CAS No.59-66-5,Acetazolamide Suppliers,MSDS download

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Basic Information

Molecular Structure:
CAS No.:	59-66-5
Name:	Acetazolamide
Article Data:	24

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
Risk Codes:	36/38-36/37/38
Safety:	26-36
Transport Information:	UN 2811
PSA:	151.66000
LogP:	0.99800

Synthetic route

: 14949-00-9
5-amino-1, 3, 4-thiadiazole-2-sulfonamide

: 507-09-5
thioacetic acid

: 59-66-5
acetazolamide

Conditions

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

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

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

: 1318259-33-4
PSA

A: 59-66-5
acetazolamide

B: 68905-61-3
C20H25NO5

Conditions

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

: PMA

A: 59-66-5
acetazolamide

B: 687620-14-0
C20H23NO5

Conditions

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

: 1318259-37-8
PPA

A: 59-66-5
acetazolamide

B: C24H25NO5

Conditions

Conditions	Yield
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

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

: Acetazolamide sodium salt

Conditions

Conditions	Yield
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

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%

Raw Materials

32873-57-7

64387-67-3

Downstream Products

14949-00-9

64-19-7

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Consensus Reports

Reported in EPA TSCA Inventory.

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