[(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编号: 72869
• 分子式: C22H31N3O6S2
• 平均质量: 497.62804
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: [(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传统名: [(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
• 别名: 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

登记号

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

理论计算性质

• Acid pKa: 14.998237
• 质子受体: 6
• 质子供体: 1
• LogD (pH = 5.5): 0.7667995
• LogD (pH = 7.4): 1.5615025
• Log P: 1.5921878
• 摩尔折射率: 127.4265 cm^3
• 极化性: 49.59826 Å^3
• 极化表面积: 108.74 Å^2
• 可自由旋转的化学键: 9
• 里宾斯基五规则: true

分子性质

安全信息

• 保存条件: -20°C

产品相关信息

• 成盐信息: Free Base

详细说明

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.

参考文献

• 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)