ceftiolene   Click here for help

GtoPdb Ligand ID: 10784

Synonyms: 42980RP | cefatiolene | RP 42,980 | RP 42980 | RP-42980 | RP42980
Compound class: Synthetic organic
Comment: Ceftiolene is a semisynthetic, broad-spectrum, third-generation cephalosporin antibiotic [1].
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 10
Hydrogen bond donors 4
Rotatable bonds 11
Topological polar surface area 310.87
Molecular weight 594.04
XLogP -2.12
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Click here for help
Canonical SMILES O=CCn1c(S/C=C/C2=C(C(=O)O)N3[C@H](SC2)[C@@H](C3=O)NC(=O)/C(=N\OC)/c2csc(n2)N)n[nH]c(=O)c1=O
Isomeric SMILES O=CCn1c(S/C=C/C2=C(C(=O)O)N3[C@H](SC2)[C@@H](C3=O)NC(=O)/C(=N\OC)/c2csc(n2)N)n[nH]c(=O)c1=O
InChI InChI=1S/C20H18N8O8S3/c1-36-26-10(9-7-39-19(21)22-9)13(30)23-11-15(32)28-12(18(34)35)8(6-38-17(11)28)2-5-37-20-25-24-14(31)16(33)27(20)3-4-29/h2,4-5,7,11,17H,3,6H2,1H3,(H2,21,22)(H,23,30)(H,24,31)(H,34,35)/b5-2+,26-10-/t11-,17-/m1/s1
InChI Key WJXAHFZIHLTPFR-JLRJEBFFSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
(6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[(E)-2-[[5,6-dioxo-4-(2-oxoethyl)-1H-1,2,4-triazin-3-yl]sulfanyl]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
5291 ceftiolene
Synonyms Click here for help
42980RP | cefatiolene | RP 42,980 | RP 42980 | RP-42980 | RP42980
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo 1088
Other databases
CAS Registry No. 77360-52-2 (source: WHO INN record)
ChEMBL Ligand CHEMBL2106102
GtoPdb PubChem SID 405560225
PubChem CID 6537430
Search Google for chemical match using the InChIKey WJXAHFZIHLTPFR-JLRJEBFFSA-N
Search Google for chemicals with the same backbone WJXAHFZIHLTPFR
Search PubMed clinical trials ceftiolene
Search PubMed titles ceftiolene
Search PubMed titles/abstracts ceftiolene
Search UniChem for chemical match using the InChIKey WJXAHFZIHLTPFR-JLRJEBFFSA-N
Search UniChem for chemicals with the same backbone WJXAHFZIHLTPFR