DT-Web

DB01331 - Cefoxitin


Identification
Name Cefoxitin
Accession Number DB01331 (EXPT00897)
Type small molecule
Description Cefoxitin is a semi-synthetic, broad-spectrum cepha antibiotic for intravenous administration. It is derived from cephamycin C, which is produced by Streptomyces lactamdurans.
Structure
MOL SDF PDB SMILES InChI
Categories (*)
Molecular Weight 427.452
Groups approved
Monoisotopic Weight 427.050791293
Pharmacology
Indication For the treatment of serious infections caused by susceptible strains microorganisms.
Mechanism of action The bactericidal action of cefoxitin results from inhibition of cell wall synthesis.
Absorption Not Available
Protein binding Not Available
Biotransformation Minimal (approximately 85 percent of cefoxitin is excreted unchanged by the kidneys over a 6-hour period).
Route of elimination Approximately 85 percent of cefoxitin is excreted unchanged by the kidneys over a 6-hour period, resulting in high urinary concentrations. Cefoxitin passes into pleural and joint fluids and is detectable in antibacterial concentrations in bile.
Toxicity The acute intravenous LD50 in the adult female mouse and rabbit was about 8.0 g/kg and greater than 1.0 g/kg, respectively. The acute intraperitoneal LD50 in the adult rat was greater than 10.0 g/kg.
Affected organisms
  • Enteric bacteria and other eubacteria
Interactions
Drug Interactions
Drug Mechanism of interaction
Acenocoumarol The cephalosporin, cefoxitin, may increase the anticoagulant effect of acenocoumarol.
Amikacin Increased risk of nephrotoxicity
Anisindione The cephalosporin, cefoxitin, may increase the anticoagulant effect of anisindione.
Dicumarol The cephalosporin, cefoxitin, may increase the anticoagulant effect of dicumarol.
Gentamicin Increased risk of nephrotoxicity
Kanamycin Increased risk of nephrotoxicity
Neomycin Increased risk of nephrotoxicity
Netilmicin Increased risk of nephrotoxicity
Probenecid Probenecid may increase the serum level of cefoxitin.
Streptomycin Increased risk of nephrotoxicity
Tobramycin Increased risk of nephrotoxicity
Warfarin The cephalosporin, cefoxitin, may increase the anticoagulant effect of warfarin.
Food Interactions Not Available

Targets


D-alanyl-D-alanine carboxypeptidase dacC
Name D-alanyl-D-alanine carboxypeptidase dacC
Gene Name dacC
Pharmacological action yes
Actions inhibitor
References
  • Matsuhashi M, Tamaki S: Enzymatic studies on the mechanism of action of cefoxitin. Correlation between the affinities of cefoxitin to penicillin-binding proteins and its rates of inhibition of the respective penicillin-sensitive reactions in E. coli. J Antibiot (Tokyo). 1978 Dec;31(12):1292-5. - Pubmed
DTHybrid score 0.572
Penicillin-binding protein 5 precursor
Name Penicillin-binding protein 5 precursor
Gene Name dacA
Pharmacological action yes
Actions inhibitor
References
  • Matsuhashi M, Tamaki S: Enzymatic studies on the mechanism of action of cefoxitin. Correlation between the affinities of cefoxitin to penicillin-binding proteins and its rates of inhibition of the respective penicillin-sensitive reactions in E. coli. J Antibiot (Tokyo). 1978 Dec;31(12):1292-5. - Pubmed
DTHybrid score 0.601
Penicillin-binding protein 7
Name Penicillin-binding protein 7
Gene Name pbpG
Pharmacological action yes
Actions inhibitor
References
  • Matsuhashi M, Tamaki S: Enzymatic studies on the mechanism of action of cefoxitin. Correlation between the affinities of cefoxitin to penicillin-binding proteins and its rates of inhibition of the respective penicillin-sensitive reactions in E. coli. J Antibiot (Tokyo). 1978 Dec;31(12):1292-5. - Pubmed
DTHybrid score Not Available
Penicillin-binding protein 4
Name Penicillin-binding protein 4
Gene Name dacB
Pharmacological action yes
Actions inhibitor
References
  • Matsuhashi M, Tamaki S: Enzymatic studies on the mechanism of action of cefoxitin. Correlation between the affinities of cefoxitin to penicillin-binding proteins and its rates of inhibition of the respective penicillin-sensitive reactions in E. coli. J Antibiot (Tokyo). 1978 Dec;31(12):1292-5. - Pubmed
DTHybrid score 0.6978
Penicillin-binding protein 1A
Name Penicillin-binding protein 1A
Gene Name mrcA
Pharmacological action yes
Actions inhibitor
References
  • Matsuhashi M, Tamaki S: Enzymatic studies on the mechanism of action of cefoxitin. Correlation between the affinities of cefoxitin to penicillin-binding proteins and its rates of inhibition of the respective penicillin-sensitive reactions in E. coli. J Antibiot (Tokyo). 1978 Dec;31(12):1292-5. - Pubmed
DTHybrid score 0.9029
Penicillin-binding protein 1B
Name Penicillin-binding protein 1B
Gene Name mrcB
Pharmacological action yes
Actions inhibitor
References
  • Matsuhashi M, Tamaki S: Enzymatic studies on the mechanism of action of cefoxitin. Correlation between the affinities of cefoxitin to penicillin-binding proteins and its rates of inhibition of the respective penicillin-sensitive reactions in E. coli. J Antibiot (Tokyo). 1978 Dec;31(12):1292-5. - Pubmed
DTHybrid score 0.9004
Peptidoglycan synthetase ftsI
Name Peptidoglycan synthetase ftsI
Gene Name ftsI
Pharmacological action yes
Actions inhibitor
References
  • Matsuhashi M, Tamaki S: Enzymatic studies on the mechanism of action of cefoxitin. Correlation between the affinities of cefoxitin to penicillin-binding proteins and its rates of inhibition of the respective penicillin-sensitive reactions in E. coli. J Antibiot (Tokyo). 1978 Dec;31(12):1292-5. - Pubmed
DTHybrid score 0.1315
Penicillin-binding protein 3
Name Penicillin-binding protein 3
Gene Name pbp3
Pharmacological action yes
Actions inhibitor
References
  • Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. - Pubmed
DTHybrid score 0.1828
Penicillin-binding protein 1b
Name Penicillin-binding protein 1b
Gene Name pbp1b
Pharmacological action yes
Actions inhibitor
References
  • Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. - Pubmed
DTHybrid score 0.9004
Penicillin-binding protein 2a
Name Penicillin-binding protein 2a
Gene Name pbp2a
Pharmacological action yes
Actions inhibitor
References
  • Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. - Pubmed
DTHybrid score Not Available
Penicillin-binding protein 1A
Name Penicillin-binding protein 1A
Gene Name pbpA
Pharmacological action yes
Actions inhibitor
References
  • Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. - Pubmed
DTHybrid score 0.9029
Penicillin-binding protein 2B
Name Penicillin-binding protein 2B
Gene Name penA
Pharmacological action yes
Actions inhibitor
References
  • Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. - Pubmed
DTHybrid score 0.8285

Enzymes


Beta-lactamase
Name Beta-lactamase
Gene Name penP
Actions substrate
References
  • Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. - Pubmed
  • Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. - Pubmed
  • Song W, Lee KM, Kim HS, Kim JS, Kim J, Jeong SH, Roh KH: Clonal spread of both oxyimino-cephalosporin- and cefoxitin-resistant Klebsiella pneumoniae isolates co-producing SHV-2a and DHA-1 beta-lactamase at a burns intensive care unit. Int J Antimicrob Agents. 2006 Dec;28(6):520-4. Epub 2006 Nov 13. - Pubmed
  • d'Azevedo PA, Goncalves AL, Musskopf MI, Ramos CG, Dias CA: Laboratory tests in the detection of extended spectrum beta-lactamase production: National Committee for Clinical Laboratory Standards (NCCLS) screening test, the E-test, the double disk confirmatory test, and cefoxitin susceptibility testing. Braz J Infect Dis. 2004 Oct;8(5):372-7. Epub 2005 Mar 17. - Pubmed
  • Ke YY, Lin TH: A theoretical study on the activation of Ser70 in the acylation mechanism of cephalosporin antibiotics. Biophys Chem. 2005 Apr 22;114(2-3):103-13. Epub 2004 Nov 30. - Pubmed
DTHybrid score 0.0448

Predictions


Id Partner name Gene Name Score
5805 Penicillin-binding protein 1A ponA 0.9029
6185 Penicillin-binding protein 1A mrcA 0.9029
6186 Penicillin-binding protein 1B ponB 0.9004
6822 Penicillin-binding protein 1b pbp1b 0.9004
159 Penicillin-binding protein 2B penA 0.8285
1539 Oligopeptide transporter, small intestine isoform SLC15A1 0.3671
1974 Oligopeptide transporter, kidney isoform SLC15A2 0.3437
1729 Solute carrier family 22 member 6 SLC22A6 0.2167
4252 Penicillin-binding protein 5 dacA 0.2107
587 Serum albumin ALB 0.2094
6067 Penicillin binding protein 2a mecA 0.1963
6113 MecA PBP2' (penicillin binding protein 2') mecA 0.192
867 Penicillin-binding protein 3 pbpC 0.1828
6119 Penicillin-binding protein 3 pbp3 0.1828
7157 Penicillin-binding protein 3 LMHCC_2184 0.1828
7162 Penicillin-binding protein 3 pbpB 0.1828
7172 Penicillin-binding protein 3 pbp3 0.1828
633 Penicillin-binding proteins 1A/1B pbpA 0.1705
118 Organic cation/carnitine transporter 2 SLC22A5 0.1483
6142 Solute carrier family 22 member 8 SLC22A8 0.1455
1 Peptidoglycan synthetase ftsI ftsI 0.1315
115 Penicillin-binding protein 2 mrdA 0.1153
6069 Penicillin-binding protein 2 mrdA 0.1153
6118 Penicillin-binding protein 2 penA 0.1153
6187 Penicillin-binding protein 2 pbpA 0.1153
6686 Penicillin-binding protein 2 pbp2 0.1153
6939 Penicillin-binding protein 2 mrdA 0.1153
7163 Penicillin-binding protein 2 pbpA 0.1153
1024 Solute carrier family 22 member 11 SLC22A11 0.1
2340 Beta-lactamase PSE-2 bla 0.0976
2461 D-alanyl-D-alanine carboxypeptidase Not Available 0.0747
5756 D-alanyl-D-alanine carboxypeptidase dac 0.0747
6143 Solute carrier family 22 member 7 SLC22A7 0.0733
4512 Cytochrome P450 3A4 CYP3A4 0.047
332 Beta-lactamase blaZ 0.0448
2478 Beta-lactamase ampC 0.0448
2613 Beta-lactamase ampC 0.0448
2635 Beta-lactamase ampC 0.0448
5445 Beta-lactamase blaB 0.0448
6019 Beta-lactamase SHV-7 0.0448
6701 Beta-lactamase cphA 0.0448
1198 Serum paraoxonase/arylesterase 1 PON1 0.0409
6223 Penicillin-binding protein 1C pbpC 0.0409
2385 Penicillin acylase Not Available 0.0391
3195 Beta-lactamase Toho-1 bla 0.0357
738 Monocarboxylate transporter 1 SLC16A1 0.0238
1405 Thiopurine S-methyltransferase TPMT 0.0238
6154 Multidrug and toxin extrusion protein 1 SLC47A1 0.0198
4200 Cytochrome P450 1A2 CYP1A2 0.0193
2164 Multidrug resistance-associated protein 4 ABCC4 0.016
3426 Glutamine synthetase glnA 0.0097
3987 Glutamine synthetase GLUL 0.0097
5577 N5-carboxyaminoimidazole ribonucleotide mutase purE 0.0096
2838 Ribose-5-phosphate isomerase A rpiA 0.0096
2952 Ribose-5-phosphate isomerase A rpiA 0.0096
5595 Ribose-5-phosphate isomerase A rpiA 0.0096
5598 Glycerol uptake operon antiterminator-related protein TM_1436 0.0096
2300 Lysozyme E 0.0096
3633 Lysozyme R 0.0096
5597 Lysozyme 17 0.0096
5591 Complement component C8 gamma chain C8G 0.0096
5582 Regulator of transcription; stringent starvation protein A sspA 0.0096
4238 50S ribosomal protein L4 rplD 0.0096
5578 50S ribosomal protein L4 rplD 0.0096
6173 50S ribosomal protein L4 rplD 0.0096
6219 50S ribosomal protein L4 rplD 0.0096
4695 UPF0124 protein yfiH yfiH 0.0096
5590 N utilization substance protein B homolog nusB 0.0096
5588 Cell division protein FtsY TM_0570 0.0096
5592 Ribonucleoside-diphosphate reductase subunit beta nrdF 0.0096
5583 RNA 3'-terminal phosphate cyclase rtcA 0.0096
5587 Iron(III)-binding periplasmic protein fbpA 0.0096
5600 Pyruvate decarboxylase pdc 0.0096
3792 KHG/KDPG aldolase [Includes: 4-hydroxy-2-oxoglutarate aldolase eda 0.0096
5586 Pleckstrin homology domain-containing family A member 1 PLEKHA1 0.0096
5593 Transferase Not Available 0.0096
5581 Beta-fructosidase bfrA 0.0096
5060 Intron-associated endonuclease 1 ITEVIR 0.0096
4375 Glutamine synthetase 1 glnA1 0.0096
5575 Short tail fiber protein 12 0.0096
5574 Invasin YPTB1668 0.0096
5580 Hexon protein PII 0.0096
4119 Cytochrome P450 2D6 CYP2D6 0.0091
3087 Nicotinate-nucleotide adenylyltransferase nadD 0.009
4469 Nicotinate-nucleotide adenylyltransferase nadD 0.009
4992 Cytochrome c peroxidase Not Available 0.009
5006 RNASE4 protein RNASE4 0.0084
3729 Citrate synthase gltA 0.0084
4575 Citrate synthase cit 0.0084
4580 Citrate synthase gltA 0.0084
4533 Glyoxalase family protein BC_1747 0.0084
3132 Tryptophan synthase alpha chain trpA 0.0084
6568 Tryptophan synthase alpha chain trpA 0.0084
2555 Pol polyprotein pol 0.0084
3242 Pol polyprotein gag-pol 0.0084
3471 Pol polyprotein gag-pro-pol 0.0084
5256 Pol polyprotein pol 0.0084
6469 Pol polyprotein gag-pol 0.0084
6565 Pol polyprotein Not Available 0.0084
5328 Prostaglandin F synthase Tb11.02.2310 0.0084
3085 Molybdopterin-guanine dinucleotide biosynthesis protein A mobA 0.0083
355 GMP synthase [glutamine-hydrolyzing] GMPS 0.0083
4353 GMP synthase [glutamine-hydrolyzing] guaA 0.0083
5599 3-carboxy-cis,cis-muconate cycloisomerase pcaB 0.0083
1467 Tumor necrosis factor ligand superfamily member 13B TNFSF13B 0.0081
2149 Angiogenin ANG 0.0077
2603 Beta-lactamase II blm 0.0077
3583 6-phosphogluconolactonase pgl 0.0077
4373 Medium-chain-fatty-acid--CoA ligase Not Available 0.0077
2521 Cell division protein ftsZ ftsZ 0.0077
3301 Cell division protein ftsZ ftsZ 0.0077
4366 Riboflavin kinase/FMN adenylyltransferase TM_0857 0.0076
2942 Sialidase nanH 0.0073
3546 Sialidase nedA 0.0073
3486 Fumarate hydratase class II fumC 0.0073
2869 1-deoxy-D-xylulose 5-phosphate reductoisomerase dxr 0.0073
2286 Isocitrate dehydrogenase [NADP] icd 0.0073
2302 Isocitrate dehydrogenase [NADP] icd 0.0073
2771 Isocitrate dehydrogenase [NADP] icd 0.0073
941 Betaine--homocysteine S-methyltransferase 1 BHMT 0.0071
857 Malate dehydrogenase, mitochondrial MDH2 0.0071
2805 Heparan sulfate glucosamine 3-O-sulfotransferase 3A1 HS3ST3A1 0.007
1123 Eosinophil cationic protein RNASE3 0.0069
2697 Uridine-cytidine kinase 2 UCK2 0.0069
2452 Tryptophanyl-tRNA synthetase trpS 0.0068
2936 Oxygen-insensitive NAD(P)H nitroreductase nfnB 0.0067
5184 Oxygen-insensitive NAD(P)H nitroreductase nfnB 0.0067
411 Glycine N-methyltransferase GNMT 0.0064
5579 Carboxypeptidase B CPB1 0.0064
3384 Macrophage migration inhibitory factor MIF 0.0062
3478 Glucose-1-phosphate thymidylyltransferase rmlA 0.0062
4277 Glucose-1-phosphate thymidylyltransferase rmlA 0.0062
128 Adenine phosphoribosyltransferase APRT 0.0056
204 cGMP-specific 3',5'-cyclic phosphodiesterase PDE5A 0.0049
5682 Ribonuclease pancreatic RNASE1 0.0049
822 Aldose reductase AKR1B1 0.0048
933 Proto-oncogene tyrosine-protein kinase Src SRC 0.0045
1632 Solute carrier organic anion transporter family member 2B1 SLCO2B1 0.0038
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