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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
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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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Click here for structure editor
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 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

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 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

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. UK MHRA (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
Specialist databases
Antibiotic DB Antibiotic DB Database logo Temocillin
Other databases
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
UniChem Compound Search for chemical match using the InChIKey BVCKFLJARNKCSS-DWPRYXJFSA-N
UniChem Connectivity Search for chemical match using the InChIKey BVCKFLJARNKCSS-DWPRYXJFSA-N