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]
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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)

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

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: 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
UNII: 6OEV9DX57Y
DrugBank ID: DB01331
INTEDE ID: DR2492

Combinatorial Drugs (CBD)

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Repurposed Drugs (RPD)

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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]

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Drug Transporter (DTP)

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

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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]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
HLA class I histocompatibility antigen, A alpha chain (HLA-A)	OTAH14LU	HLAA_HUMAN	Gene/Protein Processing	[13]
HLA class II histocompatibility antigen, DP alpha 1 chain (HLA-DPA1)	OT7OG7Y2	DPA1_HUMAN	Gene/Protein Processing	[13]

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Molecular Interaction Atlas (MIA)

MIA Detail

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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]
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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.".