関: mecillinam

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2012/12/09 21:58:59」(JST)

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Mecillinam (INN) or amdinocillin (USAN), trade name Coactin, is an extended-spectrum penicillin antibiotic that binds specifically to penicillin binding protein 2 (PBP2),^[2] and is only considered to be active against Gram-negative bacteria. It is used primarily in the treatment of urinary tract infections, and has also been used to treat typhoid and paratyphoid fever.^[3]^[4] Because mecillinam has very low oral bioavailability, an orally active prodrug was developed: pivmecillinam. Neither drug is available in the United States.^[5]

History

With the codename FL 1060, mecillinam was developed by the Danish pharmaceutical company Leo Pharmaceutical Products (now LEO Pharma). It was first described in the scientific literature in a 1972 paper.^[6]^[7]

Activity

Mecillinam is active against most pathogenic Gram-negative bacteria, except Pseudomonas aeruginosa and some species of Proteus.^[5] Several studies have also found it to be as effective as other antibiotics for treating Staphylococcus saprophyticus infection, even though it is Gram-positive, possibly because mecillinam reaches very high concentrations in urine.^[1]

Worldwide resistance to mecillinam in bacteria causing urinary tract infection has remained very low since its introduction; a 2003 study conducted in 16 European countries and Canada found resistance to range from 1.2% (Escherichia coli) to 5.2% (Proteus mirabilis).^[8] Another large study conducted in Europe and Brazil obtained similar results — 95.9% of E. coli strains, for instance, were sensitive to mecillinam.^[9]

Adverse effects

See also: Beta-lactam antibiotic: Adverse effects

The adverse effect profile of mecillinam is similar to that of other penicillins.^[2] The most common side effects of mecillinam use are rash and gastrointestinal upset, including nausea and vomiting.^[1]

References

^ ^a ^b ^c Nicolle LE (August 2000). = long&pmid = 10969050 "Pivmecillinam in the treatment of urinary tract infections". J Antimicrob Chemother 46 (Suppl A): 35–39. doi:10.1093/jac/46.suppl_1.35. PMID 10969050. http://jac.oxfordjournals.org/cgi/pmidlookup?view = long&pmid = 10969050.
^ ^a ^b Neu HC (1985). "Amdinocillin: a novel penicillin. Antibacterial activity, pharmacology and clinical use". Pharmacotherapy 5 (1): 1–10. PMID 3885172.
^ Clarke PD, Geddes AM, McGhie D, Wall JC (July 1976). "Mecillinam: a new antibiotic for enteric fever". Br Med J 2 (6026): 14–5. doi:10.1136/bmj.2.6026.14. PMC 1687648. PMID 820402. //www.ncbi.nlm.nih.gov/pmc/articles/PMC1687648/.
^ Geddes AM, Clarke PD (July 1977). "The treatment of enteric fever with mecillinam". J Antimicrob Chemother 3 Suppl B: 101–2. PMID 408321.
^ ^a ^b Pham P, Bartlett JG (August 28, 2008). "Amdinocillin (Mecillinam)". Point-of-Care Information Technology ABX Guide. Johns Hopkins University. http://prod.hopkins-abxguide.org/antibiotics/antibacterial/pcn_others/amdinocillin__mecillinam_.html. Retrieved on August 31, 2008. Freely available with registration.
^ Lund F, Tybring L (April 1972). "6β-amidinopenicillanic acids—a new group of antibiotics". Nature New Biol 236 (66): 135–7. doi:10.1038/236135c0. PMID 4402006.
^ Tybring L, Melchior NH (September 1975). "Mecillinam (FL 1060), a 6β-Amidinopenicillanic Acid Derivative: Bactericidal Action and Synergy In Vitro". Antimicrob Agents Chemother 8 (3): 271–6. PMC 429305. PMID 170856. http://aac.asm.org/cgi/pmidlookup?view=long&pmid=170856.
^ Kahlmeter G (January 2003). "An international survey of the antimicrobial susceptibility of pathogens from uncomplicated urinary tract infections: the ECO·SENS Project". J Antimicrob Chemother 51 (1): 69–76. doi:10.1093/jac/dkg028. PMID 12493789. http://jac.oxfordjournals.org/cgi/pmidlookup?view=long&pmid=12493789.
^ Naber KG, Schito G, Botto H, Palou J, Mazzei T (May 2008). "Surveillance Study in Europe and Brazil on Clinical Aspects and Antimicrobial Resistance Epidemiology in Females with Cystitis (ARESC): Implications for Empiric Therapy". Eur Urol 54 (5): 1164–75. doi:10.1016/j.eururo.2008.05.010. PMID 18511178.

English Journal

Mecillinam/clavulanate combination: a possible option for the treatment of community-acquired uncomplicated urinary tract infections caused by extended-spectrum β-lactamase-producing Escherichia coli.

Lampri N, Galani I, Poulakou G, Katsarolis I, Petrikkos G, Giamarellou H, Souli M.Source4th Department of Internal Medicine, University of Athens Medical School, 'Attikon' University General Hospital, Athens, Greece.
The Journal of antimicrobial chemotherapy.J Antimicrob Chemother.2012 Oct;67(10):2424-8. doi: 10.1093/jac/dks215. Epub 2012 Jun 4.
BACKGROUND: Extended-spectrum β-lactamases (ESBLs) have emerged as an important mechanism of β-lactam resistance among community uropathogens. We characterized the ESBLs of a collection of Escherichia coli isolates recovered from outpatients with urinary tract infection during nationwide surveilla
PMID 22665388

Efficacy of pivmecillinam for treatment of lower urinary tract infection caused by extended-spectrum β-lactamase-producing Escherichia coli and Klebsiella pneumoniae.

Titelman E, Iversen A, Kalin M, Giske CG.SourceDivision of Medicine, Department of Infectious Diseases, Karolinska University Hospital, Huddinge, Stockholm, Sweden. emilia.titelman@karolinska.se
Microbial drug resistance (Larchmont, N.Y.).Microb Drug Resist.2012 Apr;18(2):189-92. doi: 10.1089/mdr.2011.0161. Epub 2011 Dec 28.
To evaluate the clinical and bacteriological efficacy of pivmecillinam against lower urinary tract infection (UTI) caused by extended-spectrum β-lactamase (ESBL)-producing Escherichia coli and Klebsiella pneumoniae, patients treated for lower UTI with pivmecillinam (n=8) were studied. Patients trea
PMID 22204597

French results of the ARESC study: clinical aspects and epidemiology of antimicrobial resistance in female patients with cystitis. Implications for empiric therapy.

Neuzillet Y, Naber KG, Schito G, Gualco L, Botto H.SourceService d'urologie, hôpital Foch, université de Versailles - Saint-Quentin-en-Yvelines, 40, rue Worth, 92150 Suresnes, France.
Médecine et maladies infectieuses.Med Mal Infect.2012 Feb;42(2):66-75. doi: 10.1016/j.medmal.2011.07.005. Epub 2012 Jan 20.
OBJECTIVE: Uncomplicated cystitis is one of the most frequent community infections. We report the French results of the international ARESC study on the clinical aspects, epidemiology, and antimicrobial susceptibility of uropathogens.PATIENT AND METHODS: Female patients between 18 and 65 years of ag
PMID 22264668

Japanese Journal

Penicillin-binding proteins and role of amdinocillin in causing bacterial cell death

NEU HC.
Am J Med 75, 9-20, 1983
NAID 30008559510

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リンク元	「アムジノシリン」「mecillinam」
拡張検索	「amdinocillin pivoxil」

「アムジノシリン」

Amdinocillin
Systematic (IUPAC) name
	(2S,5R,6R)-6-[(azepan-1-ylmethylene)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Clinical data
AHFS/Drugs.com	International Drug Names
Pregnancy cat.	B (US); Appears safe in pregnancy
Legal status	℞ Prescription only
Routes	Intravenous, intramuscular
Pharmacokinetic data
Bioavailability	Negligible
Protein binding	5 to 10%
Metabolism	Some hepatic metabolism
Half-life	1 to 3 hours
Excretion	Renal and biliary, mostly unchanged
Identifiers
CAS number	32887-01-7
ATC code	J01CA11
PubChem	CID 36273
DrugBank	DB01163
ChemSpider	33357
UNII	V10579P3QZ
KEGG	D02888
ChEMBL	CHEMBL530
Chemical data
Formula	C15H23N3O3S
Mol. mass	325.426 g/mol
	SMILES CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)N=CN3CCCCCC3)C(=O)O)C;
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