temocillin   Click here for help

GtoPdb Ligand ID: 10926

Synonyms: BRL-17421 | BRL17421 | Negaban®
Approved drug
temocillin is an approved drug (UK (2005))
Compound class: Synthetic organic
Comment: Temocillin is a penicillinase (β-lactamase)-resistant penicillin that is active against Gram-negative bacteria. It is primarily used to treat infections caused by multiple drug-resistant strains of Enterobacteriaceae, especially those that produce extended-spectrum β-lactamase or AmpC β-lactamase. Temocillin is not effective against Acinetobacter species or Pseudomonas aeruginosa.
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 9
Hydrogen bond donors 3
Rotatable bonds 7
Topological polar surface area 186.78
Molecular weight 414.06
XLogP 0.87
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Click here for help
Canonical SMILES CO[C@@]1(NC(=O)C(c2cscc2)C(=O)O)C(=O)N2[C@@H]1SC([C@@H]2C(=O)O)(C)C
Isomeric SMILES CO[C@@]1(NC(=O)C(c2cscc2)C(=O)O)C(=O)N2[C@@H]1SC([C@@H]2C(=O)O)(C)C
InChI InChI=1S/C16H18N2O7S2/c1-15(2)9(12(22)23)18-13(24)16(25-3,14(18)27-15)17-10(19)8(11(20)21)7-4-5-26-6-7/h4-6,8-9,14H,1-3H3,(H,17,19)(H,20,21)(H,22,23)/t8?,9-,14+,16-/m0/s1
InChI Key BVCKFLJARNKCSS-DWPRYXJFSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (UK (2005))
IUPAC Name Click here for help
(2S,5R,6S)-6-[(2-carboxy-2-thiophen-3-ylacetyl)amino]-6-methoxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
International Nonproprietary Names Click here for help
INN number INN
5097 temocillin
Synonyms Click here for help
BRL-17421 | BRL17421 | Negaban®
Database Links Click here for help
CAS Registry No. 66148-78-5 (source: WHO INN record)
ChEMBL Ligand CHEMBL1276310
DrugBank Ligand DB12343
DrugCentral Ligand 2587
GtoPdb PubChem SID 405560367
PubChem CID 171758
Search Google for chemical match using the InChIKey BVCKFLJARNKCSS-DWPRYXJFSA-N
Search Google for chemicals with the same backbone BVCKFLJARNKCSS
Search PubMed clinical trials temocillin
Search PubMed titles temocillin
Search PubMed titles/abstracts temocillin
Search UniChem for chemical match using the InChIKey BVCKFLJARNKCSS-DWPRYXJFSA-N
Search UniChem for chemicals with the same backbone BVCKFLJARNKCSS