3577-01-3

• 常用中文名：头孢来星
• 常用英文名：Cefaloglycin
• CAS号：3577-01-3
• 分子式：C₁₈H₁₉N₃O₆S
• 分子量：405.42500
• 相关类别： 原料药 抗生素类药物 头孢菌素类药
• 发布时间：2018-08-17 10:31:31
• 更新时间：2024-01-06 04:19:10
• Cefaloglycin (Cephaloglycin) 是一种具有口服活性的肾毒性 β-内酰胺类 (β-lactam) 头孢菌素抗生素,具有抗菌活性。Cefaloglycin 对肠球菌以外的革兰氏阳性球菌 (Gram-Positive cocci) 有活性。Cefaloglycin 对线粒体底物的摄取和呼吸也具有毒性。

名称

• 中文名: 头孢来星
• 英文名: cefaloglycin
• 英文别名: Cefaloglycin; Cephaloglycine; (6R)-3-acetoxymethyl-7t-((R)-2-amino-2-phenyl-acetylamino)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid; Cephaoglycin acid; (6R,7R)-3-(acetyloxymethyl)-7-[[(2R)-2-amino-2-phenylacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; Cefaloglycine; Cefaloglicina; CEPHALOGLYCIN; D-Cephaloglycine; Kafocin; Cefaloglycinum; Cephaloglycin anhydrous

物化性质

• 密度: 1.52 g/cm3
• 沸点: 761.8ºC at 760mmHg
• 熔点: 236.5°C (rough estimate)
• 分子式: C₁₈H₁₉N₃O₆S
• 分子量: 405.42500
• 闪点: 414.5ºC
• 精确质量: 405.09900
• PSA: 164.33000
• LogP: 1.01720
• 折射率: 1.678
• 储存条件: 库房通风低温干燥

生物活性

• 描述: Cefaloglycin (Cephaloglycin) 是一种具有口服活性的肾毒性 β-内酰胺类 (β-lactam) 头孢菌素抗生素,具有抗菌活性。Cefaloglycin 对肠球菌以外的革兰氏阳性球菌 (Gram-Positive cocci) 有活性。Cefaloglycin 对线粒体底物的摄取和呼吸也具有毒性。
• 相关类别:
  研究领域 >> 感染
  信号通路 >> 抗感染 >> 细菌
• 靶点:

  Gram-Positive cocci[2]

• 体外研究: 头孢克洛在体外抗化脓链球菌的活性方面与头孢菌素相当,并略优于头孢氨苄[2]。
• 体内研究: 在每毫升暴露2至6小时至300至3000微克头孢甘氨酸(头孢甘氨酸)的兔肾皮质线粒体中,测量琥珀酸盐和ADP的呼吸和摄取,然后清洗以去除抗生素。头孢菌素(Cefaloglycin)不可逆地降低呼吸和琥珀酸摄取。头孢氨苄对线粒体底物摄取和呼吸的体外损伤模式具有时间依赖性和浓度依赖性[1]。
• 参考文献:

  [1]. B M Tune, et al. The Renal Mitochondrial Toxicity of Beta-Lactam Antibiotics: In Vitro Effects of Cephaloglycin and Imipenem. J Am Soc Nephrol. 1990 Nov;1(5):815-21.

  [2]. S Shadomy, et al. In Vitro Activities of Five Oral Cephalosporins Against Aerobic Pathogenic Bacteria. Antimicrob Agents Chemother. 1977 Nov;12(5):609-13.

  [3]. E Bergogne-Bérézin. Continuous Activity of Significant Antibiotics. Clin Ther. Jan-Feb 1991;13(1):181-8.

毒性和生态

CHEMICAL IDENTIFICATION RTECS NUMBER : XI0345000 CHEMICAL NAME : 5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-(2-amino-2-phenylacetamido)- 3-(hydroxymethyl)-8-oxo-, acetate (ester), D- CAS REGISTRY NUMBER : 3577-01-3 LAST UPDATED : 199603 DATA ITEMS CITED : 8 MOLECULAR FORMULA : C18-H19-N3-O6-S MOLECULAR WEIGHT : 405.46 WISWESSER LINE NOTATION : T46 ANV EM GUTJ CMVYZR& G1OV1 HVQ 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 : >10 gm/kg TOXIC EFFECTS : Liver - other changes REFERENCE : NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 18,22,1970 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intraperitoneal SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 1300 mg/kg TOXIC EFFECTS : Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis) REFERENCE : NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 18,22,1970 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Subcutaneous SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 2800 mg/kg TOXIC EFFECTS : Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis) REFERENCE : NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 18,22,1970 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : >10 gm/kg TOXIC EFFECTS : Liver - other changes REFERENCE : NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 18,22,1970 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intraperitoneal SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 1030 mg/kg TOXIC EFFECTS : Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis) REFERENCE : NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 18,22,1970 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Subcutaneous SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 3700 mg/kg TOXIC EFFECTS : Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis) REFERENCE : NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 18,22,1970 ** REPRODUCTIVE DATA ** TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral DOSE : 1200 mg/kg SEX/DURATION : female 9-14 day(s) after conception TOXIC EFFECTS : Reproductive - Maternal Effects - other effects Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced 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: 18,39,1970 TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral DOSE : 12 gm/kg SEX/DURATION : female 7-12 day(s) after conception TOXIC EFFECTS : Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) REFERENCE : NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 18,39,1970

安全

• 危害码 (欧洲): Xn
• 风险声明 (欧洲): 42/43
• 安全声明 (欧洲): 36

合成路线

19883-41-1 957-68-6 ~% 3577-01-3

文献：Ogasa; Saito; Hashimoto; Sato; Hirata Chemical and Pharmaceutical Bulletin, 1989 , vol. 37, # 2 p. 315 - 321

7765-60-8 ~% 3577-01-3

文献：Spencer; Flynn; Roeske; Siu; Chauvette Journal of medicinal chemistry, 1966 , vol. 9, # 5 p. 746 - 750

33125-05-2 ~% 3577-01-3

文献：Spencer; Flynn; Roeske; Siu; Chauvette Journal of medicinal chemistry, 1966 , vol. 9, # 5 p. 746 - 750

24461-61-8 957-68-6 ~% 3577-01-3

文献：Kawamori; Hashimoto; Katsumata; et al. Agricultural and Biological Chemistry, 1983 , vol. 47, # 11 p. 2503 - 2509

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19883-41-1 957-68-6 7765-60-8 33125-05-2
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