25953-19-9

• 常用中文名：头孢唑林
• 常用英文名：Cefazolin
• CAS号：25953-19-9
• 分子式：C₁₄H₁₄N₈O₄S₃
• 分子量：454.507
• 相关类别： 原料药 抗生素类药物 头孢菌素类药
• 发布时间：2018-07-14 18:37:03
• 更新时间：2026-07-03 19:20:39
• Cefazolin 是第一代头孢类抗生素, 用于多种细菌感染的研究。

名称

• 中文名: 头孢唑啉
• 英文名: cefazolin
• 中文别名: 头孢唑啉 RS; 头孢唑林/头孢唑啉酸; 头孢唑啉 标准品; 先锋霉素Ⅴ; 13C2,15N-头孢唑林; 头孢拉定V; (6R,7R)-7-(2-(1H-四唑-1-基)乙酰胺)-3-(((5-甲基-1,3,4-噻二唑-2-基)硫基)甲基)-8-氧代-5-硫杂-1-氮杂双环[4.2.0]辛-2-烯-2-羧酸; 头孢拉啶; Cefazolin 头孢唑啉（唑啉头孢菌素）; 头孢唑林,10 MM DMSO 溶液; 头孢唑林钠 标准品; 头孢唑啉(标准品); 头孢唑啉检测标准品; 头孢唑林-[13C2, 15N]/精确称量; 头孢唑啉钠有关杂质 L; 唑啉头孢菌素; 头孢拉定V/头孢五号/西孢唑啉/先锋霉素V/唑啉头孢菌素/头孢拉啶/头孢菌素Ⅴ; 头孢唑啉对照品; 先锋霉素V; 头孢菌素Ⅴ; 头孢唑啉,唑啉头孢菌素; 西孢唑啉; Cefazolin 头孢唑啉(唑啉头孢菌素); 头孢唑林酸; 湖北威德利优势产品,类白色粉末; 头孢五号; (6R,7R)-3-[(5-甲基-1,3,4-噻二唑-2-基)硫甲基]-8-氧代-7-[[2-(四唑-1-基)乙酰]氨基]-5-硫杂-1-氮杂双环[4.2.0]辛-2-烯-2-甲酸
• 英文别名: 7-(1-(1H)-Tetrazolylacetamido)-3-[2-(5-methyl-1,3,4-thiadiazolyl)thiomethyl]-D3-cephem-4-carboxylic Acid; 7-(1-(1h-)-tetrazolylacetamido)-3-[2-(5-methyl-1,3,4-thiadiazolyl)thiomethyl]d; elta3-chem-4-cboxylicacid; Cefazolina; Cefazolin vial; Cefazolin, Antibiotic for Culture Media Use Only; Cefazoline; CEFAZOLIN; (6R)-3-[[(5-Methyl-1,3,4-thiadiazol-2-yl)thio]methyl]-7α-[[2-(1H-tetrazol-1-yl)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-cboxylic acid; Ancef; CefazoilnV; (6R,7R)-3-{[(5-methyl-1,3,4-thiadiazol-2-yl)thio]methyl}-8-oxo-7-[(1H-tetrazol-1-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; diazol-2-yl)thio)methyl)-8-oxo-7-(2-(1h-t; 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-cboxylic acid, 3-[[(5-methyl-1,3,4-thiadiazol-2-yl)thio]methyl]-8-oxo-7-[(1H-tetrazol-1-ylacetyl)amino]-, (6R,7R); Cefazolin Sodium Impurity L; diazol-2-yl)thio)methyl)-8-oxo-7-(2-(1h-tetrazol-1-yl)acetamido); Cefazolin (C0682800); chamezine; chazolin; 7-[1-(1H)-tetrazolylacetoamido]-3-[2-(5-methyl-1,3,4-thiadiazolyl)-thiomethyl]-.DELTA.-3-chem-4-cboxylic acid; 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-cboxylicacid,3-(((5-methyl-1,3,4-thia; MFCD00243010; (6R,7R)-3-[[(5-Methyl-1,3,4-thiadiazol-2-yl)thio]methyl]-8-oxo-7-[2-(1H-tetrazol-1-yl)acetylamino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-cboxylic acid; cefamezin; Cefazolin AcidQ: What is Cefazolin Acid Q: What is the CAS Number of Cefazolin Acid Q: What is the storage condition of Cefazolin Acid Q: What e the applications of Cefazolin Acid; 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-cboxylic acid, 3-[[(5-methyl-1,3,4-thiadiazol-2-yl)thio]methyl]-8-oxo-7-[2-(1H-tetrazol-1-yl)acetamido]- (8CI); Chazolin,sodium salt; Cefazolin CRS; Cefaprim; Cephazolin; (6r-trans)-3-[[(5-methyl-1,3,4-thiadiazol-2-yl)thio]methyl]-8-oxo-7-[[(1h-tetr; Cefazolin, 10 mM in DMSO; Cefazolinum; Cafazolin; elzoam; (6R,7R)-3-{[(5-Methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl}-8-oxo-7-[(1H-tetrazol-1-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; Cefazolin Acid L; cez; Cefazolin //BP; Cefamezin; (6R,7R)-7-(2-(1H-Tetrazol-1-yl)acetamido)-3-(((5-methyl-1,3,4-thiadiazol-2-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-cboxylic acid; cefazoline; diazol-2-yl)thio)methyl)-8-oxo-7-((1h-tetra; Cephamezine; Cefazolin Acid; 7-(1H-Tetrazol-1-ylacetamido)-3-(5-methyl-1,3,4-thiadiazol-2-yl)thiomethyl-3-chem-4-cboxylic acid; CeftazidinMe; Cephazoline; (6R,7R)-3-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanylmethyl]-8-oxo-7-[[2-(tetrazol-1-yl)acetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; chazoline; Cephazolidin; 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-cboxylic acid, 3-[[(5-methyl-1,3,4-thiadiazol-2-yl)thio]methyl]-8-oxo-7-[[2-(1H-tetrazol-1-yl)acetyl]amino]-, (6R,7R); 7-(1-(1H)-Tetrazolylacetamido)-3-[2-(5-methyl-1,3,4-thiadiazolyl)thiomethyl]-D3-chem-4-cboxylic acid; EINECS 247-362-8; CEFAZOLIN ACID; (6R,7R)-3-[[(5-methyl-1,3,4-thiadiazol-2-yl)thio]methyl]-8-oxo-7-[[1-oxo-2-(1-tetrazolyl)ethyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-cboxylic acid; (6R)-3-(5-methyl-[1,3,4]thiadiazol-2-ylsulfanylmethyl)-8-oxo-7t-(2-tetrazol-1-yl-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid; Cefazoline sodium sterile IP/Bp; Cefazolin 1000 μg/mL in Acetonitrile; (6R,7R)-3-[(5-Methyl-1,3,4-thiadiazol-2-yl)sulfanylmethyl]-8-oxo-7-[[2-(tetrazol-1-yl)acetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-cboxylic acid; azol-1-yl)acetyl]-amino]-5-thia-1-azabicylo; 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-cboxylic acid, 3-[[(5-methyl-1,3,4-thiadiazol-2-yl)thio]methyl]-8-oxo-7-[(1H-tetrazol-1-ylacetyl)amino]-, (6R-trans)

物化性质

• 密度: 2.0±0.1 g/cm3
• 熔点: 198-200ºC
• 分子式: C₁₄H₁₄N₈O₄S₃
• 分子量: 454.507
• 精确质量: 454.029999
• PSA: 234.93000
• LogP: 1.13
• 外观性状: 针状
• 折射率: 1.961
• 储存条件: 室温

生物活性

• 描述: Cefazolin 是第一代头孢类抗生素, 用于多种细菌感染的研究。
• 相关类别:
  研究领域 >> 感染
  研究领域 >> 炎症/免疫
  研究领域 >> 神经疾病
  信号通路 >> 抗感染 >> 细菌
• 靶点:

  Antibiotic[1]

• 体外研究: 头孢唑林(50-300μg/mL；6或24小时)对LPS(1μg/mL)刺激的C8-B4细胞有直接抗炎作用[1]。细胞活力测定[1]细胞系：小鼠C8-B4小胶质细胞浓度：50、100、150、200、250和300μg/mL孵育时间：6或24小时结果：抑制促炎细胞因子的产生。在50和100μg/mL时抑制IL-6的产生。
• 体内研究: 头孢唑林(300mg/kg,术前1h腹腔注射,术后每日1次,连续5d)可减轻术后记忆和学习障碍。单用头孢唑林可导致小鼠认知功能障碍,可能是由于未经手术的小鼠出现短暂的肠道失调[1]。动物模型：6～8周龄CD-1雄性小鼠(体重31～36g)[1]剂量：300～500mg/kg给药：10mg/0.1ml,术前30min腹腔注射,每日1次,共5天。结果：术后小鼠学习记忆能力提高,非手术组小鼠学习记忆能力下降。
• 参考文献:

  [1]. Peng Liang, et al. Perioperative use of cefazolin ameliorates postoperative cognitive dysfunction but induces gut inflammation in mice. J Neuroinflammation. 2018 Aug 22;15(1):235.

毒性和生态

CHEMICAL IDENTIFICATION RTECS NUMBER : XI0389900 CHEMICAL NAME : 5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 3-(((5-methyl-1,3,4-thiadiazol-2-yl) thio)methyl)-8-oxo-7-(2-(1H-tetrazol-1-yl)acetamido)- CAS REGISTRY NUMBER : 25953-19-9 LAST UPDATED : 199612 DATA ITEMS CITED : 7 MOLECULAR FORMULA : C14-H14-N8-O4-S3 MOLECULAR WEIGHT : 454.54 HEALTH HAZARD DATA ACUTE TOXICITY DATA TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 3 gm/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : BYYADW Byoin Yakugaku. Hospital Pharmacology. (Yakuji Nippon Sha, 1-11 Izumi-cho, Kanda, Chiyoda-ku, Tokyo 101, Japan) V.1- 1975- Volume(issue)/page/year: 3,220,1978 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intramuscular SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 4 gm/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : BYYADW Byoin Yakugaku. Hospital Pharmacology. (Yakuji Nippon Sha, 1-11 Izumi-cho, Kanda, Chiyoda-ku, Tokyo 101, Japan) V.1- 1975- Volume(issue)/page/year: 3,220,1978 ** OTHER MULTIPLE DOSE TOXICITY DATA ** TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intraperitoneal SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 164 gm/kg/26W-I TOXIC EFFECTS : Blood - normocytic anemia Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - transaminases REFERENCE : NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 28(Suppl 7),1089,1980 TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 44100 mg/kg/35D-I TOXIC EFFECTS : Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - transaminases Related to Chronic Data - death REFERENCE : NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 28(Suppl 7),1007,1980 TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Rodent - rabbit DOSE/DURATION : 11200 mg/kg/28D-I TOXIC EFFECTS : Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis) REFERENCE : BYYADW Byoin Yakugaku. Hospital Pharmacology. (Yakuji Nippon Sha, 1-11 Izumi-cho, Kanda, Chiyoda-ku, Tokyo 101, Japan) V.1- 1975- Volume(issue)/page/year: 3,220,1978 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - A1317 No. of Facilities: 33 (estimated) No. of Industries: 1 No. of Occupations: 1 No. of Employees: 528 (estimated) NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - A1317 No. of Facilities: 318 (estimated) No. of Industries: 1 No. of Occupations: 5 No. of Employees: 16111 (estimated) No. of Female Employees: 13596 (estimated)

安全

• 危害码 (欧洲): Xn
• 风险声明 (欧洲): R20/21/22
• 安全声明 (欧洲): 26-36
• 危险品运输编码: NONH for all modes of transport
• 海关编码: 3004909090

合成路线

27164-46-1 ~76% 25953-19-9

文献：WO2005/20904 A2, ; Page/Page column 19 ;

43194-95-2 98493-37-9 ~92% 25953-19-9

文献：Tetrahedron, , vol. 41, # 22 p. 5133 - 5139

32510-61-5 29490-19-5 ~70% 25953-19-9

文献：Tetrahedron Letters, , vol. 38, # 26 p. 4693 - 4696

30246-33-4 55633-19-7 ~78% 25953-19-9

文献：Journal of Organic Chemistry, , vol. 62, # 26 p. 9099 - 9106

957-68-6 ~% 25953-19-9

文献：Tetrahedron Letters, , vol. 38, # 26 p. 4693 - 4696

61-24-5 ~% 25953-19-9

文献：Tetrahedron Letters, , vol. 38, # 26 p. 4693 - 4696

30246-33-4 55633-19-7 ~% 21732-17-2 25953-19-9

文献：Journal of Organic Chemistry, , vol. 62, # 26 p. 9099 - 9106

79239-19-3 ~% 25953-19-9

文献：Chemical and Pharmaceutical Bulletin, , vol. 44, # 3 p. 599 - 601

上下游产品

上游产品  9
27164-46-1 43194-95-2 98493-37-9 29490-19-5
30246-33-4 55633-19-7 957-68-6 61-24-5
79239-19-3
下游产品  0

制备

【方法一】
以头孢菌素C为原料制得。

海关

海关编码	3004909090