Tebipenem

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.^[1][2] Tebipenem is formulated as the ester tebipenem pivoxil due to the better absorption and improved bioavailability of this form.^[3] It has performed well in clinical trials for ear infection and looks likely to be further developed in future.^[4] It is only marketed in Japan.^[5] Tebipenem is the first carbapenem whose prodrug form, the pivalyl ester, is orally available.^[6]

Tebipenem

Tebipenem pivoxil
Clinical data
Trade names	Orapenem
Routes of administration	Oral
ATC code	J01DH06 (WHO)
Legal status
Legal status	Prescription-only in Japan; investigational elsewhere
Identifiers
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
CAS Number	161715-24-8 N
UNII	95AK1A52I8
KEGG	D09598
PDB ligand	1TE (PDBe, RCSB PDB)
CompTox Dashboard (EPA)	DTXSID00167228
Chemical and physical data
Formula	C22H31N3O6S2
Molar mass	497.63 g·mol−1
3D model (JSmol)	Interactive image
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