4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[[2-carboxy-2-(3-thienyl)acetyl]amino]-3,3-dimethyl-7-oxo-, sodium salt (1:2), (2S,5R,6R)- (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
CAS 4697-14-7 MFCD07787410
化学结构图
SMILES: CC1(C)S[C@@H]2[C@H](NC(=O)C(C(=O)[O-])c3ccsc3)C(=O)N2[C@@H]1C(=O)[O-].[Na+].[Na+]
化学属性
| Mol. Formula | C15 |
|---|---|
| Mol. Weight | 428 |
| Appearance | 乳白色非结晶性粉末，有引湿性。易溶于水(＞100g/100m1)，得到的澄清溶液的Ph值为6.0～8.0。水溶液相对稳定；酸性溶液相对不稳定。 |
| pH | :A |
别名和识别编码
| Chemical Name | 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[[2-carboxy-2-(3-thienyl)acetyl]amino]-3,3-dimethyl-7-oxo-, sodium salt (1:2), (2S,5R,6R)- |
|---|---|
| MDL Number | MFCD00864998 |
| CAS Number | 4697-14-7 |
| Synonym | (2S,5R,6R)-6-[[(2R)-CARBOXY-3-THIENYLACETYL]AMINO]-3,3-DIMETHYL-7-OXO-4-THIA-1-AZABICYCLO[3.2.0]HEPTANE-2-CARBOXYLIC ACID DISODIUM SALT (2S,5R,6R)-6-[[(2R)-Carboxy-3-thienylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid disodium salt (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 (2S,5S,6R)-6-[[(2R)-CARBOXY-3-THIENYLACETYL]AMINO]-3,3-DIMETHYL-7-OXO-4-THIA-1-AZABICYCLO[3,2,0]HEPT (2s,5r,6r)-6-[[(2r)-carboxy-3-thienylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid disodium salt 3-thiophenemalonamicacid,n-(2-carboxy-3,3-dimethyl-7-oxo-4-thia-1-azabicylo(3 Aerugipen BRL 2288 BRL-2288 BRL2288 CSL Ticillin , Tarcil Disodium, Ticarcillin Neoanabactyl SmithKline Beecham Sodium Ticarcillin |
| PubChem Substance ID | 470375 |
| Chemical Name Translation | (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 |
| Merck Number | 13,9505 |
| Wiswesser Line Notation | T45 ANV ESTJ GVO CMVYVO&- CT5SJ &-NA- 2 |
| InChIKey | ZBBCUBMBMZNEME-UBXQQCHXSA-L |
| LabNetwork Molecule ID | LN01312872 |
| InChI | InChI=1S/C15H16N2O6S2.2Na/c1-15(2)9(14(22)23)17-11(19)8(12(17)25-15)16-10(18)7(13(20)21)6-3-4-24-5-6;;/h3-5,7-9,12H,1-2H3,(H,16,18)(H,20,21)(H,22,23);;/q;2*+1/p-2/t7-,8-,9+,12-;;/m1../s1 |
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分类
- {SNA} Antibacterial, Antibiotics, Antibiotics A to Z, Antibiotics T-Z, Antibiotics by Application, Biochemicals and Reagents, Chemical Structure Class, Genetic Marker Selection, Interferes with Cell Wall Synthesis, L - Z, Mechanism of Action, Penicillins and Cephalosporins (beta-Lact
- {SNA} Antibacterial, Antibiotics, Antibiotics A to Z, Antibiotics T-Z, Antibiotics by Application, Chemical Structure Class, Genetic Marker Selection, Interferes with Cell Wall Synthesis, L - Z, Mechanism of Action, Penicillins and Cephalosporins (beta-Lactams), Spectrum of Activity
- {SNA} Antibacterial,
安全信息
GHS Symbol
- P261 Avoid breathing dust/fume/gas/mist/vapours/spray. 避免吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
- P264 Wash hands thoroughly after handling. 处理后要彻底洗净双手。
- P271 Use only outdoors or in a well-ventilated area.? 只能在室外或通风良好的地方使用。
- P272 Contaminated work clothing should not be allowed out of the workplace. 污染的工作服不得带出工作场所。
- P280 Wear protective gloves/protective clothing/eye protection/face protection. 戴防护手套/防护服/眼睛的保护物/面部保护物。
- P285 In case of inadequate ventilation wear respiratory protection. 在通风不足的情况下，戴呼吸防护。
- P302+P352
- P304+P340
- P304+P341
- P305+P351+P338
- P312 Call a POISON CENTER or doctor/physician if you feel unwell. 如果你感觉不适，呼叫解毒中心或医生/医师。
- P321 Specific treatment (see … on this label). 具体治疗（见本标签上的）。
- P332+P313
- P333+P313
- P337+P313
- P342+P311
- P362 Take off contaminated clothing and wash before reuse. 脱掉污染的衣服，清洗后方可重新使用
- P363 Wash contaminated clothing before reuse. 被污染的衣服洗净后方可重新使用。
- P403+P233
- P405 Store locked up. 上锁保管。
- P501 Dispose of contents/container to..… 处理内容物/容器.....
- H315 Causes skin irritation 会刺激皮肤
- H317 May cause an allergic skin reaction 可能导致皮肤过敏
- H319 Causes serious eye irritation 严重刺激眼睛
- H334 May cause allergy or asthma symptoms or breathing difficulties if inhaled 吸入可能导致过敏或哮喘症状或呼吸困难
- H335 May cause respiratory irritation 可能导致呼吸道刺激
- S26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 眼睛接触后，立即用大量水冲洗并征求医生意见；
- S36/37 Wear suitable protective clothing and gloves 穿戴适当的防护服和手套；
- R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性
- R43 May cause sensitisation by skin contact 皮肤接触会产生过敏反应
- R42 May cause sensitisation by inhalation 吸入会产生过敏反应
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 sma
TYPE OF TEST :
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 : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Rodent - rat 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
TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Subcutaneous SPECIES OBSERVED : Rodent - rat 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
其他信息
- MOL 文件:4697-14-7.mol
- Sigma Aldrich:4697-14-7(sigmaaldrich)
- 方法一:方法l：1.38g(5mm01)(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1 ml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(Ⅱ)溶于10ml干燥丙酮，在搅拌和蒸汽浴上，加入1.08g(5mmo1)6-APA、15m11mol/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(3×25m1)洗后，再用约11 m11mol/L盐酸酸化至Ph=2，然后用乙醚(3×15m1)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4m11mol/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%。 10.65g 5%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(4.3mmo1)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干燥，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。
- 上游原料:氧氯化硫 --> 硅藻土 --> 青霉素钠 --> 酰氯 --> 钯催化剂 --> 苄酯
- 用途一:半合成青霉素，对绿脓杆菌有高效，临床治疗绿脓杆菌感染有效率为90%左右。对耐药性绿脓杆菌产生的β-内酰胺酶稳定，但易受大肠杆菌、奇异变形杆菌以及个别绿脓杆菌菌株产生的β-内酰胺酶所破坏。和庆大霉素、多粘菌素合用对绿脓杆菌有协同作用。临床用于治疗败血症、泌尿道感染、呼吸道感染和胆道感染，也用于白血病及恶性肿瘤患者的继发感染，对伤寒也有效。替卡西林钠常和克拉维酸配伍制成新抗生素复合剂——泰门汀(Timentin)，临床用于治疗严重感染。
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