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 CDK toolkit. 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
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.

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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
References
1. Machka K, Braveny I. (1983)
In vitro activity of HR 810, a new broad-spectrum cephalosporin.
Eur J Clin Microbiol, 2 (4): 345-9. [PMID:6313358]
2. Norrby SR, Geddes AM, Shah PM. (1998)
Randomized comparative trial of cefpirome versus ceftazidime in the empirical treatment of suspected bacteraemia or sepsis. Multicentre Study Group.
J Antimicrob Chemother, 42 (4): 503-9. [PMID:9818750]
3. (1992)
Cefpirome versus ceftazidime in the treatment of urinary tract infections.
J Antimicrob Chemother, 29 Suppl A: 95-104. [PMID:1601765]