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

General Information of Drug (ID: DR2704)
Drug Name
VUFB-11502
Synonyms
Ciadox; Ciadox [INN]; Cyadox; Ciadoxum [INN-Latin]; SCHEMBL1817373; VUFB 11502; 2-formylquinoxaline-1,4-dioxide cyanoacetylhydrazone; 65884-46-0; ACETIC ACID, CYANO-, (2-QUINOXALINYLMETHYLENE)HYDRAZIDE, N,N-DIOXIDE; BRN 0826894; C12H8N5O3; Cyanoacetic acid (2-quinoxalinylmethylene)hydrazide, N(sup 1),N(sup 4)-dioxide; Cyanoacetylhydrazone 2-formylquinoxaline-1,4-dioxide; EINECS 265-963-3; N'-(2-Chinoxalinylmethylen)cyanacetohydrazid 1,4-dioxid; SCHEMBL10793569
Indication Amebiasis [ICD11: 1A36] Preclinical [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 271.23 Topological Polar Surface Area 116
Heavy Atom Count 20 Rotatable Bond Count 3
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
135412736
CAS Number
65884-46-0
Formula
C12H9N5O3
Canonical SMILES
C1=CC=C2C(=C1)[N+](=CC(=[N+]2[O-])C=NNC(=O)CC#N)[O-]
InChI
1S/C12H9N5O3/c13-6-5-12(18)15-14-7-9-8-16(19)10-3-1-2-4-11(10)17(9)20/h1-4,7-8H,5H2,(H,15,18)/b14-7+
InChIKey
MBCZYLSVSCJJJQ-VGOFMYFVSA-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
CYA-1-monoxide DM006504 N. A. Oxidation - Oxidationn 1 [2]
CYA-4-monoxide DM006505 N. A. Oxidation - Oxidationn 1 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR006999 VUFB-11502 CYA-1-monoxide Oxidation - Oxidationn XDH [2]
MR007000 VUFB-11502 CYA-4-monoxide Oxidation - Oxidationn AOX1 [2]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Aldehyde oxidase (AOX1) DME0052 Homo sapiens
AOXA_HUMAN
1.2.3.1
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
NADPH-dependent carbonyl reductase 1 (CBR1) DME0067 Homo sapiens
CBR1_HUMAN
1.1.1.184
[2]
Unclear metabolic mechanism (DME-unclear) DME1265 Escherichia coli Not Available Not Available [3]
Xanthine dehydrogenase/oxidase (XDH) DME0070 Homo sapiens
XDH_HUMAN
1.17.1.4
[2]
References
1 Pharmacokinetic and pharmacodynamic modeling of cyadox against Clostridium perfringens in swine. Sci Rep. 2017 Jun 22;7(1):4064.
2 The critical role of oxidative stress in the toxicity and metabolism of quinoxaline 1,4-di-N-oxides in vitro and in vivo. Drug Metab Rev. 2016 May;48(2):159-82.
3 Effects of cyadox and olaquindox on intestinal mucosal immunity and on fecal shedding of Escherichia coli in piglets. J Anim Sci. 2006 Sep;84(9):2367-73. Randomized Controlled Trial

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