ceftriaxone   

GtoPdb Ligand ID: 5326

Synonyms: Rocephin®
ceftriaxone is an approved drug (FDA (1984))
Compound class: Synthetic organic
Comment: Ceftriaxone is a cephalosporin antibiotic.
2D Structure
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Physico-chemical Properties
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
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
Compound class Synthetic organic
Approved drug? Yes (FDA (1984))
WHO Essential Medicine WHO Model List of Essential Medicines (21st List, 2019). Access PDF version.
IUPAC Name
(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
INN number INN
4923 ceftriaxone
Synonyms
Rocephin®
Database Links
Specialist databases
Antibiotic DB Antibiotic DB Database logo 1326
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
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Wikipedia Ceftriaxone