Tebipenem

Tebipenem

File:Tebipenem pivoxil2DCSD.svg Tebipenem pivoxil
Systematic (IUPAC) name
(4R,5S,6S)-(Pivaloyloxy)methyl 3-((1-(4,5-dihydrothiazol-2-yl)azetidin-3-yl)thio)-6-((R)-1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
Clinical data
Trade names	Orapenem
Legal status	Prescription-only in Japan; investigational elsewhere
Routes of administration	Oral
Identifiers
CAS Number	161715-24-8 N
PDB ligand ID	1TE (PDBe, RCSB PDB)
Chemical data
Formula	C22H31N3O6S2
Molecular mass	497.63 g/mol
SMILES [H][C@]12N(C(C(OCOC(C(C)(C)C)=O)=O)=C(SC3CN(C4=NCCS4)C3)[C@@H]2C)C([C@@]1([C@H](O)C)[H])=O

Tebipenem (brand name: Orapenem) is a broad-spectrum orally-administered antibiotic, from the carbapenem subgroup of β-lactam antibiotics. It was developed as a replacement drug to combat bacteria that had acquired antibiotic resistance to commonly used antibiotics. Tebipenem is formulated as the ester tebipenem pivoxil due to the better absorption and improved bioavailability of this form. It has performed well in clinical trials for ear infection and looks likely to be further developed in future. It is only marketed in Japan. Tebipenem is the first carbapenem whose prodrug form, the pivalyl ester, is orally available.