Mecillinam

Mecillinam
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 ;
PubChem CID	36273;
DrugBank	DB01163 ;
ChemSpider	33357 ;
UNII	V10579P3QZ;
KEGG	D02888 ;
ChEMBL	ChEMBL530 ;
CompTox Dashboard (EPA)	DTXSID3022584 ;
ECHA InfoCard	100.046.601
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;
	(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.