Amdinocillin

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Mecillinam
Clinical data
Trade names	Coactin, Leo, Selexid, Selexidin
AHFS/Drugs.com	International Drug Names
Pregnancy; category	Appears safe in pregnancy;
Routes of; administration	Intravenous, intramuscular
ATC code	J01CA11 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only) ; UK: POM (Prescription only) ; In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	Negligible
Protein binding	5 to 10%
Metabolism	Some hepatic metabolism
Elimination half-life	1 to 3 hours
Excretion	Renal and biliary, mostly unchanged
Identifiers
	IUPAC name (2S,5R,6R)-6-[(E/Z)-(azepan-1-ylmethylene)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid;
CAS Number	32887-01-7 ;
PubChem CID	36273;
DrugBank	DB01163 ;
ChemSpider	33357 ;
UNII	V10579P3QZ;
KEGG	D02888 ;
ChEMBL	ChEMBL530 ;
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
Formula	C15H23N3O3S
Molar mass	325.426 g/mol
3D model (JSmol)	Interactive image;
	SMILES CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)N=CN3CCCCCC3)C(=O)O)C;
(what is this?) (verify)

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

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

↑ ^1.0 ^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.
↑ ^2.0 ^2.1 Neu HC (1985). "Amdinocillin: a novel penicillin. Antibacterial activity, pharmacology and clinical use". Pharmacotherapy. 5 (1): 1–10. PMID 3885172.
↑ 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.
↑ 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.
↑ ^5.0 ^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.
↑ 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)
↑ 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.
↑ 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.
↑ 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.
↑ 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.

[Nicolle-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.

[Neu-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.

[POC-IT-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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