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| verifiedrevid = 403346583
| verifiedrevid = 403346583
| IUPAC_name = (2''S'',5''R'',6''R'')-6-[(''E''/''Z'')-(azepan-1-ylmethylene)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
| IUPAC_name = (2''S'',5''R'',6''R'')-6-[(''E''/''Z'')-(azepan-1-ylmethylene)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
| image = Mecillinam2DCSD.svg
| image = Mecillinam.png
| drug_name = Mecillinam
| drug_name = Mecillinam


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}}
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__NOTOC__
__NOTOC__
{{SI}}
{{SI}}
{{CMG}}
{{CMG}}
==Overview==
==Overview==
'''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 |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 [[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 |author=Clarke PD, Geddes AM, McGhie D, Wall JC |title=Mecillinam: a new antibiotic for enteric fever |journal=[[BMJ|Br Med J]] |volume=2 |issue=6026 |pages=14–5 |date=July 1976 |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 |doi=  10.1093/jac/3.suppl_b.101|journal=J Antimicrob Chemother |volume=3 Suppl B |issue= |pages=101–2 |date=July 1977 |pmid=408321|url=}}</ref> Because mecillinam has very low oral [[bioavailability]], an orally active [[prodrug]] was developed: [[pivmecillinam]]. 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=[[Johns Hopkins University]]}} Retrieved on August 31, 2008. Freely available with registration.</ref>
'''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 |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 [[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 |author=Clarke PD, Geddes AM, McGhie D, Wall JC |title=Mecillinam: a new antibiotic for enteric fever |journal=[[BMJ|Br Med J]] |volume=2 |issue=6026 |pages=14–5 |date=July 1976 |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 |doi=  10.1093/jac/3.suppl_b.101|journal=J Antimicrob Chemother |volume=3 Suppl B |issue= |pages=101–2 |date=July 1977 |pmid=408321|url=}}</ref> Because mecillinam has very low oral [[bioavailability]], an orally active [[prodrug]] was developed: [[pivmecillinam]]. 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=[[Johns Hopkins University]]}} Retrieved on August 31, 2008. Freely available with registration.</ref>
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==References==
==References==
{{Reflist|2}}
{{Reflist|2}}
{{Beta-lactam antibiotics}}


[[Category:Beta-lactam antibiotics]]
[[Category:Beta-lactam antibiotics]]
[[Category:Enantiopure drugs]]
[[Category:Azepanes]]
[[Category:Drug]]
[[Category:Drug]]

Latest revision as of 16:39, 20 August 2015

Mecillinam
Clinical data
Trade namesCoactin, Leo, Selexid, Selexidin
AHFS/Drugs.comInternational Drug Names
Pregnancy
category
  • Appears safe in pregnancy[1]
Routes of
administration		Intravenous, intramuscular
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • UK: POM (Prescription only)
  • In general: ℞ (Prescription only)
Pharmacokinetic data
BioavailabilityNegligible
Protein binding5 to 10%
MetabolismSome hepatic metabolism
Elimination half-life1 to 3 hours
ExcretionRenal and biliary, mostly unchanged
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
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
FormulaC15H23N3O3S
Molar mass325.426 g/mol
3D model (JSmol)
 ☒N☑Y (what is this?)  (verify)

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

Overview

Mecillinam (INN) or amdinocillin (USAN) 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]

Medical uses

Mecillinam is used in the treatment of infections due to susceptible gram-negative bacteria, especially urinary tract infections which are most commonly caused by Escherichia coli.[6] 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, 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).[7] Another large study conducted in Europe and Brazil obtained similar results — 95.9% of E. coli strains, for instance, were sensitive to mecillinam.[8]

Adverse effects

See also: Beta-lactam antibiotic: Adverse effects

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

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.[9][10]

References

  1. ↑ 1.0 1.1 1.2 Nicolle LE (August 2000). = long&pmid = 10969050 "Pivmecillinam in the treatment of urinary tract infections" Check |url= value (help). J Antimicrob Chemother. 46 (Suppl A): 35–39. doi:10.1093/jac/46.suppl_1.35. PMID 10969050.
  2. ↑ 2.0 2.1 Neu HC (1985). "Amdinocillin: a novel penicillin. Antibacterial activity, pharmacology and clinical use". Pharmacotherapy. 5 (1): 1–10. PMID 3885172.
  3. ↑ 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.
  4. ↑ Geddes AM, Clarke PD (July 1977). "The treatment of enteric fever with mecillinam". J Antimicrob Chemother. 3 Suppl B: 101–2. doi:10.1093/jac/3.suppl_b.101. PMID 408321.
  5. ↑ 5.0 5.1 Pham P, Bartlett JG (August 28, 2008). "Amdinocillin (Mecillinam)". Point-of-Care Information Technology ABX Guide. Johns Hopkins University. Retrieved on August 31, 2008. Freely available with registration.
  6. ↑ Wagenlehner, FME; Schmiemann, G; Hoyme, U; Fünfstück, R; Hummers-Pradier, E; Kaase, M; Kniehl, E; Selbach, I; Sester, U; Vahlensieck, W; Watermann, D; Naber, KG (12 February 2011). "Nationale S3-Leitlinie „Unkomplizierte Harnwegsinfektionen"". Der Urologe (in German). 50 (2): 153–169. doi:10.1007/s00120-011-2512-z. PMID 21312083. Unknown parameter |trans_title= ignored (help)
  7. ↑ 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.
  8. ↑ 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.
  9. ↑ 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.
  10. ↑ 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. doi:10.1128/aac.8.3.271. PMC 429305. PMID 170856.
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