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

General Information of Drug (ID: DR2431)
Drug Name
Secnidazole
Prodrug Info Secnidazole is the prodrug of Hydroxymethyl metabolite of secnidazole
Synonyms
Secnidazol; Secnidazol [INN-Spanish]; Secnidazolum; Secnidazolum [INN-Latin]; Solosec; Flagentyl; PM 185184;Secnidazole (Flagentyl); PM-185184; RP 14539; RP-14539; SYM-1219; seknidazol; 3366-95-8; EINECS 222-134-0; MLS000559043; NCGC00095158-01; SMR000149359
Indication Amebiasis [ICD11: 1A36] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 185.18 Topological Polar Surface Area 83.9
Heavy Atom Count 13 Rotatable Bond Count 2
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
71815
ChEBI ID
CHEBI:140628
CAS Number
3366-95-8
TTD Drug ID
D0V5IW
Formula
C7H11N3O3
Canonical SMILES
CC1=NC=C(N1CC(C)O)[N+](=O)[O-]
InChI
1S/C7H11N3O3/c1-5(11)4-9-6(2)8-3-7(9)10(12)13/h3,5,11H,4H2,1-2H3
InChIKey
KPQZUUQMTUIKBP-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
Glucuronide conjugates of secnidazole DM001287 N. A. Conjugation - Conjugation 1 [2] , [4]
Hydroxymethyl metabolite of secnidazole DM001286 N. A. Oxidation - Oxidation 1 [2] , [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002224 Secnidazole Hydroxymethyl metabolite of secnidazole Oxidation - Oxidation CYP3A4 ... [2], [4]
MR002225 Secnidazole Glucuronide conjugates of secnidazole Conjugation - Conjugation UGT [2], [4]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[2]
Nitroreductase (NTR) DME1247 Enterobacter cloacae
NFSB_ENTCL
1.5.1.39
[3]
References
1 Azithromycin was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 In vitro metabolic profile and drug-drug interaction assessment of secnidazole, a high-dose 5-nitroimidazole antibiotic for the treatment of bacterial vaginosis Pharmacol Res Perspect. 2020 Aug;8(4):e00634. doi: 10.1002/prp2.634.
3 Overexpression, isotopic labeling, and spectral characterization of Enterobacter cloacae nitroreductase. Protein Expr Purif. 1998 Jun;13(1):53-60.
4 Secnidazole. A review of its antimicrobial activity, pharmacokinetic properties and therapeutic use in the management of protozoal infections and bacterial vaginosis Drugs. 1996 Apr;51(4):621-38. doi: 10.2165/00003495-199651040-00007.

If you find any error in data or bug in web service, please kindly report it to Dr. Yin and Dr. Li.