Tebipenem Pivoxil

Tebipenem pivoxil was approved by Pharmaceuticals and Medical Devices Agency of Japan (PMDA) on Apr 22, 2009. It was developed and marketed as Orapenem® by Meiji Seika in Japan.

Tebipenem pivoxil is a broad-spectrum orally-administered antibiotic, from the carbapenem subgroup of β-lactam antibiotics. Carbapenems are a class of beta-lactam antibiotics, which act by inhibiting the synthesis of the peptidoglycan layer of bacterial cell walls. It is used to treat otorhinolaryngological infection, otitis media and bacterial pneumonia.

Orapenem® is available as granules for oral use, containing 100 mg Tebipenem pivoxil/g granules. According to the weight of children, 4 mg/kg, and twice a day after dinner.

General Information

Update Date:2016-05-16

Drug Name:
Tebipenem Pivoxil
Research Code:
L-084; ME-1211
Trade Name:
Orapenem®
MOA:
Carbapenem antibiotic
Indication:
Otitis Media; Otorhinolaryngological infection; Bacterial Pneumonia
Status:
Approved
Company:
Meiji Seika (Originator)
Sales:
$16.7 Million (Y2015);
$18.2 Million (Y2014);
$23 Million (Y2013);
ATC Code:
Approved Countries or Area

Update Date:2016-05-16

Approval Date Approval Type Trade Name Indication Dosage Form Strength Company Review Classification
2009-04-22 First approval Orapenem Otitis Media, Otorhinolaryngological infection, Bacterial Pneumonia Granule 10% Meiji Seika
Chemical Structure

Update Date:2016-05-09

Molecular Weight 497.63
Formula C22H31N3O6S2
CAS No. 161715-24-8 (Tebipenem Pivoxil);
Chemical Name (+)-hydroxymethyl(4R,5S,6S )-6-[(1R )-1-hydroxyethyl]-4-methyl-7-oxo-3-{[1-(2-thiazolin-2-yl)-3-azetidinyl]thio}-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate,2-pivalate
Tebipenem Pivoxil (Free Acid/Base)Parameters:
MW HD HA FRB* PSA* cLogP*
497.63 1 9 11 159 -0.598±0.842
*:Calculated by ACD/Labs software V11.02.
Synthesis & Impurities

Update Date:2016-05-27


1. EP0632039A1US5534510A.

2. WO9721712A1US5886172A.


1. EP0717042A1.

2. US5659043A.

3. US5783703A.


1. J. Antibiot. 2006, 59, 241-247.



1. WO2015070394A1.

2. US4644061AGB2128187A.

Impurity database is being updated!