TEMOCILLIN

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

Structure Search

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

HIDE SMILES / InChI

Molecular Formula	C16H18N2O7S2
Molecular Weight	414.453
Charge	0
Count

Stereochemistry	EPIMERIC
Additional Stereochemistry	No
Defined Stereocenters	3 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

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was marketed by Beecham Pharmaceuticals in the UK in the 1980s but achieved little commercial success and was withdrawn, though it remained available via the manufacturer’s medical department.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
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
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
Comparison of four commercial methods for determining temocillin susceptibility of Escherichia coli.	2009 Apr	19223303
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
Extended-spectrum β-lactamases in Gram Negative Bacteria.	2010 Sep	20927289

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

Substance Class	Chemical Created by `admin` on `Sat Dec 16 17:03:03 GMT 2023` Edited by `admin` on `Sat Dec 16 17:03:03 GMT 2023`
Record UNII	03QB156W6I
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TEMOCILLIN

Official Name

English

BRL-17421

Code

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

Systematic Name

English

Temocillin [WHO-DD]

Common Name

English

temocillin [INN]

Common Name

English

TEMOCILLIN [MI]

Common Name

English

BRL 17421 FREE ACID

Code

English

TEMOCILLIN [MART.]

Common Name

English

TEMOCILLIN [USAN]

Common Name

English

4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID, 6-((CARBOXY-3-THIENYLACETYL)AMINO)-6-METHOXY-3,3-DIMETHYL-7-OXO-, (2S-(2.ALPHA.,5.ALPHA.,6.ALPHA.))-

Systematic Name

English

BRL-17421 FREE ACID

Code

English

Classification Tree Code System Code

WHO-VATC

QJ01CA17