cephalexin   Click here for help

GtoPdb Ligand ID: 4832

Synonyms: cefalexin | Ceporex® | Keflex®
Approved drug
cephalexin is an approved drug (FDA (1971, prior history not available))
Compound class: Synthetic organic
Comment: Cephalexin is a cephalosporin antibacterial.
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 7
Hydrogen bond donors 3
Rotatable bonds 5
Topological polar surface area 138.03
Molecular weight 347.09
XLogP -2.19
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 NC(c1ccccc1)C(=O)NC1C(=O)N2C1SCC(=C2C(=O)O)C
Isomeric SMILES N[C@H](c1ccccc1)C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)O)C
InChI InChI=1S/C16H17N3O4S/c1-8-7-24-15-11(14(21)19(15)12(8)16(22)23)18-13(20)10(17)9-5-3-2-4-6-9/h2-6,10-11,15H,7,17H2,1H3,(H,18,20)(H,22,23)/t10-,11-,15-/m1/s1
InChI Key ZAIPMKNFIOOWCQ-UEKVPHQBSA-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/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1971, prior history not available))
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
IUPAC Name Click here for help
(6R,7R)-7-[(2R)-2-amino-2-phenylacetamido]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
International Nonproprietary Names Click here for help
INN number INN
2400 cefalexin
Synonyms Click here for help
cefalexin | Ceporex® | Keflex®
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Cephalexin
Other databases
CAS Registry No. 15686-71-2 (source: Scifinder)
ChEMBL Ligand CHEMBL1727
DrugBank Ligand DB00567
DrugCentral Ligand 571
GtoPdb PubChem SID 178101534
PubChem CID 27447
Search Google for chemical match using the InChIKey ZAIPMKNFIOOWCQ-UEKVPHQBSA-N
Search Google for chemicals with the same backbone ZAIPMKNFIOOWCQ
Search PubMed clinical trials cefalexin
Search PubMed titles cefalexin
Search PubMed titles/abstracts cefalexin
UniChem Compound Search for chemical match using the InChIKey ZAIPMKNFIOOWCQ-UEKVPHQBSA-N
UniChem Connectivity Search for chemical match using the InChIKey ZAIPMKNFIOOWCQ-UEKVPHQBSA-N
Wikipedia Cephalexin