Details of the Drug

General Information of Drug (ID: DMY8NC4)

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
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 427.5
Topological Polar Surface Area (xlogp) 0
Rotatable Bond Count (rotbonds) 8
Hydrogen Bond Donor Count (hbonddonor) 3
Hydrogen Bond Acceptor Count (hbondacc) 9
ADMET Property
Half-life
The concentration or amount of drug in body reduced by one-half in 41 - 59 minutes [1]
Metabolism
The drug is metabolized via the kidney [2]
Chemical Identifiers
Formula
C16H17N3O7S2
IUPAC Name
(6R,7S)-3-(carbamoyloxymethyl)-7-methoxy-8-oxo-7-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Canonical SMILES
COC1(C2N(C1=O)C(=C(CS2)COC(=O)N)C(=O)O)NC(=O)CC3=CC=CS3
InChI
WZOZEZRFJCJXNZ-ZBFHGGJFSA-N
InChIKey
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
Cross-matching ID
PubChem CID
441199
ChEBI ID
CHEBI:209807
CAS Number
35607-66-0
DrugBank ID
DB01331
INTEDE ID
DR2492

Molecular Interaction Atlas of This Drug


Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Beta-lactamase (blaB) DEP0IWS A0A378EHS6_KLEPR Substrate [3]
Beta-lactamase (blaB) DEEAL81 BLA2_KLEPO Substrate [4], [5]
Beta-lactamase (blaB) DE7IH52 AMPC_CITFR Substrate [6]
Beta-lactamase (blaB) DE5HV8P A0A4Q5I6I2_9BACE Substrate [7]
Beta-lactamase (blaB) DE47ARF B5WXV2_9BACT Substrate [7]
Beta-lactamase (blaB) DEG2PK9 B5WXV3_BACOV Substrate [7]
Beta-lactamase (blaB) DEWHJ7A B5WXV7_BACT4 Substrate [7]
Beta-lactamase (blaB) DEU1RXB BLAC_BACVU Substrate [7]
Beta-lactamase (blaB) DEMIUB2 BLAT_ECOLX Substrate [5]
Beta-lactamase (blaB) DEF01WC A0A3S4HKA9_CHRVL Substrate [8]
Beta-lactamase (blaB) DEHJVX4 A0A414C8Y0_9BACT Substrate [7]
Beta-lactamase (blaB) DEQAG48 A0A3Q9VXP1_CITAM Substrate [9]
Beta-lactamase (blaB) DE5AHG6 BLAC_CITKO Substrate [9]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
2 FDA approval: ado-trastuzumab emtansine for the treatment of patients with HER2-positive metastatic breast cancer. Clin Cancer Res. 2014 Sep 1;20(17):4436-41.
3 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.
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 Citrobacter freundii bacteremia: Risk factors of mortality and prevalence of resistance genes. J Microbiol Immunol Infect. 2018 Aug;51(4):565-572.
7 Presence of the cfxA gene in Bacteroides distasonis. Res Microbiol. 2003 Jun;154(5):369-74.
8 Beta-lactamase activity in Chromobacterium violaceum. J Infect Dis. 1976 Sep;134(3):290-3.
9 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.
10 Detection and characterization of beta-lactamase genes in subgingival bacteria from patients with refractory periodontitis. FEMS Microbiol Lett. 2005 Jan 15;242(2):319-24.
11 Antibiotic therapy for inducible AmpC beta-lactamase-producing Gram-negative bacilli: what are the alternatives to carbapenems, quinolones and aminoglycosides? Int J Antimicrob Agents. 2012 Oct;40(4):297-305.
12 Analyses of a ceftazidime-avibactam-resistant Citrobacter freundii isolate carrying blaKPC-2 reveals a heterogenous population and reversible genotype. mSphere. 2018 Sep 26;3(5). pii: e00408-18.
13 Identification and functional characterization of arylamine N-acetyltransferases in eubacteria: evidence for highly selective acetylation of 5-aminosalicylic acid. J Bacteriol. 2001 Jun;183(11):3417-27.
14 Prevalence of antimicrobial resistance genes in Bacteroides spp. and Prevotella spp. Dutch clinical isolates. Clin Microbiol Infect. 2019 Sep;25(9):1156.e9-1156.e13.
15 Cephalosporinases associated with outer membrane vesicles released by Bacteroides spp. protect gut pathogens and commensals against beta-lactam antibiotics. J Antimicrob Chemother. 2015 Mar;70(3):701-9.
16 War wound treatment complications due to transfer of an IncN plasmid harboring bla(OXA-181) from Morganella morganii to CTX-M-27-producing sequence type 131 Escherichia coli. Antimicrob Agents Chemother. 2015;59(6):3556-62.
17 Low-virulence Citrobacter species encode resistance to multiple antimicrobials. Antimicrob Agents Chemother. 2002 Nov;46(11):3555-60.
18 Novel TEM-type extended-spectrum beta-lactamase, TEM-134, in a Citrobacter koseri clinical isolate. Antimicrob Agents Chemother. 2005 Apr;49(4):1564-6.