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

General Information of Drug (ID: DR1664)
Drug Name
ASA-404
Synonyms
DMXAA (Vadimezan); Dimethyloxoxanthene acetic acid; Vadimezan; (5,6-Dimethyl-9-oxo-xanthen)-4-acetic acid; (5,6-dimethyl-9-oxo-9H-xanthen-4-yl)acetic acid; 117570-53-3; 2-(5,6-dimethyl-9-oxo-9H-xanthen-4-yl)acetic acid; 5,6-Dimethyl-9-oxo-9H-xanthene-4-acetic acid; 5,6-Dimethylxanthenone-4-acetic acid; 5,6-Dimethylxantheonone-4-acetic Acid; 5,6-Mexaa; 6-MeXAA; 9H-Xanthene-4-acetic acid, 5,6-dimethyl-9-oxo-; AS 1404; AS-1404; ASA-404; ASA404; CHEBI:75934; DMXAA; NSC 640488; NSC-640488; UNII-0829J8133H
Indication Prostate cancer [ICD11: 2C82] Phase 2 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 282.29 Topological Polar Surface Area 63.6
Heavy Atom Count 21 Rotatable Bond Count 2
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
123964
ChEBI ID
CHEBI:75934
CAS Number
117570-53-3
TTD Drug ID
D08UOY
Formula
C17H14O4
Canonical SMILES
CC1=C(C2=C(C=C1)C(=O)C3=CC=CC(=C3O2)CC(=O)O)C
InChI
1S/C17H14O4/c1-9-6-7-13-15(20)12-5-3-4-11(8-14(18)19)17(12)21-16(13)10(9)2/h3-7H,8H2,1-2H3,(H,18,19)
InChIKey
XGOYIMQSIKSOBS-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
6-OH-MXAA DM006736
53951284
Unclear 1 [3] , [2]
DMXAA acyl glucuronide DM006738 N. A. Unclear 1 [3] , [2]
6-OH-MXAA glucuronide DM006737 N. A. Unclear 2 [3] , [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR007274 ASA-404 6-OH-MXAA Unclear CYP1A2 ... [3], [2]
MR007276 ASA-404 DMXAA acyl glucuronide Unclear UGT1A9 ... [3], [2]
MR007275 6-OH-MXAA 6-OH-MXAA glucuronide Unclear UGT [3], [2]
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]
Flavin-containing monooxygenase (FMO) DMEN075 . Not Available Not Available [3] , [2]
UDP-glucuronosyltransferase 1A9 (UGT1A9) DME0042 Homo sapiens
UD19_HUMAN
2.4.1.17
[3]
UDP-glucuronosyltransferase 2B7 (UGT2B7) DME0040 Homo sapiens
UD2B7_HUMAN
2.4.1.17
[2]
References
1 ClinicalTrials.gov (NCT01057342) Paclitaxel, Carboplatin, and Dimethylxanthenone Acetic Acid in Treating Patients With Extensive-Stage Small Cell Lung Cancer.
2 Preclinical factors affecting the interindividual variability in the clearance of the investigational anti-cancer drug 5,6-dimethylxanthenone-4-acetic acid. Biochem Pharmacol. 2003 Jun 1;65(11):1853-65.
3 Predicting pharmacokinetics and drug interactions in patients from in vitro and in vivo models: the experience with 5,6-dimethylxanthenone-4-acetic acid (DMXAA), an anti-cancer drug eliminated mainly by conjugation. Drug Metab Rev. 2002 Nov;34(4):751-90.

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