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Acetazolamide

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Name

Acetazolamide

EINECS 200-440-5
CAS No. 59-66-5 Density 1.744 g/cm3
PSA 151.66000 LogP 0.99800
Solubility <0.1 g/100 mL at 22 °C in water Melting Point 256-261 °C
Formula C4H6N4O3S2 Boiling Point N/A
Molecular Weight 222.249 Flash Point N/A
Transport Information UN 2811 Appearance White to yellowish-white fine crystalline powder
Safety 26-36 Risk Codes 36/38-36/37/38
Molecular Structure Molecular Structure of 59-66-5 (Acetazolamide) Hazard Symbols IrritantXi
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;

Article Data 24

Acetazolamide Synthetic route

14949-00-9

5-amino-1, 3, 4-thiadiazole-2-sulfonamide

507-09-5

thioacetic acid

59-66-5

acetazolamide

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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

A

59-66-5

acetazolamide

B

68905-61-3

C20H25NO5

Conditions
ConditionsYield
With water at 37℃; pH=7.4;

PMA

A

59-66-5

acetazolamide

B

687620-14-0

C20H23NO5

Conditions
ConditionsYield
With water at 37℃; pH=7.4;

A

59-66-5

acetazolamide

B

C24H25NO5

Conditions
ConditionsYield
With water at 37℃; pH=7.4;
108-30-5

succinic acid anhydride

59-66-5

acetazolamide

59-66-5

acetazolamide

14949-00-9

5-amino-1, 3, 4-thiadiazole-2-sulfonamide

Conditions
ConditionsYield
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

Acetazolamide sodium salt

Conditions
ConditionsYield
With sodium hydroxide In water at 55℃; for 2h;99%
59-66-5

acetazolamide

7646-79-9

cobalt(II) chloride

Co(5-acetamido-1,3,4-thiadiazole-2-sulphonamide)2(NH3)2

Conditions
ConditionsYield
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%

Acetazolamide Consensus Reports

Reported in EPA TSCA Inventory.

Acetazolamide 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.

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

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