ceftriaxone   Click here for help

GtoPdb Ligand ID: 5326

Synonyms: Rocephin®
Approved drug
ceftriaxone is an approved drug (FDA (1984))
Compound class: Synthetic organic
Comment: Ceftriaxone 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 11
Hydrogen bond donors 4
Rotatable bonds 9
Topological polar surface area 293.8
Molecular weight 554.05
XLogP -0.89
No. Lipinski's rules broken 1

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 CON=C(c1csc(n1)N)C(=O)NC1C(=O)N2C1SCC(=C2C(=O)O)CSc1nc(=O)c(=O)[nH]n1C
Isomeric SMILES CO/N=C(/c1csc(n1)N)\C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)O)CSc1nc(=O)c(=O)[nH]n1C
InChI InChI=1S/C18H18N8O7S3/c1-25-18(22-12(28)13(29)23-25)36-4-6-3-34-15-9(14(30)26(15)10(6)16(31)32)21-11(27)8(24-33-2)7-5-35-17(19)20-7/h5,9,15H,3-4H2,1-2H3,(H2,19,20)(H,21,27)(H,23,29)(H,31,32)/b24-8-/t9-,15-/m1/s1
InChI Key VAAUVRVFOQPIGI-SPQHTLEESA-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 (1984))
Approved drug? Yes. FDA (1984)
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-methoxyiminoacetyl]amino]-3-[(2-methyl-5,6-dioxo-1H-1,2,4-triazin-3-yl)sulfanylmethyl]-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
4923 ceftriaxone
Synonyms Click here for help
Rocephin®
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Ceftriaxone
Other databases
CAS Registry No. 73384-59-5 (source: Scifinder)
ChEMBL Ligand CHEMBL161
DrugBank Ligand DB01212
DrugCentral Ligand 564
GtoPdb PubChem SID 178101992
PubChem CID 5479530
Search Google for chemical match using the InChIKey VAAUVRVFOQPIGI-SPQHTLEESA-N
Search Google for chemicals with the same backbone VAAUVRVFOQPIGI
Search PubMed clinical trials ceftriaxone
Search PubMed titles ceftriaxone
Search PubMed titles/abstracts ceftriaxone
UniChem Compound Search for chemical match using the InChIKey VAAUVRVFOQPIGI-SPQHTLEESA-N
UniChem Connectivity Search for chemical match using the InChIKey VAAUVRVFOQPIGI-SPQHTLEESA-N
Wikipedia Ceftriaxone