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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
Structure of TEBIPENEM PIVOXIL

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

HIDE SMILES / InChI
Molecular Formula C22H31N3O6S2
Molecular Weight 497.628
Charge 0
Count
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

CNS Non-penetrant
1014
Curator's Comment: Low penetration to the central nervous system was confirmed in amimal models

Originator

Wyeth
116
Curator's Comment: # Wyeth (now Pfizer)

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Approved
8429
ORAPENEM

Approved Use

Orapenem is usually used to treat pneumonia, otitis media and sinusitis.

Launch Date

1.24035845E12
Curative
Approved
8429
ORAPENEM

Approved Use

Orapenem is usually used to treat pneumonia, otitis media and sinusitis.

Launch Date

1.24035845E12
Curative
Approved
8429
ORAPENEM

Approved Use

Orapenem is usually used to treat pneumonia, otitis media and sinusitis.

Launch Date

1.24035845E12
PubMed

PubMed

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

Patents

CN103059028A
4
CN104055739A
4

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
Created
by admin
on Fri Dec 15 16:16:59 UTC 2023
Edited
by admin
on Fri Dec 15 16:16:59 UTC 2023
Record UNII
95AK1A52I8
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TEBIPENEM PIVOXIL
INN   JAN   WHO-DD  
USAN   INN  
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
LJC 11,084
Code English
TBPM-PI
Code English
ME-1211
Code English
ORAPENEM
Brand Name English
tebipenem pivoxil [INN]
Common Name English
ME1211
Code English
L-084
Code English
Tebipenem pivoxil [WHO-DD]
Common Name English
TEBIPENEM PIVOXIL [JAN]
Common Name English
LJC-11084
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
Systematic Name English
Classification Tree Code System Code
WHO-ATC J01DH06
Created by admin on Fri Dec 15 16:16:59 UTC 2023 , Edited by admin on Fri Dec 15 16:16:59 UTC 2023
NCI_THESAURUS C260
Created by admin on Fri Dec 15 16:16:59 UTC 2023 , Edited by admin on Fri Dec 15 16:16:59 UTC 2023
Code System Code Type Description
USAN
FG-202
Created by admin on Fri Dec 15 16:16:59 UTC 2023 , Edited by admin on Fri Dec 15 16:16:59 UTC 2023
PRIMARY
SMS_ID
100000178191
Created by admin on Fri Dec 15 16:16:59 UTC 2023 , Edited by admin on Fri Dec 15 16:16:59 UTC 2023
PRIMARY
ChEMBL
CHEMBL2107486
Created by admin on Fri Dec 15 16:16:59 UTC 2023 , Edited by admin on Fri Dec 15 16:16:59 UTC 2023
PRIMARY
PUBCHEM
9892071
Created by admin on Fri Dec 15 16:16:59 UTC 2023 , Edited by admin on Fri Dec 15 16:16:59 UTC 2023
PRIMARY
DRUG CENTRAL
2574
Created by admin on Fri Dec 15 16:16:59 UTC 2023 , Edited by admin on Fri Dec 15 16:16:59 UTC 2023
PRIMARY
NCI_THESAURUS
C76566
Created by admin on Fri Dec 15 16:16:59 UTC 2023 , Edited by admin on Fri Dec 15 16:16:59 UTC 2023
PRIMARY
EPA CompTox
DTXSID00167228
Created by admin on Fri Dec 15 16:16:59 UTC 2023 , Edited by admin on Fri Dec 15 16:16:59 UTC 2023
PRIMARY
FDA UNII
95AK1A52I8
Created by admin on Fri Dec 15 16:16:59 UTC 2023 , Edited by admin on Fri Dec 15 16:16:59 UTC 2023
PRIMARY
INN
7924
Created by admin on Fri Dec 15 16:16:59 UTC 2023 , Edited by admin on Fri Dec 15 16:16:59 UTC 2023
PRIMARY
CAS
161715-24-8
Created by admin on Fri Dec 15 16:16:59 UTC 2023 , Edited by admin on Fri Dec 15 16:16:59 UTC 2023
PRIMARY
MERCK INDEX
m11935
Created by admin on Fri Dec 15 16:16:59 UTC 2023 , Edited by admin on Fri Dec 15 16:16:59 UTC 2023
PRIMARY
Related Record Type Details
Structure of TEBIPENEM PIVOXIL HYDROCHLORIDE
SALT/SOLVATE -> PARENT
Structure of TEBIPENEM PIVOXIL HYDROBROMIDE
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of TEBIPENEM
METABOLITE ACTIVE -> PRODRUG
Related Record Type Details
Structure of TEBIPENEM
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