Mecillinam

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.

Mecillinam
Clinical data
Trade namesCoactin, Leo, Selexid, Selexidin
AHFS/Drugs.comInternational Drug Names
Pregnancy
category
  • Appears safe in pregnancy
Routes of
administration		Intravenous, intramuscular
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • UK: POM (Prescription only)
  • In general: ℞ (Prescription only)
Pharmacokinetic data
BioavailabilityNegligible
Protein binding5 to 10%
MetabolismSome hepatic metabolism
Elimination half-life1 to 3 hours
ExcretionRenal and biliary, mostly unchanged
Identifiers
  • (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
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.046.601
Chemical and physical data
FormulaC15H23N3O3S
Molar mass325.43 g·mol−1
3D model (JSmol)
  • CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)N=CN3CCCCCC3)C(=O)O)C
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