74011-58-8

• 常用中文名：依诺沙星
• 常用英文名：Enoxacin
• CAS号：74011-58-8
• 分子式：C₁₅H₁₇FN₄O₃
• 分子量：320.319
• 相关类别： 原料药 人工合成抗感染类药 喹诺酮类药
• 发布时间：2018-08-15 08:12:07
• 更新时间：2024-01-02 12:10:24
• 【用途一】
  广谱抗菌素，用于治疗革兰阴性及阳性细菌引起的泌尿、耳、鼻、喉及浅表化脓性疾患等多种感染
  【用途二】
  喹诺酮类广谱抗感染药，对革兰阳性和阴性菌及葡萄糖非发酵菌有抗菌作用。适用于治疗呼吸系统感染，消化道感染，泌尿生殖系统感染以及皮肤、耳鼻眼喉感染，妇科疾病感染
  【用途三】
  该品为第三代喹诺酮类药。体内抗菌作用较氟哌酸强2-9倍。临床用球必尿系统、呼吸系统、消化系统、耳鼻喉、皮肤及软组织感染等。

名称

• 中文名: 依诺沙星
• 英文名: enoxacin
• 中文别名: 1-乙基-6-氟-1,4-二氢-4-氧代-7-(1-哌嗪基)-1,8.萘啶-3-羧酸; 1-乙基-6-氟-1,4-二氢-4-氧代-7-(1-哌嗪基)-1,8-萘啶-3-羧酸; 1-乙基-6-氟-1,4-二氢-4-氧代-7-(-哌嗪基)-1,8-萘啶-3-羧酸
• 英文别名: 1-ethyl-6-fluoro-4-oxo-7-piperazin-1-yl-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid; MFCD00133308; 1-Ethyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid; enoram; 1-Ethyl-6-fluoro-4-oxo-7-(1-piperazinyl)-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid; Enoxacin; FLUMARK; Abenox; ENX; Gyramid; 1,8-Naphthyridine-3-carboxylic acid, 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-; Enoxor; ci919; at-2266; Humark; Enoxen

物化性质

• 密度: 1.4±0.1 g/cm3
• 沸点: 569.9±50.0 °C at 760 mmHg
• 熔点: 220-224ºC
• 分子式: C₁₅H₁₇FN₄O₃
• 分子量: 320.319
• 闪点: 298.4±30.1 °C
• 精确质量: 320.128479
• PSA: 87.46000
• LogP: 0.55
• 外观性状: 灰白色至黄色晶体
• 蒸汽压: 0.0±1.6 mmHg at 25°C
• 折射率: 1.599
• 储存条件:

  存放在密封容器内，并放在阴凉，干燥处。2-8 ºC保存。

• 稳定性:

  指定条件下稳定，远离氧化物。

• 分子结构:

  1、 摩尔折射率：78.79

  2、 摩尔体积（cm³/mol）：230.6

  3、 等张比容（90.2K）：636.7

  4、 表面张力（dyne/cm）：58.0

  5、 极化率（10^-24cm³）：31.23

• 计算化学:

  1.疏水参数计算参考值（XlogP）:无

  2.氢键供体数量:2

  3.氢键受体数量:8

  4.可旋转化学键数量:3

  5.互变异构体数量:无

  6.拓扑分子极性表面积85.8

  7.重原子数量:23

  8.表面电荷:0

  9.复杂度:521

  10.同位素原子数量:0

  11.确定原子立构中心数量:0

  12.不确定原子立构中心数量:0

  13.确定化学键立构中心数量:0

  14.不确定化学键立构中心数量:0

  15.共价键单元数量:1

• 更多:

  1. 性状：白色或浅黄褐色的结晶或结晶性粉末，无臭，味苦。

  2. 密度（g/mL,25/4℃）：未确定

  3. 相对蒸汽密度（g/mL,空气=1）：未确定

  4. 熔点（ºC）：220～224

  5. 沸点（ºC,常压）：未确定

  6. 沸点（ºC,5.2kPa）：未确定

  7. 折射率：未确定

  8. 闪点（ºC）：未确定

  9. 比旋光度（º）：未确定

  10. 自燃点或引燃温度（ºC）：未确定

  11. 蒸气压（kPa,25ºC）：未确定

  12. 饱和蒸气压（kPa,60ºC）：未确定

  13. 燃烧热（KJ/mol）：未确定

  14. 临界温度（ºC）：未确定

  15. 临界压力（KPa）：未确定

  16. 油水（辛醇/水）分配系数的对数值：未确定

  17. 爆炸上限（%,V/V）：未确定

  18. 爆炸下限（%,V/V）：未确定

  19. 溶解性：易溶于冰醋酸，微溶于甲醇，极微溶于氯仿或丙酮，几不溶于乙醇，乙醚或水。

生物活性

• 描述: Enoxacin是广谱抗菌剂。
• 相关类别:
  信号通路 >> 抗感染 >> 细菌
  研究领域 >> 感染
• 参考文献:

  [1]. Chin, N.-X. and H.C. Neu, In vitro activity of enoxacin, a quinolone carboxylic acid, compared with those of norfloxacin, new beta-lactams, aminoglycosides, and trimethoprim. Antimicrobial agents and chemotherapy, 1983. 24(5): p. 754-763.

  [2]. Wijnands, W., T. Vree, and C. Herwaarden, Enoxacin decreases the clearance of theophylline in man. British journal of clinical pharmacology, 1985. 20(6): p. 583-588.

毒性和生态

生态学数据: 通常对水是不危害的，若无政府许可，勿将材料排入周围环境。 CHEMICAL IDENTIFICATION RTECS NUMBER : QN2800000 CHEMICAL NAME : 1,8-Naphthyridine-3-carboxylic acid, 1,4-dihydro-1-ethyl-6-fluoro-4-oxo-7-(1-piperazinyl)- CAS REGISTRY NUMBER : 74011-58-8 LAST UPDATED : 199806 DATA ITEMS CITED : 15 MOLECULAR FORMULA : C15-H17-F-N4-O3 MOLECULAR WEIGHT : 320.36 WISWESSER LINE NOTATION : T66 BV EN GNJ CVQ E2 IF H- DT6M DNTJ HEALTH HAZARD DATA ACUTE TOXICITY DATA TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - rat DOSE/DURATION : >5 gm/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Subcutaneous SPECIES OBSERVED : Rodent - rat DOSE/DURATION : >2 gm/kg TOXIC EFFECTS : Behavioral - altered sleep time (including change in righting reflex) Behavioral - ataxia Skin and Appendages - hair TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 236 mg/kg TOXIC EFFECTS : Behavioral - somnolence (general depressed activity) Behavioral - convulsions or effect on seizure threshold Behavioral - ataxia TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : >4 gm/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intraperitoneal SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 3600 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Subcutaneous SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 1100 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 327 mg/kg TOXIC EFFECTS : Behavioral - somnolence (general depressed activity) Behavioral - convulsions or effect on seizure threshold Behavioral - ataxia TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Mammal - dog DOSE/DURATION : >1600 mg/kg TOXIC EFFECTS : Behavioral - food intake (animal) Gastrointestinal - hypermotility, diarrhea TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Primate - monkey DOSE/DURATION : >1600 mg/kg TOXIC EFFECTS : Behavioral - food intake (animal) Gastrointestinal - hypermotility, diarrhea TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 90 gm/kg/30D-I TOXIC EFFECTS : Kidney, Ureter, Bladder - changes in bladder weight Blood - changes in leukocyte (WBC) count Nutritional and Gross Metabolic - changes in calcium TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 273 gm/kg/26W-I TOXIC EFFECTS : Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) Nutritional and Gross Metabolic - weight loss or decreased weight gain Related to Chronic Data - changes in testicular weight TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 1680 mg/kg/4W-I TOXIC EFFECTS : Skin and Appendages - dermatitis, other (after systemic exposure) Nutritional and Gross Metabolic - weight loss or decreased weight gain TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral DOSE : 91 gm/kg SEX/DURATION : male 13 week(s) pre-mating TOXIC EFFECTS : Reproductive - Fertility - male fertility index (e.g. # males impregnating females per # males exposed to fertile nonpregnant females) Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea) Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral DOSE : 11 gm/kg SEX/DURATION : female 7-17 day(s) after conception TOXIC EFFECTS : Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Specific Developmental Abnormalities - musculoskeletal system MUTATION DATA TYPE OF TEST : Mutation in microorganisms TEST SYSTEM : Bacteria - Salmonella typhimurium DOSE/DURATION : 200 ng/plate REFERENCE : MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 281,207,1992

安全

• 危害码 (欧洲): Xi
• 风险声明 (欧洲): 36/37/38
• 安全声明 (欧洲): 26-36/37
• WGK德国: 2
• RTECS号: QN2800000
• 海关编码: 29335995

合成路线

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制备

方法1：以2，6-二羟基-5-氟烟酰胺为原料，经氯化、酯化、与乙酰哌嗪缩合、与3-乙胺基丙酸乙酯缩合、环化、脱氢、水解得产品。该路线条件温和，路线较短，但需特殊试剂四氯苯醌。国内目前主要采用该法。

方法2：另一条路线是以2，6-二氯-3-硝基吡啶为原料，经与乙氧羰基哌嗪缩合后，再经氨解、乙酰化、还原、重氮化、氟化、水解、与EMME缩合、环合乙基化、水解得产品。该法氟化反应不易控制、环化需高温，工艺条件苛刻。

海关

海关编码	29335995