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SML2846

Sigma-Aldrich

Tebipenem pivoxil

≥98% (HPLC)

Synonyme(s) :

(4R,5S,6S)-pivaloyloxymethyl 3-(1-(4,5-dihydrothiazol-2-yl)azetidin-3-ylthio)-6-((R)-1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate, L 084, L-084, L084, ME1211, SPR 994, SPR-994, SPR994, TBM-PI, Tebi-pivoxil, [4R-[4a,5ß,6ß(R*)]]-3-[[1-(4,5-dihydro-2-thiazolyl)-3-azetidinyl]thio]-6-(1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (2,2-dimethyl-1-oxopropoxy)methyl ester

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About This Item

Formule empirique (notation de Hill):
C22H31N3O6S2
Numéro CAS:
161715-24-8
Poids moléculaire :
497.63
Numéro MDL:
MFCD17215369
Code UNSPSC :
12352200
Nomenclature NACRES :
NA.77

Niveau de qualité

100

Pureté

≥98% (HPLC)

Forme

powder

Couleur

white to beige

Solubilité

DMSO: 2 mg/mL, clear

Température de stockage

−20°C

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

Clé InChI

SNUDIPVBUUXCDG-QHSBEEBCSA-N

Actions biochimiques/physiologiques

Tebipenem pivoxil (L-084I; ME1211; SPR994; Tebi-pivoxil; TBM-PI) corresponds to the orally bioavailable pivalyl ester prodrug form of the carbapenem class broad-spectrum β-lactam antibiotic Tebipenem (LJC 11,036; SPR859; TBM). TBM is potent against both gram-positive and gram-negative bacteria, including penicillin-resistant S. pneumoniae (PRSP) and many β-lactamase-producing strains, while being less effective against methicillin-resistant S. aureus (MRSA), S. marcescens, and P. aeruginosa. TBM is 2- to 64-fold more potent than imipenem, cefdinir, and faropenem against clinical isolates from respiratory and urinary-tract infections.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

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Muneki Hotomi et al.
Vaccine, 25(13), 2478-2484 (2006-10-24)
An animal model of otitis media using chinchillas was developed to evaluate the efficacy of tebipenem pivoxil (TBM-PI) against experimental otitis media. Chinchillas inoculated via the transbullar approach with Streptococcus pneumoniae serogroup 6 were included in the efficacy study with
Takeshi Isoda et al.
The Journal of antibiotics, 59(4), 241-247 (2006-07-13)
We discovered an orally active carbapenem, L-084, through pharmacokinetic studies on various prodrug esters of (1R,5S,6S)-6-[(R)-1-hydroxyethyl]-l-methyl-2-[1-(1,3-thiazolin-2-yl)azetidin-3-yl]thio-1-carbapen-2-em-3-carboxylic acid (LJC11,036). L-084 showed a strong antimicrobial activity against Gram-positive and Gram-negative bacteria and exhibited the highest intestinal absorption among synthesized prodrugs of LJC11,036.
Akash Jain et al.
Expert review of anti-infective therapy, 16(7), 513-522 (2018-07-18)
Infections caused by antibiotic-resistant pathogens, particularly Gram-negative bacteria, have become increasingly challenging to successfully treat. The beta-lactam antibiotic subclass, the carbapenems, have proven valuable for the treatment of such Gram-negative bacterial infections due to their spectrum and β-lactamase stability properties.
Kazuhiko Kato et al.
Molecular pharmaceutics, 7(5), 1747-1756 (2010-08-26)
Tebipenem pivoxil (TBPM-PI) is an oral carbapenem antibiotic for treating otolaryngologic and respiratory infections in pediatric patients. This agent is a prodrug to improve intestinal absorption of TBPM, an active form, and an absorption rate of TBPM-PI is higher than
Aileen Rubio et al.
ACS infectious diseases, 4(10), 1436-1438 (2018-08-18)
Carbapenems are potent antibacterials with broad-spectrum activity. However, poor oral absorption generally confines this important drug class to in-hospital use by intravenous (IV) administration. The continued rise in drug resistant pathogens creates a need for alternative oral therapies with broad-spectrum
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