Mecillinam: Difference between revisions

{{short description|Pharmaceutical drug}}

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{{Drugbox

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| IUPAC_name = (2''S'',5''R'',6''R'')-6-[(-1-ylmethylene)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

| image2 = Mecillinam-3D-balls.png

| drug_name =

<!--Clinical data-->

| tradename = Coactin, Leo, Selexid, Selexidin

| Drugs.com = {{drugs.com|international|amdinocillin}}

| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->

| = <!-- / / / / -->

| pregnancy_category = Appears safe in pregnancy<ref name=Nicolle>{{cite journal |=Nicolle LE |title=Pivmecillinam in the treatment of urinary tract infections |journal= |volume=46 Suppl A | pages=35–39 | =August |pmid=10969050 |doi= 10.1093/jac/46.suppl_1.35|=}}</ref>

| legal_AU = S4

| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII -->

| legal_UK = POM

| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->

| legal_status = Rx-only

| routes_of_administration = [[Intravenous therapy|Intravenous]], [[intramuscular injection|intramuscular]]

<!--Pharmacokinetic data-->

| bioavailability = Negligible

| protein_bound = 5 to 10%

| metabolism = Some [[liver|hepatic]] metabolism

| elimination_half-life = 1 to 3 hours

| excretion = [[Kidney|Renal]] and biliary, mostly unchanged

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| CAS_number_Ref = {{cascite|correct|??}}

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| DrugBank = DB01163

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 33357

| UNII_Ref = {{fdacite|changed|FDA}}

| UNII = V10579P3QZ

| KEGG_Ref = {{keggcite|changed|kegg}}

| KEGG = D02888

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| C=15|H=23|N=3|O=3|S=1

'''Mecillinam''' ([[International Nonproprietary Name|INN]]) or '''amdinocillin''' ([[United States Adopted Name|USAN]]) is an extended-spectrum [[penicillin]] [[antibiotic]] that binds specifically to [[penicillin binding proteins|penicillin binding protein 2]] (PBP2),<ref name=Neu>{{cite journal |=Neu HC |title=Amdinocillin: a novel penicillin. Antibacterial activity, pharmacology and clinical use |journal=Pharmacotherapy |volume=5 |issue=1 |pages=1–10 |year=1985 |pmid=3885172 |doi= |=}}</ref> and is only considered to be active against [[Gram-negative bacteria]]. It is used primarily in the treatment of [[urinary tract infection]]s, and has also been used to treat [[typhoid fever|typhoid]] and [[paratyphoid fever]].<ref>{{cite journal |=Clarke PD, Geddes AM, McGhie D, Wall JC |title=Mecillinam: a new antibiotic for enteric fever |journal= |volume=2 |issue=6026 |pages= | =July |pmid=820402 |pmc=1687648 |doi= 10.1136/bmj.2.6026.14}}</ref><ref>{{cite journal |=Geddes AM, Clarke PD |title=The treatment of enteric fever with mecillinam |journal= |volume=3 Suppl B | pages= |=1977 | pmid=408321 |doi= }}</ref> Because mecillinam has very low oral [[bioavailability]], an orallyactive [[prodrug]] was developed: [[pivmecillinam]].

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Mecillinam is used in the treatment of infections due to susceptible gram-negative bacteria, especially [[urinary tract infection]]s which are most commonly caused by ''[[Escherichia coli]]''.<ref>{{cite journal | vauthors = Wagenlehner FM, Schmiemann G, Hoyme U, Fünfstück R, Hummers-Pradier E, Kaase M, Kniehl E, Selbach I, Sester U, Vahlensieck W, Watermann D, Naber KG | display-authors = 6 | title = [National S3 guideline on uncomplicated urinary tract infection: recommendations for treatment and management of uncomplicated community-acquired bacterial urinary tract infections in adult patients] | language = de | journal = Der Urologe. Ausg. A | volume = 50 | issue = 2 | pages = 153–169 | date = February 2011 | pmid = 21312083 | doi = 10.1007/s00120-011-2512-z | s2cid = 115699373 | trans-title = National S3 guideline on uncomplicated urinary tract infection: recommendations for treatment and management of uncomplicated community-acquired bacterial urinary tract infections in adult patients }}</ref> Mecillinam is active against most pathogenic Gram-negative bacteria, except ''[[Pseudomonas aeruginosa]]'' and some species of ''[[Proteus (bacterium)|Proteus]]''.<ref name=POC-IT>{{cite web |url=http://prod.hopkins-abxguide.org/antibiotics/antibacterial/pcn_others/amdinocillin__mecillinam_.html |title=Amdinocillin (Mecillinam) |vauthors=Pham P, Bartlett JG |date=August 28, 2008 |work=Point-of-Care Information Technology ABX Guide |publisher=[[Johns Hopkins University]] |access-date=September 1, 2008 |archive-url=https://web.archive.org/web/20090204193527/http://prod.hopkins-abxguide.org/antibiotics/antibacterial/pcn_others/amdinocillin__mecillinam_.html |archive-date=February 4, 2009 |url-status=dead }} Retrieved on August 31, 2008. Freely available with registration.</ref> Several studies have also found it to be as effective as other antibiotics for treating ''[[Staphylococcus saprophyticus]]'' infection, though it is Gram-positive, possibly because mecillinam reaches very high concentrations in urine.<ref name=Nicolle/>

Worldwide [[antibiotic resistance|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 1.2% (''[[Escherichia coli]]'') to 5.2% (''[[Proteus mirabilis]]'').<ref>{{cite journal |=Kahlmeter G |title=An international survey of the antimicrobial susceptibility of pathogens from uncomplicated urinary tract infections: the ECOSENS Project |journal= |volume=51 |issue=1 |pages=69–76 | =January |pmid=12493789 |doi= 10.1093/jac/dkg028|=}}</ref> Another large study conducted in Europe and [[Brazil]] obtained similar results — 95.9% of ''E. coli'' strains, for instance, were sensitive to mecillinam.<ref>{{cite journal |=Naber KG, Schito G, Botto H, Palou J, Mazzei T |title=Surveillance in Europe and Brazil on and Antimicrobial Resistance Epidemiology in Females with Cystitis (ARESC): for |journal= |volume= 54|issue= 5|pages= |=2008 | pmid=18511178 |doi=10.1016/j.eururo.2008.05.010 }}</ref>

{{see also|-lactam antibiotic#|l1=Beta-lactam antibiotic: Adverse effects}}

The [[adverse drug reaction|adverse effect]] profile of mecillinam is similar to that of other penicillins.<ref name=Neu/> most common side effects are [[rash]] and gastrointestinal upset, including [[nausea]] and [[vomiting]].<ref name=Nicolle/>

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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.<ref>{{cite journal |=Lund F, Tybring L |title=-amidinopenicillanic new group of antibiotics |journal=Nature |volume=236 |issue=66 |pages = |=April |pmid=4402006 |doi=10.1038/236135c0}}</ref><ref>{{cite journal |=Tybring L, Melchior NH |title=Mecillinam (FL 1060), a -amidinopenicillanic acid derivative: bactericidal action and synergy in vitro |journal=Antimicrobial Agents and Chemotherapy |volume=8 |issue=3 |pages = |=September |pmid=170856 |pmc=429305 |doi =/aac..}}</ref>

== References ==

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[[Category:Enantiopure drugs]]