Pivmecillinam

Pivmecillinam
Clinical data
Trade namesSelexid, Melysin, Coactabs, others
Other namesamdinocillin pivoxil (USAN US)
AHFS/Drugs.comMonograph
License data
Routes of
administration		By mouth
ATC code
Legal status
Legal status
Pharmacokinetic data
BioavailabilityLow
Protein binding5 to 10% (as mecillinam)
MetabolismPivmecillinam is hydrolyzed to mecillinam
Elimination half-life1 to 3 hours
ExcretionKidney and biliary, mostly as mecillinam
Identifiers
  • 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
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.046.600 Edit this at Wikidata
Chemical and physical data
FormulaC21H33N3O5S
Molar mass439.57 g·mol−1
3D model (JSmol)
  • CC1(C(N2C(S1)C(C2=O)N=CN3CCCCCC3)C(=O)OCOC(=O)C(C)(C)C)C
  • 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
 ☒NcheckY (what is this?)  (verify)

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.[2]

  1. ^ "Selexid Summary of Product Characteristics (SmPC)". (emc). 20 March 2024. Archived from the original on 8 November 2023. Retrieved 25 April 2024.
  2. ^ a b Cite error: The named reference FDA PR 20240424 was invoked but never defined (see the help page).