Pivmecillinam

Pivmecillinam
Clinical data
Trade names	Selexid, Melysin, Coactabs, others
Other names	amdinocillin pivoxil (USAN US)
AHFS/Drugs.com	Monograph
License data	US DailyMed: Amdinocillin pivoxil;
Routes of; administration	By mouth
ATC code	J01CA08 (WHO) ;
Legal status
Legal status	UK: POM (Prescription only); US: ℞-only; In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	Low
Protein binding	5 to 10% (as mecillinam)
Metabolism	Pivmecillinam is hydrolyzed to mecillinam
Elimination half-life	1 to 3 hours
Excretion	Kidney and biliary, mostly as mecillinam
Identifiers
	IUPAC name 2,2-dimethylpropanoyloxymethyl (2S,5R,6R)-6-[(azepan-1-ylmethylene)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate;
CAS Number	32886-97-8 ; 32887-03-9;
PubChem CID	115163; 115162;
DrugBank	DB01605 ; DBSALT001943;
ChemSpider	16735658 ; 19978599;
UNII	1WAM1OQ30B; 48FX7N21H2;
KEGG	D02889 ; D01499;
ChEMBL	ChEMBL1650818 ;
CompTox Dashboard (EPA)	DTXSID7048538 ;
ECHA InfoCard	100.046.600
Chemical and physical data
Formula	C21H33N3O5S
Molar mass	439.57 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC1(C(N2C(S1)C(C2=O)N=CN3CCCCCC3)C(=O)OCOC(=O)C(C)(C)C)C;
	InChI InChI=1S/C21H33N3O5S/c1-20(2,3)19(27)29-13-28-18(26)15-21(4,5)30-17-14(16(25)24(15)17)22-12-23-10-8-6-7-9-11-23/h12,14-15,17H,6-11,13H2,1-5H3/t14-,15+,17-/m1/s1; Key:NPGNOVNWUSPMDP-HLLBOEOZSA-N; ; InChI=1S/C21H33N3O5S.ClH/c1-20(2,3)19(27)29-13-28-18(26)15-21(4,5)30-17-14(16(25)24(15)17)22-12-23-10-8-6-7-9-11-23;/h12,14-15,17H,6-11,13H2,1-5H3;1H/t14-,15+,17-;/m1./s1; Key:UHPXMYLONAGUPC-WKLLBTDKSA-N;
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Pivmecillinam (INN), or amdinocillin pivoxil (USAN), sold under the brand name Selexid and Pivya among others, is an orally active prodrug of mecillinam, an extended-spectrum penicillin antibiotic. Pivmecillinam is the pivaloyloxymethyl ester of mecillinam.

The most common side effects include nausea and diarrhea.