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帕珠沙星

帕珠沙星用途

Pazufloxacin (T-3761)是氟喹诺酮类广谱抗生素。
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帕珠沙星名称

[ CAS 号 ]:
127045-41-4

[ 中文名 ]:
帕珠沙星

[ 英文名 ]:
Pazufloxacin

[中文别名 ]:

[英文别名 ]:

帕珠沙星生物活性

[ 描述 ]:

Pazufloxacin (T-3761)是氟喹诺酮类广谱抗生素。

[ 相关类别 ]:

信号通路 >> 抗感染 >> 细菌
研究领域 >> 感染

[参考文献]

[1]. Fukuoka, Y., et al., In vitro and in vivo antibacterial activities of T-3761, a new quinolone derivative. Antimicrob Agents Chemother, 1993. 37(3): p. 384-92.

[2]. Muratani, T., M. Inoue, and S. Mitsuhashi, In vitro activity of T-3761, a new fluoroquinolone. Antimicrob Agents Chemother, 1992. 36(10): p. 2293-303.


[相关活性小分子]

嘌呤霉素二盐酸盐 | G-418 硫酸盐 | 衣霉素 | 潮霉素B | 盐霉素 | 阿维巴坦钠 | 硫酸新霉素 | 法硼巴坦 | 甲氧西林钠 | 利福平 | 甲硝唑 | 羧苄青霉素钠 | 头孢他啶 | 盐酸依拉环素 | 头孢噻肟钠

帕珠沙星物理化学性质

[ 密度 ]:
1.6±0.1 g/cm3

[ 沸点 ]:
531.5±50.0 °C at 760 mmHg

[ 熔点 ]:
269-271°C

[ 分子式 ]:
C16H15FN2O4

[ 分子量 ]:
318.300

[ 闪点 ]:
275.2±30.1 °C

[ 精确质量 ]:
318.101593

[ PSA ]:
94.55000

[ LogP ]:
0.09

[ 外观性状 ]:
白色至淡,黄色结晶

[ 蒸汽压 ]:
0.0±1.5 mmHg at 25°C

[ 折射率 ]:
1.692

[ 储存条件 ]:
2-8°C

帕珠沙星毒性和生态

CHEMICAL IDENTIFICATION

RTECS NUMBER :
UU8815300
CHEMICAL NAME :
7H-Pyrido(1,2,3-de)-1,4-benzoxazine-6-carboxylic acid, 2,3-dihydro-10-(1-aminocyclopropyl)-9- fluoro-3-methyl-7-oxo-, (S)-
CAS REGISTRY NUMBER :
127045-41-4
LAST UPDATED :
199801
DATA ITEMS CITED :
14
MOLECULAR FORMULA :
C16-H15-F-N2-O4
MOLECULAR WEIGHT :
318.33

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD - Lethal dose
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
REFERENCE :
NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 43(Suppl 2),132,1995
TYPE OF TEST :
LD - Lethal dose
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>5 gm/kg
TOXIC EFFECTS :
Skin and Appendages - dermatitis, other (after systemic exposure)
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: 48,754,1995
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
341 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - dyspnea
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: 48,754,1995
TYPE OF TEST :
LD - Lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>5 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
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: 48,754,1995
TYPE OF TEST :
LD - Lethal dose
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>5 gm/kg
TOXIC EFFECTS :
Skin and Appendages - dermatitis, other (after systemic exposure)
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: 48,754,1995
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
783 mg/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - dyspnea Skin and Appendages - dermatitis, other (after systemic exposure)
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: 48,754,1995
TYPE OF TEST :
LD - Lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
>2 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
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: 48,754,1995
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
400 mg/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Gastrointestinal - nausea or vomiting Nutritional and Gross Metabolic - body temperature decrease
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: 48,754,1995 ** OTHER MULTIPLE DOSE TOXICITY DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
36400 mg/kg/13W-I
TOXIC EFFECTS :
Gastrointestinal - other changes Musculoskeletal - joints
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: 48,790,1995
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
16800 mg/kg/4W-I
TOXIC EFFECTS :
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: 43(Suppl 2),132,1995
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
2730 mg/kg/13W-I
TOXIC EFFECTS :
Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) Musculoskeletal - joints
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: 48,790,1995 ** REPRODUCTIVE DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
125 gm/kg
SEX/DURATION :
male 9 week(s) pre-mating female 2 week(s) pre-mating - 7 day(s) after conception
TOXIC EFFECTS :
Reproductive - Paternal Effects - testes, epididymis, sperm duct Reproductive - Maternal Effects - other effects Reproductive - Specific Developmental Abnormalities - musculoskeletal system
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: 48,832,1995
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
16500 mg/kg
SEX/DURATION :
female 7-17 day(s) after conception
TOXIC EFFECTS :
Reproductive - Maternal Effects - other effects Reproductive - Specific Developmental Abnormalities - musculoskeletal system Reproductive - Specific Developmental Abnormalities - cardiovascular (circulatory) system
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: 48,832,1995
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
39 gm/kg
SEX/DURATION :
female 17-21 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: 48,832,1995
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帕珠沙星安全信息

[ 符号 ]:

GHS07

[ 信号词 ]:
Warning

[ 危害声明 ]:
H302-H312-H332

[ 警示性声明 ]:
P280

[ 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) ]:
R20/21/22

[ 安全声明 (欧洲) ]:
S36/37

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

[ RTECS号 ]:
UU8815300

帕珠沙星制备

1. 2,3,4,5-四氟苯甲酸乙酯与丙二酸二叔丁酯反应,然后与三氟乙酸经脱羧反应得4-羧甲基-2,3,5-三氟苯甲酸乙酯,用二苯基重氮甲烷酯化.在甲醇钠存在下用聚甲醛处理,在侧链的活性亚甲基处生成羟甲基,再处理成亚甲基.和三甲基硫氧碘化物反应后,引入环丙基,选择性水解成4-(1-羰基环丙基)-2,3,5-三氟苯甲酸乙酯.与氯代甲酸乙酯和叠氮化钠反应,然后用苄醇酯化,再选择性水解得4-[1-(苯甲酰基羰氨基)环丙基]-2,3,5-三氟苯甲酸.和乙氧羰基醋酸镁及1,1'-羰基二咪唑反应,使侧链甲酸基转化为甲酰基醋酸乙酯,与N,N-二甲基甲酰胺缩二甲醇和(S)-氨基-1-丙醇缩合后,再环合得2,3-二氢-7H-吡啶并[1,2,3-de][1,4]苯并恶嗪的母环,最后水解、氢化得T-3761的盐酸盐,中和得帕楚沙星.
帕楚沙星(1.00g,3.14mmo1)悬浮于10ml乙醇中,在50℃和搅拌下加入甲磺酸(0.31g,3.22mmo1)，然后冷至室温。过滤收集沉淀,即得1.22g甲磺酸帕楚沙星,收率94%.2. (S)-10-(氰基乙氧羰基甲基)-9-氟-3-甲基-7-氧-2,3-二氢-7H-吡啶[1,2,3-de][1,4]苯并嗪-6-羧酸乙酯的制备
在反应瓶中加入DMSO130ml、氢化钠(60%)6.6g(0.165mol),冰盐浴冷却至0~5ºC,搅拌下滴加氰乙酸乙酯32.3ml(0.303mol),滴毕在同温度下搅拌45min,此时混合液为澄清溶液.再加入左氟羧酸酯化合物左氧氟沙星中间体12.5g(0.040mol),升温至50ºC,在该温度下搅拌反应10~15h.降至室温,加入水500ml,用乙
酸中和至pH4~5,用乙酸乙酯(2×300ml)提取,饱和氯化钠溶液洗,水洗,无水硫酸镁干燥,有机相减压蒸除乙酸乙酯后直接用于下一步反应.

3. (S)-10-乙氰基-9-氟-3-甲基-7-氧-2,3-二氢-7H-吡啶[1,2,3-de][1,4]苯并嗪-6-羧酸的制备

在反应瓶中加入上步(S)-10-(氰基乙氧羰基甲基)-9-氟-3-甲基-7-氧-2,3-二氢-7H-吡啶[1,2,3-de][1,4]苯并嗪-6-羧酸乙酯溶于二氧六环60ml的溶液和水15ml,在室温搅拌30min,后加入对甲苯磺酸(PTS)8.3g(0.041mol),加热回流24~26h.冷却至室温,加水100ml,冷却至0~-1ºC,析出晶体过滤,水洗,乙醚洗,干燥,得类白色结晶10.4g,收率85%,mp230~232ºC.

4. (S)-10-(1-氰基环丙基)-9-氟-3-甲基-7-氧-2,3-二氢-7H-吡啶[1,2,3-de][1,4]苯并噁嗪-6-羧酸的制备
在反应瓶中加入氢氧化钠13.5g(0.34mol)、水32ml,搅拌至氢氧化钠全溶,冰浴降温至0~5ºC,加入溴化三乙基苄基铵4.54g(0.0165mol),室温搅拌30min,加入(S)-10-乙氰基-9-氟-3-甲基-7-氧-2,3-二氢-7H-吡啶[1,2,3-de][1,4]苯并嗪-6-羧酸5g(0.0165mol)和丙酮45ml,室温搅拌20min,加入1,2-二溴乙烷8.4g(0.023mol),升温至40~50ºC搅拌反应3~5h.反应毕,冷却至室温,加水和丙酮混合液(1:1)25ml分出有机层,水层再用丙酮(2×10ml)提取,合并有机层,在冷却到0~5ºC下用浓盐酸调pH至4~5h,析出的结晶过滤,水洗,滤液浓缩,加水析晶,过滤,水洗,合并所得结晶,干燥得(S)-10-(1-氰基环丙基)-9-氟-3-甲基-7-氧-2,3-二氢-7H-吡啶[1,2,3-de][1,4]苯并嗪-6-羧酸4.80g,收率86.%,mp277~280ºC.该品为黄色固体.

5. (S)-10-(1-氨甲酰基环丙基)-9-氟-3-甲基-7-氧-2,3-二氢-7H-吡啶[1,2,3-de][1,4]苯并噁嗪-6-羧酸的制备
在反应瓶中加入氢氧化钠6.1g和水145ml,搅拌溶解,冷却至15ºC,加入(S)-10-(1-氰基环丙基)-9-氟-3-甲基-7-氧-2,3-二氢-7H-吡啶[1,2,3-de][1,4]苯并噁嗪-6-羧酸25g(76mmol),在(15±2)ºC下滴加过氧化氢(30%)16.3ml(0.160mol),控制2h滴完.滴毕,在室温下搅拌30min.加水120ml,在5ºC用浓盐酸调pH至1~2,冷却,过滤,水洗至中性,干燥得(S)-10-(1-氨甲酰基环丙基)-9-氟-3-甲基-7-氧-2,3-二氢-7H-吡啶[1,2,3-de][1,4]苯并噁嗪-6-羧酸15g,收率58%,mp277~279ºC.

6. (S)-10-(1-氨基环丙基)-9-氟-3-甲基-7-氧-2,3-二氢-7H-吡啶[1,2,3-de][1,4]苯并噁嗪-6-羧酸(帕珠沙星)的制备

在反应瓶中加入氢氧化钠15g(0.375mol)和水100ml,搅拌溶解,冷却至5~10ºC滴加有效氯含量11%~12%的次氯酸钠溶液60~65ml,并在该温度下加入(S)-10-(1-氨甲酰基环丙基)-9-氟-3-甲基-7-氧-2,3-二氢-7H-吡啶[1,2,3-de][1,4]苯并噁嗪-6-羧酸10g(0.0288mol),室温搅拌反应15h.在1.5h内升至65~70ºC,搅拌20min,冷却至60ºC,加入活性炭1g,搅拌20min,热过滤,滤液冷至25ºC,滴加浓盐酸调pH5~6,搅拌10min析出固体,过滤,干燥.母液用乙酸乙酯(2×100ml)提取,浓缩,共得(S)-10-(1-氨基环丙基)-9-氟-3-甲基-7-氧-2,3-二氢-7H-吡啶[1,2,3-de][1,4]苯并噁嗪-6-羧酸(帕珠沙星)6.9g,为淡黄色固体,收率75.6%,mp268~269ºC.

7. 甲磺帕珠沙星的合成
在反应瓶中加入(S)-10-(1-氨基环丙基)-9-氟-3-甲基-7-氧-2,3-二氢-7H-吡啶[1,2,3-de][1,4]苯并噁嗪-6-羧酸(帕珠沙星)10g(0.0314mol)和95%乙醇110ml,升温至60~70ºC,滴加甲烷磺酸[3.3g(0.034mol)]的乙醇(40ml),溶液.加毕搅拌反应10min,固体全溶后,加入活性炭0.5g,回流30min,热过滤,冷却#析出结晶过滤,无水乙醇洗,抽干,干燥得甲磺帕珠沙星12g,收率92%,mp257~259ºC(分解),为白色固体.
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帕珠沙星文献

[Pharmacological properties and expected clinical role of an injectable new quinolone antibiotic, pazufloxacin mesilate].

Nippon. Yakurigaku Zasshi. 122(2) , 161-78, (2003)

Pazufloxacin mesilate (PZFX: Pasil INJECTION, Pazucross INJECTION) is a novel injectable quinolone antibiotic that was discovered by Toyama Chemical Co., Ltd. and codeveloped by Toyama Chemical Co. Lt...

Pazufloxacin Toyama Chemical Co.

Curr. Opin. Investig. Drugs 1(1) , 52-7, (2000)

Toyama Chemical Co Ltd is developing pazufloxacin (T-3761), an orally active synthetic quinolone antibiotic, which is awaiting registration following successful clinical trials that demonstrated its p...


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推荐生产厂家/供应商：

公司名：上海创赛科技有限公司

区域：上海市嘉定区

价格：
￥1069.0/100mg ￥2376.0/500mg

联系人：夏言

产品详情：[Perfemiker]Pazufloxacin,98%

公司名：上海阿拉丁生化科技股份有限公司

区域：上海市浦东新区

价格：
￥894.9/25mg ￥1431.9/50mg ￥需询单/1g ￥需询单/1g

联系人：阿拉丁李高志

产品详情：帕珠沙星

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【帕珠沙星】化源网提供帕珠沙星CAS号127045-41-4，帕珠沙星MSDS及其说明、性质、英文名、生产厂家、作用/用途、分子量、密度、沸点、熔点、结构式等。CAS号查询帕珠沙星上化源网，专业又轻松。>>电脑版：帕珠沙星

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