ChemicalBook CAS DataBase List 161715-24-8

161715-24-8

Name	(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 pivaloyloxymethyl ester
CAS	161715-24-8
EINECS(EC#)	1308068-626-2
Molecular Formula	C23H32N2O6S2
MDL Number	MFCD17215369
Molecular Weight	496.64
MOL File	161715-24-8.mol

Synonyms

ME1211 TBPM-PI SPR-994 OrapeneM TebipeneM pivoxi Taibipeinan ester Tebipenem Pivoxil Tebipenem Pivoxil-d4 Tebipenem pivoxil(L-084) TEBIPENEM PIVOXIL USP/EP/BP (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 pivaloyloxymethyl ester (4R,5S,6S)-pivaloyloxymethyl 3-(1-(4,5-dihydrothiazol-2-yl)azetidin-3-ylthio)-6-((R)-1-hydroxyethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylate [(2,2-Dimethylpropanoyl)oxy]methyl (4R,5S,6S)-3-{[1-(4,5-dihydro-1,3-thiazol-2-yl)azetidin-3-yl]sulfanyl}-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (4R,5S,6S)-3-[[1-(4,5-Dihydro-2-thiazolyl)-3-azetidinyl]thio]-6-[(1R)-1-hydroxyethyl]-4-Methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic Acid (2,2-DiMethyl-1-oxopropoxy)Methyl Ester 1-Azabicyclo[3.2.0]hept-2-ene-2-carboxylicacid,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)- [4R-[4α,5β,6β(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

Chemical Properties

Melting point	140-142℃
Boiling point	661.9±65.0 °C(Predicted)
density	1.50
storage temp.	Sealed in dry,Store in freezer, under -20°C
solubility	Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
form	Solid
pka	14.36±0.20(Predicted)
color	White
InChIKey	SNUDIPVBUUXCDG-QHSBEEBCSA-N
SMILES	N12[C@@]([H])([C@@H]([C@H](O)C)C1=O)[C@@H](C)C(SC1CN(C3=NCCS3)C1)=C2C(OCOC(=O)C(C)(C)C)=O

Safety Data

Symbol(GHS)	GHS07
Signal word	Warning
WGK Germany	WGK 3
Storage Class	11 - Combustible Solids

Hazard Information

Chemical Properties

White Solid

Uses

Tebipenem Pivoxil is an oral carbapenem antibiotic. Tebipenem Pivoxil is absorbed and metabolized into Tebipenem, its active metabolite which showed excellent bactericidal activity against β-lactamase -nonproducing, ampicillin-resistant isolates.

Uses

Tebipenem pivoxil(L-084) is a novel oral carbapenem antibiotic with an IC50 of 100 μg/ml for human CYP isoforms. In mouse, rat, dog and monkey, TBPM-PI were absorbed quickly, and the bioavailability was (71.4, 59.1, 34.8 and 44.9%, respectively. There was

Definition

ChEBI: Tebipenem pivoxil is a member of carbapenems and a pivaloyloxymethyl ester.

Biological Activity

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 bacteriaincluding penicillin-resistant S. pneumoniae (PRSP) and many β-lactamase-producing strainswhile being less effective against methicillin-resistant S. aureus (MRSA)S. marcescensand P. aeruginosa. TBM is 2- to 64-fold more potent than imipenemcefdinirand faropenem against clinical isolates from respiratory and urinary-tract infections.

in vivo

Tebipenem pivoxil (L084) (0-4.00 g/kg; p.o.; once) shows minimal lethal dosage (MLD) of 4.00 g/kg and the maximum tolerance dosage (MTD) of 3.40 g/kg in mice^[1].
Tebipenem pivoxil (50 and 100 mg/kg; p.o.; once) significantly protects the sepsis mice challenged with various pathogenic bacteria^[1].

Animal Model:	KM mice weighing 18–22 g^[1]
Dosage:	2.89, 3.40 and 4.00 g/kg
Administration:	Oral administration (tablet), once
Result:	Within the 14-day observation period, only one mouse was dead in the maximum oral dosage (4.00 g/kg). The minimal lethal dosage (MLD) was 4.00 g/kg and the maximum tolerance dosage (MTD) in the mice was 3.40 g/kg. Showed dose-dependent liver and kidney damage.

Animal Model:	ICR mice, sepsis mouse models^[1]
Dosage:	50 and 100 mg/kg
Administration:	Oral administration (tablet), once
Result:	Significantly increased the survival number of the sepsis mice within a 168 h observation period.

IC 50

β-lactam

Spectrum Detail

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