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Details

Stereochemistry ACHIRAL
Molecular Formula C4H6N4O3S2
Molecular Weight 222.245
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ACETAZOLAMIDE

SMILES

CC(=O)NC1=NN=C(S1)S(N)(=O)=O

InChI

InChIKey=BZKPWHYZMXOIDC-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

Description

Acetazolamide, usually sold under the trade name Diamox in some countries. DIAMOX is used for adjunctive treatment of: chronic simple (open-angle) glaucoma, secondary glaucoma, and preoperatively in acute angle-closure glaucoma where delay of surgery is desired in order to lower intraocular pressure. DIAMOX is also indicated for the prevention or amelioration of symptoms associated with acute mountain sickness despite gradual ascent. DIAMOX is an enzyme inhibitor that acts specifically on carbonic anhydrase, the enzyme that catalyzes the reversible reaction involving the hydration of carbon dioxide and the dehydration of carbonic acid. In the eye, this inhibitory action of acetazolamide decreases the secretion of aqueous humor and results in a drop in intraocular pressure, a reaction considered desirable in cases of glaucoma and even in certain non-glaucomatous conditions. Evidence seems to indicate that DIAMOX has utility as an adjuvant in treatment of certain dysfunctions of the central nervous system (e.g., epilepsy). The diuretic effect of DIAMOX is due to its action in the kidney on the reversible reaction involving hydration of carbon dioxide and dehydration of carbonic acid. The result is renal loss of HCO3 ion, which carries out sodium, water, and potassium. It is on the World Health Organization's List of Essential Medicines, a list of the most important medications needed in a basic health system.

CNS Activity

Approval Year

PubMed

PubMed

TitleDatePubMed
Management strategies for refractory localization-related seizures.
2001
[Therapeutic use of potassium citrate].
2001
Herpes simplex virus bullous keratitis misdiagnosed as a case of pseudophakic bullous keratopathy with secondary glaucoma: an unusual presentation.
2001
Vasoconstrictive drugs increase carbonic anhydrase I in vascular smooth muscle while vasodilating drugs reduce the activity of this isozyme by a direct mechanism of action.
2001
Calcification in the planula and polyp of the hydroid Hydractinia symbiolongicarpus (Cnidaria, Hydrozoa).
2001 Aug
Acetazolamide poisoning in a toddler.
2001 Aug
Grossly false applanation tonometry associated with interface fluid in susceptible LASIK patients.
2001 Aug
Evaluation of blood flow in the cerebral microcirculation: analysis of the refill kinetics during ultrasound contrast agent infusion.
2001 Aug
[A coronary artery bypass grafting using cardiopulmonary bypass with intraaortic balloon pumping in patient with low cardiac function combined with cerebral vascular disease].
2001 Aug
Acetazolamide treatment for infantile central sleep apnea.
2001 Aug
Physiological and molecular biological characterization of intracellular carbonic anhydrase from the marine diatom Phaeodactylum tricornutum.
2001 Aug
Minocycline and Pseudotumor cerebri: The well-known but well-kept secret.
2001 Aug
Cerebrovascular reserve in patients with carotid occlusive disease assessed by stable xenon-enhanced ct cerebral blood flow and transcranial Doppler.
2001 Aug
Carbonic anhydrase isozyme distribution and characterization in metabolic fiber types of the dorsal levator muscle of the blue crab, Callinectes sapidus.
2001 Aug 1
Depolarization of the liver cell membrane by metformin.
2001 Aug 6
Preferential acetazolamide-induced vasodilation based on vessel size and organ: confirmation of peripheral vasodilation with use of colored microspheres.
2001 Jul
Liquid and ion transport by fetal airway and lung epithelia of mice deficient in sodium-potassium-2-chloride transporter.
2001 Jul
Discordance between cerebral oxygen and glucose metabolism, and hemodynamics in a mitochondrial encephalomyopathy, lactic acidosis, and strokelike episode patient.
2001 Jul
Reliable measurement of mouse intraocular pressure by a servo-null micropipette system.
2001 Jul
Medical support on a Himalayan expedition.
2001 Jun
Acute mountain sickness score and hypoxemia.
2001 May
Dilatation of renal artery distal to stenosis demonstrated using acetazolamide Tc-99m MAG3 scintigraphy.
2001 Sep
Quantitative cerebral blood flow imaging in a patient with the Heidenhain variant of Creutzfeldt-Jakob disease.
2001 Sep
Timolol may inhibit aqueous humor secretion by cAMP-independent action on ciliary epithelial cells.
2001 Sep
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Glaucoma: The recommended dosage is 1 capsule (500 mg) two times a day. Usually 1 capsule is administered in the morning and 1 capsule in the evening. It may be necessary to adjust the dose, but it has usually been found that dosage in excess of 2 capsules (1 g) does not produce an increased effect Acute Mountain Sickness: Dosage is 500 mg to 1000 mg daily, in divided doses using tablets or extended-release capsules as appropriate. In circumstances of rapid ascent, such as in rescue or military operations, the higher dose level of 1000 mg is recommended
Route of Administration: Oral
In Vitro Use Guide
In both, piriform and entorhinal cortices (PC and EC, respectively), acetazolamide (10 uM): (i) reduced the duration and the interval of ccurrence of ictal discharges along with the associated ripples and fast ripples; (ii) decreased the interval of occurrence of interictal discharges and the rates of associated fast ripples; and (iii)diminished the duration and amplitude of pharmacologically isolated GABAergic events while increasing their interval of occurrence.
Name Type Language
ACETAZOLAMIDE
EP   HSDB   INN   MART.   MI   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD   WHO-IP  
INN  
Official Name English
DEFILTRAN
Brand Name English
ATENEZO
Brand Name English
ACETAZOLAMIDE [USP-RS]
Common Name English
ACETAZOLAMIDE [INN]
Common Name English
ACETAZOLAMIDE [MART.]
Common Name English
NEPHRAMIDE
Common Name English
ACETAZOLAMIDE [HSDB]
Common Name English
PHONURIT
Common Name English
ACETAZOLAMIDE [EP]
Common Name English
FONURIT
Brand Name English
ACETAZOLAMIDE [WHO-IP]
Common Name English
ACETAZOLAMIDE [MI]
Common Name English
ACETAMOX
Brand Name English
ACETAZOLAMIDE [JAN]
Common Name English
DIDOC
Brand Name English
DIAMOX
Common Name English
DIURIWAS
Brand Name English
NSC-145177
Code English
N-(5-(AMINOSULFONYL)-1,3,4-THIADIAZOL-2-YL)ACETAMIDE
Systematic Name English
ACETAZOLAMIDE [USP]
Common Name English
ACETAZOLAMIDE [WHO-DD]
Common Name English
ACETAZOLAMIDE [VANDF]
Common Name English
ACETAZOLAMIDE [ORANGE BOOK]
Common Name English
GLAUPAX
Brand Name English
EDEMOX
Brand Name English
ACETAMIDE, N-(5-(AMINOSULFONYL)-1,3,4-THIADIAZOL-2-YL)-
Systematic Name English
DONMOX
Brand Name English
L 579486
Code English
N-(5-SULFAMOYL-1,3,4-THIADIAZOL-2-YL)ACETAMIDE
Systematic Name English
ACETAZOLAMIDUM [WHO-IP LATIN]
Common Name English
Classification Tree Code System Code
WHO-VATC QS01EC01
Created by admin on Tue Mar 06 10:29:31 UTC 2018 , Edited by admin on Tue Mar 06 10:29:31 UTC 2018
NDF-RT N0000175517
Created by admin on Tue Mar 06 10:29:31 UTC 2018 , Edited by admin on Tue Mar 06 10:29:31 UTC 2018
CFR 21 CFR 522.44
Created by admin on Tue Mar 06 10:29:31 UTC 2018 , Edited by admin on Tue Mar 06 10:29:31 UTC 2018
WHO-ATC S01EC01
Created by admin on Tue Mar 06 10:29:31 UTC 2018 , Edited by admin on Tue Mar 06 10:29:31 UTC 2018
NDF-RT N0000000235
Created by admin on Tue Mar 06 10:29:31 UTC 2018 , Edited by admin on Tue Mar 06 10:29:31 UTC 2018
WHO-ESSENTIAL MEDICINES LIST 21.4
Created by admin on Tue Mar 06 10:29:31 UTC 2018 , Edited by admin on Tue Mar 06 10:29:31 UTC 2018
CFR 21 CFR 520.28
Created by admin on Tue Mar 06 10:29:31 UTC 2018 , Edited by admin on Tue Mar 06 10:29:31 UTC 2018
LIVERTOX 9
Created by admin on Tue Mar 06 10:29:31 UTC 2018 , Edited by admin on Tue Mar 06 10:29:31 UTC 2018
Code System Code Type Description
INN
481
Created by admin on Tue Mar 06 10:29:31 UTC 2018 , Edited by admin on Tue Mar 06 10:29:31 UTC 2018
PRIMARY
MERCK INDEX
M1322
Created by admin on Tue Mar 06 10:29:31 UTC 2018 , Edited by admin on Tue Mar 06 10:29:31 UTC 2018
PRIMARY Merck Index
LactMed
59-66-5
Created by admin on Tue Mar 06 10:29:31 UTC 2018 , Edited by admin on Tue Mar 06 10:29:31 UTC 2018
PRIMARY
ChEMBL
CHEMBL20
Created by admin on Tue Mar 06 10:29:31 UTC 2018 , Edited by admin on Tue Mar 06 10:29:31 UTC 2018
PRIMARY
EVMPD
SUB05219MIG
Created by admin on Tue Mar 06 10:29:31 UTC 2018 , Edited by admin on Tue Mar 06 10:29:31 UTC 2018
PRIMARY
MESH
D000086
Created by admin on Tue Mar 06 10:29:31 UTC 2018 , Edited by admin on Tue Mar 06 10:29:31 UTC 2018
PRIMARY
WIKIPEDIA
ACETAZOLAMIDE
Created by admin on Tue Mar 06 10:29:31 UTC 2018 , Edited by admin on Tue Mar 06 10:29:31 UTC 2018
PRIMARY
CAS
59-66-5
Created by admin on Tue Mar 06 10:29:31 UTC 2018 , Edited by admin on Tue Mar 06 10:29:31 UTC 2018
PRIMARY
HSDB
59-66-5
Created by admin on Tue Mar 06 10:29:31 UTC 2018 , Edited by admin on Tue Mar 06 10:29:31 UTC 2018
PRIMARY
PUBCHEM
1986
Created by admin on Tue Mar 06 10:29:31 UTC 2018 , Edited by admin on Tue Mar 06 10:29:31 UTC 2018
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
ACETAZOLAMIDE
Created by admin on Tue Mar 06 10:29:31 UTC 2018 , Edited by admin on Tue Mar 06 10:29:31 UTC 2018
PRIMARY Description: A white, or almost white, crystalline powder; odourless. Solubility: Very slightly soluble in water; slightly soluble in ethanol (~750 g/l) TS; practically insoluble in ether R. Category: Carbonic anhydrase inhibitor. Storage: Acetazolamide should be kept in a well-closed container. Definition: Acetazolamide contains not less than 99.0% and not more than 101.0% of C4H6N4O3S2, calculated with reference to the dried substance.
EPA CompTox
59-66-5
Created by admin on Tue Mar 06 10:29:31 UTC 2018 , Edited by admin on Tue Mar 06 10:29:31 UTC 2018
PRIMARY
ECHA (EC/EINECS)
200-440-5
Created by admin on Tue Mar 06 10:29:31 UTC 2018 , Edited by admin on Tue Mar 06 10:29:31 UTC 2018
PRIMARY
NCI_THESAURUS
C28809
Created by admin on Tue Mar 06 10:29:31 UTC 2018 , Edited by admin on Tue Mar 06 10:29:31 UTC 2018
PRIMARY
DRUG BANK
DB00819
Created by admin on Tue Mar 06 10:29:31 UTC 2018 , Edited by admin on Tue Mar 06 10:29:31 UTC 2018
PRIMARY
IUPHAR
6792
Created by admin on Tue Mar 06 10:29:31 UTC 2018 , Edited by admin on Tue Mar 06 10:29:31 UTC 2018
PRIMARY
RXCUI
167
Created by admin on Tue Mar 06 10:29:31 UTC 2018 , Edited by admin on Tue Mar 06 10:29:31 UTC 2018
PRIMARY RxNorm