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Mecillinam
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
Identifiers
CAS number 32887-01-7
ATC code J01CA11
PubChem 36273
DrugBank DB01163
Chemical data
Formula C 15H23N3O3S 
Mol. mass 325.426 g/mol
SMILES eMolecules & PubChem
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
Therapeutic considerations
Pregnancy cat. B(US)
Appears safe in pregnancy[1]
Legal status Prescription only
Routes Intravenous, intramuscular

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]

Contents

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 between 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

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

  1. ^ a b c Nicolle LE (August 2000). "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.  
  2. ^ a b 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. PMID 820402.  
  4. ^ Geddes AM, Clarke PD (July 1977). "The treatment of enteric fever with mecillinam". J Antimicrob Chemother 3 Suppl B: 101–2. PMID 408321.  
  5. ^ 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.
  6. ^ Lund F, Tybring L (April 1972). "6β-amidinopenicillanic acids—a new group of antibiotics". Nature New Biol 236 (66): 135–7. PMID 4402006.  
  7. ^ 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. PMID 170856. PMC 429305. http://aac.asm.org/cgi/pmidlookup?view=long&pmid=170856.  
  8. ^ 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.  
  9. ^ 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: 1164. doi:10.1016/j.eururo.2008.05.010. PMID 18511178.  


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