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.
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
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
SMILES / InChI / InChIKey
Click here for help
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
Classification Click here for help
Compound class Synthetic organic
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