Details
Stereochemistry | EPIMERIC |
Molecular Formula | C16H18N2O7S2 |
Molecular Weight | 414.453 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 3 / 4 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@]2(NC(=O)C(C(O)=O)C3=CSC=C3)OC)C(O)=O
InChI
InChIKey=BVCKFLJARNKCSS-DWPRYXJFSA-N
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
DescriptionSources: http://www.ncbi.nlm.nih.gov/pubmed/27013887Curator's Comment: description was created based on several sources, including
https://www.medicines.org.uk/emc/medicine/22753
Sources: http://www.ncbi.nlm.nih.gov/pubmed/27013887
Curator's Comment: description was created based on several sources, including
https://www.medicines.org.uk/emc/medicine/22753
Temocillin was marketed by Beecham Pharmaceuticals in the UK in the 1980s but achieved little commercial success and was withdrawn, though it remained available via the manufacturer’s medical department. Presently licensed to Eumedica, temocillin is being re-launched in the UK and Belgium for treating UTI, sepsis, and respiratory infections by ESBL (Extended-spectrum beta-lactamases) and AmpC-producing Enterobacteriaceae. It acts by inhibiting the synthesis of the peptidoglycan layer of bacterial cell walls. It irreversibly binds to the active site of specific transpeptidases and carboxypeptidases known as Penicillin Binding Proteins (PBP), preventing peptidoglycan production.
Originator
Sources: http://www.ncbi.nlm.nih.gov/pubmed/16531428
Curator's Comment: Temocillin was marketed by Beecham Pharmaceuticals in the UK in the 1980s but achieved little commercial success and was withdrawn
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: Penicillin Binding Proteins Sources: http://www.ncbi.nlm.nih.gov/pubmed/3307621 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Curative | Unknown Approved UseUnknown |
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Sources: http://www.ncbi.nlm.nih.gov/pubmed/27013887 |
Curative | Unknown Approved UseUnknown |
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Curative | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Temocillin in the treatment of pyelonephritis in children. | 1987 |
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Probing the penicillin sidechain selectivity of recombinant deacetoxycephalosporin C synthase. | 2001 May |
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Comparative in vitro activity of temocillin and other antimicrobial agents against Enterobacteriaceae isolated from patients admitted to five Belgian hospitals. | 2001 Nov-Dec |
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Successful medical management of multifocal psoas abscess following cesarean section: report of a case and review of the literature. | 2002 May 10 |
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Temocillin susceptibility by BSAC methodology. | 2007 Jul |
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In vitro activity of temocillin against prevalent extended-spectrum beta-lactamases producing Enterobacteriaceae from Belgian intensive care units. | 2007 Nov |
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Effects of treatment with antimicrobial agents on the human colonic microflora. | 2008 Dec |
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Case report: subacute synovitis of the knee after a rose thorn injury: unusual clinical picture. | 2008 Dec |
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Continuous versus intermittent infusion of temocillin, a directed spectrum penicillin for intensive care patients with nosocomial pneumonia: stability, compatibility, population pharmacokinetic studies and breakpoint selection. | 2008 Feb |
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beta-Lactams without a suicide inhibitor. | 2008 Jan |
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Recovery of antimicrobial-resistant Pseudomonas aeruginosa from sputa of cystic fibrosis patients by culture on selective media. | 2008 May |
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Temocillin in cystic fibrosis: a retrospective pilot study. | 2008 Nov |
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Spinal infection caused by ESBL-producing Klebsiella pneumoniae treated with temocillin. | 2008 Oct |
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Comparison of four commercial methods for determining temocillin susceptibility of Escherichia coli. | 2009 Apr |
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Clinical efficacy of temocillin. | 2009 Aug |
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Aqua-(2,2'-bipyridine-κN,N')bis-(thio-phene-2-carboxyl-ato-κO)copper(II). | 2009 Jul 11 |
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Infections with extended-spectrum beta-lactamase-producing enterobacteriaceae: changing epidemiology and drug treatment choices. | 2010 Feb 12 |
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[Update on antimicrobial chemotherapy]. | 2010 Mar |
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Extended-spectrum β-lactamases in Gram Negative Bacteria. | 2010 Sep |
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Long-term stability of temocillin in elastomeric pumps for outpatient antibiotic therapy in cystic fibrosis patients. | 2010 Sep |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.medicines.org.uk/emc/medicine/22753
Curator's Comment: Negaban (temocillin sodium) may be administered by intravenous injection, intermittent intravenous infusion or intramuscular injection.
1-2 g every 12 hours.
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6348653
Temocillin is a carboxypenicillin; a methoxy group in the 6-alpha position should confer to the molecule greater stability to beta-lactamases. 236 strains isolated from clinical specimens were tested. Enterobacteriaceae were very susceptible, MICs being generally less than or equal to 8 micrograms/ml and always less than 32 micrograms/ml. The activity of the drug was equal against the beta-lactamases producing strains
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WHO-VATC |
QJ01CA17
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NCI_THESAURUS |
C1500
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J01CA17
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100000082926
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SUB10886MIG
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C76858
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171758
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X-27
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m10550
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CHEMBL1276310
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266-184-1
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TEMOCILLIN
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DTXSID201009398
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37775
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03QB156W6I
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C031367
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5097
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DB12343
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2587
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66148-78-5
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)