthrom; Sinthrome; Sintrom; Sintroma; Syncoumar; Syncumar; Syntrom; Trombostop; 152-72-7; 3-(alpha-Acetonyl-4-nitrobenzyl)-4-hydroxycoumarin; ACENOCOUMAROL; Acenocoumarin; Acenocoumarol (INN); Acenocoumarol [INN]; Acenocoumarolum; Acenocoumarolum [INN-Latin]; Acenocumarol; Acenocumarolo; Acenocumarolo [DCIT]; Acenocumarolum; Acenokumarin; Acenokumarin [Czech]; G 23350; G-23350; Nitrophenylacetylethyl-4-hydroxycoumarine; Zotil
Indication Venous thromboembolism [ICD11: BD72] Phase 1 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 353.3 Topological Polar Surface Area 109
Heavy Atom Count 26 Rotatable Bond Count 4
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 6
Cross-matching ID
PubChem CID
54676537
ChEBI ID
CHEBI:53766
CAS Number
152-72-7
TTD Drug ID
D05HFY
Formula
C19H15NO6
Canonical SMILES
CC(=O)CC(C1=CC=C(C=C1)[N+](=O)[O-])C2=C(C3=CC=CC=C3OC2=O)O
InChI
1S/C19H15NO6/c1-11(21)10-15(12-6-8-13(9-7-12)20(24)25)17-18(22)14-4-2-3-5-16(14)26-19(17)23/h2-9,15,22H,10H2,1H3
InChIKey
VABCILAOYCMVPS-UHFFFAOYSA-N
The Predicted Metabolic Roadmap of This Drug
The Full List of Predicted Drug Metabolites (PDM) of This Drug
PDM Name PDM ID PubChem ID Reaction PDM Level Biosystem
G-23350 M1 PDM007891
57369794
Oxidation - Aromatic hydroxylation of fused benzene ring AndFromCyProduct 1 Human
G-23350 M11 PDM007901 N. A. Reduction - Nitroreduction of nitroarene to hydroxylamine 1 Human
G-23350 M12 PDM007902 N. A. Oxidation - Hydroxylation of non-terminal aliphatic carbon adjacent to aromatic ring 1 Human
G-23350 M13 PDM007903 N. A. Oxidation - Aromatic hydroxylation of fused benzene ring 1 Human
G-23350 M14 PDM007904
71357560
Reduction - Reduction of ketone to alcohol 1 Human
G-23350 M15 PDM007905 N. A. Reduction - Nitroreduction of nitroarene to nitrosoarene 1 Gut microbial environment
G-23350 M2 PDM007892
57369793
Oxidation - Aromatic hydroxylation of fused benzene ring AndFromCyProduct 1 Human
G-23350 M3 PDM007893 N. A. Oxidation - Aromatic hydroxylation of fused benzene ring AndFromCyProduct 1 Human
G-23350 M4 PDM007894 N. A. Oxidation - alpha-Hydroxylation of carbonyl group AndFromCyProduct 1 Human
G-23350 M5 PDM007895 N. A. Oxidation - alpha-Hydroxylation of carbonyl group AndFromCyProduct 1 Human
G-23350 M10 PDM007900 N. A. Conjugation - Sulfation of secondary alcohol 2 Human
G-23350 M6 PDM007896 N. A. Conjugation - Aromatic OH-glucuronidation 2 Human
G-23350 M7 PDM007897 N. A. Conjugation - Aromatic OH-glucuronidation 2 Human
G-23350 M8 PDM007898 N. A. Conjugation - Aromatic OH-glucuronidation 2 Human
G-23350 M9 PDM007899 N. A. Conjugation - Sulfation of primary alcohol 2 Human
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[2]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[3]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[4]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[2]
References
1 ClinicalTrials.gov (NCT03015025) Pharmacogenetic Dosage Algorithm for Acenocoumarol.
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 Prediction of pharmacokinetic drug/drug interactions from In vitro data: interactions of the nonsteroidal anti-inflammatory drug lornoxicam with oral anticoagulants. Drug Metab Dispos. 2000 Feb;28(2):161-8.
4 Possible interaction between topical terbinafine and acenocoumarol. Ann Pharmacother. 2009 Nov;43(11):1911-2.

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