cefpirome   Click here for help

GtoPdb Ligand ID: 12033

Synonyms: HR 810 | Romecef®
Approved drug
cefpirome is an approved drug (Thailand (2016))
Compound class: Synthetic organic
Comment: Cefpirome is a semisynthetic, fourth generation cephalosporin belonging to the β-lactam class of antibacterial compounds [1].
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 8
Hydrogen bond donors 2
Rotatable bonds 8
Topological polar surface area 207.46
Molecular weight 514.11
XLogP -0.85
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES CO/N=C(\C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)[O-])C[n+]1cccc2c1CCC2)/c1csc(n1)N
Isomeric SMILES CO/N=C(/c1csc(n1)N)\C(=O)N[C@H]1[C@@H]2N(C1=O)C(=C(CS2)C[n+]1cccc2c1CCC2)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
InChI Key DKOQGJHPHLTOJR-WHRDSVKCSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
No information available.
Summary of Clinical Use Click here for help
Comparative studies indicate that parenteral cefpirome is at least as effective as ceftazidime for the treatment of suspected bacteraemia in patients with severe sepsis [2] and urinary tract infections in hospitalized patients [3].
There is no information regarding approval for clinical use of this drug on the US FDA website. Other national approval agencies may have granted marketing authorisation, including Thailand where it is approved for the treatment of septicaemia and infections of the skin, the urinary tract and the lower respiratory tract, caused by susceptible bacteria.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
In common with other β-lactams, cefpirome binds to penicillin-binding proteins leading to inhibition of bacterial cell wall synthesis and resulting in bacterial cell lysis and death.