|Systematic (IUPAC) name|
|Protein binding||5 to 10%|
|Metabolism||Some hepatic metabolism|
|Half-life||1 to 3 hours|
|Excretion||Renal and biliary, mostly unchanged|
|Mol. mass||325.426 g/mol|
Mecillinam (INN) or amdinocillin (USAN), trade name Coactin, is an extended-spectrum penicillin antibiotic that binds specifically to penicillin binding protein 2 (PBP2), 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. Because mecillinam has very low oral bioavailability, an orally active prodrug was developed: pivmecillinam. Neither drug is available in the United States.
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.
Mecillinam is active against most pathogenic Gram-negative bacteria, except Pseudomonas aeruginosa and some species of Proteus. 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.
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). Another large study conducted in Europe and Brazil obtained similar results — 95.9% of E. coli strains, for instance, were sensitive to mecillinam.
For an alternative synthesis, see:
- Nicolle LE (August 2000). = long&pmid = 10969050 "Pivmecillinam in the treatment of urinary tract infections". J Antimicrob Chemother 46 (Suppl A): 35–39.
- Neu HC (1985). "Amdinocillin: a novel penicillin. Antibacterial activity, pharmacology and clinical use". Pharmacotherapy 5 (1): 1–10.
- Clarke PD, Geddes AM, McGhie D, Wall JC (July 1976). "Mecillinam: a new antibiotic for enteric fever".
- Geddes AM, Clarke PD (July 1977). "The treatment of enteric fever with mecillinam". J Antimicrob Chemother. 3 Suppl B: 101–2.
- Pham P, Bartlett JG (August 28, 2008). "Amdinocillin (Mecillinam)". Point-of-Care Information Technology ABX Guide. 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.
- Tybring L, Melchior NH (September 1975). "Mecillinam (FL 1060), a 6β-Amidinopenicillanic Acid Derivative: Bactericidal Action and Synergy In Vitro".
- 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.
- 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.
- Sakamoto, F.; Ikeda, S.; Hirayama, R.; Moriyama, M.; Sotomura, M.; Tsukamoto, G. (1987). "Studies on prodrugs. VI Preparation and characterization of (5-substituted 2-oxo-1,3-dioxol-4-yl)methyl esters of mecillinam". Chemical & Pharmaceutical Bulletin 35 (2): 642.
- Lund, F.; Tybring, L. (1972). "6β-Amidinopenicillanic Acids—a New Group of Antibiotics". Nature New Biology 236 (66): 135.