cefapirin   Click here for help

GtoPdb Ligand ID: 12191

Synonyms: Cefadyl® | cephapirin
Approved drug
cefapirin is an approved drug (FDA (1974))
Compound class: Synthetic organic
Comment: Cefapirin is a semisynthetic, first 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 9
Hydrogen bond donors 2
Rotatable bonds 9
Topological polar surface area 176.5
Molecular weight 423.06
XLogP -2.25
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 O=C(N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)O)COC(=O)C)CSc1ccncc1
Isomeric SMILES CC(=O)OCC1=C(N2[C@@H]([C@@H](C2=O)NC(=O)CSc2ccncc2)SC1)C(=O)O
InChI InChI=1S/C17H17N3O6S2/c1-9(21)26-6-10-7-28-16-13(15(23)20(16)14(10)17(24)25)19-12(22)8-27-11-2-4-18-5-3-11/h2-5,13,16H,6-8H2,1H3,(H,19,22)(H,24,25)/t13-,16-/m1/s1
InChI Key UQLLWWBDSUHNEB-CZUORRHYSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1974))
IUPAC Name Click here for help
(6R,7R)-3-(acetyloxymethyl)-8-oxo-7-[(2-pyridin-4-ylsulfanylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
International Nonproprietary Names Click here for help
INN number INN
2871 cefapirin
Synonyms Click here for help
Cefadyl® | cephapirin
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Cephapirin
Other databases
CAS Registry No. 21593-23-7 (source: Scifinder)
ChEBI CHEBI:554446
ChEMBL Ligand CHEMBL1599
DrugBank Ligand DB01139
DrugCentral Ligand 575
GtoPdb PubChem SID 472319313
PubChem CID 30699
Search Google for chemical match using the InChIKey UQLLWWBDSUHNEB-CZUORRHYSA-N
Search Google for chemicals with the same backbone UQLLWWBDSUHNEB
Search PubMed clinical trials cefapirin
Search PubMed titles cefapirin
Search PubMed titles/abstracts cefapirin
UniChem Compound Search for chemical match using the InChIKey UQLLWWBDSUHNEB-CZUORRHYSA-N
UniChem Connectivity Search for chemical match using the InChIKey UQLLWWBDSUHNEB-CZUORRHYSA-N