TEBIPENEM PIVOXIL HYDROBROMIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C22H31N3O6S2.BrH
Molecular Weight	578.54
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of TEBIPENEM PIVOXIL HYDROBROMIDE

Structure Search

SMILES

Br.[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=MMWWBQNLJKFAIN-HXLQFWNVSA-N

InChI=1S/C22H31N3O6S2.BrH/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;1H/t11-,12-,14-,15-;/m1./s1

HIDE SMILES / InChI

Description
Sources: http://www.rad-ar.or.jp/siori/english/kekka.cgi?n=2372 | https://www.ncbi.nlm.nih.gov/pubmed/26751436

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 Target ID: CHEMBL2362973 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15728880 \| https://www.ncbi.nlm.nih.gov/pubmed/26751436	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Otitis media 41 Sources: http://www.rad-ar.or.jp/siori/english/kekka.cgi?n=2372 http://adisinsight.springer.com/drugs/800010812	Curative	Approved 8429	ORAPENEM Approved Use Orapenem is usually used to treat pneumonia, otitis media and sinusitis. Launch Date 2009
Pneumonia 90 Sources: http://www.rad-ar.or.jp/siori/english/kekka.cgi?n=2372 http://adisinsight.springer.com/drugs/800010812	Curative	Approved 8429	ORAPENEM Approved Use Orapenem is usually used to treat pneumonia, otitis media and sinusitis. Launch Date 2009
Sinusitis 26 Sources: http://www.rad-ar.or.jp/siori/english/kekka.cgi?n=2372 http://adisinsight.springer.com/drugs/800010812	Curative	Approved 8429	ORAPENEM Approved Use Orapenem is usually used to treat pneumonia, otitis media and sinusitis. Launch Date 2009

PubMed

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

Patents

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.

Name

Type

Language

TEBIPENEM PIVOXIL HYDROBROMIDE

Official Name

English

SPR-994

Code

English

TEBIPENEM PIVOXIL HYDROBROMIDE [USAN]

Common Name

English

TBPM-PI-HBR

Code

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, HYDROBROMIDE (1:1), (4R,5S,6S)-

Systematic Name

English

SPR994

Code

English

[(2,2-Dimethylpropanoyl)oxy]methyl (4R,5S,6S)-3-{[1-(4,5-dihydrothiazol-2-yl)azetidin-3-yl]sulfanyl}-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate monohydrobromide

Systematic Name

English

Code System Code Type Description

FDA UNII

NT65DX774J