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

General Information of Drug (ID: DR2492)
Drug Name
Cefoxitin
Synonyms
Cefoxitina; Cefoxitine; Cefoxitinum; Cefoxotin; Cenomycin; Mefoxin; Mefoxitin; Rephoxitin; cefoxitin; ceftoxitin; 35607-66-0; CEPHOXITIN; 4kow; 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[[(aminocarbonyl)oxy]methyl]-7-methoxy-8-oxo-7-[(2-thienylacetyl)amino]-, (6R,7S)-; 6OEV9DX57Y; AK118716; CAS-35607-66-0; CFX; CHEBI:209807; CHEMBL996; DSSTox_CID_2764; DSSTox_GSID_22764; DSSTox_RID_76721; NCGC00183034-01; UNII-6OEV9DX57Y
Indication Peritonitis [ICD11: DC50] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 427.5 Topological Polar Surface Area 202
Heavy Atom Count 28 Rotatable Bond Count 8
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 9
Cross-matching ID
PubChem CID
441199
ChEBI ID
CHEBI:209807
CAS Number
35607-66-0
Formula
C16H17N3O7S2
Canonical SMILES
COC1(C2N(C1=O)C(=C(CS2)COC(=O)N)C(=O)O)NC(=O)CC3=CC=CS3
InChI
1S/C16H17N3O7S2/c1-25-16(18-10(20)5-9-3-2-4-27-9)13(23)19-11(12(21)22)8(6-26-15(17)24)7-28-14(16)19/h2-4,14H,5-7H2,1H3,(H2,17,24)(H,18,20)(H,21,22)/t14-,16+/m1/s1
InChIKey
WZOZEZRFJCJXNZ-ZBFHGGJFSA-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
Decarbamylcefoxitin DM000752
23620315
Unclear 1 [6]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000584 Cefoxitin Decarbamylcefoxitin Unclear blaB [6]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Beta-lactamase (blaB) DME1094 Citrobacter freundii
AMPC_CITFR
3.5.2.6
[2]
Beta-lactamase (blaB) DME1643 Chromobacterium violaceum
A0A3S4HKA9_CHRVL
3.5.2.6
[3]
Beta-lactamase (blaB) DME1024 Klebsiella variicola
BLA2_KLEPO
3.5.2.6
[4] , [5]
Beta-lactamase (blaB) DME1223 Escherichia coli
BLAT_ECOLX
3.5.2.6
[5]
Beta-lactamase (blaB) DME1349 Bifidobacterium breve
A0A0L0LVQ7_BIFBR
3.5.2.6
[6]
Beta-lactamase (blaB) DME1733 Citrobacter koseri
BLAC_CITKO
3.5.2.6
[7]
Beta-lactamase (blaB) DME1320 Citrobacter amalonaticus
A0A3Q9VXP1_CITAM
3.5.2.6
[7]
Beta-lactamase (blaB) DME1023 Klebsiella pneumoniae
A0A378EHS6_KLEPR
3.5.2.6
[8]
Beta-lactamase (blaB) DME1215 Bacteroides caccae
A0A4Q5I6I2_9BACE
3.5.2.6
[9]
Beta-lactamase (blaB) DME1216 Parabacteroides distasonis
B5WXV2_9BACT
3.5.2.6
[9]
Beta-lactamase (blaB) DME1217 Parabacteroides merdae
A0A414C8Y0_9BACT
3.5.2.6
[9]
Beta-lactamase (blaB) DME1218 Bacteroides ovatus
B5WXV3_BACOV
3.5.2.6
[9]
Beta-lactamase (blaB) DME1219 Bacteroides thetaiotaomicron
B5WXV7_BACT4
3.5.2.6
[9]
Beta-lactamase (blaB) DME1220 Bacteroides vulgatus
BLAC_BACVU
3.5.2.6
[9]
⏷ Show the Full List of 14  DME(s)
References
1 Cefoxitin was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Citrobacter freundii bacteremia: Risk factors of mortality and prevalence of resistance genes. J Microbiol Immunol Infect. 2018 Aug;51(4):565-572.
3 Beta-lactamase activity in Chromobacterium violaceum. J Infect Dis. 1976 Sep;134(3):290-3.
4 Antibiotic resistance and production of extended-spectrum beta-lactamases amongst Klebsiella spp. from intensive care units in Europe. J Antimicrob Chemother. 1996 Sep;38(3):409-24.
5 Oral streptococcal strains isolated from odontogenic infections and their susceptibility to antibiotics. Rev Med Chir Soc Med Nat Iasi. 2006 Oct-Dec;110(4):1012-5.
6 Analysis of cefoxitin, cephalothin and their deacylated metabolites in human urine by high-performance liquid chromatography J Chromatogr. 1974 Nov 6;99(0):609-18. doi: 10.1016/s0021-9673(00)90889-6.
7 Citrobacter koseri and Citrobacter amalonaticus isolates carry highly divergent beta-lactamase genes despite having high levels of biochemical similarity and 16S rRNA sequence homology. J Antimicrob Chemother. 2004 Jun;53(6):1076-80.
8 Analysis of the drug-resistant characteristics of Klebsiella pneumoniae isolated from the respiratory tract and CTX-M ESBL genes. Genet Mol Res. 2015 Oct 5;14(4):12043-8.
9 Presence of the cfxA gene in Bacteroides distasonis. Res Microbiol. 2003 Jun;154(5):369-74.

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