| 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 | |
| Clinical data | |
| AHFS/Drugs.com | International Drug Names |
| Pregnancy cat. | B(US) Appears safe in pregnancy[1] |
| Legal status | ℞ Prescription only |
| Routes | Intravenous, intramuscular |
| 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 |
| Identifiers | |
| CAS number | 32887-01-7 |
| ATC code | J01CA11 |
| PubChem | CID 36273 |
| DrugBank | DB01163 |
| ChemSpider | 33357 |
| UNII | V10579P3QZ |
| KEGG | D02888 |
| ChEMBL | CHEMBL530 |
| Chemical data | |
| Formula | C15H23N3O3S |
| Mol. mass | 325.426 g/mol |
| SMILES | eMolecules & PubChem |
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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]
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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]
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]
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]