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Substance Name: Acetazolamide [USP:INN:BAN:JAN]
RN: 59-66-5
UNII: O3FX965V0I
InChIKey: BZKPWHYZMXOIDC-UHFFFAOYSA-N

Note

  • One of the CARBONIC ANHYDRASE INHIBITORS that is sometimes effective against absence seizures. It is sometimes useful also as an adjunct in the treatment of tonic-clonic, myoclonic, and atonic seizures, particularly in women whose seizures occur or are exacerbated at specific times in the menstrual cycle. However, its usefulness is transient often because of rapid development of tolerance. Its antiepileptic effect may be due to its inhibitory effect on brain carbonic anhydrase, which leads to an increased transneuronal chloride gradient, increased chloride current, and increased inhibition. (From Smith and Reynard, Textbook of Pharmacology, 1991, p337)

Molecular Formula

  • C4-H6-N4-O3-S2

Molecular Weight

  • 222.2484
 

Classification Codes

  • Anticonvulsants
  • Carbonic Anhydrase Inhibitor
  • Carbonic Anhydrase Inhibitors
  • Central Nervous System Agents
  • Diuretics
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Human Data
  • Natriuretic Agents
  • Reproductive Effect

Names and Synonyms

Name of Substance

  • Acetazolamide
  • Acetazolamide [USP:INN:BAN:JAN]

MeSH Heading

  • Acetazolamide

Synonyms

  • 1,3,4-Thiadiazole-2-sulfonamide, 5-acetamido-
  • 2-Acetamido-5-sulfonamido-1,3,4-thiadiazole
  • 2-Acetylamino-1,3,4-thiadiazole-5-sulfonamide
  • 5-Acetamide-1,3,4-thiadiazole-2-sulfonamide
  • 6063
  • Acetamide, N-(5-(aminosulfonyl)-1,3,4-thiadiazol-2-yl)-
  • Acetamidothiadiazolesulfonamide
  • Acetamox
  • Acetazolamid
  • Acetazolamida
  • Acetazolamida [INN-Spanish]
  • Acetazolamide
  • Acetazolamidum
  • Acetazolamidum [INN-Latin]
  • AI3-52458
  • Carbonic Anhydrase Inhibitor No. 6063
  • CCRIS 5811
  • Cidamex
  • Defiltran
  • Dehydratin
  • Diacarb
  • Diakarb
  • Diamox
  • Diamox sequels
  • Didoc
  • Diluran
  • Diuramid
  • Diureticum-holzinger
  • Diuriwas
  • Diutazol
  • Donmox
  • Duiramid
  • Edemox
  • EINECS 200-440-5
  • Eumicton
  • Fonurit
  • Glaumox
  • Glaupax
  • Glupax
  • HSDB 3002
  • N-(5-(Aminosulfonyl)-1,3,4-thiadiazol-2-yl)acetamide
  • N-(5-Sulfamoyl-1,3,4-thiadiazol-2-yl)acetamide
  • Natrionex
  • Nephramid
  • Nephramide
  • NSC 145177
  • Phonurit
  • SK-acetazolamide
  • UNII-O3FX965V0I
  • Vetamox

Systematic Names

  • Acetamide, N-(5-(aminosulfonyl)-1,3,4-thiadiazol-2-yl)-
  • Acetamide, N-(5-sulfamoyl-1,3,4-thiadiazol-2-yl)-
  • Acetazolamide

Superlist Name

  • Acetazolamide

Registry Numbers

CAS Registry Number

  • 59-66-5

FDA UNII

  • O3FX965V0I

Other Registry Numbers

  • 5661-25-6
  • 8017-69-4

Related Registry Number

  • 1424-27-7 (mono-hydrochloride salt)

System Generated Number

  • 0000059665

Structure Descriptors

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)

InChIKey

BZKPWHYZMXOIDC-UHFFFAOYSA-N

Smiles

CC(=O)Nc1nnc(s1)S(=O)(=O)N

Toxicity

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.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 260.5 deg C   EXP
pKa Dissociation Constant 7.2 (none)   EXP
log P (octanol-water) -0.26 (none)   EXP
Water Solubility 980 mg/L 30 EXP
Vapor Pressure 4.09E-09 mm Hg 25 EST
Henry's Law Constant 1.40E-16 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 8.02E-13 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.