Drug Information

Drug (ID: DG00447) and It's Reported Resistant Information

• Name: Cefpirome
• Synonyms: CEFPIROME; 84957-29-9; Cefpiroma; Cefpiromum; Cefrom; HR 810; UNII-S72Q2F09HY; cefpirome sulfate; CHEBI:3503; S72Q2F09HY; (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-(6,7-dihydro-5H-cyclopenta[b]pyridin-1-ium-1-ylmethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate; cefpirome sulphate; HR-810; (6R,7R)-7-{[(2Z)-2-(2-Amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino}-3-(6,7-dihydro-5H-cyclopenta[b]pyridinium-1-ylmethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate; 5H-Cyclopenta[b]pyridinium,1-[[(6R,7R)-7-[[(2Z)-(2-amino-4-thiazolyl)(methoxyimino)acetyl]amino]-2-carboxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl]-6,7-dihydro-, inner salt; Cefpiromum [Latin]; Cefpiroma [Spanish]; Cefpirome [INN:BAN]; NCGC00181339-01; Broact; Keiten; Cefir; Cefpirome (INN); Cefir (TN); HR-810 FREE BASE; SCHEMBL49406; MLS006010792; CHEMBL65794; DTXSID2048244; SCHEMBL22207951; C22H22N6O5S2; AKOS016013926; DB13682; (6R,7R)-7-(()-2-(2-Amino-4-thiazolyl)-2-methoxyiminoacetamido)-8-oxo-3-(2beta-trimethylenpyridinio)methyl)-5-thia-1-azabicyclo(4.2.0)oct-2-en-2-carboxylat; 1-(((6R,7R)-7-(2-(2-Amino-4-thiazolyl)glyoxylamino)-2-carboxy-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-en-3-yl)methyl)-6,7-dihydro-5H-1-pyridinium hydroxide, inner salt; 5H-1-Pyrindinium, 1-((7-(((2-amino-4-thiazolyl)(methoxyimino)acetyl)amino)-2-carboxy-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-en-3-yl)methyl)-6,7-dihydro-, hydroxide, inner salt, (6R-(6alpha,7beta(Z)))-; H828; SMR004701476; 98753-19-6; D07649; 1-{[(6R,7R)-2-carboxylato-7-{[(2Z)-1-hydroxy-2-(2-imino-2,3-dihydro-1,3-thiazol-4-yl)-2-(methoxyimino)ethylidene]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl}-5H,6H,7H-cyclopenta[b]pyridin-1-ium; 5H-1-Pyrindinium, 1-((7-(((2-amino-4-thiazolyl)(methoxyimino)acetyl)amino)-2-carboxy-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-en-3-yl)methyl)-5,6,7,8-tetrahydro-, hydroxide, inner salt, (6R-(6alpha,7beta(Z)))-; 7-{[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino}-3-(6,7-dihydro-5H-cyclopenta[b]pyridinium-1-ylmethyl)-3,4-didehydrocepham-4-carboxylic acid
• Drug Resistance Disease(s):
  Disease(s) with Clinically Reported Resistance for This Drug (1 diseases)
  Bacterial infection [ICD-11: 1A00-1C4Z]; [1], [2], [3]
• Formula: C22H22N6O5S2
• IsoSMILES: CO/N=C(/C1=CSC(=N1)N)\\C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)C[N+]4=CC=CC5=C4CCC5)C(=O)[O-]
• InChI: 1S/C22H22N6O5S2/c1-33-26-15(13-10-35-22(23)24-13)18(29)25-16-19(30)28-17(21(31)32)12(9-34-20(16)28)8-27-7-3-5-11-4-2-6-14(11)27/h3,5,7,10,16,20H,2,4,6,8-9H2,1H3,(H3-,23,24,25,29,31,32)/b26-15-/t16-,20-/m1/s1
• InChIKey: DKOQGJHPHLTOJR-WHRDSVKCSA-N
• PubChem CID: 5479539
• INTEDE ID: DR2656
• DrugBank ID: DB13682

Type(s) of Resistant Mechanism of This Drug

  DISM: Drug Inactivation by Structure Modification

  UAPP: Unusual Activation of Pro-survival Pathway

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], [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 DH10B; 316385
• In Vitro Model: Citrobacter freundii 2526/96; 546
• In Vitro Model: Escherichia coli isolates; 562
• Experiment for Molecule Alteration: Whole genome sequence assay
• Experiment for Drug Resistance: Agar dilution method assay
• Mechanism Description: We have reported recently the DNA sequence of another Beta-lactamase, CTX- M-15, from Indian enterobacterial isolates that were resistant to both cefotaxime and ceftazidime.CTX-M-15 has a single amino acid change [Asp-240-Gly (Ambler numbering)]7 compared with CTX-M-3.

Unusual Activation of Pro-survival Pathway (UAPP)

Key Molecule: Pyruvate decarboxylase 5 (PDC5) [4], [3]

• Molecule Alteration: Missense mutation; p.R79Q+p.T105A
• 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: Pseudomonas aeruginosa isolates; 287
• In Vitro Model: Pseudomonas aeruginosa PAO1; 208964
• In Vitro Model: Pseudomonas aeruginosa 12B; 287
• In Vitro Model: Pseudomonas aeruginosa kG2505; 287
• Experiment for Molecule Alteration: Whole genome sequence assay
• Experiment for Drug Resistance: Agar dilution method assay; Etest method assay
• Mechanism Description: Reduced susceptibility to imipenem, ceftazidime, and cefepime was observed only with recombinant P. aeruginosa strains expressing an AmpC Beta-lactamase that had an alanine residue at position 105.Recently, several ESACs have been described from Escherichia coli contributing to reduced susceptibility to imipenem.

Key Molecule: Pyruvate decarboxylase 3 (PDC3) [4], [3]

• Molecule Alteration: Missense mutation; p.T97A
• 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: Pseudomonas aeruginosa isolates; 287
• In Vitro Model: Pseudomonas aeruginosa PAO1; 208964
• In Vitro Model: Pseudomonas aeruginosa 12B; 287
• In Vitro Model: Pseudomonas aeruginosa kG2505; 287
• Experiment for Molecule Alteration: Whole genome sequence assay
• Experiment for Drug Resistance: Agar dilution method assay; Etest method assay
• Mechanism Description: Reduced susceptibility to imipenem, ceftazidime, and cefepime was observed only with recombinant P. aeruginosa strains expressing an AmpC Beta-lactamase that had an alanine residue at position 105.Recently, several ESACs have been described from Escherichia coli contributing to reduced susceptibility to imipenem.

References

• Ref 1: Plasmid-mediated extended-spectrum beta-lactamase (CTX-M-3 like) from India and gene association with insertion sequence ISEcp1. FEMS Microbiol Lett. 2001 Jul 24;201(2):237-41. doi: 10.1111/j.1574-6968.2001.tb10762.x.
• Ref 2: Biochemical analysis of the ceftazidime-hydrolysing extended-spectrum beta-lactamase CTX-M-15 and of its structurally related beta-lactamase CTX-M-3. J Antimicrob Chemother. 2002 Dec;50(6):1031-4. doi: 10.1093/jac/dkf240.
• 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: Extended-spectrum cephalosporinases in Pseudomonas aeruginosa. Antimicrob Agents Chemother. 2009 May;53(5):1766-71. doi: 10.1128/AAC.01410-08. Epub 2009 Mar 2.