CAS 4697-14-7 MFCD07787410-4-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 TAO{mole}

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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安全信息

WGK Germany2

GHS Symbol

Precautionary statements

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.....

Hazard statements

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

RTECSXM9410000

Signal word Danger

Personal Protective Equipment dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Hazard Codes Xn Xn,Xi

Safety Statements

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；

Risk Statements

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

Storage condition 2-8°C

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。