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盐酸洛美沙星

盐酸洛美沙星用途

Lomefloxacin盐酸盐是氟喹诺酮类抗生素。

盐酸洛美沙星名称

[ CAS 号 ]:
98079-52-8

[ 中文名 ]:
盐酸洛美沙星

[ 英文名 ]:
Lomefloxacin hydrochloride

[中文别名 ]:

[英文别名 ]:

MFCD00214312
Lomefloxacin hydrochloride
Lomefloxacin (hydrochloride)

盐酸洛美沙星生物活性

[ 描述 ]:

Lomefloxacin盐酸盐是氟喹诺酮类抗生素。

[ 相关类别 ]:

信号通路 >> 抗感染 >> 细菌

研究领域 >> 感染

[参考文献]

[1]. http://www.drugbank.ca/drugs/DB00978

[相关活性小分子]

盐酸洛美沙星物理化学性质

[ 沸点 ]:
542.7ºC at 760 mmHg

[ 熔点 ]:
290-3000C

[ 分子式 ]:
C₁₇H₂₀ClF₂N₃O₃

[ 分子量 ]:
387.809

[ 闪点 ]:
282ºC

[ 精确质量 ]:
387.116119

[ PSA ]:
74.57000

[ LogP ]:
2.99170

[ 外观性状 ]:
白色粉末

[ 储存条件 ]:
−20°C

盐酸洛美沙星MSDS

详细MSDS(安全技术说明书)

盐酸洛美沙星毒性和生态

CHEMICAL IDENTIFICATION

RTECS NUMBER :: VB1997500

CHEMICAL NAME :: 3-Quinolinecarboxylic acid, 1,4-dihydro-6,8-difluoro-1-ethyl-7-(3-methyl-1-pipera zinyl)-4- oxo-, monohydrochloride

CAS REGISTRY NUMBER :: 98079-52-8

LAST UPDATED :: 199607

DATA ITEMS CITED :: 13

MOLECULAR FORMULA :: C17-H19-F2-N3-O3.Cl-H

MOLECULAR WEIGHT :: 387.85

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 :: 1556 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Behavioral - changes in motor activity (specific assay) Lungs, Thorax, or Respiration - respiratory depression

REFERENCE :: NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 36(Suppl 2),338,1988

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1637 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Behavioral - changes in motor activity (specific assay) Lungs, Thorax, or Respiration - respiratory depression

REFERENCE :: NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 36(Suppl 2),338,1988

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 328 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Behavioral - changes in motor activity (specific assay) Lungs, Thorax, or Respiration - respiratory depression

REFERENCE :: NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 36(Suppl 2),338,1988

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1608 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Behavioral - changes in motor activity (specific assay) Lungs, Thorax, or Respiration - respiratory depression

REFERENCE :: NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 36(Suppl 2),338,1988

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 995 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: ZKZAEY Zhongguo Kangshengsu Zazhi. Chinese Journal of Antibiotics. (Zhongguo Kangshengsu Zazhi Bianjibu, 9 Shanbanqiaolu, Chenqdu, 610051 Peop. Rep. China) V.13- 1988- Volume(issue)/page/year: 19,154,1994

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 253 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Behavioral - changes in motor activity (specific assay) Lungs, Thorax, or Respiration - respiratory depression

REFERENCE :: NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 36(Suppl 2),338,1988 ** OTHER MULTIPLE DOSE TOXICITY DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 27300 mg/kg/13W-I

TOXIC EFFECTS :: Gastrointestinal - other changes Kidney, Ureter, Bladder - other changes in urine composition Liver - other changes

REFERENCE :: NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 36(Suppl 2),343,1988

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Primate - monkey

DOSE/DURATION :: 36500 mg/kg/52W-I

TOXIC EFFECTS :: Gastrointestinal - nausea or vomiting Blood - changes in platelet count Nutritional and Gross Metabolic - changes in sodium

REFERENCE :: JZKEDZ Jitchuken Zenrinsho Kenkyuho. Central Institute for Experimental Animals, Research Reports. (Jikken Dobutsu Chuo Kenkyusho, 1433 Nogawa, Takatsu-ku, Kawasaki 211, Japan) V.1- 1975- Volume(issue)/page/year: 14,23,1988

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 2800 mg/kg/2W-I

TOXIC EFFECTS :: Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) Nutritional and Gross Metabolic - weight loss or decreased weight gain Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - phosphatases

REFERENCE :: NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 36(Suppl 2),391,1988

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 1400 mg/kg/7D-I

TOXIC EFFECTS :: Behavioral - food intake (animal) Nutritional and Gross Metabolic - weight loss or decreased weight gain

REFERENCE :: NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 36(Suppl 2),449,1988 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 3300 mg/kg

SEX/DURATION :: female 7-17 day(s) after conception

TOXIC EFFECTS :: Reproductive - Maternal Effects - other effects Reproductive - Effects on Embryo or Fetus - extra-embryonic structures (e.g., placenta, umbilical cord) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)

REFERENCE :: JJANAX Japanese Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo 141, Japan) V.21- 1968- Volume(issue)/page/year: 41,1352,1988

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 8100 mg/kg

SEX/DURATION :: female 17-22 day(s) after conception lactating female 21 day(s) post-birth

TOXIC EFFECTS :: Reproductive - Maternal Effects - parturition Reproductive - Maternal Effects - other effects

REFERENCE :: JJANAX Japanese Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo 141, Japan) V.21- 1968- Volume(issue)/page/year: 41,1370,1988

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 650 mg/kg

SEX/DURATION :: female 6-18 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - extra-embryonic structures (e.g., placenta, umbilical cord) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Specific Developmental Abnormalities - musculoskeletal system

REFERENCE :: NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 36(Suppl 2),391,1988

盐酸洛美沙星安全信息

[ 符号 ]:

GHS07

[ 信号词 ]:
Warning

[ 危害声明 ]:
H302

[ 个人防护装备 ]:
dust mask type N95 (US);Eyeshields;Gloves

[ 危害码 (欧洲) ]:
Xn:Harmful;

[ 风险声明 (欧洲) ]:
R22

[ 危险品运输编码 ]:
NONH for all modes of transport

[ WGK德国 ]:
3

[ RTECS号 ]:
VB1997500

[ 海关编码 ]:
2933990090

盐酸洛美沙星制备

(1).6,7,8-三氟-1-(2-氟乙基)-1,4二氢-4-氧代-3-喹啉酸乙酯的制备

在反应瓶中加入6,7,8-三氟-1,4-二氢-4-氧代-3-喹啉羧酸乙酯60g(0.22mol)、无水碳酸钾50g(0.36mol)、碘化钾18g(0.11mol)和DMF240ml,搅拌

加热至90 ºC,滴加1-溴-2-氟乙烷42g(0.33mol),滴毕,保温搅拌反应10h.减压回收DMF,冷至室温,入水适量,过滤,滤饼用水洗,乙醇洗,得类白色固体64.5g,收率92.5%,mp182~184 ºC.

(2).6,8- 二氟-1-(2-氟乙基)-1,4-二氢-7-(4-甲基-1-哌嗪基)-4-氧代-3-喹啉羧酸乙酯的制备

在反应瓶中加入6,7,8-三氟-1-(2-氟乙基)-1,4二氢-4-氧代-3-喹啉酸乙酯64g(0.2mol)和N-甲基哌嗪160g(1.6mol),搅拌加热至110 ºC,搅拌反应6h.减压回收N-甲基哌嗪(约110g),冷却,加适量水稀释,析出固体过滤,水洗滤饼,得类白色固体6,8- 二氟-1-(2-氟乙基)-1,4-二氢-7-(4-甲基-1-哌嗪基)-4-氧代-3-喹啉羧酸乙酯 70.5g,收率88.8%,mp155~159 ºC.(该步反应中加适量K2CO3对反应有促反应完全作用.)

(3).盐酸氟罗沙星的合成

在反应瓶中加入6,8- 二氟-1-(2-氟乙基)-1,4-二氢-7-(4-甲基-1-哌嗪基)-4-氧代-3-喹啉羧酸乙酯60g(0.15mol)与3% NaOH溶液600ml,搅拌加热至85 ºC,保温搅拌反应1h.过滤,滤液用乙酸调至PH7.2,降温,过滤,滤饼依次用适量水、乙醇洗，干燥得白色固体 45.5g,收率82.2%.

取36.9g(0.1mol)、370ml乙醇,搅拌混合,加入18%盐酸水溶液,加热回流4h.冷却析晶,过滤,滤液依次用冷乙醇洗,乙醚洗,抽干,用水重结晶得6,8- 二氟-1-(2-氟乙基)-1,4-二氢-7-(4-甲基-1-哌嗪基)-4-氧代-3-喹啉羧酸乙酯 38.0g,收率93.6%，mp269~271 ºC.

4. 2,3,4-三氟苯胺的制备
首先介绍镍催化剂的制备.在100ml烧杯中加入100gNaOH和水400ml,搅拌溶解,冷至室温,向其中分批加入200目的镍铝合金粉75g,加时有H2放出.加完后,将其在水浴加热煮沸4h.用倾泻法水洗至中性(800ml×4).再加入100ml10%NaOH水溶液,水浴加热煮沸2h.水洗至中性(800ml×4).再用乙醇(100ml×3)洗涤,并用200ml乙醇将其制得的活性镍催化剂覆盖,以防与空气接触.

在加氢高压釜中加入2,3,4-三氟硝基苯177g、乙醇500ml及上述制备的Raney Ni催化剂一批量.用N2置换釜中空气3次,用H2置换釜中N2气2次,充入H2,维持H2压力0.1~0.2MPa,于常温搅拌反应6h.过滤,滤液蒸除乙醇,剩余物减压蒸馏,收集84~86ºC/0.09MPa馏分(或92/2.67kPa馏分),得2,3,4-三氟苯胺142g,收率96%.

5. 6,7,8-三氟-4-羟基喹啉-3-羧酸乙酯的制备

在反应瓶中加入上步制备的化合物2,3,4-三氟苯胺1.47g(0.01mol) 和乙氧基亚甲基丙二酸二乙酯2.16g(0.01mol). 搅拌加热至40~50 ºC, 在该温度下搅拌反应2h. 蒸去反应生成的乙醇,加入二苯乙烷18ml, 升温至220~240 ºC, 在该温度下搅拌反应2h. 冷却,过滤, 滤饼用石油醚洗涤,得6,7,8-三氟-4-羟基喹啉-3-羧酸乙酯2.71g, 收率88.3%,无需进一步纯化,直接用于下步反应.

6. 1-乙基-6,7,8-三氟-1,4-二氢-4-氧代喹啉-3-羧酸乙酯的制备

在反应瓶中加入上步制备的化合物6,7,8-三氟-4-羟基喹啉-3-羧酸乙酯1.355g(5mmol)、DMF15ml和K2CO31.38g(10mmol), 搅拌下于室温慢慢滴加溴乙烷0.82g(7.5mmol), 滴毕, 然后于50~60 ºC搅拌反应4h. 冷却至室温,过滤, 滤液浓缩回收DMF, 析出固体,用二氯乙烷重结晶, 得1-乙基-6,7,8-三氟-1,4-二氢-4-氧代喹啉-3-羧酸乙酯3.45g, 收率90.3%,mp:197~200 ºC.

7. 1-乙基-6,7,8-三氟-1,4-二氢-4-氧代喹啉-3-羧酸根·二乙酸根合硼的制备

在反应瓶中加入硼酸0.37g(5.98mmol) 和乙酸酐2ml(8.98mmol), 搅拌混合,于室温搅拌反应3h. 再升温至110 ºC, 在110 ºC搅拌回流1h. 冷却.加入上步制备的化合物1-乙基-6,7,8-三氟-1,4-二氢-4-氧代喹啉-3-羧酸乙酯1.2g(4mmol), 升温至90 ºC, 在该温度搅拌反应2h. 加水6ml, 搅拌片刻. 过滤,滤饼用水洗涤,抽干,得1.45g, 收率90.6%,mp:209~211 ºC (分解).

8. 1-乙基-6,8-二氟-7-(8-甲基-1-哌嗪基)-1,4-二氢-4-氧代喹啉-3-羧酸根·二乙酸根合硼的制备

在反应瓶中加入上步制备的化合物1-乙基-6,7,8-三氟-1,4-二氢-4-氧代喹啉-3-羧酸根·二乙酸根合硼0.4g(1mmol)、三乙胺2ml(1.45g,14.33mmol) 和2-甲基哌嗪0.12g(1.2mmol), 搅拌混合,于室温反应4h. 减压蒸除三乙胺,剩余物加入乙醇适量,将析出固体过滤,得0.394g, 收率82.1%,mp 221.2~224 ºC.

9. 1-乙基-6,8-二氟-7-(3-甲基-1-哌嗪基)-1,4-二氢-4-氧代喹啉-3-羧酸(洛美沙星)的制备

在反应瓶中加入上步制备的化合物1-乙基-6,8-二氟-7-(8-甲基-1-哌嗪基)-1,4-二氢-4-氧代喹啉-3-羧酸根·二乙酸根合硼0.479g(1mmol)、95%乙醇2.4ml和三乙胺0.1g(0.9mmol), 搅拌回流1h. 冷却,析出固体,过滤, 用少许乙醇洗涤滤饼,抽干,得白色粉状结晶1-乙基-6,8-二氟-7-(3-甲基-1-哌嗪基)-1,4-二氢-4-氧代喹啉-3-羧酸(洛美沙星)0.31g, 收率87.5%,将其用DMF重结晶,得无色针状结晶,mp 241~241.9 ºC.

10 1-乙基-6,8-二氟-7-(3-甲基-1-哌嗪基)-1,4-二氢-4-氧代喹啉-3-羧酸盐酸盐(盐酸洛美沙星)的合成

在反应瓶中加入洛美沙星游离酸1-乙基-6,8-二氟-7-(3-甲基-1-哌嗪基)-1,4-二氢-4-氧代喹啉-3-羧酸(洛美沙星)0.55g、乙醇5.5ml, 搅拌混合后加入18%盐酸水溶液,调至pH3左右,加热搅拌回流4h. 冷却#析出固体,过滤,滤饼依次用乙醇、乙醚洗涤,抽干后用水重结晶,得1-乙基-6,8-二氟-7-(3-甲基-1-哌嗪基)-1,4-二氢-4-氧代喹啉-3-羧酸盐酸盐(盐酸洛美沙星)0.43g, 收率约71%,mp296~300 ºC(分解).

盐酸洛美沙星海关

[ 海关编码 ]: 2933990090

[ 中文概述 ]:
2933990090. 其他仅含氮杂原子的杂环化合物. 增值税率:17.0%. 退税率:13.0%. 监管条件:无. 最惠国关税:6.5%. 普通关税:20.0%

[ 申报要素 ]: 品名, 成分含量, 用途, 乌洛托品请注明外观, 6－己内酰胺请注明外观, 签约日期

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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