[(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-carbonyloxy]methyl 2,2-dimethylpropanoate

• ChemBase ID: 72869
• Molecular Formular: C22H31N3O6S2
• Molecular Mass: 497.62804
• Monoisotopic Mass: 497.16542773
• SMILES: [C@@H]1(C(=O)N2[C@@H]1[C@H](C(=C2C(=O)OCOC(=O)C(C)(C)C)SC1CN(C1)C1=NCCS1)C)[C@@H](C)O
• Canonical SMILES: C[C@H]([C@H]1C(=O)N2[C@@H]1[C@@H](C)C(=C2C(=O)OCOC(=O)C(C)(C)C)SC1CN(C1)C1=NCCS1)O
• InChI: 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
• InChIKey: SNUDIPVBUUXCDG-QHSBEEBCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(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-carbonyloxy]methyl 2,2-dimethylpropanoate
• IUPAC Traditional name: [(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-carbonyloxy]methyl 2,2-dimethylpropanoate
• Synonyms: L-084; TBPM-PI; ME1211; Tebipenem pivoxil; (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; L 084; Orapenem; [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

Database IDs

• CAS Number: 161715-24-8
• PubChem SID: 162037790
• PubChem CID: 9892071

CALCULATED PROPERTIES

• Acid pKa: 14.998237
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 0.7667995
• LogD (pH = 7.4): 1.5615025
• Log P: 1.5921878
• Molar Refractivity: 127.4265 cm^3
• Polarizability: 49.59826 Å^3
• Polar Surface Area: 108.74 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• Storage Condition: -20°C

Product Information

• Salt Data: Free Base

DETAILS

Selleck Chemicals - S2159

Research Area: Infection
Biological Activity:
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 no other tissue than the kidney, in which TBPM was highly distributed and remained for a long time. In addition, low penetration to the central nervous system was confirmed. The penetration ratio of TBPM to ELF, that is the ratio of ELF concentration to plasma concentration of TBPM, was 21.8 +/- 14.7%. [1][2]

Toronto Research Chemicals - T012900

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.

REFERENCES

• Kijima K et al. Jpn J Antibiot. 2009 Jun; 62(3):214-40
• Nakashima, M. et al.: Nip. Kag. Ryo. Gak., 57, 90 (2009)
• Kishii, K. etal.: Antimicrob. Agents Chemother., 54, 3970 (2009)