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
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
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was marketed by Beecham Pharmaceuticals in the UK in the 1980s but achieved little commercial success and was withdrawn, though it remained available via the manufacturer’s medical department.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was marketed by Beecham Pharmaceuticals in the UK in the 1980s but achieved little commercial success and was withdrawn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 |
---|---|---|---|
Target ID: Penicillin Binding Proteins Sources: http://www.ncbi.nlm.nih.gov/pubmed/3307621 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Curative | Unknown Approved UseUnknown |
|||
Sources: http://www.ncbi.nlm.nih.gov/pubmed/27013887 |
Curative | Unknown Approved UseUnknown |
||
Curative | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
---|---|---|
Probing the penicillin sidechain selectivity of recombinant deacetoxycephalosporin C synthase. | 2001 May |
|
Comparative in vitro activity of temocillin and other antimicrobial agents against Enterobacteriaceae isolated from patients admitted to five Belgian hospitals. | 2001 Nov-Dec |
|
Effects of treatment with antimicrobial agents on the human colonic microflora. | 2008 Dec |
|
Case report: subacute synovitis of the knee after a rose thorn injury: unusual clinical picture. | 2008 Dec |
|
Temocillin in cystic fibrosis: a retrospective pilot study. | 2008 Nov |
|
Comparison of four commercial methods for determining temocillin susceptibility of Escherichia coli. | 2009 Apr |
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
Name | Type | Language | ||
---|---|---|---|---|
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
EU-Orphan Drug |
EU/3/03/183
Created by
admin on Fri Dec 15 18:00:41 GMT 2023 , Edited by admin on Fri Dec 15 18:00:41 GMT 2023
|
||
|
FDA ORPHAN DRUG |
182903
Created by
admin on Fri Dec 15 18:00:41 GMT 2023 , Edited by admin on Fri Dec 15 18:00:41 GMT 2023
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
11583399
Created by
admin on Fri Dec 15 18:00:41 GMT 2023 , Edited by admin on Fri Dec 15 18:00:41 GMT 2023
|
PRIMARY | |||
|
DTXSID50977112
Created by
admin on Fri Dec 15 18:00:41 GMT 2023 , Edited by admin on Fri Dec 15 18:00:41 GMT 2023
|
PRIMARY | |||
|
96IIP39ODH
Created by
admin on Fri Dec 15 18:00:41 GMT 2023 , Edited by admin on Fri Dec 15 18:00:41 GMT 2023
|
PRIMARY | |||
|
DBSALT002179
Created by
admin on Fri Dec 15 18:00:41 GMT 2023 , Edited by admin on Fri Dec 15 18:00:41 GMT 2023
|
PRIMARY | |||
|
61545-06-0
Created by
admin on Fri Dec 15 18:00:41 GMT 2023 , Edited by admin on Fri Dec 15 18:00:41 GMT 2023
|
PRIMARY | |||
|
262-835-9
Created by
admin on Fri Dec 15 18:00:41 GMT 2023 , Edited by admin on Fri Dec 15 18:00:41 GMT 2023
|
PRIMARY | |||
|
m10550
Created by
admin on Fri Dec 15 18:00:41 GMT 2023 , Edited by admin on Fri Dec 15 18:00:41 GMT 2023
|
PRIMARY | Merck Index | ||
|
SUB128094
Created by
admin on Fri Dec 15 18:00:41 GMT 2023 , Edited by admin on Fri Dec 15 18:00:41 GMT 2023
|
PRIMARY | |||
|
52434
Created by
admin on Fri Dec 15 18:00:41 GMT 2023 , Edited by admin on Fri Dec 15 18:00:41 GMT 2023
|
PRIMARY | |||
|
100000153807
Created by
admin on Fri Dec 15 18:00:41 GMT 2023 , Edited by admin on Fri Dec 15 18:00:41 GMT 2023
|
PRIMARY |
ACTIVE MOIETY
SUBSTANCE RECORD