Compound ID | 3228

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Cefpirome

Synonym(s): HR-810  |  HR810

Class: Beta-lactam

Agent Type: Semisynthetic; Small molecule; Direct acting;
Spectrum of activity: Gram-positive & Gram-negative
Mechanism of action: Cell wall synthesis inhibitor
Target Pathogen: Active against Staphylococcus aureus, Enterobacter cloacae, Streptococcus sp., Pseudomonas aeruginosa
Description: A fourth-generation synthetic compound derived from cephalosporin C; shows synergistic effect with gentamicin in Pseudomonas and Enterobacter strains
Institute where first reported: Hoechst AG
Year first mentioned: 1983
Highest developmental phase: Approved (not in US)
Development status: Approved
Reason Dropped: Discontinued in many countries
Chemical structure(s):
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Molecular weight: 514.58
Iso. SMILES: 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 Key: DKOQGJHPHLTOJR-WHRDSVKCSA-N
Can. SMILES: CO/N=C(/C1=CSC(=N1)N)\C(=O)N[C@@H]2C(=O)N3C(=C(C[N+]4=C5CCCC5=CC=C4)CS[C@H]23)C(=O)[O-]
InChI: 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
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/5479539
Guide to Pharmacology: cefpirome
Citations:
  • https://pubmed.ncbi.nlm.nih.gov/1601761/
  • https://pubmed.ncbi.nlm.nih.gov/9211085/
  • https://pubmed.ncbi.nlm.nih.gov/8261711/
  • https://www.jstage.jst.go.jp/article/antibiotics1968/37/8/37_8_929/_article/-char/en

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