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Details

Stereochemistry ABSOLUTE
Molecular Formula C16H21N3O4S2
Molecular Weight 383.486
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TEBIPENEM

SMILES

[H][C@]1([C@@H](C)O)C(=O)N2C(C(O)=O)=C(SC3CN(C3)C4=NCCS4)[C@H](C)[C@]12[H]

InChI

InChIKey=GXXLUDOKHXEFBQ-YJFSRANCSA-N
InChI=1S/C16H21N3O4S2/c1-7-11-10(8(2)20)14(21)19(11)12(15(22)23)13(7)25-9-5-18(6-9)16-17-3-4-24-16/h7-11,20H,3-6H2,1-2H3,(H,22,23)/t7-,8-,10-,11-/m1/s1

HIDE SMILES / InChI

Molecular Formula C16H21N3O4S2
Molecular Weight 383.486
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

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

Curator's Comment: Low penetration to the central nervous system was confirmed in amimal models

Originator

Curator's Comment: # Wyeth (now Pfizer)

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
ORAPENEM

Approved Use

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

Launch Date

2009
Curative
ORAPENEM

Approved Use

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

Launch Date

2009
Curative
ORAPENEM

Approved Use

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

Launch Date

2009
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

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
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 Sat Dec 16 01:33:03 GMT 2023
Edited
by admin
on Sat Dec 16 01:33:03 GMT 2023
Record UNII
Q2TWQ1I31U
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TEBIPENEM
WHO-DD  
Common Name English
(1R,5S,6S)-6-(1(R)-HYDROXYETHYL)-1-METHYL-2-(1-(2-THIAZOLIN-2-YL)AZETIDIN-3-YLSULFANYL)-1-CARBA-2-PENEM-3-CARBOXYLIC ACID
Common Name English
TEBIPENEM [MI]
Common Name English
LJC-11036
Common Name English
Tebipenem [WHO-DD]
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-, (4R,5S,6S)-
Common Name English
Code System Code Type Description
EVMPD
SUB04685MIG
Created by admin on Sat Dec 16 01:33:03 GMT 2023 , Edited by admin on Sat Dec 16 01:33:03 GMT 2023
PRIMARY
WIKIPEDIA
Tebipenem
Created by admin on Sat Dec 16 01:33:03 GMT 2023 , Edited by admin on Sat Dec 16 01:33:03 GMT 2023
PRIMARY
FDA UNII
Q2TWQ1I31U
Created by admin on Sat Dec 16 01:33:03 GMT 2023 , Edited by admin on Sat Dec 16 01:33:03 GMT 2023
PRIMARY
MESH
C500135
Created by admin on Sat Dec 16 01:33:03 GMT 2023 , Edited by admin on Sat Dec 16 01:33:03 GMT 2023
PRIMARY
EPA CompTox
DTXSID40167227
Created by admin on Sat Dec 16 01:33:03 GMT 2023 , Edited by admin on Sat Dec 16 01:33:03 GMT 2023
PRIMARY
MERCK INDEX
m11936
Created by admin on Sat Dec 16 01:33:03 GMT 2023 , Edited by admin on Sat Dec 16 01:33:03 GMT 2023
PRIMARY
PUBCHEM
9800194
Created by admin on Sat Dec 16 01:33:03 GMT 2023 , Edited by admin on Sat Dec 16 01:33:03 GMT 2023
PRIMARY
CAS
161715-21-5
Created by admin on Sat Dec 16 01:33:03 GMT 2023 , Edited by admin on Sat Dec 16 01:33:03 GMT 2023
PRIMARY
SMS_ID
100000084770
Created by admin on Sat Dec 16 01:33:03 GMT 2023 , Edited by admin on Sat Dec 16 01:33:03 GMT 2023
PRIMARY
Related Record Type Details
PRODRUG -> METABOLITE ACTIVE