曲伐沙星
| 中文名称 | 曲伐沙星 |
|---|---|
| 中文同义词 | 曲伐沙星;特伐沙星;(1Α,5Α,6Α)-7-(6-氨基-3-氮杂二环[3.1.0]己-3-基)-1-(2,4-二氟苯基)-6-氟-1,4-二氢-4-氧-1,8-萘啶-3-羧酸;曲伐沙星,曲氟沙星;聚苯乙烯磺酸钙;曲氟沙星;曲伐沙星杂质 |
| 英文名称 | TROVAFLOXACIN |
| 英文同义词 | TROVAFLOXACIN;1,8-Naphthyridine-3-carboxylic acid, 7-(1.alpha.,5.alpha.,6.alpha.)-6-amino-3-azabicyclo3.1.0hex-3-yl-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-;(1α，5α，6α)-7-(6-Amino-3-azabi-cyclo[3.1.0]hex-3-y1)-1-(2，4-difluomphenyl)-6-fluom-1，4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid;CP-99219;Trovan：CP-99219-27;7-[(1R,5S)-6-amino-3-azabicyclo[3.1.0]hexan-3-yl]-1-(2,4-difluorophenyl)-6-fluoro-4-keto-1,8-naphthyridine-3-carboxylic acid;7-[(1R,5S)-6-amino-3-azabicyclo[3.1.0]hexan-3-yl]-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid;7-[(1R,5S)-6-azanyl-3-azabicyclo[3.1.0]hexan-3-yl]-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid |
| CAS号 | 147059-72-1 |
| 分子式 | C20H15F3N4O3 |
| 分子量 | 416.36 |
| EINECS号 | |
| 相关类别 | 抗病源性微生物药;喹诺酮类药物;药物;合成抗菌药;精细化工原料;API |
| Mol文件 | 147059-72-1.mol |
| 结构式 |  |
曲伐沙星 性质
| 熔点 | >195oC (dec.) |
|---|---|
| 沸点 | 630.5±55.0 °C(Predicted) |
| 密度 | 1.612±0.06 g/cm3(Predicted) |
| 储存条件 | -20°C Freezer, Under inert atmosphere |
| 溶解度 | 可溶于乙腈（少许）、DMSO（少许） |
| 形态 | 固体 |
| 酸度系数(pKa) | 5.80±0.70(Predicted) |
| 颜色 | 淡米色至浅米色 |
| CAS 数据库 | 147059-72-1 |
IC50: 4 μM (Pannexin 1 channel (PANX1))
Gram-positive, Gram-negative and anaerobic organisms
DNA gyrase
Topoisomerase IV
Trovafloxacin (20 µM; 24 hours; HepG2 cells) and tumor necrosis factor (TNF; 4 ng/mL) incubation induces apoptosis and increases leakage of lactate dehydrogenase (LDH) in HepG2 cells.
Trovafloxacin (20 µM; 24 hours; HepG2 cells) and TNF (4 ng/mL) incubation increases expression of early NF-κB-related factors A20 and IκBα.
Trovafloxacin prolongs TNF-induced activation of MAPKs and IKKα/β activation in HepG2.
Trovafloxacin is a potent inhibitor of TO-PRO-3 uptake by apoptotic cells. Trovafloxacin also inhibits ATP release from apoptotic cells. Trovafloxacin does not inhibit caspase 3/7 activation, or caspase-mediated PANX1 cleavage during apoptosis.
Trovafloxacin is equally active against both penicillin-susceptible and -resistant pneumococci, with MICs of 0.06-0.25 mg/mL reported for more than 700 isolates. The MICs of Trovafloxacin at which 90% of isolates are inhibited for 55 isolates of pneumococci is 0.125 μg/mL.
Apoptosis Analysis
| Cell Line: | HepG2 cells |
| Concentration: | 20 µM |
| Incubation Time: | 24 hours |
| Result: | Showed a gradual increase of Annexin V-staining and an increased leakage of lactate dehydrogenase (LDH) at 24 h. |
RT-PCR
| Cell Line: | HepG2 cells |
| Concentration: | 20 µM |
| Incubation Time: | 24 hours |
| Result: | Caused a higher increase in the transcription of A20 and IκBα in HepG2 cells. |
Trovafloxacin (150 mg/kg; oral administration; male C57BL/6 J mice) treatment disrupts TNF-induced p65 nuclear translocation. Trovafloxacin treatment increases expression of early NF-κB-related factors A20 and IκBα.
Trovafloxacin, when administered in combination with lipopolysaccharide (LPS) or TNF to mice induces severe liver toxicity associated with vast apoptotic areas in the liver, increased serum levels of alanine amino transferases (ALT) and pro-inflammatory cytokines.
| Animal Model: | Male C57BL/6 J mice (9-11-week-old) injected with recombinant murine TNF ion |
| Dosage: | 150 mg/kg |
| Administration: | Oral administration |
| Result: | Showed a greater number of cells with increased nuclear/cytoplasmic p65 ratio in liver. |
500mg 7-氯-1-(2，4-二氟苯基)-7-氟-1，4-二氢-4-氧代-1，8-喹啉-3-羧酸、624mg(1α，5α，6α)-6-氨基-3-氮杂二环[3.1.0]己烷二甲苯磺酸盐、0.6ml三乙胺和5ml甲醇，一起回流16h。过滤收集形成的白色固体，在THF中回流，再过滤收集。得450ml特伐沙星，收率75%，mp 225～228℃(分解)。