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Antiinfective agent stubs
Tebipenem
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Tebipenem

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Tebipenem
Tebipenem pivoxil2DCSD.svg
Tebipenem pivoxil
Clinical data
Trade names Orapenem
Routes of
administration		 Oral
ATC code
Legal status
Legal status
  • Prescription-only in Japan; investigational elsewhere
Identifiers
  • (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
UNII
KEGG
PDB ligand
CompTox Dashboard (EPA)
Chemical and physical data
Formula C22H31N3O6S2
Molar mass 497.63 g·mol−1
3D model (JSmol)
  • [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.


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