Drug Information

Drug (ID: DG00299) and It's Reported Resistant Information

• Name: Cefuroxime
• Synonyms: Anaptivan; Biociclin; Biofuroksym; Bioxima; CXM; Cefofix; Cefumax; Cefurex; Cefuril; Cefuroxim; Cefuroximesodium; Cefuroximine; Cefuroximo; Cefuroximum; Cephuroxime; Cetroxil; Colifossim; Curocef; Curoxim; Curoxima; Curoxime; Froxal; Furoxil; Kesint; Ketocef; Lifurox; Medoxim; Sharox; Spectrazolr; Ultroxim; Zinacef;CEFUROXIME AND DEXTROSE IN DUPLEX CONTAINER; CEFUROXIME SODIUM; Cefuroxim AJ; Cefuroxim Fresenius; Cefuroxim Genericsn; Cefuroxim Hexal; Cefuroxim Lilly; Cefuroxim MN; Cefuroxim Norcox; Cefuroxim curasan; Cefuroxima Fabra; Cefuroxima Richet; Cefuroxime for Injection and Dextrose for Injection in Duplex Container; Cefuroxime na; Cefuroxime sodium salt; KEFUROX IN PLASTIC CONTAINER; Sodium cefuroxime; ZINACEF IN PLASTIC CONTAINER; Zinacef Danmark; Ceftin (TN); Cefuroxim Norcox [inj.]; Cefuroxime (TN); Cefuroximo [INN-Spanish]; Cefuroximum [INN-Latin]; Cetroxil [inj.]; Froxal [inj.]; KS-1040; Sharox [inj.]; Zinacef (TN); Zinnat (TN); Zinnat [inj.]; Cefuroxime (USAN/INN); Cefuroxime [USAN:INN:BAN]; Cefuroxime sodium (JP15/USP); Cefuroxime sodium [USAN:BAN:JAN]; Sodium (6R-(6alpha,7beta(Z)))-3-(((aminocarbonyl)oxy)methyl)-7-(2-furyl(methoxyimino)acetamido)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate; Sodium (6R,7R)-7-(2-(2-furyl)glyoxylamido)-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate, 7(sup 2)-(Z)-(O-methyloxime), carbamate (ester); (6R,7R)-3-(carbamoyloxymethyl)-7-[[(2Z)-2-(furan-2-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; (6R,7R)-3-[(carbamoyloxy)methyl]-7-[(2Z)-2-(furan-2-yl)-2-(methoxyimino)acetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; (6R,7R)-3-[(carbamoyloxy)methyl]-7-{[(2Z)-2-furan-2-yl-2-(methoxyimino)acetyl]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; (6R,7R)-7-(2-(2-Furyl)glyoxylamido)-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid 7(sup 2)-(Z)-(O-methyloxime) carbamate (ester); 3-[(carbamoyloxy)methyl]-7beta-[(2Z)-2-(furan-2-yl)-2-(methoxyimino)acetamido]-3,4-didehydrocepham-4-carboxylic acid
• Indication:
  In total 1 Indication(s)
  Acute bronchitis [ICD-11: CA42]; Approved; [1]
• Drug Resistance Disease(s):
  Disease(s) with Clinically Reported Resistance for This Drug (1 diseases)
  Bacterial infection [ICD-11: 1A00-1C4Z]; [2], [3]
• Target: Bacterial Penicillin binding protein (Bact PBP); NOUNIPROTAC; [1]
• Formula: C16H16N4O8S
• IsoSMILES: CO/N=C(/C1=CC=CO1)\\C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)COC(=O)N)C(=O)O
• InChI: 1S/C16H16N4O8S/c1-26-19-9(8-3-2-4-27-8)12(21)18-10-13(22)20-11(15(23)24)7(5-28-16(17)25)6-29-14(10)20/h2-4,10,14H,5-6H2,1H3,(H2,17,25)(H,18,21)(H,23,24)/b19-9-/t10-,14-/m1/s1
• InChIKey: JFPVXVDWJQMJEE-IZRZKJBUSA-N
• PubChem CID: 5479529
• ChEBI ID: CHEBI:3515
• TTD Drug ID: D0Y2IE
• DrugBank ID: DB01112

Type(s) of Resistant Mechanism of This Drug

  DISM: Drug Inactivation by Structure Modification

Drug Resistance Data Categorized by Their Corresponding Diseases

ICD-01: Infectious/parasitic diseases

Bacterial infection [ICD-11: 1A00-1C4Z]

Drug Resistance Data Categorized by Their Corresponding Mechanisms

Drug Inactivation by Structure Modification (DISM)

Key Molecule: Beta-lactamase (BLA) [1]

• Molecule Alteration: Missense mutation; p.Y221H
• Resistant Disease: Bacterial infection [ICD-11: 1A00-1C4Z]
• Experimental Note: Identified from the Human Clinical Data
• In Vitro Model: Escherichia coli TOP10; 83333
• In Vitro Model: Escherichia coli EC13; 562
• Experiment for Molecule Alteration: Whole genome sequencing assay
• Experiment for Drug Resistance: Disk diffusion test assay
• Mechanism Description: The CMY-136 Beta-lactamase, a Y221H point mutant derivative of CMY-2,confers an increased level of resistance to ticarcillin, cefuroxime, cefotaxime, and ceftolozane/tazobactam.

Key Molecule: Beta-lactamase (BLA) [4]

• Molecule Alteration: Expression; Inherence
• Resistant Disease: Pseudomonas aeruginosa infection [ICD-11: 1A00-1C4Z]
• Experimental Note: Identified from the Human Clinical Data
• In Vitro Model: Pseudomonas aeruginosa PAO1; 208964
• Experiment for Molecule Alteration: DNA sequencing and protein assay
• Experiment for Drug Resistance: Disk diffusion assay
• Mechanism Description: P. aeruginosa harbors two naturally encoded Beta-lactamase genes, one of which encodes an inducible cephalosporinase and the other of which encodes a constitutively expressed oxacillinase. AmpC is a kind of cephalosporinase which lead to drug resistance.

Key Molecule: Beta-lactamase (BLA) [2], [3]

• Molecule Alteration: Missense mutation; p.D240G
• Resistant Disease: Bacterial infection [ICD-11: 1A00-1C4Z]
• Experimental Note: Identified from the Human Clinical Data
• In Vitro Model: Escherichia coli; 668369
• In Vitro Model: Escherichia coli Gre-1; 562
• Experiment for Molecule Alteration: Whole genome sequence assay
• Experiment for Drug Resistance: Agar dilution method assay
• Mechanism Description: The first extended-spectrum Beta-lactamase (ESBL) of the CTX-M type (MEN-1/CTX-M-1) was reported at the beginning of the 1990s.CTX-M-27 differed from CTX-M-14 only by the substitution D240G and was the third CTX-M enzyme harbouring this mutation after CTX-M-15 and CTX-M-16. The Gly-240-harbouring enzyme CTX-M-27 conferred to Escherichia coli higher MICs of ceftazidime (MIC, 8 versus 1 mg/L) than did the Asp-240-harbouring CTX-M-14 enzyme.

References

• Ref 1: Genetic, Biochemical, and Structural Characterization of CMY-136 Beta-Lactamase, a Peculiar CMY-2 Variant. ACS Infect Dis. 2019 Apr 12;5(4):528-538. doi: 10.1021/acsinfecdis.8b00240. Epub 2019 Mar 7.
• Ref 2: Effect of D240G substitution in a novel ESBL CTX-M-27. J Antimicrob Chemother. 2003 Jul;52(1):29-35. doi: 10.1093/jac/dkg256. Epub 2003 May 29.
• Ref 3: Identifying novel Beta-lactamase substrate activity through in silico prediction of antimicrobial resistance. Microb Genom. 2021 Jan;7(1):mgen000500. doi: 10.1099/mgen.0.000500.
• Ref 4: Biochemical characterization of the naturally occurring oxacillinase OXA-50 of Pseudomonas aeruginosa. Antimicrob Agents Chemother. 2004 Jun;48(6):2043-8. doi: 10.1128/AAC.48.6.2043-2048.2004.