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
Indication
Disease Entry ICD 11 Status REF
Acute gonococcal cervicitis N.A. Approved [1]
Bacteremia 1A73 Approved [1]
Bacterial infection 1A00-1C4Z Approved [2]
Endometritis N.A. Approved [1]
Lung abscess N.A. Approved [1]
Peritonitis N.A. Approved [1]
Staphylococcal pneumonia N.A. Approved [1]
Staphylococcus aureus infection N.A. Approved [1]
Pelvic inflammatory disease GA05 Investigative [1]
⏷ Show the Full List of Indication(s)
Affected Organisms
Enteric bacteria and other eubacteria
ATC Code
J01DC01: Cefoxitin
J01DC: Second-generation cephalosporins
J01D: OTHER BETA-LACTAM ANTIBACTERIALS
J01: ANTIBACTERIALS FOR SYSTEMIC USE
J: ANTIINFECTIVES FOR SYSTEMIC USE
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 427.5
Logarithm of the Partition Coefficient (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 [3]
Metabolism
The drug is metabolized via the kidney []
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
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
Cross-matching ID
PubChem CID
441199
ChEBI ID
CHEMBL996
CAS Number
35607-66-0
UNII
6OEV9DX57Y
DrugBank ID
DB01331
TTD ID
D02VFC
INTEDE ID
DR2492
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA Information of This Drug
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Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Bacterial Penicillin binding protein (Bact PBP) TTJP4SM NOUNIPROTAC Binder [4]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
Peptide transporter 1 (SLC15A1) DT9G7XN S15A1_HUMAN Substrate [5]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Beta-lactamase (blaB) DEP0IWS A0A378EHS6_KLEPR Substrate [6]
Beta-lactamase (blaB) DEEAL81 BLA2_KLEPO Substrate [7], [8]
Beta-lactamase (blaB) DE7IH52 AMPC_CITFR Substrate [9]
Beta-lactamase (blaB) DE5HV8P A0A4Q5I6I2_9BACE Substrate [10]
Beta-lactamase (blaB) DE47ARF B5WXV2_9BACT Substrate [10]
Beta-lactamase (blaB) DEG2PK9 B5WXV3_BACOV Substrate [10]
Beta-lactamase (blaB) DEWHJ7A B5WXV7_BACT4 Substrate [10]
Beta-lactamase (blaB) DEU1RXB BLAC_BACVU Substrate [10]
Beta-lactamase (blaB) DEMIUB2 BLAT_ECOLX Substrate [8]
Beta-lactamase (blaB) DEF01WC A0A3S4HKA9_CHRVL Substrate [11]
Beta-lactamase (blaB) DEHJVX4 A0A414C8Y0_9BACT Substrate [10]
Beta-lactamase (blaB) DEQAG48 A0A3Q9VXP1_CITAM Substrate [12]
Beta-lactamase (blaB) DE5AHG6 BLAC_CITKO Substrate [12]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
HLA class II histocompatibility antigen, DP alpha 1 chain (HLA-DPA1) OT7OG7Y2 DPA1_HUMAN Gene/Protein Processing [13]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Cefoxitin (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Givosiran DM5PFIJ Moderate Increased risk of nephrotoxicity by the combination of Cefoxitin and Givosiran. Inborn porphyrin/heme metabolism error [5C58] [14]
Plazomicin DMKMBES Moderate Increased risk of nephrotoxicity by the combination of Cefoxitin and Plazomicin. Urinary tract infection [GC08] [15]

References

1 Cefoxitin FDA Label
2 Natural products as sources of new drugs over the last 25 years. J Nat Prod. 2007 Mar;70(3):461-77.
3 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
4 Staphylococcus aureus PBP4 is essential for beta-lactam resistance in community-acquired methicillin-resistant strains. Antimicrob Agents Chemother. 2008 Nov;52(11):3955-66.
5 Three-dimensional quantitative structure-activity relationship analyses of beta-lactam antibiotics and tripeptides as substrates of the mammalian H+/peptide cotransporter PEPT1. J Med Chem. 2005 Jun 30;48(13):4410-9.
6 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.
7 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.
8 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.
9 Citrobacter freundii bacteremia: Risk factors of mortality and prevalence of resistance genes. J Microbiol Immunol Infect. 2018 Aug;51(4):565-572.
10 Presence of the cfxA gene in Bacteroides distasonis. Res Microbiol. 2003 Jun;154(5):369-74.
11 Beta-lactamase activity in Chromobacterium violaceum. J Infect Dis. 1976 Sep;134(3):290-3.
12 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.
13 Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis. Chem Res Toxicol. 2015 May 18;28(5):927-34. doi: 10.1021/tx5005248. Epub 2015 Apr 3.
14 Cerner Multum, Inc. "Australian Product Information.".
15 Agencia Espaola de Medicamentos y Productos Sanitarios Healthcare "Centro de informacion online de medicamentos de la AEMPS - CIMA.".