| Identification | Back Directory | [Name]
Tebipenem | [CAS]
161715-21-5 | [Synonyms]
LJC11036
LJC-11036
Tebipenem
LJC 11036
Tebipenem USP/EP/BP
Tebipenem Impurity 5
Tibipenem intermediate 2
(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
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)-
(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-carboxylicaci
(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-carboxylic acid | [Molecular Formula]
C16H21N3O4S2 | [MDL Number]
MFCD00936545 | [MOL File]
161715-21-5.mol | [Molecular Weight]
383.49 |
| Chemical Properties | Back Directory | [Boiling point ]
624.5±65.0 °C(Predicted) | [density ]
1.75 | [storage temp. ]
Sealed in dry,Store in freezer, under -20°C | [solubility ]
insoluble in EtOH; ≥19.15 mg/mL in H2O with gentle warming; ≥24.9 mg/mL in DMSO | [form ]
solid | [pka]
4.29±0.60(Predicted) | [color ]
White to khaki | [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 | [InChIKey]
GXXLUDOKHXEFBQ-YJFSRANCSA-N | [SMILES]
S1CCN=C1N2CC(C2)SC3=C(N4[C@H]([C@H]3C)[C@H](C4=O)[C@H](O)C)C(=O)O |
| Hazard Information | Back Directory | [Uses]
Tebipenem is an orally available carbapenem antibiotic, shows broad-spectrum activity against Gram-positive and -negative bacteria, except for Pseudomonas aeruginosa. | [Biological Activity]
tebipenem is an orally available carbapenem antibiotic. tebipenem is active against a panel of clinical isolates from a variety of bacterial species (mic50s ≤ 0.0039 ~ 8 μg/ml), including methicillin-resistant strains of staphylococcus aureus (s. aureus) and staphylococcus epidermidis (s. epidermidis), as well as penicillin-resistant streptococcus pneumoniae (s. pneumonia). tebipenem also inhibits β-lactamase in a time- and concentration-dependent manner. tebipenem pivoxil, a derivative of tebipenem, has been under development as the first orally available carbapenem antibiotic for the treatment of respiratory and otolaryngological infections caused by drug-resistant s. pneumonia in pediatric patients.1. hazra s, xu h, blanchard js. tebipenem, a new carbapenem antibiotic, is a slow substrate that inhibits the β-lactamase from mycobacterium tuberculosis. biochemistry, 2014, 53(22): 3671-3678.2. fujimoto k, takemoto k, hatano k, et al. novel carbapenem antibiotics for parenteral and oral applications: in vitro and in vivo activities of 2-aryl carbapenems and their pharmacokinetics in laboratory animals. antimicrobial agents and chemotherapy, 2013, 57(2): 697-707. | [Synthesis]
The general procedure for the synthesis of (4R,5S,6S)-3-((1-(4,5-dihydrothiazol-2-yl)azetidin-3-yl)thio)-6-((R)-1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid from tepipenem condensate is as follows: to compound (II) (R is p-nitrobenzyl ) (15.0 g, 29.0 mmol) was added 200 mL of n-butanol and 200 mL of water and stirred until completely dissolved. Subsequently 8.00 g of Raney Ni was added and the hydrogenation reaction was carried out at 60 °C. The reaction was carried out at 2.0 MPa hydrogen pressure and 20 °C for 4 hours. Upon completion of the reaction, the solid was collected by filtration and the filter cake was washed with 15 mL of water. The filtrate was adjusted to pH 6.5 with 4-dimethylaminopyridine and then washed with 150 mL of ethyl acetate. After the solution was cooled to 0 °C, 700 mL of acetone was added drop by drop and stirred for 10 minutes, 700 mL of acetone was again added drop by drop and stirring was continued for 1 hour. Finally, 12.5 g of white solid tebutamidine was obtained with a yield of 94.5% and a purity of 99.6%. | [IC 50]
β-lactam | [References]
[1] Hazra S, et al. Tebipenem, a new carbapenem antibiotic, is a slow substrate that inhibits the β-lactamase from Mycobacterium tuberculosis. Biochemistry. 2014 Jun 10;53(22):3671-8 DOI:10.1021/bi500339j
[2] Seenama C, et al. In vitro activity of tebipenem against Burkholderia pseudomallei. Int J Antimicrob Agents. 2013 Oct;42(4):375. DOI:10.1016/j.ijantimicag.2013.06.016
[3] Li H, et al. In vitro antibacterial activities of two novel oral antibiotics, tebipenem and cefditoren, and other comparators against community-acquired respiratory tract infection-associated bacterial pathogens: A multicentre study in China. Int J Antimicrob Agents. 2014 Jan;43(1):92-3. DOI:10.1016/j.ijantimicag.2013.09.009 |
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