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  • Acetazolamide
Name:Acetazolamide
CAS No:59-66-5

PRODUCT DESCRIPTION

【Name】
acetazolamide
【CAS Registry number】
59-66-5
【Synonyms】
2-acetamido-5-sulfamoyl-1,3,4-thiadiazole
2-acetylamino-1,3,4-thiadiazole-5-sulfonamide
5-acetamido-1,3,4-thiadiazole-2-sulfonamide
【EINECS(EC#)】
200-440-5
【Molecular Formula】
C4H6N4O3S2 (Products with the same molecular formula)
【Molecular Weight】
222.24
【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)
【Canonical SMILES】
CC(=O)NC1=NN=C(S1)S(=O)(=O)N
【MOL File】
59-66-5.mol

Chemical and Physical Properties

【Appearance】
white to off-white crystalline powder
【Density】
1.744 g/cm3
【Melting Point】
256-261℃
【Boiling Point】
°Cat760mmHg
【Flash Point】
°C
【Water】
<0.1 g/100 mL at 22 ºC
【Solubilities】
<0.1 g/100 mL at 22 oC in water
【Color/Form】
CRYSTALS FROM WATER
WHITE TO FAINTLY YELLOWISH WHITE, CRYSTALLINE, POWDER
【Stability】
Sensitive to light.
【Storage temp】
Store between 15 and 30C (59 and 86F), in a well-closed container, unless otherwise specified by manufacturer.
【Computed Properties】
Molecular Weight:222.24544 [g/mol]
Molecular Formula:C4H6N4O3S2
XLogP3:-0.3
H-Bond Donor:2
H-Bond Acceptor:5
Rotatable Bond Count:2
Tautomer Count:5
Exact Mass:221.988131
MonoIsotopic Mass:221.988131
Topological Polar Surface Area:152
Heavy Atom Count:13
Formal Charge:0
Complexity:297
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:4
Feature 3D Donor Count:2
Feature 3D Ring Count:1
Effective Rotor Count:3
Conformer Sampling RMSD:0.6
CID Conformer Count:10

Safety and Handling

【Hazard Codes】
Xi:Irritant
【Risk Statements】
R36/38
【Safety Statements 】
S26
【HazardClass】
6.1
【Safety】
Hazard Codes:Xi
Risk Statements:36/38-36/37/38
36/38:Irritating to eyes and skin
36/37/38:Irritating to eyes, respiratory system and skin
Safety Statements:26-36
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36:Wear suitable protective clothing
RIDADR:2811
HazardClass:6.1
PackingGroup:III
Hazardous Substances Data:59-66-5(Hazardous Substances Data)
【PackingGroup 】
III
【Transport】
2811
【Exposure Standards and Regulations】
Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).
【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
【Octanol/Water Partition Coefficient】
Log P= -0.45
【Report】

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
【Disposal Methods】
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

REACTION OF HYDRAZINE HYDRATE WITH AMMONIUM THIOCYANATE, TO PRODUCE 5-AMINO-2-MERCAPTO-1,3,4-THIADIAZOLE, WHICH IS ACETYLATED AND OXIDIZED, THEN AMIDATED WITH AMMONIA
Hydrazine + ammonium thiocyanate + acetic anhydride + ammonia (thiocyanate addition/cyclization/acetylation/oxidation/sulfonamide formation)
Oxidative chlorination of 2-acetyl-amino-5-mercapto-1,3,4-thiadiazole or its S-benzyl or S-acyl derivatives to the corresponding sulfonyl chlorides followed by reaction with ammonia has proved to be an optimal method for the synthesis of acetazolamide.
U.S. Production

(1977) PROBABLY GREATER THAN 4.54X10+5 GRAMS
(1979) PROBABLY GREATER THAN 4.54X10+5 GRAMS
Consumption Patterns

ESSENTIALLY 100% AS A DIURETIC
【Usage】

Carbonic anhydrase inhibitor. Diuretic.

Biomedical Effects and Toxicity

【Pharmacological Action】
- Drugs used to prevent SEIZURES or reduce their severity.
- A class of compounds that reduces the secretion of H+ ions by the proximal kidney tubule through inhibition of CARBONIC ANHYDRASES.
- Agents that promote the excretion of urine through their effects on kidney function.
【Therapeutic Uses】
Anticonvulsants; Carbonic Anhydrase Inhibitors; Diuretics
MEDICATION (VET): IN LAMINITIS, UDDER EDEMA, ENTEROTOXEMIA, ASCITES, & GLAUCOMA IN VARIOUS SPECIES.
Carbonic anhydrase inhibitors are indicated primarily as adjuncts to other agents in the treatment of open-angle (chronic simple) glaucoma and secondary glaucoma, and to lower intraocular pressure prior to surgery for some types of glaucoma. /Carbonic anhydrase inhibitors; Included in US product labeling/
Acetazolamide is used to lower intraocular pressure in the treatment of malignant (ciliary block) glaucoma, which may occur after inflammation surgery, trauma, or use of miotics. /NOT included in US product labeling/
Acetazolamide is indicated as an adjunct to other anticonvulsants in the management of absence seizures (petit mal), generalized tonic-clonic seizures (grand mal), mixed seizure patterns. It may be especially useful for intermittent therapy in females who experience increased seizure activity at the time of menstruation. /Included in US product labeling/
Oral acetazolamide is indicated to decrease the incidence and/or severity of symptoms (such as headache, nausea, shortness of breath, dizziness, drowsiness, and fatigue) associated with acute altitude sickness in mountain climbers who are attempting rapid ascent and in those who are very susceptible to altitude sickness despite gradual ascent. Gradual ascent is desirable for prevention of acute altitude sickness even when acetazolamide is used. However, prompt descent may still be necessary if severe manifestations of acute altitude sickness, such as pulmonary edema or cerebral edema, occur. /Included in US product labeling/
Acetazolamide is used to treat both the hypokalemic and hyperkalemic forms of familial periodic paralysis. It terminates the acute attacks and, with chronic use, prevents their recurrence. It may be the drug of choice in the hypokalemic form of the condition. /NOT included in US or Canadian product labeling/
Parenteral acetazolamide is used to produce a forced alkaline diuresis as a method of increasing the elimination of certain weakly acidic medications. /NOT included in US product labeling/
Oral acetazolamide is used to alkalinize the urine as a means of preventing the occurrence or recurrence of uric acid renal stones, especially in patients receiving uricosuric antigout agents, or of cystine renal stones. /NOT included in US or Canadian product labeling/
Acetazolamide has also been used to prevent or counteract metabolic alkalosis, including that which may occur following open heart surgery; however, it is no longer used for these indications.
Acetazolamide has also been used as a diuretic in the treatment of edema due to congestive heart disease and drug-induced edema. However, it has been replaced by newer diuretics for these indications.
MEDICATION (VET): DIURETIC IN CATTLE UDDER EDEMA, IN ANIMAL CARDIAC & RESPIRATORY PROBLEMS
A placebo controlled study of the therapy of acute altitude sickness in 12 mountain climbers, 6 of whom were given 250 mg of oral acetazolamide every 8 hr for 2 doses, is reported. After 24 hr, the patients treated with acetazolamide were asymptomatic, whereas those given the placebo still had acute altitude sickness. The alveolar to arterial oxygen pressure difference decr slightly over 24 hr in the acetazolamide group, but incr slightly in the placebo group. Acetazolamide improved the arterial partial oxygen pressure over 24 hr when compared with placebo. It was concluded that in established cases of acute altitude sickness, treatment with acetazolamide relieves symptoms, improves arterial oxygenation, and prevents further impairment of pulmonary gas exchange. [Grissom CK et al; Ann Intern Med 116: 461-5 (1992)]
【Biomedical Effects and Toxicity】
Carbonic anhydrase inhibitors are avidly bound by carbonic anhydrase and, accordingly, tissues rich in this enzyme will have higher concentrations of carbonic anhydrase inhibitors following systemic administration. /Carbonic Anhydrase Inhibitors/
Inhibitors of Carbonic Anhydrase. Drug: acetazolamide; Oral Absorption: nearly complete; Plasma Half-Life: 6-9 hours; and Route of Elimination: renal excretion of intact drug. /From table/
ACETAZOLAMIDE RELATED TO RESPONSE IN RABBIT; KIDNEY RESPONSE, MEASURED BY MONITORING URINE FLOW & NA ELIMINATION, URINE FLOW & NA ELIMINATION OCCUR IMMEDIATELY AFTER INJECTION CORRELATED WITH LOG DOSE. [KUNKA RL, MATTOCKS AM; J PHARM SCI 68 (3): 347-349 (1979)] PubMed Abstract
IV BOLUS INJECTIONS OF (14)C-LABELED, ACETAZOLAMIDE WERE MADE IN RABBITS. PLASMA, URINE, & WASHED RED BLOOD CELL CONCN WERE MEASURED, THE LATTER INDICATING BOUND DRUG. [KUNKA RL, MATTOCKS AM; J PHARM SCI 68 (3): 342-346 (1979)] PubMed Abstract
ACETAZOLAMIDE BINDING TO HIGH ACTIVITY AND LOW ACTIVITY CARBONIC ANHYDRASE ISOENZYMES WAS STUDIED; MAX. BINDING CAPACIETIES OF 17.2 & 155 MUM WERE FOUND. [BAYNE WF ET AL; J PHARM SCI 68 (7): 912-3 (1979)] PubMed Abstract
Acetazolamide is a carbonic anhydrase inhibitor commonly used to reduce intraocular pressure (IOP). /This is the first report/ of a pharmacokinetic study of acetazolamide in a patient undergoing continuous ambulatory peritoneal dialysis (CAPD). The patient was a Type I diabetic with end stage renal disease (ESRD) undergoing CAPD who received acetazolamide for elevated IOP after surgery for a detached retina. Serum acetazolamide concn were measured prior to a 250 mg oral dose and 12 additional times during a 24 hr dosing interval. All dialysate effluent was collected and assayed for acetazolamide. Serum concn at the beginning and end during the dosing interval were 18 and 17 mcg/ml, respectively, with a maximum concn of 27 mcg/ml at 6.5 hr (therapeutic range = 5-10 mcg/ml). The elimination half life was prolonged, 28.5 compared to that seen in subjects with normal renal function (5-10 hr). CAPD did not remove a clinically significant amount of drug (17.1 mg, or 6.8% of dose recovered in dialysate). The patient was very lethargic during therapy, a possible manifestation of acetazolamide toxicity. Marked reduction in acetazolamide dosage (in this /instance/ 125 mg/day) would be required to prevent drug accumulation and toxicity. [Schwenk MH et al; Adv Perit Dial 10: 44-6 (1994)] PubMed Abstract

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】
No Data

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