4697-14-7

• 常用中文名：替卡西林二钠
• 常用英文名：Ticarcillin disodium salt
• CAS号：4697-14-7
• 分子式：C₁₅H₁₄N₂Na₂O₆S₂
• 分子量：428.391
• 相关类别： 原料药 抗生素类药物 β-内酰胺酶抑制剂
• 发布时间：2018-09-21 17:49:48
• 更新时间：2024-01-01 20:12:20
• Ticarcillin二钠盐主要用于抗革兰氏阴性菌, 尤其是绿脓杆菌, 也是少数能够治疗嗜麦芽感染的抗生素。

名称

• 中文名: 替卡西林二钠
• 英文名: ticarcillin disodium
• 中文别名: [2S-[2Α,5Α,6Β(S^^)]]-6-[(羧基-3-噻吩乙酰基)氨基]-3,3-二甲基-7-氧代-4-硫-1-氮杂双环[3.2.0]庚烷-2-羧酸二钠盐; 的卡西林; (2S,5R,6R)-6-[[(2R)-羧基-3-噻吩基乙酰]氨基]-3,3-二甲基-7-氧代-4-硫杂-1-氮杂二环[3.2.0]庚烷-2-羧酸二钠盐; 替卡西林; 替卡西林钠
• 英文别名: Ticillin Disodium Salt; Neoanabactyl; CSL Ticillin,Tarcil; Timentin sodium; Ticalpenin; 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[[(2R)-2-carboxy-2-(3-thienyl)acetyl]amino]-3,3-dimethyl-7-oxo-, sodium salt, (2S,5R,6R)- (1:2); Disodium (2S,5R,6R)-6-{[(2R)-2-carboxylato-2-(3-thienyl)acetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate; TIMENTIN; ticarpen; MFCD07787410; Ticarcillin disodium; Disodium Ticarcillin; Aerugipen; Ticarcillin disodium salt; TICAR

物化性质

• 沸点: 768.3ºC at 760 mmHg
• 分子式: C₁₅H₁₄N₂Na₂O₆S₂
• 分子量: 428.391
• 闪点: 418.4ºC
• 精确质量: 428.008881
• PSA: 183.21000
• 外观性状: 结晶粉末
• 储存条件: 2-8°C
• 稳定性:

  水溶液相对稳定；酸性溶液相对不稳定。

• 更多:

  1.性状：乳白色非结晶性粉末，有引湿性。

  2.溶于水：易溶于水

生物活性

• 描述: Ticarcillin二钠盐主要用于抗革兰氏阴性菌, 尤其是绿脓杆菌, 也是少数能够治疗嗜麦芽感染的抗生素。
• 相关类别:
  信号通路 >> 抗感染 >> 细菌
  研究领域 >> 感染

毒性和生态

CHEMICAL IDENTIFICATION RTECS NUMBER : XM9410000 CHEMICAL NAME : 3-Thiophenemalonamic acid, N-(2-carboxy-3,3-dimethyl-7-oxo-4-thia-1-azabicylo(3. 2.0) hept-6-yl)-, disodium salt CAS REGISTRY NUMBER : 4697-14-7 LAST UPDATED : 199707 DATA ITEMS CITED : 18 MOLECULAR FORMULA : C15-H14-N2-O6-S2.2Na MOLECULAR WEIGHT : 428.41 WISWESSER LINE NOTATION : T45 ANV ESTJ GVO CMVYVO&- CT5SJ &-NA- 2 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 : 16 gm/kg TOXIC EFFECTS : Behavioral - somnolence (general depressed activity) Gastrointestinal - hypermotility, diarrhea REFERENCE : KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 12,556,1978 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intraperitoneal SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 7200 mg/kg TOXIC EFFECTS : Behavioral - somnolence (general depressed activity) Gastrointestinal - ulceration or bleeding from stomach Gastrointestinal - ulceration or bleeding from small intestine REFERENCE : KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 12,556,1978 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Subcutaneous SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 10 gm/kg TOXIC EFFECTS : Behavioral - somnolence (general depressed activity) Gastrointestinal - ulceration or bleeding from small intestine REFERENCE : KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 12,556,1978 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 5350 mg/kg TOXIC EFFECTS : Behavioral - somnolence (general depressed activity) Kidney, Ureter, Bladder - other changes REFERENCE : KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 12,556,1978 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : >16 gm/kg TOXIC EFFECTS : Gastrointestinal - ulceration or bleeding from small intestine REFERENCE : KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 12,556,1978 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intraperitoneal SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 7800 mg/kg TOXIC EFFECTS : Behavioral - somnolence (general depressed activity) Gastrointestinal - ulceration or bleeding from small intestine Kidney, Ureter, Bladder - other changes REFERENCE : KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 12,556,1978 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Subcutaneous SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 10700 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 12,556,1978 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 5200 mg/kg TOXIC EFFECTS : Behavioral - somnolence (general depressed activity) REFERENCE : KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 12,556,1978 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Subcutaneous SPECIES OBSERVED : Mammal - dog DOSE/DURATION : 7 gm/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 12,556,1978 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Mammal - dog DOSE/DURATION : >4 gm/kg TOXIC EFFECTS : Behavioral - somnolence (general depressed activity) Gastrointestinal - nausea or vomiting REFERENCE : KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 12,556,1978 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Subcutaneous SPECIES OBSERVED : Rodent - rabbit DOSE/DURATION : >11 gm/kg TOXIC EFFECTS : Gastrointestinal - ulceration or bleeding from stomach REFERENCE : KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 12,556,1978 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Rodent - rabbit DOSE/DURATION : >8 gm/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 12,556,1978 ** OTHER MULTIPLE DOSE TOXICITY DATA ** TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intraperitoneal SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 60 gm/kg/30D-C TOXIC EFFECTS : Liver - changes in liver weight Endocrine - changes in thymus weight Blood - changes in leukocyte (WBC) count REFERENCE : KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 12,556,1978 TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Subcutaneous SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 26 gm/kg/30D-I TOXIC EFFECTS : Endocrine - changes in spleen weight Endocrine - changes in thymus weight Blood - normocytic anemia REFERENCE : KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 12,556,1978 TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Subcutaneous SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 91 gm/kg/26W-C TOXIC EFFECTS : Endocrine - changes in adrenal weight Endocrine - changes in thymus weight Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) REFERENCE : KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 12,556,1978 ** REPRODUCTIVE DATA ** TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Subcutaneous DOSE : 5500 mg/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 REFERENCE : KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 12,556,1978 TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intravenous DOSE : 5500 mg/kg SEX/DURATION : female 7-17 day(s) after conception TOXIC EFFECTS : Reproductive - Specific Developmental Abnormalities - musculoskeletal system REFERENCE : KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 12,556,1978 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X2885 No. of Facilities: 535 (estimated) No. of Industries: 2 No. of Occupations: 9 No. of Employees: 14268 (estimated) No. of Female Employees: 10723 (estimated)

安全

• 符号: GHS07, GHS08
• 信号词: Danger
• 危害声明: H315-H319-H334-H335
• 警示性声明: P261-P305 + P351 + P338-P342 + P311
• 个人防护装备: dust mask type N95 (US);Eyeshields;Faceshields;Gloves
• 危害码 (欧洲): Xi:Irritant;
• 风险声明 (欧洲): R36/37/38;R42;R43
• 安全声明 (欧洲): S26-S36/37
• 危险品运输编码: NONH for all modes of transport
• WGK德国: 2
• RTECS号: XM9410000

制备

方法1:1.38g(5mmol)(噻吩-3-基)丙二酸单苄酯(Ⅰ)和2.5ml二氯亚砜，在50~55℃下加热1h，再在60~65℃下加热10min。在减压和低于30℃下，除去过剩的二氯亚砜，最后可以加入1ml苯，在高真空下利用共沸去除痕量的二氯亚砜，剩下的是黄色油状的(噻吩-3-基)丙二酸单苄酯酰氯(Ⅱ)。把该酰氯9Ⅱ)溶于10ml干燥丙酮，在搅拌和蒸汽浴上，加入1.08g(55mmol)6-APA、15ml1mol/L碳酸氢钠和5ml丙酮的混合溶液。当反应开始进行后，将反应液在室温下继续搅拌45min。反应液用乙醚(3×25ml)洗后，再用约11ml1mol/L盐酸酸化至PH＝2，然后用乙醚(3×15ml)萃取该酸性水溶液。萃取液用活性炭和硫酸镁一起脱色5min。过滤，摇晃淡黄色的滤液和约4ml1mol/L碳酸氢钠，得到PH值为7~7.5的水
溶性萃取液。该水溶性萃取液在低温低压浓缩后，剩余物加入异丙醇一起搅拌，直到混合物中含10％水为止。此时开始结晶，在0℃下放置过夜使结晶完全。得白色结晶的α-(苄氧羰基)-3-噻吩甲基青霉素钠(Ⅲ)，收率50％。

10.65g5％载于碳酸钙的钯催化剂悬浮于32ml水中，预先氢化1h，然后加入2.13g(4.3mmol)上面得到的钠盐(Ⅲ)溶于30ml水的溶液，在略高于大气压的压力下氢化1.5h。用装有Dicalite(一种硅藻土)的装置进行过滤。澄清的滤液在低温低压下浓缩，剩余物在五氧化二磷存在下真空燥，得白色固体的替卡西林钠。

方法2:2-噻吩-2-苄氧羰基乙酰氯(Ⅱ)对6-APA的苄酯进行酰化，得到化合物(Ⅳ)，再氢解脱去两个苄基保护基，然后用碳酸氢钠中和即可得到替卡西林钠。