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

General Information of Drug (ID: DR2165)
Drug Name
GW9662
Synonyms
Lopac-M-6191; Lopac0_000798; SCHEMBL420231; SR-01000075999; Spectrum5_001989; Tocris-1508; cid_644213; (2-chloro-5-nitrophenyl)-N-benzamide; 2-Chloro-5-nitro-N-4-phenylbenzamide; 2-Chloro-5-nitro-N-phenyl-benzamide; 2-Chloro-5-nitro-N-phenylbenzamide; 2-Chloro-5-nitrobenzanilide; 22978-25-2; AC1LD8S0; BSPBio_001021; CHEBI:79993; CHEMBL375270; DSSTox_CID_20723; DSSTox_GSID_40723; DSSTox_RID_79570; GTPL3442; GW 9662; GW-9662; GW9662; KBioGR_000361; KBioSS_000361; MLS001056751; SMR000326735; benzamide, 2-chloro-5-nitro-N-phenyl-
Indication Breast cancer [ICD11: 2C60] Investigative [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 276.67 Topological Polar Surface Area 74.9
Heavy Atom Count 19 Rotatable Bond Count 2
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
644213
PubChem SID
841875 ; 877487 ; 6873016 ; 8707317 ; 11111477 ; 11114114 ; 11121686 ; 11122166 ; 11362775 ; 11365337 ; 11367899 ; 11370801 ; 11370802 ; 11373500 ; 11376061 ; 14824325 ; 17396617 ; 17405359 ; 22395870 ; 24278560 ; 24883187 ; 26732595 ; 26752209 ; 26752210 ; 26752211 ; 26758841 ; 43765920 ; 47719268 ; 47793670 ; 47942452 ; 47942453 ; 48392499 ; 50104878 ; 50104879 ; 50104880 ; 53777904 ; 53790960 ; 53800743 ; 56355093 ; 57408227 ; 77530674 ; 85202868 ; 85231138 ; 85787762 ; 88369062 ; 90341221 ; 92304217 ; 92310037 ; 99300949 ; 99302469
ChEBI ID
CHEBI:79993
CAS Number
22978-25-2
TTD Drug ID
D00ACX
Formula
C13H9ClN2O3
Canonical SMILES
C1=CC=C(C=C1)NC(=O)C2=C(C=CC(=C2)[N+](=O)[O-])Cl
InChI
1S/C13H9ClN2O3/c14-12-7-6-10(16(18)19)8-11(12)13(17)15-9-4-2-1-3-5-9/h1-8H,(H,15,17)
InChIKey
DNTSIBUQMRRYIU-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-amino-2-chloro-N-phenyl benzamide DM006519 N. A. Reduction - Reduction 1 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR007024 GW9662 5-amino-2-chloro-N-phenyl benzamide Reduction - Reduction Unclear [2]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Oxygen-insensitive NADPH nitroreductase A (nfsA) DME1971 Salmonella enterica
NFSA_SALTY
1.5.1.38
[2]
Oxygen-insensitive NADPH nitroreductase B (nfsB) DME1617 Salmonella enterica
NFSB_SALTY
1.5.1.34
[2]
References
1 GW9662, a potent antagonist of PPARgamma, inhibits growth of breast tumour cells and promotes the anticancer effects of the PPARgamma agonist rosiglitazone, independently of PPARgamma activation. Br J Pharmacol. 2004 Dec;143(8):933-7.
2 Effects of bacterial and presystemic nitroreductase metabolism of 2-chloro-5-nitro-N-phenylbenzamide on its mutagenicity and bioavailability. Chem Biol Interact. 2012 Apr 15;197(1):16-22.

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