TEBIPENEM PIVOXIL

Possibly Marketed Outside US

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

C[C@@H](O)[C@@H]1[C@H]2[C@@H](C)C(SC3CN(C3)C4=NCCS4)=C(N2C1=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

HIDE SMILES / InChI

Molecular Formula	C22H31N3O6S2
Molecular Weight	497.628
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description

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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Penicillin-binding protein 31	Inhibitor 8,504

Conditions

Condition	Modality	Highest Phase	Product
Otitis media 42	Curative	Approved 8,583	ORAPENEM
Pneumonia 91	Curative	Approved 8,583	ORAPENEM
Sinusitis 26	Curative	Approved 8,583	ORAPENEM

C_max

Value	Dose	Analyte	Population
11.81 μg/mL	250 mg single, oral	TEBIPENEM plasma	Homo sapiens
3.9 μg/mL	250 mg single, oral	TEBIPENEM plasma	Homo sapiens
6087.5 ng/mL	100 mg single, oral	TEBIPENEM plasma	Homo sapiens
11099.17 ng/mL	200 mg single, oral	TEBIPENEM plasma	Homo sapiens
17825 ng/mL	400 mg single, oral	TEBIPENEM plasma	Homo sapiens
256 ng/mL	100 mg single, oral	TEBIPENEM plasma	Homo sapiens
1209 ng/mL	300 mg single, oral	TEBIPENEM plasma	Homo sapiens
1944 ng/mL	600 mg single, oral	TEBIPENEM plasma	Homo sapiens
2943 ng/mL	900 mg single, oral	TEBIPENEM plasma	Homo sapiens
4062 ng/mL	300 mg single, oral	TEBIPENEM plasma	Homo sapiens
3064 ng/mL	300 mg single, oral	TEBIPENEM plasma	Homo sapiens
6216 ng/mL	600 mg single, oral	TEBIPENEM plasma	Homo sapiens
1810 ng/mL	300 mg single, oral	TEBIPENEM plasma	Homo sapiens
2893 ng/mL	100 mg single, oral	TEBIPENEM plasma	Homo sapiens
4006 ng/mL	300 mg single, oral	TEBIPENEM plasma	Homo sapiens
6203 ng/mL	600 mg single, oral	TEBIPENEM plasma	Homo sapiens
12652 ng/mL	900 mg single, oral	TEBIPENEM plasma	Homo sapiens
1892 ng/mL	300 mg single, oral	TEBIPENEM plasma	Homo sapiens
3014 ng/mL	600 mg single, oral	TEBIPENEM plasma	Homo sapiens
1852 ng/mL	300 mg single, oral	TEBIPENEM plasma	Homo sapiens
1677 ng/mL	300 mg single, oral	TEBIPENEM plasma	Homo sapiens
5830 ng/mL	600 mg single, oral	TEBIPENEM plasma	Homo sapiens
2288 ng/mL	300 mg single, oral	TEBIPENEM plasma	Homo sapiens
2058 ng/mL	300 mg single, oral	TEBIPENEM plasma	Homo sapiens
6451 ng/mL	600 mg single, oral	TEBIPENEM plasma	Homo sapiens
7759 ng/mL	300 mg 3 times / day multiple, oral	TEBIPENEM plasma	Homo sapiens
13428 ng/mL	600 mg 3 times / day multiple, oral	TEBIPENEM plasma	Homo sapiens
6493 ng/mL	300 mg 3 times / day multiple, oral	TEBIPENEM plasma	Homo sapiens
15090 ng/mL	600 mg 3 times / day multiple, oral	TEBIPENEM plasma	Homo sapiens
2.71 μg/mL	100 mg 3 times / day multiple, oral	TEBIPENEM plasma	Homo sapiens
6.08 μg/mL	200 mg 3 times / day multiple, oral	TEBIPENEM plasma	Homo sapiens
4.74 μg/mL	300 mg 3 times / day multiple, oral	TEBIPENEM plasma	Homo sapiens
5.08 μg/mL	150 mg 3 times / day multiple, oral	TEBIPENEM plasma	Homo sapiens
7.92 μg/mL	250 mg 2 times / day multiple, oral	TEBIPENEM plasma	Homo sapiens
8.69 μg/mL	300 mg 3 times / day multiple, oral	TEBIPENEM plasma	Homo sapiens
9.85 μg/mL	250 mg single, oral	TEBIPENEM plasma	Homo sapiens
7.17 μg/mL	250 mg single, oral	TEBIPENEM plasma	Homo sapiens
13.26 μg/mL	250 mg single, oral	TEBIPENEM plasma	Homo sapiens
13.88 μg/mL	250 mg single, oral	TEBIPENEM plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
10.46 μg × h/mL	250 mg single, oral	TEBIPENEM plasma	Homo sapiens
9.52 μg × h/mL	250 mg single, oral	TEBIPENEM plasma	Homo sapiens
6407.34 ng × h/mL	100 mg single, oral	TEBIPENEM plasma	Homo sapiens
12517.7 ng × h/mL	200 mg single, oral	TEBIPENEM plasma	Homo sapiens
23126.57 ng × h/mL	400 mg single, oral	TEBIPENEM plasma	Homo sapiens
872 ng × h/mL	100 mg single, oral	TEBIPENEM plasma	Homo sapiens
3738 ng × h/mL	300 mg single, oral	TEBIPENEM plasma	Homo sapiens
5192 ng × h/mL	600 mg single, oral	TEBIPENEM plasma	Homo sapiens
10571 ng × h/mL	900 mg single, oral	TEBIPENEM plasma	Homo sapiens
7268 ng × h/mL	300 mg single, oral	TEBIPENEM plasma	Homo sapiens
6267 ng × h/mL	300 mg single, oral	TEBIPENEM plasma	Homo sapiens
13602 ng × h/mL	600 mg single, oral	TEBIPENEM plasma	Homo sapiens
4456 ng × h/mL	300 mg single, oral	TEBIPENEM plasma	Homo sapiens
2875 ng × h/mL	100 mg single, oral	TEBIPENEM plasma	Homo sapiens
6488 ng × h/mL	300 mg single, oral	TEBIPENEM plasma	Homo sapiens
12715 ng × h/mL	600 mg single, oral	TEBIPENEM plasma	Homo sapiens
21913 ng × h/mL	900 mg single, oral	TEBIPENEM plasma	Homo sapiens
7175 ng × h/mL	300 mg single, oral	TEBIPENEM plasma	Homo sapiens
14727 ng × h/mL	600 mg single, oral	TEBIPENEM plasma	Homo sapiens
6215 ng × h/mL	300 mg single, oral	TEBIPENEM plasma	Homo sapiens
6549 ng × h/mL	300 mg single, oral	TEBIPENEM plasma	Homo sapiens
16547 ng × h/mL	600 mg single, oral	TEBIPENEM plasma	Homo sapiens
6579 ng × h/mL	300 mg single, oral	TEBIPENEM plasma	Homo sapiens
6137 ng × h/mL	300 mg single, oral	TEBIPENEM plasma	Homo sapiens
14200 ng × h/mL	600 mg single, oral	TEBIPENEM plasma	Homo sapiens
7726 ng × h/mL	300 mg 3 times / day multiple, oral	TEBIPENEM plasma	Homo sapiens
20592 ng × h/mL	600 mg 3 times / day multiple, oral	TEBIPENEM plasma	Homo sapiens
7484 ng × h/mL	300 mg 3 times / day multiple, oral	TEBIPENEM plasma	Homo sapiens
17924 ng × h/mL	600 mg 3 times / day multiple, oral	TEBIPENEM plasma	Homo sapiens
3.2 μg × h/mL	100 mg 3 times / day multiple, oral	TEBIPENEM plasma	Homo sapiens
6.68 μg × h/mL	200 mg 3 times / day multiple, oral	TEBIPENEM plasma	Homo sapiens
11.35 μg × h/mL	300 mg 3 times / day multiple, oral	TEBIPENEM plasma	Homo sapiens
5.22 μg × h/mL	150 mg 3 times / day multiple, oral	TEBIPENEM plasma	Homo sapiens
7.93 μg × h/mL	250 mg 2 times / day multiple, oral	TEBIPENEM plasma	Homo sapiens
13.62 μg × h/mL	300 mg 3 times / day multiple, oral	TEBIPENEM plasma	Homo sapiens
12.29 μg × h/mL	250 mg single, oral	TEBIPENEM plasma	Homo sapiens
16.45 μg × h/mL	250 mg single, oral	TEBIPENEM plasma	Homo sapiens
29.22 μg × h/mL	250 mg single, oral	TEBIPENEM plasma	Homo sapiens
92.59 μg × h/mL	250 mg single, oral	TEBIPENEM plasma	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
0.77 h	250 mg single, oral	TEBIPENEM plasma	Homo sapiens
0.91 h	250 mg single, oral	TEBIPENEM plasma	Homo sapiens
0.84 h	100 mg single, oral	TEBIPENEM plasma	Homo sapiens
0.76 h	200 mg single, oral	TEBIPENEM plasma	Homo sapiens
0.92 h	400 mg single, oral	TEBIPENEM plasma	Homo sapiens
2 h	100 mg single, oral	TEBIPENEM plasma	Homo sapiens
3.8 h	600 mg single, oral	TEBIPENEM plasma	Homo sapiens
2.5 h	900 mg single, oral	TEBIPENEM plasma	Homo sapiens
0.8 h	300 mg single, oral	TEBIPENEM plasma	Homo sapiens
0.8 h	300 mg single, oral	TEBIPENEM plasma	Homo sapiens
1 h	600 mg single, oral	TEBIPENEM plasma	Homo sapiens
1.2 h	300 mg single, oral	TEBIPENEM plasma	Homo sapiens
0.9 h	100 mg single, oral	TEBIPENEM plasma	Homo sapiens
0.8 h	300 mg single, oral	TEBIPENEM plasma	Homo sapiens
1.1 h	600 mg single, oral	TEBIPENEM plasma	Homo sapiens
1 h	900 mg single, oral	TEBIPENEM plasma	Homo sapiens
1.3 h	600 mg single, oral	TEBIPENEM plasma	Homo sapiens
1.1 h	300 mg single, oral	TEBIPENEM plasma	Homo sapiens
0.9 h	300 mg single, oral	TEBIPENEM plasma	Homo sapiens
1.1 h	600 mg single, oral	TEBIPENEM plasma	Homo sapiens
0.9 h	300 mg single, oral	TEBIPENEM plasma	Homo sapiens
0.9 h	600 mg single, oral	TEBIPENEM plasma	Homo sapiens
0.82 h	300 mg 3 times / day multiple, oral	TEBIPENEM plasma	Homo sapiens
0.79 h	600 mg 3 times / day multiple, oral	TEBIPENEM plasma	Homo sapiens
0.72 h	300 mg 3 times / day multiple, oral	TEBIPENEM plasma	Homo sapiens
0.83 h	600 mg 3 times / day multiple, oral	TEBIPENEM plasma	Homo sapiens
0.44 h	100 mg 3 times / day multiple, oral	TEBIPENEM plasma	Homo sapiens
0.36 h	200 mg 3 times / day multiple, oral	TEBIPENEM plasma	Homo sapiens
0.67 h	300 mg 3 times / day multiple, oral	TEBIPENEM plasma	Homo sapiens
0.4 h	150 mg 3 times / day multiple, oral	TEBIPENEM plasma	Homo sapiens
0.34 h	250 mg 2 times / day multiple, oral	TEBIPENEM plasma	Homo sapiens
0.54 h	300 mg 3 times / day multiple, oral	TEBIPENEM plasma	Homo sapiens
0.88 h	250 mg single, oral	TEBIPENEM plasma	Homo sapiens
1.49 h	250 mg single, oral	TEBIPENEM plasma	Homo sapiens
1.44 h	250 mg single, oral	TEBIPENEM plasma	Homo sapiens
4.11 h	250 mg single, oral	TEBIPENEM plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
26.1%			TEBIPENEM serum	Homo sapiens

PubMed

Show entries

Title	Date	PubMed
Syntheses and pharmacokinetic studies of prodrug esters for the development of oral carbapenem, L-084.	2006 Apr	16830892
[Convulsive liability of an oral carbapenem antibiotic, tebipenem pivoxil].	2009 Jun	19882983

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Sample Use Guides

In Vivo Use Guide

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

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.

Substance Class	Chemical
Record UNII	95AK1A52I8
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ORAPENEM

Preferred Name

English

TEBIPENEM PIVOXIL

Official Name

English

TEBIPENEM PIVOXIL [USAN]

Common Name

English

TEBIPENEM PIVOXIL [MI]

Common Name

English

1-AZABICYCLO(3.2.0)HEPT-2-ENE-2-CARBOXYLIC ACID, 3-((1-(4,5-DIHYDRO-2-THIAZOLYL)-3-AZETIDINYL)THIO)-6-((1R)-1-HYDROXYETHYL)-4-METHYL-7-OXO-, (2,2-DIMETHYL-1-OXOPROPOXY)METHYL ESTER, (4R,5S,6S)-

Systematic Name

English

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