CEFOXITIN

First approved in 1978

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C16H17N3O7S2
Molecular Weight	427.452
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CO[C@]2(NC(=O)CC1=CC=CS1)[C@H]3SCC(COC(N)=O)=C(N3C2=O)C(O)=O

InChI

InChIKey=WZOZEZRFJCJXNZ-ZBFHGGJFSA-N

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

HIDE SMILES / InChI

Molecular Formula	C16H17N3O7S2
Molecular Weight	427.452
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.drugbank.ca/drugs/DB01331
Curator's Comment: Description was created based on several sources, including https://www.drugs.com/pro/cefoxitin.html

Cefoxitin is a cephamycin antibiotic often grouped with the second-generation cephalosporins. It is active against a broad range of gram-negative bacteria including anaerobes. The methoxy group in the 7a position provides cefoxitin with a high degree of stability in the presence of beta-lactamases, both penicillinases and cephalosporinases, of gram-negative bacteria. The bactericidal action of cefoxitin results from inhibition of cell wall synthesis.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Escherichia coli growth 23 Target ID: Escherichia coli growth Sources: https://www.ncbi.nlm.nih.gov/pubmed/2663161	Inhibitor 8504
Klebsiella pneumoniae growth 4 Target ID: Klebsiella pneumoniae growth Sources: https://www.ncbi.nlm.nih.gov/pubmed/2663161	Inhibitor 8504
D-alanyl-D-alanine carboxypeptidase DacC 3 Target ID: P08506 Gene ID: 945455.0 Gene Symbol: dacC Target Organism: Escherichia coli (strain K12) Sources: http://www.drugbank.ca/drugs/DB01331	Inhibitor 8504
D-alanyl-D-alanine carboxypeptidase DacA 4 Target ID: P0AEB2 Gene ID: 945222.0 Gene Symbol: dacA Target Organism: Escherichia coli (strain K12) Sources: http://www.drugbank.ca/drugs/DB01331	Inhibitor 8504
D-alanyl-D-alanine endopeptidase 2 Target ID: P0AFI5 Gene ID: 946662.0 Gene Symbol: pbpG Target Organism: Escherichia coli (strain K12) Sources: http://www.drugbank.ca/drugs/DB01331	Inhibitor 8504
Penicillin-binding protein 1B 22 Target ID: P02919 Gene ID: 944843.0 Gene Symbol: mrcB Target Organism: Escherichia coli (strain K12) Sources: http://www.drugbank.ca/drugs/DB01331	Inhibitor 8504
Penicillin-binding protein 2B 10 Target ID: P0A3M6 Gene ID: 933948.0 Gene Symbol: penA Target Organism: Streptococcus pneumoniae (strain ATCC BAA-255 / R6) Sources: http://www.drugbank.ca/drugs/DB01331	Inhibitor 8504	8.0 nM [IC50]
Penicillin-binding protein 1A 45 Target ID: Q8DR59 Gene ID: 934791.0 Gene Symbol: pbpA Target Organism: Streptococcus pneumoniae (strain ATCC BAA-255 / R6) Sources: https://www.ncbi.nlm.nih.gov/pubmed/7447421	Inhibitor 8504	6.8 nM [IC50]
penicillin-binding protein 2A 2 Target ID: 933569.0 Gene Symbol: pbp2a Sources: https://www.ncbi.nlm.nih.gov/pubmed/7447421	Inhibitor 8504	2.4 nM [IC50]
penicillin-binding protein 1B 2 Target ID: 934893.0 Gene Symbol: pbp1b Sources: https://www.ncbi.nlm.nih.gov/pubmed/7447421	Inhibitor 8504	0.145 nM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Lower respiratory tract infections 52 Sources: https://www.drugs.com/pro/cefoxitin.html	Curative	Approved 8583	Cefoxitin Approved Use Cefoxitin for Injection, USP is indicated for the treatment of serious infections caused by susceptible strains of the designated microorganisms in the diseases listed below. (1) Lower respiratory tract infections, including pneumonia and lung abscess, caused by Streptococcus pneumoniae, other streptococci (excluding enterococci, e.g., Enterococcus faecalis [formerly Streptococcus faecalis]), Staphylococcus aureus (including penicillinase-producing strains), Escherichia coli, Klebsiella species, Haemophilus influenzae, and Bacteroides species. (2) Urinary tract infections caused by Escherichia coli, Klebsiella species, Proteus mirabilis, Morganella morganii, Proteus vulgaris and Providencia species (including P. rettgeri). (3) Intra-abdominal infections, including peritonitis and intra-abdominal abscess, caused by Escherichia coli, Klebsiella species, Bacteroides species including Bacteroides fragilis, and Clostridium species. (4) Gynecological infections, including endometritis, pelvic cellulitis, and pelvic inflammatory disease caused by Escherichia coli, Neisseria gonorrhoeae (including penicillinase-producing strains), Bacteroides species including B. fragilis, Clostridium species, Peptococcus niger, Peptostreptococcus species and Streptococcus agalactiae. Cefoxitin for injection, like cephalosporins, has no activity against Chlamydia trachomatis. Therefore, when Cefoxitin for injection is used in the treatment of patients with pelvic inflammatory disease and C. trachomatis is one of the suspected pathogens, appropriate anti-chlamydial coverage should be added. (5) Septicemia caused by Streptococcus pneumoniae, Staphylococcus aureus (including penicillinase-producing strains), Escherichia coli, Klebsiella species, and Bacteroides species including B. fragilis. (6) Bone and joint infections caused by Staphylococcus aureus (including penicillinase-producing strains). (7) Skin and skin structure infections caused by Staphylococcus aureus (including penicillinase-producing strains), Staphylococcus epidermidis, Streptococcus pyogenes and other streptococci (excluding enterococci e.g., Enterococcus faecalis [formerly Streptococcus faecalis]), Escherichia coli, Proteus mirabilis, Klebsiella species, Bacteroides species including B. fragilis, Clostridium species, Peptococcus niger, and Peptostreptococcus species. Launch Date 2010
Urinary tract infections 207 Sources: https://www.drugs.com/pro/cefoxitin.html	Curative	Approved 8583	Cefoxitin Approved Use Cefoxitin for Injection, USP is indicated for the treatment of serious infections caused by susceptible strains of the designated microorganisms in the diseases listed below. (1) Lower respiratory tract infections, including pneumonia and lung abscess, caused by Streptococcus pneumoniae, other streptococci (excluding enterococci, e.g., Enterococcus faecalis [formerly Streptococcus faecalis]), Staphylococcus aureus (including penicillinase-producing strains), Escherichia coli, Klebsiella species, Haemophilus influenzae, and Bacteroides species. (2) Urinary tract infections caused by Escherichia coli, Klebsiella species, Proteus mirabilis, Morganella morganii, Proteus vulgaris and Providencia species (including P. rettgeri). (3) Intra-abdominal infections, including peritonitis and intra-abdominal abscess, caused by Escherichia coli, Klebsiella species, Bacteroides species including Bacteroides fragilis, and Clostridium species. (4) Gynecological infections, including endometritis, pelvic cellulitis, and pelvic inflammatory disease caused by Escherichia coli, Neisseria gonorrhoeae (including penicillinase-producing strains), Bacteroides species including B. fragilis, Clostridium species, Peptococcus niger, Peptostreptococcus species and Streptococcus agalactiae. Cefoxitin for injection, like cephalosporins, has no activity against Chlamydia trachomatis. Therefore, when Cefoxitin for injection is used in the treatment of patients with pelvic inflammatory disease and C. trachomatis is one of the suspected pathogens, appropriate anti-chlamydial coverage should be added. (5) Septicemia caused by Streptococcus pneumoniae, Staphylococcus aureus (including penicillinase-producing strains), Escherichia coli, Klebsiella species, and Bacteroides species including B. fragilis. (6) Bone and joint infections caused by Staphylococcus aureus (including penicillinase-producing strains). (7) Skin and skin structure infections caused by Staphylococcus aureus (including penicillinase-producing strains), Staphylococcus epidermidis, Streptococcus pyogenes and other streptococci (excluding enterococci e.g., Enterococcus faecalis [formerly Streptococcus faecalis]), Escherichia coli, Proteus mirabilis, Klebsiella species, Bacteroides species including B. fragilis, Clostridium species, Peptococcus niger, and Peptostreptococcus species. Launch Date 2010
Peritonitis 22 Sources: https://www.drugs.com/pro/cefoxitin.html	Curative	Approved 8583	Cefoxitin Approved Use Cefoxitin for Injection, USP is indicated for the treatment of serious infections caused by susceptible strains of the designated microorganisms in the diseases listed below. (1) Lower respiratory tract infections, including pneumonia and lung abscess, caused by Streptococcus pneumoniae, other streptococci (excluding enterococci, e.g., Enterococcus faecalis [formerly Streptococcus faecalis]), Staphylococcus aureus (including penicillinase-producing strains), Escherichia coli, Klebsiella species, Haemophilus influenzae, and Bacteroides species. (2) Urinary tract infections caused by Escherichia coli, Klebsiella species, Proteus mirabilis, Morganella morganii, Proteus vulgaris and Providencia species (including P. rettgeri). (3) Intra-abdominal infections, including peritonitis and intra-abdominal abscess, caused by Escherichia coli, Klebsiella species, Bacteroides species including Bacteroides fragilis, and Clostridium species. (4) Gynecological infections, including endometritis, pelvic cellulitis, and pelvic inflammatory disease caused by Escherichia coli, Neisseria gonorrhoeae (including penicillinase-producing strains), Bacteroides species including B. fragilis, Clostridium species, Peptococcus niger, Peptostreptococcus species and Streptococcus agalactiae. Cefoxitin for injection, like cephalosporins, has no activity against Chlamydia trachomatis. Therefore, when Cefoxitin for injection is used in the treatment of patients with pelvic inflammatory disease and C. trachomatis is one of the suspected pathogens, appropriate anti-chlamydial coverage should be added. (5) Septicemia caused by Streptococcus pneumoniae, Staphylococcus aureus (including penicillinase-producing strains), Escherichia coli, Klebsiella species, and Bacteroides species including B. fragilis. (6) Bone and joint infections caused by Staphylococcus aureus (including penicillinase-producing strains). (7) Skin and skin structure infections caused by Staphylococcus aureus (including penicillinase-producing strains), Staphylococcus epidermidis, Streptococcus pyogenes and other streptococci (excluding enterococci e.g., Enterococcus faecalis [formerly Streptococcus faecalis]), Escherichia coli, Proteus mirabilis, Klebsiella species, Bacteroides species including B. fragilis, Clostridium species, Peptococcus niger, and Peptostreptococcus species. Launch Date 2010

C_max

Value	Dose	Co-administered	Analyte	Population
24 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/318227/	1 g single, intramuscular dose: 1 g route of administration: Intramuscular experiment type: SINGLE co-administered:		CEFOXITIN plasma	Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
33.5 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/318227/	1 g single, intramuscular dose: 1 g route of administration: Intramuscular experiment type: SINGLE co-administered:		CEFOXITIN plasma	Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
0.67 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/318227/	1 g single, intramuscular dose: 1 g route of administration: Intramuscular experiment type: SINGLE co-administered:		CEFOXITIN plasma	Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
27% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/318227/	1 g single, intramuscular dose: 1 g route of administration: Intramuscular experiment type: SINGLE co-administered:		CEFOXITIN plasma	Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
2 g single, intramuscular Dose: 2 g Route: intramuscular Route: single Dose: 2 g Sources: https://pubmed.ncbi.nlm.nih.gov/3578148	unhealthy, 17 years Health Status: unhealthy Age Group: 17 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/3578148	Disc. AE: Hoigne's syndrome... AEs leading to discontinuation/dose reduction: Hoigne's syndrome (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/3578148
12 g 1 times / day multiple, intravenous Highest studied dose Dose: 12 g, 1 times / day Route: intravenous Route: multiple Dose: 12 g, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/318219	unhealthy, 22 years Health Status: unhealthy Age Group: 22 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/318219	Sources: https://pubmed.ncbi.nlm.nih.gov/318219
2 g 3 times / day multiple, intravenous Dose: 2 g, 3 times / day Route: intravenous Route: multiple Dose: 2 g, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/21042010	unhealthy, 45 years Health Status: unhealthy Age Group: 45 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/21042010	Disc. AE: Hemolytic anemia... AEs leading to discontinuation/dose reduction: Hemolytic anemia (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/21042010
1 g 4 times / day multiple, intravenous Dose: 1 g, 4 times / day Route: intravenous Route: multiple Dose: 1 g, 4 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/6641504	unhealthy, 77 years Health Status: unhealthy Age Group: 77 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/6641504	Disc. AE: Hemolytic anemia, Pancytopenia... AEs leading to discontinuation/dose reduction: Hemolytic anemia (1 patient) Pancytopenia (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/6641504

AEs

AE	Significance	Dose	Population
Hoigne's syndrome	1 patient Disc. AE	2 g single, intramuscular Dose: 2 g Route: intramuscular Route: single Dose: 2 g Sources: https://pubmed.ncbi.nlm.nih.gov/3578148	unhealthy, 17 years Health Status: unhealthy Age Group: 17 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/3578148
Hemolytic anemia	1 patient Disc. AE	2 g 3 times / day multiple, intravenous Dose: 2 g, 3 times / day Route: intravenous Route: multiple Dose: 2 g, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/21042010	unhealthy, 45 years Health Status: unhealthy Age Group: 45 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/21042010
Hemolytic anemia	1 patient Disc. AE	1 g 4 times / day multiple, intravenous Dose: 1 g, 4 times / day Route: intravenous Route: multiple Dose: 1 g, 4 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/6641504	unhealthy, 77 years Health Status: unhealthy Age Group: 77 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/6641504
Pancytopenia	1 patient Disc. AE	1 g 4 times / day multiple, intravenous Dose: 1 g, 4 times / day Route: intravenous Route: multiple Dose: 1 g, 4 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/6641504	unhealthy, 77 years Health Status: unhealthy Age Group: 77 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/6641504

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:209807	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:209807
ChemicalBook	CB9490581	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB9490581
MolPort	MolPort-006-127-091	https://www.molport.com/shop/molecule-link/MolPort-006-127-091
ZINC	ZINC000003830449	http://zinc15.docking.org/substances/ZINC000003830449

PubMed

Title	Date	PubMed
Antimicrobial resistance of strains of the Bacteroides fragilis group isolated from the intestinal tract of children and adults in Brazil.	2001 Aug	11516935
Anti-anaerobic activity of antibacterial agents.	2001 Feb	11178339
Antimicrobial resistance surveillance of bacteria in 1999 in Korea with a special reference to resistance of enterococci to vancomycin and gram-negative bacilli to third generation cephalosporin, imipenem, and fluoroquinolone.	2001 Jun	11447969
Cephalosporins in surgical prophylaxis.	2001 Nov	11936371
Probing substrate binding to metallo-beta-lactamase L1 from Stenotrophomonas maltophilia by using site-directed mutagenesis.	2002	11876827
A luminescent Escherichia coli biosensor for the high throughput detection of beta-lactams.	2002 Apr	12006111
Klebsiella pneumoniae: epidemiology and analysis of risk factors for infections caused by resistant strains.	2002 Aug	12215282
Cross-reactivity of cefotetan and ceftriaxone antibodies, associated with hemolytic anemia, with other: cephalosporins and penicillin.	2002 Aug	12162687
Increase in resistance to new fluoroquinolones from 1998 to 2001 in the Bacteroides fragilis group.	2002 Dec	12461033
Antibacterial activity of moxifloxacin against periodontal anaerobic pathogens involved in systemic infections.	2002 Dec	12458140
Mycobacterium fortuitum complex endocarditis-case report and literature review.	2002 Feb	11952729
[Identification of plasmid-encoded cephalosporinase ACC-1 among various enterobacteria (Klebsiella pneumoniae, Proteus mirabilis, Salmonella) isolated from a Tunisian hospital (Sfax 997-2000)].	2002 Feb	11873633
Characterization of blaCMY-11, an AmpC-type plasmid-mediated beta-lactamase gene in a Korean clinical isolate of Escherichia coli.	2002 Feb	11815567
Surgical prophylaxis in practice.	2002 Jan	11993642
Natural antibiotic susceptibility and biochemical profiles of Yersinia enterocolitica-like strains: Y. bercovieri, Y. mollaretii, Y. aldovae and 'Y. ruckeri'.	2002 Jan	11800473
Primary liver abscess caused by one clone of Klebsiella pneumoniae with two colonial morphotypes and resistotypes.	2002 Jan	11749761
A pathway-specific cell based screening system to detect bacterial cell wall inhibitors.	2002 Mar	12014443
The ACT-1 plasmid-encoded AmpC beta-lactamase is inducible: detection in a complex beta-lactamase background.	2002 Mar	11864960
[Genotypic exploration of a hospital neonatal outbreak due to Klebsiella pneumoniae producing extended-spectrum-betalactamase].	2002 May	12053539
Proposed protocol to reduce bacterial infectious complications in living related small bowel transplant recipients.	2002 May	12034255
Effectiveness of inpatient and outpatient treatment strategies for women with pelvic inflammatory disease: results from the Pelvic Inflammatory Disease Evaluation and Clinical Health (PEACH) Randomized Trial.	2002 May	12015517
Cefepime MIC as a predictor of the extended-spectrum beta-lactamase type in Klebsiella pneumoniae, Taiwan.	2002 May	11996691
Rapidly growing members of the genus Mycobacterium affecting dogs and cats.	2002 May-Jun	12022405
Comparison of screening methods for TEM- and SHV-derived extended-spectrum beta-lactamase detection.	2002 Nov	12445009
Comparative in vitro activities of ertapenem against bacterial pathogens from patients with acute pelvic infection.	2002 Nov	12407133
Natural antibiotic susceptibility of Enterobacter spp., with special reference to Enterobacter aerogenes and Enterobacter intermedius strains.	2002 Oct	12462424
[Activity of 14 antimicrobials against Eikenella corrodens].	2002 Oct-Dec	12600009
Natural antibiotic susceptibility of Enterobacter amnigenus, Enterobacter cancerogenus, Enterobacter gergoviae and Enterobacter sakazakii strains.	2002 Sep	12427217
Multilaboratory comparison of anaerobe susceptibility results using 3 different agar media.	2002 Sep 1	12173107
Biochemical characterization of a novel extended-spectrum beta-lactamase from Pseudomonas aeruginosa 802.	2002 Spring	12002654
A clinical strain of Escherichia coli possessing CMY-2 plasmid-mediated amp C beta-lactamase: an emerging concern in pediatrics?	2002 Winter	12523630
Natural antimicrobial susceptibilities of strains of 'unusual' Serratia species: S. ficaria, S. fonticola, S. odorifera, S. plymuthica and S. rubidaea.	2003 Apr	12654765
Pelvic inflammatory disease: how should it be managed?	2003 Feb	12821828
Efficacy and safety of azithromycin as monotherapy or combined with metronidazole compared with two standard multidrug regimens for the treatment of acute pelvic inflammatory disease.	2003 Jan-Feb	12635534
Multiple antibiotic-resistance mechanisms including a novel combination of extended-spectrum beta-lactamases in a Klebsiella pneumoniae clinical strain isolated in Argentina.	2003 Jul	12775675
Group 1 beta-lactamases of Aeromonas caviae and their resistance to beta-lactam antibiotics.	2003 Mar	12795407
Isolation of Escherichia coli O157:H7 from intact colon fecal samples of swine.	2003 Mar	12643837
Emergence of ceftriaxone-resistant Salmonella isolates and rapid spread of plasmid-encoded CMY-2-like cephalosporinase, Taiwan.	2003 Mar	12643826
Changes in sensitivity patterns to selected antibiotics in Clostridium difficile in geriatric in-patients over an 18-month period.	2003 Mar	12621092
Faropenem, a new oral penem: antibacterial activity against selected anaerobic and fastidious periodontal isolates.	2003 Mar	12615878
A seven-year survey of Klebsiella pneumoniae producing TEM-24 extended-spectrum beta-lactamase in Nice University Hospital (1994-2000).	2003 May	12767843
Beta-lactamase characterization in Escherichia coli isolates with diminished susceptibility or resistance to extended-spectrum cephalosporins recovered from sick animals in Spain.	2003 Summer	12820806

Patents

Sample Use Guides

In Vivo Use Guide

Adults The usual adult dosage range is 1 gram to 2 grams every six to eight hours.

Route of Administration: Intravenous

In Vitro Use Guide

CEFOXITIN inhibited Mycobacterium fortuitum growth with MIC 32 ug/ml

Substance Class	Chemical Created by `admin` on `Wed Apr 02 08:45:38 GMT 2025` Edited by `admin` on `Wed Apr 02 08:45:38 GMT 2025`
Record UNII	6OEV9DX57Y
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

J01DC01

Preferred Name

English

CEFOXITIN

Official Name

English

(6R,7S)-3-(Hydroxymethyl)-7-methoxy-8-oxo-7-[2-(2-thienyl)acetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid carbamate (ester)

Systematic Name

English

CEFOXITIN [USAN]

Common Name

English

Cefoxitin [WHO-DD]

Common Name

English

CEFOXITIN [VANDF]

Common Name

English

CEFOXITIN [USP-RS]

Common Name

English

CEFOXITIN [ORANGE BOOK]

Common Name

English

CEFOXITIN [MI]

Common Name

English

cefoxitin [INN]

Common Name

English

Classification Tree Code System Code

NDF-RT

N0000011161