cefixime   Click here for help

GtoPdb Ligand ID: 10898

Synonyms: (E)-Cefixime | Cefspan® | CFIX | FK-027 | FR-17027 | Suprax®
Approved drug PDB Ligand
cefixime is an approved drug (FDA (1989))
Compound class: Synthetic organic
Comment: Cefixime is a broad-spectrum, third-generation, orally active 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 10
Hydrogen bond donors 4
Rotatable bonds 9
Topological polar surface area 238.05
Molecular weight 453.04
XLogP -2.53
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 Nc1nc(cs1)/C(=N/OCC(=O)O)/C(=O)N[C@H]1[C@H]2SCC(=C(N2C1=O)C(=O)O)C=C
Isomeric SMILES Nc1nc(cs1)/C(=N/OCC(=O)O)/C(=O)N[C@H]1[C@H]2SCC(=C(N2C1=O)C(=O)O)C=C
InChI InChI=1S/C16H15N5O7S2/c1-2-6-4-29-14-10(13(25)21(14)11(6)15(26)27)19-12(24)9(20-28-3-8(22)23)7-5-30-16(17)18-7/h2,5,10,14H,1,3-4H2,(H2,17,18)(H,19,24)(H,22,23)(H,26,27)/b20-9-/t10-,14-/m1/s1
InChI Key OKBVVJOGVLARMR-QSWIMTSFSA-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 (1989))
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-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(carboxymethoxyimino)acetyl]amino]-3-ethenyl-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
5678 cefixime
Synonyms Click here for help
(E)-Cefixime | Cefspan® | CFIX | FK-027 | FR-17027 | Suprax®
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Cefixime
Other databases
BindingDB Ligand 84007
CAS Registry No. 79350-37-1 (source: WHO INN record)
ChEMBL Ligand CHEMBL1541
DrugBank Ligand DB00671
DrugCentral Ligand 537
GtoPdb PubChem SID 405560339
PubChem CID 5362065
RCSB PDB Ligand C04
Search Google for chemical match using the InChIKey OKBVVJOGVLARMR-QSWIMTSFSA-N
Search Google for chemicals with the same backbone OKBVVJOGVLARMR
Search PubMed clinical trials cefixime
Search PubMed titles cefixime
Search PubMed titles/abstracts cefixime
UniChem Compound Search for chemical match using the InChIKey OKBVVJOGVLARMR-QSWIMTSFSA-N
UniChem Connectivity Search for chemical match using the InChIKey OKBVVJOGVLARMR-QSWIMTSFSA-N