Mecillinam

Mecillinam

File:Mecillinam skeletal formula.svg
File:Mecillinam ball-and-stick model from xtal 1981.png
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 checkY
PubChem CID	36273
DrugBank	DB01163 checkY
ChemSpider	33357 ☒N
UNII	V10579P3QZ
KEGG	D02888 ☒N
ChEMBL	ChEMBL530 checkY
E number	{{#property:P628}}
CompTox Dashboard (EPA)	{{#property:P3117}}
ECHA InfoCard	{{#property:P2566}}
Chemical and physical data
Formula	C15H23N3O3S
Molar mass	325.43 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)N=CN3CCCCCC3)C(=O)O)C
☒NcheckY (what is this?)  (verify)

Mecillinam (INN) or amdinocillin (USAN) is an extended-spectrum penicillin antibiotic of the amidinopenicillin class 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.

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. 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.

Adverse effects

See also: Beta-lactam antibiotic: Adverse effects

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

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.