CAS Number59-66-5
SynonymsCidamex; Diamox; N-[5-(Aminosulfonyl)-1,3,4-thiadiozol-2-yl]-Acetamide; DIACARB; Glupax; Diluran; N-(5-Sulfamoyl-1,3,4-thiadiazol-2-yl)acetamide; 5-acetamido-1,3,4-thiadiazole-2-sulphonamide; EINECS 200-440-5; acetazolamide; Atenezol; MFCD00003105; Didoc; Edemox; Diakarb
Molecular FormulaC4H6N4O3S2
Molecular Weight261.32
Purity98%
Density1.7±0.1 g/cm3
Melting Point256-261°C
AppearanceWhite to off-white crystalline powder
EINECS200-440-5
Symbol
Signal WordWarning
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 59-66-5 |
| Catalog No. | 2A-9007057 |
| Chinese Name | 乙酰唑胺 |
| Synonyms | Cidamex; Diamox; N-[5-(Aminosulfonyl)-1,3,4-thiadiozol-2-yl]-Acetamide; DIACARB; Glupax; Diluran; N-(5-Sulfamoyl-1,3,4-thiadiazol-2-yl)acetamide; 5-acetamido-1,3,4-thiadiazole-2-sulphonamide; EINECS 200-440-5; acetazolamide; Atenezol; MFCD00003105; Didoc; Edemox; Diakarb |
| Molecular Formula | C4H6N4O3S2 |
| Molecular Weight | 261.32 |
| Purity | 98 |
| Density | 1.7±0.1 g/cm3 |
| Melting Point | 256-261°C |
| Appearance | White to off-white crystalline powder |
| Water Solubility | <0.1 g/100 mL at 22 ºC |
| Storage Condition | Keep sealed. |
| Packaging | III |
| Application | Acetazolamide is a carbonic anhydrase (CA) IX inhibitor that inhibits hCA IX with an IC50 of 30 nM [1]. diuretics[4]. |
| EINECS | 200-440-5 |
| HTC | 2935009090 |
| MDL Number | MFCD30861492 |
| SMILES | CC(=O)Nc1nnc(S(N)(=O)=O)s1 |
| InChI | InChI=1S/C4H6N4O3S2/c1-2(9)6-3-7-8-4(12-3)13(5,10)11/h1H3,(H2,5,10,11)(H,6,7,9) |
| InChI Key | BZKPWHYZMXOIDC-UHFFFAOYSA-N |
| NACRES Code | NA.24 |
| UNSPSC | 41116107 |
| Hazard Symbols | 6.1 |
| Risk Codes | R36/38 |
| Safety Description | S26 |
| MSDS | msds/7057_1_59_66_5.pdf |
| Bioactivity | Acetazolamide is a carbonic anhydrase (CA) IX inhibitor with an IC50 of 30 nM for hCA IX[1]. Diuretic effects[4]. Related Catalog Signaling Pathways >> Autophagy >> Autophagy Signaling Pathways >> Metabolic Enzyme/Protease >> Carbonic Anhydrase Research Areas >> Cardiovascular Disease In Vitro Acetazolamide also inhibits hCA II with an IC50 of 130 nM[1]. Acetazolamide (Ace) is a small heteroaromatic sulfonamide that binds to various carbonic anhydrases with high affinity, acting as a carbonic anhydrase (CA) inhibitor[2]. Compared with the control group, the high Acetazolamide concentration (AceH, 50 nM), Cisplatin (Cis; 1 µg/mL) and Cis combined with the low Acetazolamide concentration (AceL, 10 nM) treatments significantly reduces viability of Hep-2 cells[2]. Treatment with the Acetazolamide/Cis combination significantly increases the expression levels of P53, as both AceL+Cis and AceH+Cis treatments result in significantly increased P53 protein expression levels compared with the control group. The Ace/Cis combination treatment significantly reduces the bcl-2/bax expression ratio, and increases the expression of caspase-3 protein, compared with the control group. AceL, AceH, Cis and AceL+Cis treatments significantly reduce the bcl-2/bax ratio compared with the control group[2]. Combined Ace and Cis treatment effectively promotes apoptosis in Hep-2 cells[2]. Combined treatment with Ace/Cis markedly decreases the expression of AQP1 mRNA in Hep-2 cells. Both AceH and AceL+Cis treatments decrease the expression of aquaporin-1 (AQP1) mRNA in Hep-2 cells compared with the control group[2]. In Vivo Acetazolamide (40 mg/kg) significantly potentiates the inhibitory effect of MS-275 on tumorigenesis in neuroblastoma (NB) SH-SY5Y xenografts[3]. Acetazolamide (40 mg/kg) and/or MS-275 treatment reduce expression of HIF1-α and CAIX in NB SH-SY5Y xenograft[3]. Acetazolamide (40 mg/kg), MS-275 and Acetazolamide+MS-275 reduce expression of mitotic and proliferative markers in NB SH-SY5Y xenografts[3]. Cell Assay Cell Viability Assay[2] Cell line: Hep-2 cells and HUVECs Concentration: 10 nM and 50 nM Incubation time: 48 h Assay: The cell viability of Hep-2 cells and HUVECs is measured by MTT assay. Hep-2 cells and HUVECs in logarithmic growth phase are plated in 96-well plates. Following 48 h of drug treatment as indicated, 200 µL MTT (5 mg/mL) is added to each well. Cells are incubated with the MTT solution at 37°C for 4 h. Then, 150 µL DMSO is added for 5 min. The optical density (OD) values are measured at 490 nm with a Versamax Microplate reader. Note: Combined treatment effectively reduced viability in Hep-2 cells. Animal Admin In vivo studies[3] Animal model: 4-6 weeks-old female NOD/SCID mice Dosage: 40 mg/kg, intraperitoneal injection, every day for 2 weeks Administration: Mice are randomized into four groups (5 mice per group). The control and treatment groups receive intraperitoneal injections of vehicle (PBS) or Acetazolamide (40 mg/kg), MS-275 (20 mg/kg) or the combination, respectively, every day for 2 weeks. Experiments are terminated when tumor sizes exceed 2 cm3 in volume or animals show signs of morbidity. Tumor diameters are measured on a daily basis until termination. Note: Inhibited tumor growth of NB xenografts with significant anti-tumor growth potentiation effect. References [1]. 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. [2]. 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. [3]. 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. [4]. Kassamali R, et al. Acetazolamide: a forgotten diuretic agent. Cardiol Rev. 2011 Nov-Dec;19(6):276-8. Chemical & Physical Properties Density 1.7±0.1 g/cm3 Melting Point 256-261°C Molecular Formula C4H6N4O3S2 Molecular Weight 222.245 Exact Mass 221.988129 PSA 151.66000 LogP -0.26 Index of Refraction 1.641 InChIKey BZKPWHYZMXOIDC-UHFFFAOYSA-N SMILES CC(=O)Nc1nnc(S(N)(=O)=O)s1 Water Solubility <0.1 g/100 mL at 22 ºC |
| Use of | Acetazolamide is a carbonic anhydrase (CA) IX inhibitor with an IC50 of 30 nM for hCA IX[1]. Diuretic effects[4]. Properties Articles91 Name acetazolamide Synonym More Synonyms acetazolamide Biological Activity Description Acetazolamide is a carbonic anhydrase (CA) IX inhibitor with an IC50 of 30 nM for hCA IX[1]. Diuretic effects[4]. Related Catalog Signaling Pathways >> Autophagy >> Autophagy Signaling Pathways >> Metabolic Enzyme/Protease >> Carbonic Anhydrase Research Areas >> Cardiovascular Disease References [1]. 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]. 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. [4]. Kassamali R, et al. Acetazolamide: a forgotten diuretic agent. Cardiol Rev. 2011 Nov-Dec;19(6):276-8. Chemical & Physical Properties Molecular Formula C4H6N4O3S2 Exact Mass 221.988129 PSA 151.66000 LogP -0.26 Index of Refraction 1.641 InChIKey BZKPWHYZMXOIDC-UHFFFAOYSA-N SMILES CC(=O)Nc1nnc(S(N)(=O)=O)s1 |
| Tax Rebate | 9.0% |
| Supervision | None MFN tariff: 6.5% Ordinary tariff: 35.0% |
| Transport Info | Product name: Summary 2935009090 other sulphonamides VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:6.5% General tariff:35.0% |
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