153-61-7

• 常用中文名：头孢噻吩酸
• 常用英文名：Cephalothin
• CAS号：153-61-7
• 分子式：C₁₆H₁₆N₂O₆S₂
• 分子量：396.438
• 相关类别： 信号通路 抗感染 细菌
• 发布时间：2018-07-20 19:59:57
• 更新时间：2024-01-03 19:40:24
• Cephalotin (Cephalotin) 是一种 β-内酰胺抗生素,可抑制 C 类 β-内酰胺酶 (β-lactamase AmpC) 的活性,Ki 值为 0.32 µM。

名称

• 中文名: 头孢噻吩
• 英文名: cefalotin
• 中文别名: (6R,7R)-3-[(乙酰氧基)甲基]-7-[2-(2-噻吩基)乙酰氨基]-8-氧代-5-硫杂-1-氮杂双环[4.2.0]辛-2-烯-2-甲酸; 头孢噻吩酸
• 英文别名: Cemastin; Toricelocin; Ceporacin; Cefalothin; Tokiosarl Ampullen; EINECS 205-815-7; 3-(Hydroxymethyl)-8-oxo-7-[2-(2-thienyl)acetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxyli; Lospoven; Cephalothin; Cephalotin; 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[(acetyloxy)methyl]-8-oxo-7-[(2-thienylacetyl)amino]-, (6R,7R)-; Cefalotina; Microtin; Cefalotine; (6R,7R)-3-[(acetyloxy)methyl]-8-oxo-7-[(2-thienylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; (6R-trans)-3-[(Acetyloxy)methyl]-8-oxo-7-[(2-thienylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carbo; (6R,7R)-3-[(acetyloxy)methyl]-8-oxo-7-[(thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[(acetyloxy)methyl]-8-oxo-7-[[2-(2-thienyl)acetyl]amino]-, (6R,7R)-; Cepovenin; Coaxin; (6R,7R)-3-(Acetoxymethyl)-8-oxo-7-[(2-thienylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; Cefalotinum; (6R,7R)-3-(acetyloxymethyl)-8-oxo-7-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; Cephalothinum; Synclotin; Cefalotin

物化性质

• 密度: 1.6±0.1 g/cm3
• 沸点: 757.2±60.0 °C at 760 mmHg
• 熔点: 160-161ºC
• 分子式: C₁₆H₁₆N₂O₆S₂
• 分子量: 396.438
• 闪点: 411.8±32.9 °C
• 精确质量: 396.044983
• PSA: 166.55000
• LogP: 1.45
• 外观性状: 白色晶体粉末
• 蒸汽压: 0.0±2.7 mmHg at 25°C
• 折射率: 1.676
• 储存条件:

  低温通风干燥处。

• 水溶解性: 158 MG/L
• 分子结构:

  1、 摩尔折射率：95.07

  2、 摩尔体积（cm³/mol）：252.7

  3、 等张比容（90.2K）：751.4

  4、 表面张力（dyne/cm）：78.1

  5、 极化率（10-24cm3）：37.69

• 计算化学:

  1.疏水参数计算参考值（XlogP）:无

  2.氢键供体数量:2

  3.氢键受体数量:8

  4.可旋转化学键数量:7

  5.互变异构体数量:4

  6.拓扑分子极性表面积167

  7.重原子数量:26

  8.表面电荷:0

  9.复杂度:680

  10.同位素原子数量:0

  11.确定原子立构中心数量:2

  12.不确定原子立构中心数量:0

  13.确定化学键立构中心数量:0

  14.不确定化学键立构中心数量:0

  15.共价键单元数量:1

生物活性

• 描述: Cephalotin (Cephalotin) 是一种 β-内酰胺抗生素,可抑制 C 类 β-内酰胺酶 (β-lactamase AmpC) 的活性,Ki 值为 0.32 µM。
• 相关类别:
  研究领域 >> 感染
  信号通路 >> 抗感染 >> 细菌
• 靶点:

  Ki: 0.32 μM (β-lactamase AmpC)[1]

• 参考文献:

  [1]. Morandi S, et al. Structure-based optimization of cephalothin-analogue boronic acids as beta-lactamase inhibitors. Bioorg Med Chem. 2008 Feb 1;16(3):1195-205. Epub 2007 Nov 7.

毒性和生态

毒理学数据: 腹腔-大鼠 LD50: 4296 毫克/公斤; 静脉-小鼠 LD50: 4990 毫克/公斤。 CHEMICAL IDENTIFICATION RTECS NUMBER : XI0388000 CHEMICAL NAME : 5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 3-(hydroxymethyl)-8-oxo-7-(2-(2- thienyl)acetamido)-, acetate (ester) CAS REGISTRY NUMBER : 153-61-7 LAST UPDATED : 199707 DATA ITEMS CITED : 17 MOLECULAR FORMULA : C16-H16-N2-O6-S2 MOLECULAR WEIGHT : 396.46 WISWESSER LINE NOTATION : T46 ANV ES GUTJ G1OV1 HVQ CMV1- BT5SJ HEALTH HAZARD DATA ACUTE TOXICITY DATA TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intraperitoneal SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 4296 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Subcutaneous SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 10 gm/kg TOXIC EFFECTS : Kidney, Ureter, Bladder - other changes TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Rodent - rat DOSE/DURATION : >5 gm/kg TOXIC EFFECTS : Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - acute pulmonary edema Kidney, Ureter, Bladder - other changes TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Parenteral SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 23 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Subcutaneous SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : >4 gm/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 4990 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intramuscular SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 7 gm/kg TOXIC EFFECTS : Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis) TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intracerebral SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 81 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Subcutaneous SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 70 gm/kg/35D-I TOXIC EFFECTS : Blood - normocytic anemia Skin and Appendages - dermatitis, other (after systemic exposure) Nutritional and Gross Metabolic - weight loss or decreased weight gain TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 21 gm/kg/21D-I TOXIC EFFECTS : Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis) Kidney, Ureter, Bladder - other changes in urine composition Nutritional and Gross Metabolic - changes in sodium TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intramuscular SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 31 gm/kg/31D-I TOXIC EFFECTS : Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis) Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Subcutaneous DOSE : 8800 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 TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Subcutaneous DOSE : 18 gm/kg SEX/DURATION : female 9-11 day(s) after conception TOXIC EFFECTS : Reproductive - Effects on Embryo or Fetus - fetal death Reproductive - Specific Developmental Abnormalities - skin and skin appendages TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Unreported DOSE : 9 gm/kg SEX/DURATION : female 9-11 day(s) after conception TOXIC EFFECTS : Reproductive - Effects on Embryo or Fetus - fetal death Reproductive - Specific Developmental Abnormalities - other developmental abnormalities MUTATION DATA TYPE OF TEST : Phage inhibition capacity TEST SYSTEM : Microorganism - not otherwise specified DOSE/DURATION : 25 ug/plate REFERENCE : ZMMPAO Zentralblatt fuer Bakteriologie, Parasitenkunde, Infektionskrankheiten und Hygiene, Abteilung 1: Originale, Reihe A: Medizinische Mikrobiologie und Parasitologie. (Stuttgart, Fed. Rep. Ger.) V.217-245, 1971-79. Volume(issue)/page/year: 231,369,1975 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - 83991 No. of Facilities: 33 (estimated) No. of Industries: 1 No. of Occupations: 3 No. of Employees: 1452 (estimated) NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - 83991 No. of Facilities: 290 (estimated) No. of Industries: 1 No. of Occupations: 8 No. of Employees: 21013 (estimated) No. of Female Employees: 19052 (estimated)

安全

• 危害码 (欧洲): Xi

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