氟哌酸

氟哌酸用途

用途一：具有广谱高效的抗菌作用，治疗范围广，口服吸收好，毒性低，临床上主要用于尿路感染、胆道感染、肠道感染的治疗，疗效显著。
用途二：氟哌酸昌日本杏林公司1978年开发的第三代喹诺酮类抗菌剂。具有抗菌谱广、抗菌力强的特点。对大肠杆菌、肺炎干菌、产气杆菌、阴沟杆菌、变形杆菌、沙门氏菌属、志贺氏菌属、枸橼酸杆菌属及沙雷氏菌属等遥植树菌科细菌具有强大的抗菌作用。临庆用于敏感菌所致泌尿系统、肠道、乎吸系统、外科、妇科、五官科及皮肤科等感受染性疾病。还应用于治疗淋病。
用途三：抗菌药，用于治疗上呼吸道感染，泌尿系统、胃肠道系统细菌感染，对胆道、外科、妇产科等感染亦有较好疗效

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氟哌酸名称

[ CAS 号 ]:
70458-96-7

[ 中文名 ]:
氟哌酸

[ 英文名 ]:
Norfloxacin

[中文别名 ]:

诺氟沙星

[英文别名 ]:

Zomxin
Fulgram
Barazan
NORFLOXACINE
CHIBROXIN
Noflo
Utinor
EINECS 274-614-4
Nolicin
Sebercim

氟哌酸生物活性

[ 描述 ]:

Norfloxacin是广谱抗生素,能通过结合DNA旋转酶抑制革兰氏阳性和阴性菌。

[ 相关类别 ]:

信号通路 >> 抗感染 >> 细菌

研究领域 >> 感染

[参考文献]

[1]. Nelson JM, et al. Fluoroquinolone-resistant Campylobacter species and the withdrawal of fluoroquinolones from use in poultry: a public health success story. Clin Infect Dis. 2007 Apr 1;44(7):977-80. Epub 2007 Feb 14.

[2]. Pade?skaia EN. Norfloxacin: more than 20 years of clinical use, the results and place among fluoroquinolones in modern chemotherapy for infections. Antibiot Khimioter. 2003;48(9):28-36.

[3]. Rafalsky V, et al. Quinolones for uncomplicated acute cystitis in women. Cochrane Database Syst Rev. 2006 Jul 19;(3):CD003597.

[相关活性小分子]

氟哌酸物理化学性质

[ 密度 ]:
1.3±0.1 g/cm3

[ 沸点 ]:
555.8±50.0 °C at 760 mmHg

[ 熔点 ]:
220°C

[ 分子式 ]:
C₁₆H₁₈FN₃O₃

[ 分子量 ]:
319.331

[ 闪点 ]:
289.9±30.1 °C

[ 精确质量 ]:
319.133209

[ PSA ]:
74.57000

[ LogP ]:
0.82

[ 外观性状 ]:
灰白色至淡黄色结晶粉末

[ 蒸汽压 ]:
0.0±1.6 mmHg at 25°C

[ 折射率 ]:
1.595

[ 储存条件 ]:
通风低温干燥

氟哌酸MSDS

详细MSDS(安全技术说明书)

氟哌酸毒性和生态

CHEMICAL IDENTIFICATION

RTECS NUMBER :: VB2005000

CHEMICAL NAME :: 3-Quinolinecarboxylic acid, 1,4-dihydro-1-ethyl-6-fluoro-4-oxo-7-(1-piperazinyl)-

CAS REGISTRY NUMBER :: 70458-96-7

BEILSTEIN REFERENCE NO. :: 0567897

LAST UPDATED :: 199612

DATA ITEMS CITED :: 33

MOLECULAR FORMULA :: C16-H18-F-N3-O3

MOLECULAR WEIGHT :: 319.37

WISWESSER LINE NOTATION :: T66 BN EVJ B2 DVQ HF I- DT6M DNTJ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 94 mg/kg/13D-I

TOXIC EFFECTS :: Musculoskeletal - other changes

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 48 mg/kg/2D-I

TOXIC EFFECTS :: Liver - hepatitis (hepatocellular necrosis), zonal Behavioral - muscle weakness Musculoskeletal - joints

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

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 :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >1500 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 - rat

DOSE/DURATION :: 245 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - convulsions or effect on seizure threshold

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

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >500 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - other changes

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 :: 1064 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 :: >1500 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 :: 220 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - convulsions or effect on seizure threshold

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

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 470 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity)

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - species unspecified

DOSE/DURATION :: >4 gm/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 :: 1400 mg/kg/2W-I

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - retinal changes (pigmentary depositions, retinitis, other)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 9 gm/kg/30D-I

TOXIC EFFECTS :: Musculoskeletal - joints

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 1375 mg/kg

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

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - musculoskeletal system Reproductive - Effects on Newborn - behavioral

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 2750 mg/kg

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

TOXIC EFFECTS :: Reproductive - Effects on Newborn - weaning or lactation index (e.g., # alive at weaning per # alive at day 4)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 20 gm/kg

SEX/DURATION :: male 61 day(s) pre-mating female 15 day(s) pre-mating - 6 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

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 10 gm/kg

SEX/DURATION :: male 61 day(s) pre-mating female 15 day(s) pre-mating - 6 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - extra-embryonic structures (e.g., placenta, umbilical cord)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 1250 mg/kg

SEX/DURATION :: female 6-15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Newborn - behavioral

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 2 gm/kg

SEX/DURATION :: female 10-20 day(s) after conception

TOXIC EFFECTS :: Reproductive - Maternal Effects - other effects Endocrine - estrogenic 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 :: Unreported

DOSE :: 4650 mg/kg

SEX/DURATION :: female 20-50 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetal death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 1625 mg/kg

SEX/DURATION :: female 13 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Maternal Effects - ovaries, fallopian tubes Reproductive - Maternal Effects - uterus, cervix, vagina

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 1300 mg/kg

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

TOXIC EFFECTS :: 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 :: 1300 mg/kg

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

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 1300 mg/kg

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

TOXIC EFFECTS :: Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Effects on Embryo or Fetus - fetal death

TYPE OF TEST :: Micronucleus test

MUTATION DATA

TYPE OF TEST :: Unscheduled DNA synthesis

TEST SYSTEM :: Rodent - rat Liver

DOSE/DURATION :: 310 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

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氟哌酸安全信息

[ 个人防护装备 ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ 危害码 (欧洲) ]:
Xn: Harmful;

[ 风险声明 (欧洲) ]:
R20/21/22

[ 安全声明 (欧洲) ]:
26-37/39

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

[ WGK德国 ]:
2

[ RTECS号 ]:
VB2005000

[ 海关编码 ]:
2933990090

氟哌酸合成路线

详细合成路线

氟哌酸上下游产品

氟哌酸上游产品

氟哌酸下游产品

氟哌酸制备

邻二氯苯经硝化，或对硝基氯苯经氯化均可得3，4-二氯硝基苯。再在二甲亚砜中，和氟化钾回流，氟化得3-氯-4-氟硝基苯。在盐酸或乙酸水溶液存在下，用铁粉还原成3-氯-4-氟苯胺。接着和原甲酸三乙酯及丙二酸二乙酯(生成乙氧基亚甲基丙二酸二乙酯)在硝酸铵存在下回流，得缩合产物。在液体石蜡或二苯醚中加热环合，生成7-氯-6-氟-4-羟基喹啉-3-羧酸乙酯。进行乙基化后，再水解得乙基化产物。最后与哌嗪缩合得诺氟沙星。其工艺比较成熟，收率较高，一般能达到40%～65%，但7位引入哌嗪基时，6位氟原子被取代的副产物可占25%，分离困难，影响收率。以对硝基氯苯计总收率为8%以上。

在引入吡嗪环前，1-乙基-6-氟-7-氯-1，4-二氢-4-氧代喹啉-8-羧酸乙酯先和氟硼酸或三氟化硼-乙醚或乙酸硼反应，使4位上的羰基形成硼螯合物，然后再引入吡嗪基，可使7位氟被置换的副反应减少，收率可提高15%以上，且产品的质量改善。

诺氟沙星的合成，国内外研究较多，但真正用于工业生产的却不多。其合成路线的改进主要体现在两个方面。一是对成环工艺进行改进，二是在哌嗪基的引入上做些文章。

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氟哌酸海关

[ 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%

氟哌酸文献

Phenotypic heterogeneity enables uropathogenic Escherichia coli to evade killing by antibiotics and serum complement.

Infect. Immun. 83(3) , 1056-67, (2015)

Uropathogenic strains of Escherichia coli (UPEC) are the major cause of bacteremic urinary tract infections. Survival in the bloodstream is associated with different mechanisms that help to resist ser...

Genotypes and oxacillin resistance of Staphylococcus aureus from chicken and chicken meat in Poland.

Poult. Sci. 93(12) , 3179-86, (2014)

The genotypes and oxacillin resistance of 263 Staphylococcus aureus isolates cultured from chicken cloacae (n = 138) and chicken meat (n = 125) was analyzed. Fifteen spa types were determined in the s...

Efflux-related resistance to norfloxacin, dyes, and biocides in bloodstream isolates of Staphylococcus aureus.

Antimicrob. Agents Chemother. 51 , 3235-9, (2007)

Efflux is an important resistance mechanism in Staphylococcus aureus, but its frequency in patients with bacteremia is unknown. Nonreplicate bloodstream isolates were collected over an 8-month period,...

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氟哌酸相关知识

[诺氟沙星胶囊] - 说明书 - 作用 - 诺氟沙星副作用

2018-12-15 18:28:34

诺氟沙星（Norfloxacin，又名Noroxin、Fulgram），别名：力醇罗、氟哌酸、淋克星。其化学名为1-乙基-6-氟-1,4-二氢-4-氧代-7-(1-哌嗪基)-3-喹啉羧酸。本品为第二代喹诺酮类抗菌药，会阻碍消化道内致病细菌的DNA旋转酶（DNA Gyrase）的作用，阻碍细菌DNA...

诺氟沙星含量测定和制剂方法

2022-04-17 19:50:01

诺氟沙星（Norfloxacin，又名Noroxin、Fulgram），别名：力醇罗、氟哌酸、淋克星。其化学名为1-乙基-6-氟-1,4-二氢-4-氧代-7-(1-哌嗪基)-3-喹啉羧酸。本品为第三代喹诺酮类抗菌药，会阻碍消化道内致病细菌的DNA旋转酶（DNAGyrase）的作用，阻碍细菌DNA复...

氟哌酸

氟哌酸用途

氟哌酸名称

氟哌酸生物活性

氟哌酸物理化学性质

氟哌酸MSDS

详细MSDS(安全技术说明书)

氟哌酸毒性和生态

CHEMICAL IDENTIFICATION

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

MUTATION DATA

氟哌酸安全信息

氟哌酸合成路线

详细合成路线

氟哌酸上下游产品

氟哌酸上游产品

氟哌酸下游产品

氟哌酸制备

氟哌酸海关

氟哌酸文献

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