Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C22H31N3O6S2 |
Molecular Weight | 497.628 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@]12[C@@H](C)C(SC3CN(C3)C4=NCCS4)=C(N1C(=O)[C@]2([H])[C@@H](C)O)C(=O)OCOC(=O)C(C)(C)C
InChI
InChIKey=SNUDIPVBUUXCDG-QHSBEEBCSA-N
InChI=1S/C22H31N3O6S2/c1-11-15-14(12(2)26)18(27)25(15)16(19(28)30-10-31-20(29)22(3,4)5)17(11)33-13-8-24(9-13)21-23-6-7-32-21/h11-15,26H,6-10H2,1-5H3/t11-,12-,14-,15-/m1/s1
Tebipenem pivoxil is an oral carbapenem prodrug that was originated by Wyeth (now Pfizer). It 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.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19882982
Curator's Comment: Low penetration to the central nervous system was confirmed in amimal models
Originator
Sources: http://adisinsight.springer.com/drugs/800010812
Curator's Comment: # Wyeth (now Pfizer)
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL2362973 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Curative | ORAPENEM Approved UseOrapenem is usually used to treat pneumonia, otitis media and sinusitis. Launch Date2009 |
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Curative | ORAPENEM Approved UseOrapenem is usually used to treat pneumonia, otitis media and sinusitis. Launch Date2009 |
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Curative | ORAPENEM Approved UseOrapenem is usually used to treat pneumonia, otitis media and sinusitis. Launch Date2009 |
Sample Use Guides
For children: In general, take 0.04 gram per kilogram of body weight (g/kg) (4 mg of the active ingredient [titer]/kg) at a time, twice a day, after meals. The dosage may be increased up to 0.06 g/kg (6 mg [titer]/kg) as needed. Strictly follow the instructions.
Standard duration of administration is for 7 days or less.
If you miss a dose, take a dose as soon as possible. However, if it is almost time for the next dose, skip the missed dose and follow your regular dosing schedule. You should never take two doses at one time.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26751436
The MIC90 values of tebipenem pivoxil against Gram-positive bacteria such as methicillin-sensitive Staphylococcus aureus (MSSA), methicillin-resistant Staphylococcus aureus (MRSA), methicillin-sensitive Staphylococcus epidermidis (MSSE), methicillin-resistant Staphylococcus epidermidis (MRSE), Pyogenic streptococcus, and Enterococcus faecalis were ≤ 0.125, 16, 0.5, 8, ≤ 0.125, and 32 ug/mL, respectively. Correspondingly, the MIC90 values of tebipenem pivoxil against Escherichia coli, Klebsiella pneumoniae, Enterobacter aerogenes, Haemophilus influenzae, Pseudomonas aeruginosa, and Acinetobacter baumannii were 1, 0.5, ≤ 0.125, 0.25, 64, 64 ug/mL, respectively. The MBC values of tebipenem pivoxil against Escherichia coli, Staphylococcus aureus, Klebsiella pneumoniae were 0.016-2, 0.063-32, 0.031-32 ug/mL, respectively.
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WHO-ATC |
J01DH06
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C260
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FG-202
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100000178191
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161715-24-8
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m11935
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)
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SUBSTANCE RECORD