Mecillinam

Mecillinam
Clinical data
Trade namesCoactin, Leo, Selexid, Selexidin
AHFS/Drugs.comInternational Drug Names
Pregnancy
category
  • Appears safe in pregnancy[1]
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 Edit this at Wikidata
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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Mecillinam (INN) or amdinocillin (USAN) is an extended-spectrum penicillin antibiotic of the amidinopenicillin class 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.

  1. ^ Nicolle LE (August 2000). "Pivmecillinam in the treatment of urinary tract infections". The Journal of Antimicrobial Chemotherapy. 46 (Suppl A): 35–39. doi:10.1093/jac/46.suppl_1.35. PMID 10969050.
  2. ^ Neu HC (1985). "Amdinocillin: a novel penicillin. Antibacterial activity, pharmacology and clinical use". Pharmacotherapy. 5 (1): 1–10. doi:10.1002/j.1875-9114.1985.tb04448.x. PMID 3885172. S2CID 46561080.
  3. ^ Clarke PD, Geddes AM, McGhie D, Wall JC (July 1976). "Mecillinam: a new antibiotic for enteric fever". British Medical Journal. 2 (6026): 14–15. 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". The Journal of Antimicrobial Chemotherapy. 3 (Suppl B): 101–102. doi:10.1093/jac/3.suppl_b.101. PMID 408321.