Mecillinam

Clinical data
Trade names| Coactin, Leo, Selexid, Selexidin
AHFS/Drugs.com| International Drug Names
Pregnancy
category|

* Appears safe in pregnancy[1]

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 Y

PubChem CID|

* 36273

DrugBank|

* DB01163 Y

ChemSpider|

* 33357 N

UNII|

* V10579P3QZ

KEGG|

* D02888 N

ChEMBL|

* ChEMBL530 Y

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

NY (what is this?) (verify)

WikiDoc Resources for Mecillinam

Articles

Most recent articles on Mecillinam

Most cited articles on Mecillinam

Review articles on Mecillinam

Articles on Mecillinam in N Eng J Med, Lancet, BMJ

Media

Powerpoint slides on Mecillinam

Images of Mecillinam

Photos of Mecillinam

Podcasts & MP3s on Mecillinam

Videos on Mecillinam

Evidence Based Medicine

Cochrane Collaboration on Mecillinam

Bandolier on Mecillinam

TRIP on Mecillinam

Clinical Trials

Ongoing Trials on Mecillinam at Clinical Trials.gov

Trial results on Mecillinam

Clinical Trials on Mecillinam at Google

Guidelines / Policies / Govt

US National Guidelines Clearinghouse on Mecillinam

NICE Guidance on Mecillinam

NHS PRODIGY Guidance

FDA on Mecillinam

CDC on Mecillinam

Books

Books on Mecillinam

News

Mecillinam in the news

Be alerted to news on Mecillinam

News trends on Mecillinam

Commentary

Blogs on Mecillinam

Definitions

Definitions of Mecillinam

Patient Resources / Community

Patient resources on Mecillinam

Discussion groups on Mecillinam

Patient Handouts on Mecillinam

Directions to Hospitals Treating Mecillinam

Risk calculators and risk factors for Mecillinam

Healthcare Provider Resources

Symptoms of Mecillinam

Causes & Risk Factors for Mecillinam

Diagnostic studies for Mecillinam

Treatment of Mecillinam

Continuing Medical Education (CME)

CME Programs on Mecillinam

International

Mecillinam en Espanol

Mecillinam en Francais

Business

Mecillinam in the Marketplace

Patents on Mecillinam

Experimental / Informatics

List of terms related to Mecillinam

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

## Overview[edit | edit source]

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[edit | edit source]

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[edit | edit source]

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[edit | edit source]

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[edit | edit source]

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.CS1 maint: Multiple names: authors list (link)
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)CS1 maint: Unrecognized language (link)
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.CS1 maint: Multiple names: authors list (link)
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.

*[AU]: Australia
*[UK]: United Kingdom
*[CID]: Compound ID