TEMOCILLIN SODIUM

Details

Stereochemistry	EPIMERIC
Molecular Formula	C16H16N2O7S2.2Na
Molecular Weight	458.417
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[Na+].[Na+].[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=MRGCZDWBFFUEES-CWBCWDDISA-L

InChI=1S/C16H18N2O7S2.2Na/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);;/q;2*+1/p-2/t8?,9-,14+,16-;;/m0../s1

HIDE SMILES / InChI

Description
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was marketed by Beecham Pharmaceuticals in the UK in the 1980s but achieved little commercial success and was withdrawn, though it remained available via the manufacturer’s medical department.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

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Penicillin Binding Proteins 2 Target ID: Penicillin Binding Proteins Sources: http://www.ncbi.nlm.nih.gov/pubmed/3307621	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Urinary tract infections 205 Sources: http://www.ncbi.nlm.nih.gov/pubmed/27013887	Curative	Approved 8429	Unknown Approved Use Unknown
Sepsis 71 Sources: http://www.ncbi.nlm.nih.gov/pubmed/27013887	Curative	Approved 8429	Unknown Approved Use Unknown
Respiratory infections 12 Sources: http://www.ncbi.nlm.nih.gov/pubmed/27013887	Curative	Approved 8429	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Temocillin in the treatment of pyelonephritis in children.	1987	3622246
Probing the penicillin sidechain selectivity of recombinant deacetoxycephalosporin C synthase.	2001 May	11437242
Comparative in vitro activity of temocillin and other antimicrobial agents against Enterobacteriaceae isolated from patients admitted to five Belgian hospitals.	2001 Nov-Dec	11881320
Successful medical management of multifocal psoas abscess following cesarean section: report of a case and review of the literature.	2002 May 10	11950495
In vitro activity of temocillin against extended spectrum beta-lactamase-producing Escherichia coli.	2006 Apr	16501056
Temocillin in the treatment of Burkholderia cepacia infection in cystic fibrosis.	2006 May	16650744
Activity of temocillin against prevalent ESBL- and AmpC-producing Enterobacteriaceae from south-east England.	2006 May	16531428
Temocillin susceptibility by BSAC methodology.	2007 Jul	17550891
Imported cutaneous melioidosis in traveler, Belgium.	2007 Jun	17582903
In vitro activity of temocillin against prevalent extended-spectrum beta-lactamases producing Enterobacteriaceae from Belgian intensive care units.	2007 Nov	17668253
Effects of treatment with antimicrobial agents on the human colonic microflora.	2008 Dec	19337440
Case report: subacute synovitis of the knee after a rose thorn injury: unusual clinical picture.	2008 Dec	18773251
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	18070831
beta-Lactams without a suicide inhibitor.	2008 Jan	18154547
Recovery of antimicrobial-resistant Pseudomonas aeruginosa from sputa of cystic fibrosis patients by culture on selective media.	2008 May	18316821
Temocillin in cystic fibrosis: a retrospective pilot study.	2008 Nov	18706868
Spinal infection caused by ESBL-producing Klebsiella pneumoniae treated with temocillin.	2008 Oct	18804871
Comparison of four commercial methods for determining temocillin susceptibility of Escherichia coli.	2009 Apr	19223303
Clinical efficacy of temocillin.	2009 Aug	19520716
Temocillin revived.	2009 Feb	19095679
Aqua-(2,2'-bipyridine-κN,N')bis-(thio-phene-2-carboxyl-ato-κO)copper(II).	2009 Jul 11	21583368
In vitro activity of temocillin against planktonic and sessile Burkholderia cepacia complex bacteria.	2010 Dec	20851061
Infections with extended-spectrum beta-lactamase-producing enterobacteriaceae: changing epidemiology and drug treatment choices.	2010 Feb 12	20166768
[Update on antimicrobial chemotherapy].	2010 Mar	19959306
Extended-spectrum β-lactamases in Gram Negative Bacteria.	2010 Sep	20927289
Long-term stability of temocillin in elastomeric pumps for outpatient antibiotic therapy in cystic fibrosis patients.	2010 Sep	20576638

Patents

Sample Use Guides

In Vivo Use Guide

1-2 g every 12 hours.

Route of Administration: Other

In Vitro Use Guide

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

Name

Type

Language

TEMOCILLIN SODIUM

Common Name

English

Temocillin disodium [WHO-DD]

Common Name

English

TEMOCILLIN SODIUM [MART.]

Common Name

English

TEMOCILLIN DISODIUM

Common Name

English

N-((2S,5R,6S)-2-CARBOXY-6-METHOXY-3,3-DIMETHYL-7-OXO-4-THIA-1-AZABICYCLO(3.2.0)HEPT-6-YL)-3-THIOPHENEMALONAMIC ACID DISODIUM SALT

Common Name

English

TEMOCILLIN DISODIUM SALT [MI]

Common Name

English

BRL 17421

Code

English

TEMOCILLIN DISODIUM SALT

Common Name

English

Classification Tree Code System Code

EU-Orphan Drug

EU/3/03/183