1424-27-7

• 常用中文名：乙酰唑胺钠
• 常用英文名：Acetazolamide
• CAS号：1424-27-7
• 分子式：C₄H₅N₄NaO₃S₂
• 分子量：244.22700
• 相关类别： 信号通路 抗感染 细菌
• 发布时间：2018-07-17 22:19:51
• 更新时间：2024-01-08 15:01:22

• 碳酸酐酶抑制剂。利尿药。

名称

• 中文名: 乙酰唑胺钠
• 英文名: acetazolamide sodium
• 英文别名: Sodium acetazolamide; Acetazolamide,Monosodium Salt; N-(5-Sulfamoyl-1,3,4-thiadiazol-2-yl)acetamide monosodium salt; Acetazolamide sodium; sodium,(5-acetamido-1,3,4-thiadiazol-2-yl)sulfonylazanide; ACETAMIDE,N-(5-SULFAMOYL-1,3,4-THIADIAZOL-2-YL)-,MONOSODIUM SALT; Acetamide,N-(5-(aminosulfonyl)-1,3,4-thiadiazol-2-yl)-,monosodium salt; Acetazolamide sodium salt; UNII-429ZT169UH

物化性质

• 熔点: 258-259ºC (EFFERVESCENCE)
• 分子式: C₄H₅N₄NaO₃S₂
• 分子量: 244.22700
• 精确质量: 243.97000
• PSA: 142.87000
• LogP: 0.78380
• 外观性状: 固体
• 储存条件:

  密封阴凉干燥避光保存。

• 分子结构:

  1、摩尔折射率：无可用的

  2、摩尔体积（cm³/mol）：无可用的

  3、等张比容（90.2K）：无可用的

  4、表面张力（dyne/cm）：无可用的

  5、介电常数：无可用的

  6、极化率（10^-24cm³）：无可用的

  7、单一同位素质量：243.970075 Da

  8、标称质量：244 Da

  9、平均质量：244.2273 Da

• 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:7

  4.可旋转化学键数量:2

  5.互变异构体数量:5

  6.拓扑分子极性表面积127

  7.重原子数量:14

  8.表面电荷:0

  9.复杂度:302

  10.同位素原子数量:0

  11.确定原子立构中心数量:0

  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:2

• 更多:

  1. 性状：白色粉末

  2. 密度（g/mL,25/4℃）：未确定

  3. 相对蒸汽密度（g/mL,空气=1）：未确定

  4. 熔点（ºC）：未确定

  5. 沸点（ºC,常压）：未确定

  6. 沸点（ºC,5.2kPa）：未确定

  7. 折射率：未确定

  8. 闪点（ºC）：未确定

  9. 比旋光度（º）：未确定

  10. 自燃点或引燃温度（ºC）：未确定

  11. 蒸气压（kPa,25ºC）：未确定

  12. 饱和蒸气压（kPa,60ºC）：未确定

  13. 燃烧热（KJ/mol）：未确定

  14. 临界温度（ºC）：未确定

  15. 临界压力（KPa）：未确定

  16. 油水（辛醇/水）分配系数的对数值：未确定

  17. 爆炸上限（%,V/V）：未确定

  18. 爆炸下限（%,V/V）：未确定

  19. 溶解性： 溶于水。

生物活性

• 描述: 乙酰唑胺钠是乙酰唑酰胺的钠盐。乙酰唑胺是碳酸酐酶(CA)IX抑制剂,对hCA IX的IC50为30 nM。乙酰唑酰胺具有利尿、降压和抗淋菌活性[1][4][5][6]。
• 相关类别:
  研究领域 >> 感染
  信号通路 >> 自噬 >> 自噬
  信号通路 >> 代谢酶/蛋白酶 >> 碳酸酐酶
  研究领域 >> 代谢疾病
  信号通路 >> 抗感染 >> 细菌
• 体外研究: 乙酰唑胺也抑制hCA II,IC50为130 nM[1]。乙酰唑胺(Ace)是一种小的杂芳磺酰胺,以高亲和力结合各种碳酸酐酶,作为碳酸酐酶(CA)抑制剂[2]。与对照组相比,高乙酰唑胺浓度(AceH,50 nM)、顺铂(Cis；1µg/mL)和Cis联合低乙酰唑酰胺浓度(AceL,10 nM)治疗显著降低了Hep-2细胞的活力[2]。与对照组相比,乙酰唑胺/顺式联合治疗显著增加P53的表达水平,因为AceL+顺式和AceH+顺式治疗均导致P53蛋白表达水平显著增加。与对照组相比,Ace/Cis联合治疗显著降低bcl-2/bax表达率,并增加caspase-3蛋白的表达。与对照组相比,AceL、AceH、Cis和AceL+Cis治疗显著降低bcl-2/bax比率[2]。Ace和Cis联合治疗可有效促进Hep-2细胞凋亡[2]。Ace/Cis联合治疗可显著降低Hep-2细胞中AQP1 mRNA的表达。与对照组相比,AceH和AceL+Cis处理均降低了Hep-2细胞中水通道蛋白-1(AQP1)mRNA的表达[2]。
• 体内研究: 乙酰唑胺(40 mg/kg)显著增强MS-275对神经母细胞瘤(NB)SH-SY5Y异种移植物肿瘤发生的抑制作用[3]。乙酰唑胺(40 mg/kg)和/或MS-275治疗可降低NB SH-SY5Y异种移植物中HIF1-α和CAIX的表达[3]。乙酰唑胺(40 mg/kg)、MS-275和乙酰唑酰胺+MS-275降低NB SH-SY5Y异种移植物中有丝分裂和增殖标记物的表达[3]。乙酰唑胺(50 mg/kg；PO,持续3天)显著降低感染小鼠阴道内淋菌负荷90%[6]。
• 参考文献:

  [1]. Bayat Mokhtari R, et al. Acetazolamide potentiates the anti-tumor potential of HDACi, MS-275, in neuroblastoma. BMC Cancer. 2017 Feb 24;17(1):156.

  [2]. Hou Z, et al. Dual-tail approach to discovery of novel carbonic anhydrase IX inhibitors by simultaneously matching the hydrophobic and hydrophilic halves of the active site. Eur J Med Chem. 2017 May 26;132:1-10.

  [3]. Gao H, et al. Combined treatment with acetazolamide and cisplatin enhances chemosensitivity in laryngeal carcinoma Hep-2 cells. Oncol Lett. 2018 Jun;15(6):9299-9306.

  [4]. Kassamali R, et al. Acetazolamide: a forgotten diuretic agent. Cardiol Rev. 2011 Nov-Dec;19(6):276-8.

  [5]. Jabeen E, et al. Interaction of antihypertensive acetazolamide with nonsteroidal anti-inflammatory drugs. J Photochem Photobiol B. 2013 Aug 5;125:155-63.

  [6]. Abutaleb NS, et al. In vivo efficacy of acetazolamide in a mouse model of Neisseria gonorrhoeae infection. Microb Pathog. 2022 Mar;164:105454.

毒性和生态

CHEMICAL IDENTIFICATION RTECS NUMBER : AC8400000 CHEMICAL NAME : Acetamide, N-(5-sulfamoyl-1,3,4-thiadiazol-2-yl)-, monosodium salt CAS REGISTRY NUMBER : 1424-27-7 LAST UPDATED : 199609 DATA ITEMS CITED : 20 MOLECULAR FORMULA : C4-H5-N4-O3-S2.Na MOLECULAR WEIGHT : 244.24 WISWESSER LINE NOTATION : T5NN DSJ CSZW EMV1 &-NA- HEALTH HAZARD DATA ACUTE TOXICITY DATA TYPE OF TEST : LD - Lethal dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - rat DOSE/DURATION : >1 gm/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : JHHBAI Bulletin of the Johns Hopkins Hospital. (Baltimore, MD) V.1-119, 1889-1966. For publisher information, see JHMJAX. Volume(issue)/page/year: 95,199,1954 TYPE OF TEST : LDLo - Lowest published lethal dose ROUTE OF EXPOSURE : Subcutaneous SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 3 gm/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : JHHBAI Bulletin of the Johns Hopkins Hospital. (Baltimore, MD) V.1-119, 1889-1966. For publisher information, see JHMJAX. Volume(issue)/page/year: 95,199,1954 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 : JHHBAI Bulletin of the Johns Hopkins Hospital. (Baltimore, MD) V.1-119, 1889-1966. For publisher information, see JHMJAX. Volume(issue)/page/year: 95,199,1954 TYPE OF TEST : LD - Lethal dose ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Mammal - dog DOSE/DURATION : >2 gm/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : JHHBAI Bulletin of the Johns Hopkins Hospital. (Baltimore, MD) V.1-119, 1889-1966. For publisher information, see JHMJAX. Volume(issue)/page/year: 95,199,1954 TYPE OF TEST : LDLo - Lowest published lethal dose ROUTE OF EXPOSURE : Subcutaneous SPECIES OBSERVED : Rodent - guinea pig DOSE/DURATION : 1500 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : JHHBAI Bulletin of the Johns Hopkins Hospital. (Baltimore, MD) V.1-119, 1889-1966. For publisher information, see JHMJAX. Volume(issue)/page/year: 95,199,1954 ** OTHER MULTIPLE DOSE TOXICITY DATA ** TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Mammal - dog DOSE/DURATION : 1 gm/kg/10D-I TOXIC EFFECTS : Nutritional and Gross Metabolic - changes in sodium Nutritional and Gross Metabolic - changes in potassium REFERENCE : JHHBAI Bulletin of the Johns Hopkins Hospital. (Baltimore, MD) V.1-119, 1889-1966. For publisher information, see JHMJAX. Volume(issue)/page/year: 95,199,1954 ** REPRODUCTIVE DATA ** TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intraperitoneal DOSE : 1 gm/kg SEX/DURATION : female 10 day(s) after conception TOXIC EFFECTS : Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - fetal death Reproductive - Specific Developmental Abnormalities - musculoskeletal system REFERENCE : TJADAB Teratology, The International Journal of Abnormal Development. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1968- Volume(issue)/page/year: 1,51,1968 TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Subcutaneous DOSE : 1 gm/kg SEX/DURATION : female 10 day(s) after conception TOXIC EFFECTS : Reproductive - Effects on Embryo or Fetus - fetal death Reproductive - Specific Developmental Abnormalities - musculoskeletal system REFERENCE : TJADAB Teratology, The International Journal of Abnormal Development. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1968- Volume(issue)/page/year: 1,51,1968 TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral DOSE : 850 mg/kg SEX/DURATION : female 10 day(s) after conception TOXIC EFFECTS : Reproductive - Specific Developmental Abnormalities - musculoskeletal system REFERENCE : TJADAB Teratology, The International Journal of Abnormal Development. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1968- Volume(issue)/page/year: 28,355,1983 TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Subcutaneous DOSE : 1 gm/kg SEX/DURATION : female 8 day(s) after conception TOXIC EFFECTS : Reproductive - Specific Developmental Abnormalities - Central Nervous System Reproductive - Specific Developmental Abnormalities - musculoskeletal system REFERENCE : TJADAB Teratology, The International Journal of Abnormal Development. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1968- Volume(issue)/page/year: 10,221,1974 TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Subcutaneous DOSE : 200 mg/kg SEX/DURATION : female 8 day(s) after conception TOXIC EFFECTS : Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue) REFERENCE : TJADAB Teratology, The International Journal of Abnormal Development. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1968- Volume(issue)/page/year: 27,51,1983 TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Subcutaneous DOSE : 1 gm/kg SEX/DURATION : female 8 day(s) after conception TOXIC EFFECTS : Reproductive - Effects on Newborn - live birth index (measured after birth) Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain) REFERENCE : TJADAB Teratology, The International Journal of Abnormal Development. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1968- Volume(issue)/page/year: 28,45,1983 TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Subcutaneous DOSE : 3 gm/kg SEX/DURATION : female 9-11 day(s) after conception TOXIC EFFECTS : Reproductive - Effects on Embryo or Fetus - fetal death REFERENCE : TJADAB Teratology, The International Journal of Abnormal Development. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1968- Volume(issue)/page/year: 28,45,1983 TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Subcutaneous DOSE : 200 mg/kg SEX/DURATION : female 8 day(s) after conception TOXIC EFFECTS : Reproductive - Specific Developmental Abnormalities - musculoskeletal system REFERENCE : TJADAB Teratology, The International Journal of Abnormal Development. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1968- Volume(issue)/page/year: 28,45,1983 TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Subcutaneous DOSE : 1500 mg/kg SEX/DURATION : female 13 day(s) after conception TOXIC EFFECTS : Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Effects on Embryo or Fetus - cytological changes (including somatic cell genetic material) REFERENCE : TJADAB Teratology, The International Journal of Abnormal Development. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1968- Volume(issue)/page/year: 15,199,1977 TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Subcutaneous DOSE : 1500 mg/kg SEX/DURATION : female 13 day(s) after conception TOXIC EFFECTS : Reproductive - Specific Developmental Abnormalities - musculoskeletal system REFERENCE : TJADAB Teratology, The International Journal of Abnormal Development. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1968- Volume(issue)/page/year: 15,199,1977 TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intraperitoneal DOSE : 300 mg/kg SEX/DURATION : female 8 day(s) after conception TOXIC EFFECTS : Reproductive - Specific Developmental Abnormalities - musculoskeletal system REFERENCE : TJADAB Teratology, The International Journal of Abnormal Development. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1968- Volume(issue)/page/year: 4,95,1971 TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intraperitoneal DOSE : 600 mg/kg SEX/DURATION : female 8 day(s) after conception TOXIC EFFECTS : Reproductive - Specific Developmental Abnormalities - Central Nervous System REFERENCE : TJADAB Teratology, The International Journal of Abnormal Development. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1968- Volume(issue)/page/year: 4,95,1971 TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intravaginal DOSE : 110 mg/kg SEX/DURATION : female 8 day(s) after conception TOXIC EFFECTS : Reproductive - Specific Developmental Abnormalities - musculoskeletal system REFERENCE : TJADAB Teratology, The International Journal of Abnormal Development. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1968- Volume(issue)/page/year: 7,209,1973 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X5616 No. of Facilities: 17 (estimated) No. of Industries: 1 No. of Occupations: 1 No. of Employees: 223 (estimated) No. of Female Employees: 137 (estimated)

安全

• 危害码 (欧洲): Xi