| Revision as of 13:31, 20 December 2010 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{drugbox}} (changes to watched fields - added verified revid - updated 'UNII_Ref', 'ChemSpiderID_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref') per Chem/Drugbox validation (report [[Misplaced Pages← Previous edit |
Latest revision as of 08:23, 6 January 2024 edit undoMaxim Masiutin (talk | contribs)Extended confirmed users, IP block exemptions, Pending changes reviewers31,058 edits Add: s2cid. Added the cs1 style template to denote Vancouver ("vanc") citation style, because references contain "vauthors" attribute to specify the list of authors. |
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{{short description|Pharmaceutical drug}} |
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{{drugbox | Watchedfields = changed |
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{{cs1 config|name-list-style=vanc}} |
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| verifiedrevid = 370473618 |
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{{Drugbox |
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| IUPAC_name = (2''S'',5''R'',6''R'')-6--3,3-dimethyl-7-oxo-4-thia-1-azabicycloheptane-2-carboxylic acid |
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| Watchedfields = changed |
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| verifiedrevid = 403346583 |
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| IUPAC_name = (2''S'',5''R'',6''R'')-6--3,3-dimethyl-7-oxo-4-thia-1-azabicycloheptane-2-carboxylic acid |
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| image = Mecillinam.svg |
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| image = Mecillinam.svg |
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| image2 = Mecillinam-3D-balls.png |
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| CASNo_Ref = {{cascite}} |
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| drug_name = |
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<!--Clinical data--> |
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| tradename = Coactin, Leo, Selexid, Selexidin |
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| Drugs.com = {{drugs.com|international|amdinocillin}} |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| pregnancy_US = <!-- A / B / C / D / X --> |
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| pregnancy_category = Appears safe in pregnancy<ref name=Nicolle>{{cite journal | vauthors = Nicolle LE | title = Pivmecillinam in the treatment of urinary tract infections | journal = The Journal of Antimicrobial Chemotherapy | volume = 46 | issue = Suppl A | pages = 35–39 | date = August 2000 | pmid = 10969050 | doi = 10.1093/jac/46.suppl_1.35 | doi-access = free }}</ref> |
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| legal_AU = S4 |
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| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII --> |
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| legal_UK = POM |
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| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> |
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| legal_status = Rx-only |
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| routes_of_administration = ], ] |
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<!--Pharmacokinetic data--> |
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| bioavailability = Negligible |
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| protein_bound = 5 to 10% |
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| metabolism = Some ] metabolism |
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| elimination_half-life = 1 to 3 hours |
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| excretion = ] and biliary, mostly unchanged |
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<!--Identifiers--> |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number = 32887-01-7 |
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| CAS_number = 32887-01-7 |
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| CAS_supplemental = |
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| CAS_supplemental = |
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| ATC_prefix = J01 |
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| ATC_prefix = J01 |
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| ATC_suffix = CA11 |
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| ATC_suffix = CA11 |
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| ATC_supplemental = |
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| ATC_supplemental = |
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| PubChem = 36273 |
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| PubChem = 36273 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = DB01163 |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 33357 |
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| UNII_Ref = {{fdacite|changed|FDA}} |
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| UNII = V10579P3QZ |
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| KEGG_Ref = {{keggcite|changed|kegg}} |
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| KEGG = D02888 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 530 |
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| ChEMBL = 530 |
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<!--Chemical data--> |
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| DrugBank = DB01163 |
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| C=15 | H=23 | N=3 | O=3 | S=1 |
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| smiles = CC1((N2(S1)(C2=O)N=CN3CCCCCC3)C(=O)O)C |
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| smiles = CC1((N2(S1)(C2=O)N=CN3CCCCCC3)C(=O)O)C |
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| C=15|H=23|N=3|O=3|S=1 |
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| molecular_weight = 325.426 g/mol |
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| bioavailability = Negligible |
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| protein_bound = 5 to 10% |
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| metabolism = Some ] metabolism |
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| elimination_half-life = 1 to 3 hours |
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| excretion = ] and biliary, mostly unchanged |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| pregnancy_US = B |
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| pregnancy_category = <br/>Appears safe in pregnancy<ref name=Nicolle>{{cite journal |author=Nicolle LE |title=Pivmecillinam in the treatment of urinary tract infections |journal=J Antimicrob Chemother |volume=46 Suppl A |issue= |pages=35–39 |year=2000 |month=August |pmid=10969050 |doi= 10.1093/jac/46.suppl_1.35|url=http://jac.oxfordjournals.org/cgi/pmidlookup?view=long&pmid=10969050}}</ref> |
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| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S8 --> |
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| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII --> |
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| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C --> |
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| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> |
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| legal_status = Rx-only |
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| routes_of_administration = ], ] |
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}} |
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}} |
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'''Mecillinam''' (]) or '''amdinocillin''' (]), trade name '''Coactin''', is an extended-spectrum ] ] that binds specifically to ] (PBP2),<ref name=Neu>{{cite journal |author=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= |url=}}</ref> and is only considered to be active against ]. It is used primarily in the treatment of ]s, and has also been used to treat ] and ].<ref>{{cite journal |author=Clarke PD, Geddes AM, McGhie D, Wall JC |title=Mecillinam: a new antibiotic for enteric fever |journal=] |volume=2 |issue=6026 |pages=14–5 |year=1976 |month=July |pmid=820402 |pmc=1687648 |doi= 10.1136/bmj.2.6026.14|url=}}</ref><ref>{{cite journal |author=Geddes AM, Clarke PD |title=The treatment of enteric fever with mecillinam |journal=J Antimicrob Chemother |volume=3 Suppl B |issue= |pages=101–2 |year=1977 |month=July |pmid=408321 |doi= |url=}}</ref> Because mecillinam has very low oral ], an orally-active ] was developed: ]. Neither drug is available in the United States.<ref name=POC-IT>{{cite web |url=http://prod.hopkins-abxguide.org/antibiotics/antibacterial/pcn_others/amdinocillin__mecillinam_.html |title=Amdinocillin (Mecillinam) |author=Pham P, Bartlett JG |date=August 28, 2008 |work=Point-of-Care Information Technology ABX Guide |publisher=]}} Retrieved on August 31, 2008. Freely available with registration.</ref> |
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'''Mecillinam''' (]) or '''amdinocillin''' (]) is an extended-spectrum ] ] of the amidinopenicillin class that binds specifically to ] (PBP2),<ref name=Neu>{{cite journal | vauthors = 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 = 10.1002/j.1875-9114.1985.tb04448.x | s2cid = 46561080 }}</ref> and is only considered to be active against ]. It is used primarily in the treatment of ]s, and has also been used to treat ] and ].<ref>{{cite journal | vauthors = Clarke PD, Geddes AM, McGhie D, Wall JC | title = Mecillinam: a new antibiotic for enteric fever | journal = British Medical Journal | volume = 2 | issue = 6026 | pages = 14–15 | date = July 1976 | pmid = 820402 | pmc = 1687648 | doi = 10.1136/bmj.2.6026.14 }}</ref><ref>{{cite journal | vauthors = Geddes AM, Clarke PD | title = The treatment of enteric fever with mecillinam | journal = The Journal of Antimicrobial Chemotherapy | volume = 3 | issue = Suppl B | pages = 101–102 | date = July 1977 | pmid = 408321 | doi = 10.1093/jac/3.suppl_b.101 }}</ref> Because mecillinam has very low oral ], an orally active ] was developed: ]. |
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==History== |
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==Medical uses== |
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Mecillinam is used in the treatment of infections due to susceptible gram-negative bacteria, especially ]s which are most commonly caused by '']''.<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 = | 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 '']'' and some species of '']''.<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=] |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 '']'' infection, though it is Gram-positive, possibly because mecillinam reaches very high concentrations in urine.<ref name=Nicolle/> |
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With the codename FL 1060, mecillinam was developed by the Danish ] Leo Pharmaceutical Products (now LEO Pharma). It was first described in the scientific literature in a 1972 paper.<ref>{{cite journal |author=Lund F, Tybring L |title=6β-amidinopenicillanic acids—a new group of antibiotics |journal=Nature New Biol |volume=236 |issue=66 |pages=135–7 |year=1972 |month=April |pmid=4402006 |doi=10.1038/236135c0}}</ref><ref>{{cite journal |author=Tybring L, Melchior NH |title=Mecillinam (FL 1060), a 6β-amidinopenicillanic acid derivative: bactericidal action and synergy in vitro |journal=] |volume=8 |issue=3 |pages=271–6 |year=1975 |month=September |pmid=170856 |pmc=429305 |doi= |url=http://aac.asm.org/cgi/pmidlookup?view=long&pmid=170856}}</ref> |
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==Activity== |
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Mecillinam is active against most pathogenic ], except '']'' and some species of '']''.<ref name=POC-IT>{{cite web |url=http://prod.hopkins-abxguide.org/antibiotics/antibacterial/pcn_others/amdinocillin__mecillinam_.html |title=Amdinocillin (Mecillinam) |author=Pham P, Bartlett JG |date=August 28, 2008 |work=Point-of-Care Information Technology ABX Guide |publisher=]}} 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 '']'' infection, even though it is ], possibly because mecillinam reaches very high concentrations in urine.<ref name=Nicolle/> |
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Worldwide ] 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 between 1.2% ('']'') to 5.2% ('']'').<ref>{{cite journal |author=Kahlmeter G |title=An international survey of the antimicrobial susceptibility of pathogens from uncomplicated urinary tract infections: the ECO·SENS Project |journal=J Antimicrob Chemother |volume=51 |issue=1 |pages=69–76 |year=2003 |month=January |pmid=12493789 |doi= 10.1093/jac/dkg028|url=http://jac.oxfordjournals.org/cgi/pmidlookup?view=long&pmid=12493789}}</ref> Another large study conducted in Europe and ] obtained similar results — 95.9% of ''E. coli'' strains, for instance, were sensitive to mecillinam.<ref>{{cite journal |author=Naber KG, Schito G, Botto H, Palou J, Mazzei T |title=Surveillance Study in Europe and Brazil on Clinical Aspects and Antimicrobial Resistance Epidemiology in Females with Cystitis (ARESC): Implications for Empiric Therapy |journal=Eur Urol |volume= 54|issue= 5|pages= 1164|year=2008 |month=May |pmid=18511178 |doi=10.1016/j.eururo.2008.05.010 |url=}}</ref> |
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Worldwide ] 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% ('']'') to 5.2% ('']'').<ref>{{cite journal | vauthors = Kahlmeter G | title = An international survey of the antimicrobial susceptibility of pathogens from uncomplicated urinary tract infections: the ECO.SENS Project | journal = The Journal of Antimicrobial Chemotherapy | volume = 51 | issue = 1 | pages = 69–76 | date = January 2003 | pmid = 12493789 | doi = 10.1093/jac/dkg028 | doi-access = free }}</ref> Another large study conducted in Europe and ] obtained similar results — 95.9% of ''E. coli'' strains, for instance, were sensitive to mecillinam.<ref>{{cite journal | vauthors = Naber KG, Schito G, Botto H, Palou J, Mazzei T | title = Surveillance study in Europe and Brazil on clinical aspects and Antimicrobial Resistance Epidemiology in Females with Cystitis (ARESC): implications for empiric therapy | journal = European Urology | volume = 54 | issue = 5 | pages = 1164–1175 | date = November 2008 | pmid = 18511178 | doi = 10.1016/j.eururo.2008.05.010 }}</ref> |
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==Adverse effects== |
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==Adverse effects== |
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{{see also|Beta-lactam antibiotic#Adverse effects|l1=Beta-lactam antibiotic: Adverse effects}} |
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{{see also|Β-lactam antibiotic#Adverse_effects|l1=Beta-lactam antibiotic: Adverse effects}} |
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The ] profile of mecillinam is similar to that of other penicillins.<ref name=Neu/> The most common side effects of mecillinam use are ] and gastrointestinal upset, including ] and ].<ref name=Nicolle/> |
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The ] profile of mecillinam is similar to that of other penicillins.<ref name=Neu/> Its most common side effects are ] and gastrointestinal upset, including ] and ].<ref name=Nicolle/> |
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==References== |
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==History== |
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With the codename FL 1060, mecillinam was developed by the Danish ] Leo Pharmaceutical Products (now ]). It was first described in the scientific literature in a 1972 paper.<ref>{{cite journal | vauthors = Lund F, Tybring L | title = 6 -amidinopenicillanic acids--a new group of antibiotics | journal = Nature | volume = 236 | issue = 66 | pages = 135–137 | date = April 1972 | pmid = 4402006 | doi = 10.1038/236135c0 | s2cid = 4293996 | doi-access = free }}</ref><ref>{{cite journal | vauthors = Tybring L, Melchior NH | title = Mecillinam (FL 1060), a 6beta-amidinopenicillanic acid derivative: bactericidal action and synergy in vitro | journal = Antimicrobial Agents and Chemotherapy | volume = 8 | issue = 3 | pages = 271–276 | date = September 1975 | pmid = 170856 | pmc = 429305 | doi = 10.1128/aac.8.3.271 }}</ref> |
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== References == |
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{{Reflist}} |
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{{Reflist}} |
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{{Clear}} |
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{{Beta-lactam antibiotics}} |
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{{Beta-lactam antibiotics}} |
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