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| CAS No.: | 59-66-5 |
|---|---|
| Name: | Acetazolamide |
| Molecular Structure: | |
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| Formula: | C4H6N4O3S2 |
| Molecular Weight: | 222.249 |
| Synonyms: | Acetamide, N-(5-sulfamoyl-1,3,4-thiadiazol-2-yl)- (8CI);2-Acetamido-1,3,4-thiadiazole-5-sulfonamide;2-Acetylamino-1,3,4-thiadiazole-5-sulfonamide;5-Acetamide-1,3,4-thiadiazole-2-sulfonamide;5-Acetylamino-1,3,4-thiadiazol-2-ylsulfonamide;Acetamox;Acetazolamid;Acetazolamide;Atenezol;Cidamex;Diakarb;Diamox;Diluran;Diuramide;Diuriwas;Diutazol;Eumicton;Glaupax;L 579486;N-(5-Sulfamoyl-1,3,4-thiadiazol-2-yl)acetamide;N-[5-(Aminosulfonyl)-1,3,4-thiadiazol-2-yl]acetamide;NSC 145177;Natrionex;Phonurit; |
| EINECS: | 200-440-5 |
| Density: | 1.744 g/cm3 |
| Melting Point: | 256-261 °C |
| Solubility: | <0.1 g/100 mL at 22 °C in water |
| Appearance: | White to yellowish-white fine crystalline powder |
| Hazard Symbols: |
 Xi
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| Risk Codes: | 36/38-36/37/38 |
| Safety: | 26-36 |
| Transport Information: | UN 2811 |
| PSA: | 151.66000 |
| LogP: | 0.99800 |
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| Conditions | Yield |
|---|---|
| With 10-methyl-9-(2,4,6-trimethylphenyl) acridinium tetrafluoroborate In acetonitrile at 20℃; for 5h; Irradiation; | 76% |
- 32873-57-7
5-acetamido-1,3,4-thiadiazolyl-2-sulfonyl chloride
- 59-66-5
acetazolamide
| Conditions | Yield |
|---|---|
| With 1,1,1-triphenylsilylamine In acetonitrile for 1h; Reflux; Inert atmosphere; | 74% |
| With ammonium hydroxide In water for 1h; Cooling with ice; | 72% |
| With ammonium hydroxide at 20℃; for 0.5h; | 46% |
- 64387-67-3
2-acetylamino-5-benzylmercapto-1,3,4-thiadiazole
- 59-66-5
acetazolamide
| Conditions | Yield |
|---|---|
| With chlorine; acetic acid anschliessendes Behandeln mit fluessigem NH3; | |
| Stage #1: 2-acetylamino-5-benzylmercapto-1,3,4-thiadiazole With chlorine; acetic acid at 50℃; for 0.5h; Stage #2: With ammonia | |
| Stage #1: 2-acetylamino-5-benzylmercapto-1,3,4-thiadiazole With water; chlorine; acetic acid at 5℃; for 0.5h; Stage #2: With ammonia |
| Conditions | Yield |
|---|---|
| With water at 37℃; pH=7.4; |
| Conditions | Yield |
|---|---|
| With water at 37℃; pH=7.4; |
| Conditions | Yield |
|---|---|
| With water at 37℃; pH=7.4; |
- 59-66-5
acetazolamide
- 14949-00-9
5-amino-1, 3, 4-thiadiazole-2-sulfonamide
| Conditions | Yield |
|---|---|
| With hydrogenchloride In ethanol for 4h; Reflux; | 100% |
| With hydrogenchloride In methanol; water for 18h; Reflux; | 98% |
| With hydrogenchloride; water In methanol for 18h; Reflux; | 98% |
- 59-66-5
acetazolamide
| Conditions | Yield |
|---|---|
| With sodium hydroxide In water at 55℃; for 2h; | 99% |
| Conditions | Yield |
|---|---|
| With NH3 In ethanol addn. of the ligand to a soln. of CoCl2 in ethanol, warming, stirring, addn. of NH3; filtn. of ppt., washing (EtOH), dried at 40 °C, elem. anal.; | 98% |
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Consensus Reports
Specification
The Acetazolamide has the cas register number 59-66-5, and its IUPAC name is N-(5-sulfamoyl-1,3,4-thiadiazol-2-yl)acetamide. It belongs to the product category which is Miscellaneous Enzyme.
This is a kind of white to yellowish-white fine crystalline powder with no odor or taste. Besides, it is slightly soluble in water, ethanol, nearly insoluble in chloroform and ethyl ether, and easily soluble in ammonia solution.
The characteristics of this chemical are as follows: (1)ACD/LogP: -0.26; (2)ACD/LogD (pH 5.5): -0.26; (3)ACD/LogD (pH 7.4): -0.48; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 17.06; (7)ACD/KOC (pH 7.4): 10.47; (8)#H bond acceptors: 7; (9)#H bond donors: 3; (10)#Freely Rotating Bonds: 1; (11)Polar Surface Area: 120.09; (12)Index of Refraction: 1.64; (13)Molar Refractivity: 45.95 cm3; (14)Molar Volume: 127.3 cm3; (15)Polarizability: 18.21 ×10-24 cm3; (16)Surface Tension: 97.9 dyne/cm; (17)Density: 1.744 g/cm3.
The production method of Acetazolamide: It could be produce from the amination. Firstly, mix the ammonia water and trash ice till the temperature cools to below 5℃, and then add oxychloride to have heat preservation reation for about half an hour; Secondly, adjust PH to 5-6 with hydrochloric acid and then filter with filter cake to have the PH7, and then dry to get the acetazolamide crude products; Thirdly, heat the mixture of crude products, water, activated carbon and Na2S2O5 to 95℃, and then go through the decoloration for 1-1.5hour to get crystal after filtering and cooling; Lastly, have a listing process of filtering, washing and drying to get the products.
Use of Acetazolamide: Acetazolamide reacts to produce 5-amino-[1,3,4]thiadiazole-2-sulfonic acid amide, with the following condition: reagent: HCL (37 percent); reaction time: 2 hours; yield: 2.75g; other condition: heating.
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As to its usage, it is widely applied in pharmeceutics. It is a kind of diuretic, and also as carbonic anhydrase inhibitor to resist carbonic anhydrase in kidney tubules epithelial cell; It has the function of controlling Aqueous Humour secretion to release the intraocular tension, which could be applied in curing glaucoma and mild cardiac edema.
In addition, you could obtain the molecular structure by converting the following datas:
(1)SMILES:O=S(=O)(c1nnc(s1)NC(=O)C)N
(2)InChI:InChI=1/C4H6N4O3S2/c1-2(9)6-3-7-8-4(12-3)13(5,10)11/h1H3,(H2,5,10,11)(H,6,7,9)
(3)InChIKey:BZKPWHYZMXOIDC-UHFFFAOYAA
Below are the toxicity information of this chemical:
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| dog | LD50 | intravenous | > 2gm/kg (2000mg/kg) | Drugs in Japan Vol. 6, Pg. 15, 1982. | |
| guinea pig | LD50 | subcutaneous | > 1500mg/kg (1500mg/kg) | Drugs in Japan Vol. 6, Pg. 15, 1982. | |
| man | TDLo | oral | 54mg/kg/5D-I (54mg/kg) | LUNGS, THORAX, OR RESPIRATION: DYSPNEA | Archives of Internal Medicine. Vol. 143, Pg. 1278, 1983. |
| mouse | LD50 | intraperitoneal | 1175mg/kg (1175mg/kg) | Russian Pharmacology and Toxicology Vol. 39, Pg. 255, 1976. | |
| mouse | LD50 | intravenous | > 3gm/kg (3000mg/kg) | Drugs in Japan Vol. 6, Pg. 15, 1982. | |
| mouse | LD50 | oral | 4300mg/kg (4300mg/kg) | Acta Biologica et Medica Germanica. Vol. 21, Pg. 193, 1968. | |
| mouse | LD50 | subcutaneous | > 3gm/kg (3000mg/kg) | Drugs in Japan Vol. 6, Pg. 15, 1982. | |
| rat | LD50 | intraperitoneal | 2750mg/kg (2750mg/kg) | Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 56(4), Pg. 134S, 1960 |