70458-92-3

• 常用中文名：培氟沙星
• 常用英文名：Pefloxacin
• CAS号：70458-92-3
• 分子式：C₁₇H₂₀FN₃O₃
• 分子量：333.357
• 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：2018-02-06 08:00:00
• 更新时间：2026-07-03 22:43:41
• Pefloxacin是抗菌化合物,通过抑制DNA旋转酶来阻断DNA复制。

名称

• 中文名: 培氟沙星
• 英文名: 1-ethyl-6-fluoro-7-(4-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid
• 中文别名: 1-乙基-6-氟-7-(4-甲基哌嗪-1-基)-4-氧代-1,4-二氢喹啉-3-羧酸; 培氟沙星, 100PPM; 培氟沙星Pefloxacinium; 1-乙基-1,4-二氢-6-氟-7-(4-甲基-1-哌嗪)-4-氧代-3-喹啉羧酸; 1-乙基-6-氟-1,4-二氢-7-(4-佳绩-哌嗪基)-4-氧代-3-喹啉羧酸; 培氟哌酸; 甲醇中培氟沙星溶液标准物质; 甲氟哌酸; 1-乙基-6-氟-7-(4-甲基哌嗪基)-4-氧代-1,4-二氢喹啉-3-羧酸
• 英文别名: 1589mRB：Peflox; am-725; PEFLOXACIN METHANESULFONATE; am725; 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(4-methyl-1-piperazinyl)-3-quinolinec; Penaeine; EU-5306; 1-Ethyl-6-fluoro-7-(4-methyl-1-piperazinyl)-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid; Pefloxacino; 1-ethyl-6-fluoro-7-(4-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; PEFLOXACIN MESYLATE; PERFLOXACINE; EINECS 274-611-8; 1-Ethyl-1，4-dihydro-6-fluoro-7-(4-methyl-1-piperazinyl)-4-oxo-3-quinolinecboxylic acid; PFLX; Abactal; Labocton; 1-Ethyl-6-fluoro-7-(4-methyl-1-piperazinyl)-1,4-dihydro-4-oxo-3-quinolinecboxylic acid; Acrylamide Impurity 31; Pefloxacin in Methanol; pefloxacine; 1589RB; Pefloxacin (USAN); PEFLOXACIN(SUBJECTTOPATENTFREE); MFCD01685696; peflacin; nyl)-4-oxo; Silver Pefloxacin; Penoxacine; RB-1589; N-Methylnorfloxacin; Pefloxacinium; Pefloxacine; 3-quinolinecboxylicacid,1,4-dihydro-1-ethyl-6-fluoro-7-(4-methyl-1-piperazi; PEFLOXACINE METHANSULFONATE DIHYDRATE; Pefloxacin //BP; PEFLOXACINE MESYLATE DIHYDRATE; 1-ETHYL-6-FLUORO-1,4-DIHYDRO-7-(4-METHYL-1-PIPERAZINYL-4-OXO-3-QUINOLINE CBOXYLIC ACID) METHANE SULPHONATE DIHYDRATE; 1584rb; 1-Ethyl-6-fluoro-1,4-dihydro-7-(4-methylpiperazino)-4-oxo-3-quinolinecboxylic acid; 1,4-Didhydro-7(4-methylpiperazinyl)-fluoro-1-ethyl-4-oxosynolin cbonoic acid; 1-Ethyl-6-fluoro-7-(4-methyl-1-piperazinyl)-4-oxo-1,4-dihydro-3-quinolinecboxylic acid; SULPHONATE DIHYDRATE; 3-Quinolinecboxylic acid, 1-ethyl-6-fluoro-1,4-dihydro-7-(4-methyl-1-piperazinyl)-4-oxo; 1-Ethyl-4-oxo-6-fluoro-7-(4-methyl-1-piperazinyl)-1,4-dihydro-3-quinolinecboxylic acid; PEFLOXACIN MESYLATE DIHYDRATE; Pefloxacinum; 1-ETHYL-6-FLUORO-7-(4-METHYLPIPERAZIN-1-YL)-4-OXO-QUINOLINE-3-CBOXYLIC ACID; PEFLOXACIN; PEFLOXACIN METHANE SULFONATE DIHYDRATE

物化性质

• 密度: 1.3±0.1 g/cm3
• 沸点: 529.1±50.0 °C at 760 mmHg
• 分子式: C₁₇H₂₀FN₃O₃
• 分子量: 333.357
• 闪点: 273.8±30.1 °C
• 精确质量: 333.148865
• PSA: 65.78000
• LogP: 1.51
• 蒸汽压: 0.0±1.5 mmHg at 25°C
• 折射率: 1.594
• 储存条件: 2-8℃
• 分子结构:

  1、 摩尔折射率：85.63

  2、 摩尔体积（cm³/mol）：252.4

  3、 等张比容（90.2K）：679.3

  4、 表面张力（dyne/cm）：52.4

  5、 极化率（10-24cm3）：33.94

• 计算化学:

  1.疏水参数计算参考值（XlogP）:无

  2.氢键供体数量:1

  3.氢键受体数量:7

  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64.1

  7.重原子数量:24

  8.表面电荷:0

  9.复杂度:545

  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：类白色晶体。

  2.熔点（ºC）：270--272

  3.溶解性：溶于碱性和酸性溶液，微溶于水。

生物活性

• 描述: Pefloxacin是抗菌化合物,通过抑制DNA旋转酶来阻断DNA复制。
• 相关类别:
  信号通路 >> 抗感染 >> 细菌
  天然产物 >> 生物碱
  研究领域 >> 感染
• 参考文献:

  [1]. Drlica K, et al. DNA gyrase, topoisomerase IV, and the 4-quinolones. Microbiol Mol Biol Rev. 1997 Sep;61(3):377-92.

  [2]. Hussy P, et al. Effect of 4-quinolones and novobiocin on calf thymus DNA polymerase alpha primase complex, topoisomerases I and II, and growth of mammalian lymphoblasts. Antimicrob Agents Chemother. 1986 Jun;29(6):1073-8.

毒性和生态

CHEMICAL IDENTIFICATION RTECS NUMBER : VB2002000 CHEMICAL NAME : 3-Quinolinecarboxylic acid, 1,4-dihydro-1-ethyl-6-fluoro-7-(4-methyl-1-piperaziny l)-4-oxo- CAS REGISTRY NUMBER : 70458-92-3 BEILSTEIN REFERENCE NO. : 0567618 LAST UPDATED : 199806 DATA ITEMS CITED : 9 MOLECULAR FORMULA : C17-H20-F-N3-O3 MOLECULAR WEIGHT : 333.40 WISWESSER LINE NOTATION : T66 BN VVJ B2 DVQ HF I- AT6N DNTJ D1 HEALTH HAZARD DATA ACUTE TOXICITY DATA TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Human - man DOSE/DURATION : 1714 mg/kg/21W-I TOXIC EFFECTS : Peripheral Nerve and Sensation - paresthesis Peripheral Nerve and Sensation - structural change in nerve or sheath TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Human - man DOSE/DURATION : 343 mg/kg/30D-I TOXIC EFFECTS : Musculoskeletal - joints Musculoskeletal - other changes TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Human - woman DOSE/DURATION : 16 mg/kg TOXIC EFFECTS : Behavioral - hallucinations, distorted perceptions Behavioral - muscle contraction or spasticity 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 : Intravenous SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 225 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value TYPE OF TEST : LD - Lethal dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Mammal - dog DOSE/DURATION : >50 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 7500 mg/kg/30D-C TOXIC EFFECTS : Liver - changes in liver weight Kidney, Ureter, Bladder - other changes in urine composition Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral DOSE : 30 gm/kg SEX/DURATION : male 30 day(s) pre-mating TOXIC EFFECTS : Reproductive - Paternal Effects - testes, epididymis, sperm duct Reproductive - Paternal Effects - prostate, seminal vesicle, Cowper's gland, accessory glands MUTATION DATA TYPE OF TEST : Unscheduled DNA synthesis TEST SYSTEM : Rodent - rat Liver DOSE/DURATION : 780 umol/L REFERENCE : MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 221,263,1989

安全

• 危害码 (欧洲): N
• 风险声明 (欧洲): R51/53:Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment .
• 安全声明 (欧洲): S61
• 危险品运输编码: UN 3082
• RTECS号: WM6250000

合成路线

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制备

1.诺氟沙星为原料，经甲基化而得产品。

2.从诺氟沙星中的中间体硼螯合物开始制备。该硼螫合物、乙腈、N- 甲基哌嗪和三乙胺混合，室温反应后再回流。蒸除溶剂，加水，浓盐酸调至Ph=3后再回流。加入活性炭脱色，过滤。滤液碱化至Ph=11，再加活性炭脱色，过滤，用30%醋酸中和至Ph=6.7-7.2，冰箱中过夜。过滤，水洗，干燥得类白色的培氟沙星，收率82%，熔点270-272℃。培氟沙星溶入无水乙醇中，在60～70℃下滴加甲磺酸，反应。冷至15℃，过滤析出的结晶，用10倍乙醇重结晶，得甲磺酸培氟沙星，收率88.5%。

3.也可硼螯合物、N-甲基哌嗪和三乙胺一起回流。再碱性水解，酸化至Ph=7.2，得培氟沙星；将其加入甲磺酸的水溶液中，反应得到的粗品用85%乙醇重结晶，得甲磺酸培氟沙星，收率79.4%，熔点284℃。