Temocillin: Difference between revisions

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Temocillin
Clinical data
AHFS/Drugs.com	International Drug Names
ATC code	J01CA17 (WHO) ;
Identifiers
	IUPAC name (2S,5R,6S)-6-[(Carboxy-3-thienylacetyl)amino]- 6-methoxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0] heptane-2-carboxylic acid,;
CAS Number	66148-78-5 ;
PubChem CID	171758;
ChemSpider	150149 ;
UNII	03QB156W6I;
KEGG	D06064 ;
ChEBI	CHEBI:51817 ;
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C16H18N2O7S2
Molar mass	414.453 g/mol
3D model (JSmol)	Interactive image;
	SMILES O=C(O)[C@@H]2N3C(=O)[C@@](OC)(NC(=O)C(c1ccsc1)C(=O)O)[C@H]3SC2(C)C;
	InChI 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 ; Key:BVCKFLJARNKCSS-DWPRYXJFSA-N ;
(verify)

← Older edit

VisualWikitext

Latest revision as of 14:56, 13 April 2015

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

Temocillin is a β-lactamase-resistant penicillin^[1]^[2] introduced by Beecham, marketed by Eumedica Pharmaceuticals as Negaban. It is used primarily for the treatment of multiple drug-resistant, Gram-negative bacteria. It is a carboxypenicillin.^[3]

Pharmacology

Temocillin is a β-lactamase-resistant penicillin. It is not active against Gram-positive bacteria or bacteria with altered penicillin-binding proteins.

It is normally active against Moraxella catarrhalis, Brucella abortus, Burkholderia cepacia, Citrobacter species, Escherichia coli, Haemophilus influenzae, Klebsiella pneumoniae, Pasteurella multocida, Proteus mirabilis, Salmonella typhimurium, and Yersinia enterocolitica. It is also active against some Enterobacter species, Morganella morganii, and Serratia species. Temocillin has no useful activity against Acinetobacter species or Pseudomonas aeruginosa.

Its primary use is against Enterobacteriaceae, and in particular against strains producing extended-spectrum β-lactamase or AmpC β-lactamase.^[4]

Dosage

The common dose is 2 g intravenously every 12 hours. Theoretical reasons exist for giving temocillin as a continuous intravenous infusion in severe disease:^[5] a single loading dose of 2 g is given intravenously followed by a 4-g infusion over 24 hours. Temocillin for intravenous injection is diluted in 20 ml of sterile water; it is diluted in less than 2.7 ml of sterile water when being prepared for intramuscular injection; the continuous infusion is diluted in 48 ml of sterile water for ease of administration (1 ml per half hour). To reduce pain, the intramuscular injection may be made up using sterile 1% lignocaine instead of sterile water.

Temocillin may be given to patients with impaired renal function. No adjustment needs to be made to the dose in mild to moderate renal impairment (creatinine clearance greater than 30 ml/min). Temocillin is cleared by haemodialysis, so in dialysis patients, the dose should be given after dialysis.

No oral preparation of temocillin is licensed.

Adverse effects

The undesirable effects of temocillin are those of any β-lactam antibiotic. In particular, it has been associated with angioedema and anaphylaxis in penicillin-allergic patients. Animal studies have not shown any induction of Clostridium difficile infection.^[6] As with any other penicillin, convulsions can occur if very high doses are given.

Synthesis

References

↑ Andrews JM, Jevons G, Walker R, Ashby J, Fraise AP (July 2007). "Temocillin susceptibility by BSAC methodology". J. Antimicrob. Chemother. 60 (1): 185–7. doi:10.1093/jac/dkm179. PMID 17550891.
↑ Van Landuyt HW, Pyckavet M, Lambert A, Boelaert J (October 1982). "In vitro activity of temocillin (BRL 17421), a novel beta-lactam antibiotic". Antimicrob. Agents Chemother. 22 (4): 535–40. doi:10.1128/aac.22.4.535. PMC 183789. PMID 7181470.
↑ Chanal M, Sirot J, Cluzel M, Joly B, Glanddier Y (June 1983). "[In vitro study of the bacteriostatic and bactericidal activity of temocillin (BRL 17421)]". Pathol. Biol. (in French). 31 (6): 467–70. PMID 6348653.
↑ Livermore DM et al. (2006) Activity of temocillin vs. prevalent ESBL- and AmpC-producing Enterobacteriaceae from SE England. J Antimicrob Chemother. 2006 May;57(5):1012-4.
↑ De Jongh R et al. (2008) 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. J Antimicrob Chemother. 2008 Feb;61(2):382-8.
↑ Boon RJ; et al. (1985). "Studies with temocillin in a hamster model of antibiotic-associated colitis". Antimicrob Agents Chemother. 27 (6): 980–1. doi:10.1128/aac.27.6.980. PMC 180203. PMID 3875312.
↑ Template:Cite doi

@@ Line 1: / Line 1: @@
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-| IUPAC_name        = (2S,5R,6S)-6-[(Carboxy-3-thienylacetyl)amino]- 6-methoxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0] heptane-2-carboxylic acid,
+| Watchedfields = changed
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+| verifiedrevid = 447429921
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-| ATC_prefix        = J01
+| image =Temocillin.png
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+| ATC_suffix = CA17
+| PubChem = 171758
+| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
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+| KEGG_Ref = {{keggcite|correct|kegg}}
+| KEGG = D06064
+| ChEBI_Ref = {{ebicite|correct|EBI}}
+| ChEBI = 51817
+<!--Chemical data-->
+| C=16 | H=18 | N=2 | O=7 | S=2
+| molecular_weight = 414.453 g/mol
+| smiles = O=C(O)[C@@H]2N3C(=O)[C@@](OC)(NC(=O)C(c1ccsc1)C(=O)O)[C@H]3SC2(C)C
+| InChI = 1/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
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 }}
+__Notoc__
 {{SI}}
+{{CMG}}
+==Overview==
+'''Temocillin''' is a [[beta-lactamase|β-lactamase]]-resistant [[penicillin]]<ref name="pmid17550891">{{cite journal |author=Andrews JM, Jevons G, Walker R, Ashby J, Fraise AP |title=Temocillin susceptibility by BSAC methodology |journal=[[J. Antimicrob. Chemother.]] |volume=60 |issue=1 |pages=185–7 |date=July 2007 |pmid=17550891 |doi=10.1093/jac/dkm179 |url=http://jac.oxfordjournals.org/cgi/pmidlookup?view=long&pmid=17550891}}</ref><ref name="pmid7181470">{{cite journal |author=Van Landuyt HW, Pyckavet M, Lambert A, Boelaert J |title=In vitro activity of temocillin (BRL 17421), a novel beta-lactam antibiotic |journal=Antimicrob. Agents Chemother. |volume=22 |issue=4 |pages=535–40 |date=October 1982 |pmid=7181470 |pmc=183789 |doi= 10.1128/aac.22.4.535|url=http://aac.asm.org/cgi/pmidlookup?view=long&pmid=7181470}}</ref> introduced by [[Beecham (pharmaceutical company)|Beecham]], marketed by Eumedica Pharmaceuticals as Negaban. It is used primarily for the treatment of multiple drug-resistant, [[Gram-negative]] bacteria.  It is a [[carboxypenicillin]].<ref name="pmid6348653">{{cite journal |author=Chanal M, Sirot J, Cluzel M, Joly B, Glanddier Y |title=[In vitro study of the bacteriostatic and bactericidal activity of temocillin (BRL 17421)] |language=French |journal=Pathol. Biol. |volume=31 |issue=6 |pages=467–70 |date=June 1983 |pmid=6348653 |doi= |url=}}</ref>
-'''Temocillin''' is a [[beta-lactamase|β-lactamase]] resistant [[penicillin]] marketed by [[Eumedica Pharmaceuticals]] as Negaban® primarily for the treatment of multiresistant [[Gram negative]] bacteria.
 ==Pharmacology==
-Temocillin is a [[beta-lactamase|β-lactamase]] resistance [[penicillin]].  It is not active against [[Gram positive]] bacteria or bacteria with altered [[penicillin-binding protein]]s.
+Temocillin is a β-lactamase-resistant penicillin.  It is not active against [[Gram-positive]] bacteria or bacteria with altered [[penicillin-binding protein]]s.
-It is normally active against ''[[Moraxella catarrhalis]]'', ''[[Brucella abortus]]'', ''[[Burkholderia cepacia]]'', ''[[Citrobacter]]'' species, ''[[Escherichia coli]]'', ''[[Haemophilus influenzae]]'', ''[[Klebsiella pneumoniae]]'', ''[[Pasteurella multocida]]'', ''[[Proteus mirabilis]]'', ''[[Salmonella typhimurium]]'' and ''[[Yersinia enterocolitica]]''.  It is also active against some ''[[Enterobacter]]'' species, ''[[Morganella morganii]]'', and ''[[Serratia]]'' species.  Temocillin has no useful activity against [[Gram positive]] organisms, ''[[Acinetobacter]]'' species, or ''[[Pseudomonas aeruginosa]]''.
+It is normally active against ''[[Moraxella catarrhalis]]'', ''[[Brucella abortus]]'', ''[[Burkholderia cepacia]]'', ''[[Citrobacter]]'' species, ''[[Escherichia coli]]'', ''[[Haemophilus influenzae]]'', ''[[Klebsiella pneumoniae]]'', ''[[Pasteurella multocida]]'', ''[[Proteus mirabilis]]'', ''[[Salmonella typhimurium]]'', and ''[[Yersinia enterocolitica]]''.  It is also active against some ''[[Enterobacter]]'' species, ''[[Morganella morganii]]'', and ''[[Serratia]]'' species.  Temocillin has no useful activity against ''[[Acinetobacter]]'' species or ''[[Pseudomonas aeruginosa]]''.
-Its primary use is against [[Enterobacteriaceae]], and in particular against strains producing [[extended spectrum beta-lamase|extended spectrum β-lactamase]] or [[AmpC]] [[beta-lactamase|β-lactamase]] (Livermore, 2005).
+Its primary use is against [[Enterobacteriaceae]], and in particular against strains producing [[extended spectrum beta-lactamase|extended-spectrum β-lactamase]] or [[beta-lactamase#AmpC-type β-lactamases (Class C)|AmpC β-lactamase]].<ref>Livermore DM ''et al.'' (2006) Activity of temocillin vs. prevalent ESBL- and AmpC-producing Enterobacteriaceae from SE England. J Antimicrob Chemother. 2006 May;57(5):1012-4.</ref>
 ==Dosage==
-The common dosage is 1[[gram|g]] intravenously or intramuscularly every 12 hours.  For severe infections, the dose is 2g intravenously every 12 hours.  There are good theoretical reasons for giving Temocillin as a continuous intravenous infusion in severe disease (Claeysoone, 2005): a single loading dose of 2g is given intravenously followed by a 4g infusion over 24 hours.  Temocillin for intravenous injection is diluted in 20ml of sterile water; it is diluted in less than 2.7ml of sterile water when being prepared for intramuscular injection; the continuous infusion is diluted in 48ml of sterile water for ease of administration (1ml per half hour).  To reduce pain, the intramuscular injection may be made up using sterile 1% lignocaine instead of sterile water.
+The common dose is 2 g intravenously every 12 hours.  Theoretical reasons exist for giving temocillin as a continuous intravenous infusion in severe disease:<ref>De Jongh R ''et al.'' (2008) 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. J Antimicrob Chemother. 2008 Feb;61(2):382-8.</ref> a single loading dose of 2 g is given intravenously followed by a 4-g infusion over 24 hours.  Temocillin for intravenous injection is diluted in 20 ml of sterile water; it is diluted in less than 2.7 ml of sterile water when being prepared for intramuscular injection; the continuous infusion is diluted in 48 ml of sterile water for ease of administration (1 ml per half hour).  To reduce pain, the intramuscular injection may be made up using sterile 1% lignocaine instead of sterile water.
-Temocillin may be given to patient with impaired renal function.  No adjustment needs to be made to the dose in mild to moderate renal impairment ([[creatinine clearance]]  greater than 30ml/min).  The manufacturer does not recommend using reduced doses, instead they recommend increasing the duration between doses.  In severe renal impairment when it is 10 to 30, the dose is 1g in 24 hours; when less than 10, the dose is 1g every 48 hours.  Temocillin is cleared by [[haemodialysis]], which means that in dialysis patients, the dose should be given ''after'' dialysis.
+Temocillin may be given to patients with impaired renal function.  No adjustment needs to be made to the dose in mild to moderate renal impairment ([[creatinine clearance]] greater than 30 ml/min).  <!-- The manufacturer does not recommend using reduced doses, instead they recommend increasing the duration between doses.  In severe renal impairment when CC is 10 to 30, the dose is 1 g in 24 hours; when less than 10, the dose is 1 g every 48 hours. -->  Temocillin is cleared by [[haemodialysis]], so in dialysis patients, the dose should be given after dialysis.
-There is no licensed oral preparation of Temocillin.
+No oral preparation of temocillin is licensed.
-==Undesirable effects==
-The undesirable effects of Temocillin are those of any β-lactam antibiotic.  In particular, Temocillin has been associated with angioedema and anaphylaxis in penicillin allergic patients.  Animal studies have not shown any induction of ''[[Clostridium difficile]]'' infection (Boon, 1985).  As with any other penicillin, convulsions can occur if very high doses are given.
+==Adverse effects==
+The undesirable effects of temocillin are those of any β-lactam antibiotic.  In particular, it has been associated with angioedema and anaphylaxis in penicillin-allergic patients.  Animal studies have not shown any induction of ''[[Clostridium difficile]]'' infection.<ref>{{cite journal | author=Boon RJ ''et al.'' | title=Studies with temocillin in a hamster model of antibiotic-associated colitis| journal=Antimicrob Agents Chemother | year=1985 | volume=27 | issue=6 | pages=980–1 | url= | pmid=3875312 | pmc=180203 | doi=10.1128/aac.27.6.980}}</ref>  As with any other penicillin, convulsions can occur if very high doses are given.
+==Synthesis==
+[[File:Temocillin synthesis.png|thumb|center|700px|Temocillin synthesis:<ref>{{Cite doi|10.1039/P19790002455}}</ref>]]
 ==References==
-* {{cite web | title=Eumedica | work=Eumedica Pharmaceuticals | url=http://www.eumedica.com | accessdate=November 20 | accessyear=2005}}
+{{reflist|2}}
-* {{cite journal | author=Bonacorsi S ''et al'' | title=Comparative in vitro activities of meropenem, imipenem, temocillin, piperacillin, and ceftazidime in combination with tobramycin, rifampin, or ciprofloxacin against Burkholderia cepacia isolates from patients with cystic fibrosis| journal=Antimicrob Agents Chemother | year=1999 | volume=43 | issue=2 | pages=213&ndash;7 | url= }}
-* {{cite journal | author=Boon RJ ''et al'' | title=Studies with temocillin in a hamster model of antibiotic-associated colitis| journal=Antimicrob Agents Chemother | year=1985 | volume=27 | issue=6 | pages=980&ndash;1 | url= }}
-* Livermore DM ''et al'' (2005) Activity of temocillin vs. prevalent ESBL- and AmpC-producing Enterobacteriaceae from SE England. FIS Meeting, November 2005, Cardiff, UK
-* Claeysoone K ''et al'' (2005) Continuous vs. Intermittent infusion of Temocillin in ICU patients.  25th ISICEM, March 2005, Brussels, Belgium, poster A351
+==Further reading==
+*{{cite journal |author=Livermore DM, Tulkens PM |title=Temocillin revived |journal=[[Journal of Antimicrobial Chemotherapy]] |volume=63 |issue=2 |pages=243–5 |date=February 2009 |pmid=19095679 |doi=10.1093/jac/dkn511}}
-[[th:เทโมซิลลิน]]
 [[Category:Beta-lactam antibiotics]]
+[[Category:Thiophenes]]
-{{WH}}
+[[Category:Drug]]
-{{WikiDoc Sources}}