TEMOCILLIN

Possibly Marketed Outside US

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

CO[C@]2(NC(=O)C(C(O)=O)C1=CSC=C1)[C@H]3SC(C)(C)[C@@H](N3C2=O)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was marketed by Beecham Pharmaceuticals in the UK in the 1980s but achieved little commercial success and was withdrawn, though it remained available via the manufacturer’s medical department.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 8504

Conditions

Condition	Modality	Highest Phase	Product
Urinary tract infections 207 Sources: http://www.ncbi.nlm.nih.gov/pubmed/27013887	Curative	Approved 8583	Unknown Approved Use Unknown
Sepsis 74 Sources: http://www.ncbi.nlm.nih.gov/pubmed/27013887	Curative	Approved 8583	Unknown Approved Use Unknown
Respiratory infections 12 Sources: http://www.ncbi.nlm.nih.gov/pubmed/27013887	Curative	Approved 8583	Unknown Approved Use Unknown

C_max

Value	Dose	Analyte	Population
233.5 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32433753/	2 g single, intravenous dose: 2 g route of administration: Intravenous experiment type: SINGLE co-administered:	TEMOCILLIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
100 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32433753/	2 g single, subcutaneous dose: 2 g route of administration: Subcutaneous experiment type: SINGLE co-administered:	TEMOCILLIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
77.9 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4029032/ \| https://pubmed.ncbi.nlm.nih.gov/28849402/	0.5 g single, intravenous dose: 0.5 g route of administration: Intravenous experiment type: SINGLE co-administered:	TEMOCILLIN serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
160.8 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4029032/ \| https://pubmed.ncbi.nlm.nih.gov/28849402/	1 g single, intravenous dose: 1 g route of administration: Intravenous experiment type: SINGLE co-administered:	TEMOCILLIN serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
236.1 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4029032/ \| https://pubmed.ncbi.nlm.nih.gov/28849402/	2 g single, intravenous dose: 2 g route of administration: Intravenous experiment type: SINGLE co-administered:	TEMOCILLIN serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
127 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6853404/	15 mg single, intravenous dose: 15 mg route of administration: Intravenous experiment type: SINGLE co-administered:	TEMOCILLIN serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
122 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6853404/	15 mg single, intravenous dose: 15 mg route of administration: Intravenous experiment type: SINGLE co-administered:	TEMOCILLIN serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
118 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6853404/	15 mg single, intravenous dose: 15 mg route of administration: Intravenous experiment type: SINGLE co-administered:	TEMOCILLIN serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
31.33 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6619046/	3.75 mg/kg single, intravenous dose: 3.75 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	TEMOCILLIN serum	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED
75.08 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6619046/	7.5 mg/kg single, intravenous dose: 7.5 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	TEMOCILLIN serum	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED
75.08 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6619046/	15 mg/kg single, intravenous dose: 15 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	TEMOCILLIN serum	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED
26.71 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6619046/	7.5 mg/kg single, intramuscular dose: 7.5 mg/kg route of administration: Intramuscular experiment type: SINGLE co-administered:	TEMOCILLIN serum	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED
69.8 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6619046/	7.5 mg/kg single, intravenous dose: 7.5 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	TEMOCILLIN serum	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FASTED
49.41 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6619046/	7.5 mg/kg single, intravenous dose: 7.5 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	TEMOCILLIN serum	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FASTED
49.52 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6619046/	7.5 mg/kg single, intravenous dose: 7.5 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	TEMOCILLIN serum	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FASTED
173.1 mg/L OTHER https://www.medicines.org.uk/emc/product/466#PHARMACOKINETIC_PROPS	1 g single, intravenous dose: 1 g route of administration: Intravenous experiment type: SINGLE co-administered:	TEMOCILLIN serum	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
281.2 mg/L OTHER https://www.medicines.org.uk/emc/product/466#PHARMACOKINETIC_PROPS	2 g single, intravenous dose: 2 g route of administration: Intravenous experiment type: SINGLE co-administered:	TEMOCILLIN serum	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
482.9 mg/L OTHER https://www.medicines.org.uk/emc/product/466#PHARMACOKINETIC_PROPS	4 g single, intravenous dose: 4 g route of administration: Intravenous experiment type: SINGLE co-administered:	TEMOCILLIN serum	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
72.7 mg/L OTHER https://www.medicines.org.uk/emc/product/466#PHARMACOKINETIC_PROPS	1 g single, intramuscular dose: 1 g route of administration: Intramuscular experiment type: SINGLE co-administered:	TEMOCILLIN serum	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
93.2 mg/L OTHER https://www.medicines.org.uk/emc/product/466#PHARMACOKINETIC_PROPS	1 g single, intravenous dose: 1 g route of administration: Intravenous experiment type: SINGLE co-administered:	TEMOCILLIN serum	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
49.5 mg/L OTHER https://www.medicines.org.uk/emc/product/466#PHARMACOKINETIC_PROPS	7.5 mg/kg single, intravenous dose: 7.5 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	TEMOCILLIN serum	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
1197.1 mg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32433753/	2 g single, intravenous dose: 2 g route of administration: Intravenous experiment type: SINGLE co-administered:	TEMOCILLIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
1314 mg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32433753/	2 g single, subcutaneous dose: 2 g route of administration: Subcutaneous experiment type: SINGLE co-administered:	TEMOCILLIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
344.1 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4029032/ \| https://pubmed.ncbi.nlm.nih.gov/28849402/	0.5 g single, intravenous dose: 0.5 g route of administration: Intravenous experiment type: SINGLE co-administered:	TEMOCILLIN serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
573.3 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4029032/ \| https://pubmed.ncbi.nlm.nih.gov/28849402/	1 g single, intravenous dose: 1 g route of administration: Intravenous experiment type: SINGLE co-administered:	TEMOCILLIN serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
784.5 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4029032/ \| https://pubmed.ncbi.nlm.nih.gov/28849402/	2 g single, intravenous dose: 2 g route of administration: Intravenous experiment type: SINGLE co-administered:	TEMOCILLIN serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
418 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6853404/	15 mg single, intravenous dose: 15 mg route of administration: Intravenous experiment type: SINGLE co-administered:	TEMOCILLIN serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
1301 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6853404/	15 mg single, intravenous dose: 15 mg route of administration: Intravenous experiment type: SINGLE co-administered:	TEMOCILLIN serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
1553 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6853404/	15 mg single, intravenous dose: 15 mg route of administration: Intravenous experiment type: SINGLE co-administered:	TEMOCILLIN serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
1749 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26603304/	1 g 1 times / day multiple, intravenous dose: 1 g route of administration: Intravenous experiment type: MULTIPLE co-administered:	TEMOCILLIN serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
5088 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26603304/	2 g 1 times / 2 days multiple, intravenous dose: 2 g route of administration: Intravenous experiment type: MULTIPLE co-administered:	TEMOCILLIN serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
7621 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26603304/	3 g 1 times / 3 days multiple, intravenous dose: 3 g route of administration: Intravenous experiment type: MULTIPLE co-administered:	TEMOCILLIN serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Analyte	Population
5.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32433753/	2 g single, intravenous dose: 2 g route of administration: Intravenous experiment type: SINGLE co-administered:	TEMOCILLIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
6.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32433753/	2 g single, subcutaneous dose: 2 g route of administration: Subcutaneous experiment type: SINGLE co-administered:	TEMOCILLIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
5.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4029032/ \| https://pubmed.ncbi.nlm.nih.gov/28849402/	0.5 g single, intravenous dose: 0.5 g route of administration: Intravenous experiment type: SINGLE co-administered:	TEMOCILLIN serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4029032/ \| https://pubmed.ncbi.nlm.nih.gov/28849402/	1 g single, intravenous dose: 1 g route of administration: Intravenous experiment type: SINGLE co-administered:	TEMOCILLIN serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4029032/ \| https://pubmed.ncbi.nlm.nih.gov/28849402/	2 g single, intravenous dose: 2 g route of administration: Intravenous experiment type: SINGLE co-administered:	TEMOCILLIN serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
3.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6853404/	15 mg single, intravenous dose: 15 mg route of administration: Intravenous experiment type: SINGLE co-administered:	TEMOCILLIN serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
12.7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6853404/	15 mg single, intravenous dose: 15 mg route of administration: Intravenous experiment type: SINGLE co-administered:	TEMOCILLIN serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
17.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6853404/	15 mg single, intravenous dose: 15 mg route of administration: Intravenous experiment type: SINGLE co-administered:	TEMOCILLIN serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
4.75 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6619046/	3.75 mg/kg single, intravenous dose: 3.75 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	TEMOCILLIN serum	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED
5.88 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6619046/	7.5 mg/kg single, intravenous dose: 7.5 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	TEMOCILLIN serum	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED
5.18 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6619046/	15 mg/kg single, intravenous dose: 15 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	TEMOCILLIN serum	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED
5.53 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6619046/	7.5 mg/kg single, intramuscular dose: 7.5 mg/kg route of administration: Intramuscular experiment type: SINGLE co-administered:	TEMOCILLIN serum	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED
13.57 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6619046/	7.5 mg/kg single, intravenous dose: 7.5 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	TEMOCILLIN serum	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FASTED
18.86 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6619046/	7.5 mg/kg single, intravenous dose: 7.5 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	TEMOCILLIN serum	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FASTED
28.22 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6619046/	7.5 mg/kg single, intravenous dose: 7.5 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	TEMOCILLIN serum	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FASTED
22.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26603304/	1 g 1 times / day multiple, intravenous dose: 1 g route of administration: Intravenous experiment type: MULTIPLE co-administered:	TEMOCILLIN serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
26 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26603304/	2 g 1 times / 2 days multiple, intravenous dose: 2 g route of administration: Intravenous experiment type: MULTIPLE co-administered:	TEMOCILLIN serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
35.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26603304/	3 g 1 times / 3 days multiple, intravenous dose: 3 g route of administration: Intravenous experiment type: MULTIPLE co-administered:	TEMOCILLIN serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
4.2 h OTHER https://www.medicines.org.uk/emc/product/466#PHARMACOKINETIC_PROPS	1 g single, intravenous dose: 1 g route of administration: Intravenous experiment type: SINGLE co-administered:	TEMOCILLIN serum	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
4.2 h OTHER https://www.medicines.org.uk/emc/product/466#PHARMACOKINETIC_PROPS	2 g single, intravenous dose: 2 g route of administration: Intravenous experiment type: SINGLE co-administered:	TEMOCILLIN serum	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
4.2 h OTHER https://www.medicines.org.uk/emc/product/466#PHARMACOKINETIC_PROPS	4 g single, intravenous dose: 4 g route of administration: Intravenous experiment type: SINGLE co-administered:	TEMOCILLIN serum	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
5.4 h OTHER https://www.medicines.org.uk/emc/product/466#PHARMACOKINETIC_PROPS	1 g single, intramuscular dose: 1 g route of administration: Intramuscular experiment type: SINGLE co-administered:	TEMOCILLIN serum	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
11.7 h OTHER https://www.medicines.org.uk/emc/product/466#PHARMACOKINETIC_PROPS	1 g single, intravenous dose: 1 g route of administration: Intravenous experiment type: SINGLE co-administered:	TEMOCILLIN serum	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
28.2 h OTHER https://www.medicines.org.uk/emc/product/466#PHARMACOKINETIC_PROPS	7.5 mg/kg single, intravenous dose: 7.5 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	TEMOCILLIN serum	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
15% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32433753/	2 g single, intravenous dose: 2 g route of administration: Intravenous experiment type: SINGLE co-administered:		TEMOCILLIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
15% OTHER https://www.medicines.org.uk/emc/product/466#PHARMACOKINETIC_PROPS			TEMOCILLIN serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
2 g 3 times / day multiple, intravenous Recommended Dose: 2 g, 3 times / day Route: intravenous Route: multiple Dose: 2 g, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/25433006/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/25433006/	Sources: https://pubmed.ncbi.nlm.nih.gov/25433006/
6 mg 1 times / day multiple, intravenous Recommended Dose: 6 mg, 1 times / day Route: intravenous Route: multiple Dose: 6 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/25433006/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/25433006/	Disc. AE: Pseudomembranous colitis... AEs leading to discontinuation/dose reduction: Pseudomembranous colitis (grade 3, 7.1%) Sources: https://pubmed.ncbi.nlm.nih.gov/25433006/

AEs

AE	Significance	Dose	Population
Pseudomembranous colitis	grade 3, 7.1% Disc. AE	6 mg 1 times / day multiple, intravenous Recommended Dose: 6 mg, 1 times / day Route: intravenous Route: multiple Dose: 6 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/25433006/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/25433006/

PubMed

Title	Date	PubMed
In vitro activity of temocillin against planktonic and sessile Burkholderia cepacia complex bacteria.	2010-12	20851061
Extended-spectrum β-lactamases in Gram Negative Bacteria.	2010-09	20927289
Long-term stability of temocillin in elastomeric pumps for outpatient antibiotic therapy in cystic fibrosis patients.	2010-09	20576638
[Update on antimicrobial chemotherapy].	2010-03	19959306
Infections with extended-spectrum beta-lactamase-producing enterobacteriaceae: changing epidemiology and drug treatment choices.	2010-02-12	20166768
Clinical efficacy of temocillin.	2009-08	19520716
Aqua-(2,2'-bipyridine-κN,N')bis-(thio-phene-2-carboxyl-ato-κO)copper(II).	2009-07-11	21583368
Comparison of four commercial methods for determining temocillin susceptibility of Escherichia coli.	2009-04	19223303
Temocillin revived.	2009-02	19095679
Effects of treatment with antimicrobial agents on the human colonic microflora.	2008-12	19337440
Case report: subacute synovitis of the knee after a rose thorn injury: unusual clinical picture.	2008-12	18773251
Temocillin in cystic fibrosis: a retrospective pilot study.	2008-11	18706868
Spinal infection caused by ESBL-producing Klebsiella pneumoniae treated with temocillin.	2008-10	18804871
Recovery of antimicrobial-resistant Pseudomonas aeruginosa from sputa of cystic fibrosis patients by culture on selective media.	2008-05	18316821
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.	2008-02	18070831
beta-Lactams without a suicide inhibitor.	2008-01	18154547
In vitro activity of temocillin against prevalent extended-spectrum beta-lactamases producing Enterobacteriaceae from Belgian intensive care units.	2007-11	17668253
Temocillin susceptibility by BSAC methodology.	2007-07	17550891
Imported cutaneous melioidosis in traveler, Belgium.	2007-06	17582903
Temocillin in the treatment of Burkholderia cepacia infection in cystic fibrosis.	2006-05	16650744
Activity of temocillin against prevalent ESBL- and AmpC-producing Enterobacteriaceae from south-east England.	2006-05	16531428
In vitro activity of temocillin against extended spectrum beta-lactamase-producing Escherichia coli.	2006-04	16501056
Successful medical management of multifocal psoas abscess following cesarean section: report of a case and review of the literature.	2002-05-10	11950495
Comparative in vitro activity of temocillin and other antimicrobial agents against Enterobacteriaceae isolated from patients admitted to five Belgian hospitals.	2002-03-08	11881320
Probing the penicillin sidechain selectivity of recombinant deacetoxycephalosporin C synthase.	2001-05	11437242
Temocillin in the treatment of pyelonephritis in children.	1987	3622246

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 `Wed Apr 02 08:42:44 GMT 2025` Edited by `admin` on `Wed Apr 02 08:42:44 GMT 2025`
Record UNII	03QB156W6I
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TEMOCILLIN

Official Name

English

BRL 17421 FREE ACID

Preferred 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

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