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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

Molecular Formula C4H6N4O3S2
Molecular Weight 222.245
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Renal failure associated with acetazolamide therapy for glaucoma.
1975 Apr
Management strategies for refractory localization-related seizures.
2001
Diuretic therapy for newborn infants with posthemorrhagic ventricular dilatation.
2001
Treatment of typical absence seizures and related epileptic syndromes.
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
Carbonic anhydrase inhibitors for hypercapnic ventilatory failure in chronic obstructive pulmonary disease.
2001
Treatment options for sleep apnoea.
2001
[A case of potassium-sensitive periodic paralysis with cardiac dysrhythmia controlled with imipramine and acetazolamide].
2001 Apr
Abolition of pentagastrin-stimulated alkaline tide using the carbonic anhydrase inhibitor acetazolamide.
2001 Apr
What factors are related to impairment of cerebrovascular reserve before and after arteriovenous malformation resection? A cerebral blood flow study using xenon-enhanced computed tomography.
2001 Apr
Benign intracranial hypertension: correlation of cerebral blood flow with disease severity.
2001 Apr
Preretinal neovascularization associated with acetazolamide-induced systemic acidosis in the neonatal rat.
2001 Apr
Calcification in the planula and polyp of the hydroid Hydractinia symbiolongicarpus (Cnidaria, Hydrozoa).
2001 Aug
Grossly false applanation tonometry associated with interface fluid in susceptible LASIK patients.
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
Cerebrovascular reserve in patients with carotid occlusive disease assessed by stable xenon-enhanced ct cerebral blood flow and transcranial Doppler.
2001 Aug
Dissolution of poorly crystalline apatite crystals by osteoclasts determined on artificial thin-film apatite.
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
Beta-adrenergic blocker therapy and the trabecular meshwork.
2001 Feb
The effect of acetazolamide on the kinetics of four newer beta-lactams in the aqueous humor.
2001 Feb
Assessment of cerebrovascular reactivity with functional magnetic resonance imaging: comparison of CO(2) and breath holding.
2001 Jan
[Evaluation of time dependency of the acetazolamide effect on cerebral hemodynamics as measured by 99mTc-ECD single-photon emission computed tomography].
2001 Jan
Discordance between cerebral oxygen and glucose metabolism, and hemodynamics in a mitochondrial encephalomyopathy, lactic acidosis, and strokelike episode patient.
2001 Jul
Anticonvulsant medications.
2001 Jul
Reliable measurement of mouse intraocular pressure by a servo-null micropipette system.
2001 Jul
Anticonvulsant activity of omeprazole in rats.
2001 Jul
High-altitude illness.
2001 Jul 12
Extracellular carbonic anhydrase in the dogfish, Squalus acanthias: a role in CO2 excretion.
2001 Jul-Aug
Indomethacin activates carbonic anhydrase and antagonizes the effect of the specific carbonic anhydrase inhibitor acetazolamide, by a direct mechanism of action.
2001 Jun
Long-term follow-up study on patients with sleep apnea syndrome.
2001 Jun
Acetazolamide in women with catamenial epilepsy.
2001 Jun
Langerhans' cell histiocytosis presenting as intracranial hypertension.
2001 Jun
Serous macular detachments in a patient with IgM paraproteinemia: an optical coherence tomography study.
2001 Jun
Correlation of optic nerve head tomography with visual field sensitivity in papilledema.
2001 Jun
Pharmacological enhancement of synaptic efficacy, spatial learning, and memory through carbonic anhydrase activation in rats.
2001 Jun
Hypokalaemic periodic paralysis type 2 caused by mutations at codon 672 in the muscle sodium channel gene SCN4A.
2001 Jun
Model of ionic transport for bovine ciliary epithelium: effects of acetazolamide and HCO.
2001 Jun
Sporadic late onset paroxysmal cerebellar ataxia in four unrelated patients: a new disease?
2001 Mar
Compromised hemodynamics associated with multipedicular lesions of cerebral arteries.
2001 Mar
Characterization of carbonic anhydrase from Neisseria gonorrhoeae.
2001 Mar
Acute mountain sickness score and hypoxemia.
2001 May
HCO3- potentiates the cAMP-dependent secretory response of the human distal colon through a DIDS-sensitive pathway.
2001 May
Transient renal tubular acidosis in a neonate following transplacental acetazolamide.
2001 May
Revisiting the question, "is the acetazolamide test valid for quantitative assessment of maximal cerebral autoregulatory vasodilation?".
2001 May
Correlation of cerebrovascular reserve as measured by acetazolamide-challenged SPECT with angiographic flow patterns and intra- or extracranial arterial stenosis.
2001 May
Identification and localization of acid-base transporters in the conjunctival epithelium.
2001 May
Nongenomic effect of testosterone on chloride secretion in cultured rat efferent duct epithelia.
2001 May
Characterisation of carbonic anhydrase in Plasmodium falciparum.
2001 May 15
Quantitative cerebral blood flow imaging in a patient with the Heidenhain variant of Creutzfeldt-Jakob disease.
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.
Substance Class Chemical
Created
by admin
on Tue Oct 22 00:46:34 UTC 2019
Edited
by admin
on Tue Oct 22 00:46:34 UTC 2019
Record UNII
O3FX965V0I
Record Status Validated (UNII)
Record Version
  • Download
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 Oct 22 00:46:34 UTC 2019 , Edited by admin on Tue Oct 22 00:46:34 UTC 2019
NCI_THESAURUS C448
Created by admin on Tue Oct 22 00:46:34 UTC 2019 , Edited by admin on Tue Oct 22 00:46:34 UTC 2019
NDF-RT N0000175517
Created by admin on Tue Oct 22 00:46:34 UTC 2019 , Edited by admin on Tue Oct 22 00:46:34 UTC 2019
CFR 21 CFR 522.44
Created by admin on Tue Oct 22 00:46:34 UTC 2019 , Edited by admin on Tue Oct 22 00:46:34 UTC 2019
NCI_THESAURUS C29577
Created by admin on Tue Oct 22 00:46:34 UTC 2019 , Edited by admin on Tue Oct 22 00:46:34 UTC 2019
WHO-ATC S01EC01
Created by admin on Tue Oct 22 00:46:34 UTC 2019 , Edited by admin on Tue Oct 22 00:46:34 UTC 2019
NDF-RT N0000000235
Created by admin on Tue Oct 22 00:46:34 UTC 2019 , Edited by admin on Tue Oct 22 00:46:34 UTC 2019
WHO-ESSENTIAL MEDICINES LIST 21.4
Created by admin on Tue Oct 22 00:46:34 UTC 2019 , Edited by admin on Tue Oct 22 00:46:34 UTC 2019
CFR 21 CFR 520.28
Created by admin on Tue Oct 22 00:46:34 UTC 2019 , Edited by admin on Tue Oct 22 00:46:34 UTC 2019
LIVERTOX 9
Created by admin on Tue Oct 22 00:46:34 UTC 2019 , Edited by admin on Tue Oct 22 00:46:34 UTC 2019
Code System Code Type Description
INN
481
Created by admin on Tue Oct 22 00:46:34 UTC 2019 , Edited by admin on Tue Oct 22 00:46:34 UTC 2019
PRIMARY
MERCK INDEX
M1322
Created by admin on Tue Oct 22 00:46:34 UTC 2019 , Edited by admin on Tue Oct 22 00:46:34 UTC 2019
PRIMARY Merck Index
LactMed
59-66-5
Created by admin on Tue Oct 22 00:46:34 UTC 2019 , Edited by admin on Tue Oct 22 00:46:34 UTC 2019
PRIMARY
ChEMBL
CHEMBL20
Created by admin on Tue Oct 22 00:46:34 UTC 2019 , Edited by admin on Tue Oct 22 00:46:34 UTC 2019
PRIMARY
EVMPD
SUB05219MIG
Created by admin on Tue Oct 22 00:46:34 UTC 2019 , Edited by admin on Tue Oct 22 00:46:34 UTC 2019
PRIMARY
MESH
D000086
Created by admin on Tue Oct 22 00:46:34 UTC 2019 , Edited by admin on Tue Oct 22 00:46:34 UTC 2019
PRIMARY
WIKIPEDIA
ACETAZOLAMIDE
Created by admin on Tue Oct 22 00:46:34 UTC 2019 , Edited by admin on Tue Oct 22 00:46:34 UTC 2019
PRIMARY
CAS
59-66-5
Created by admin on Tue Oct 22 00:46:34 UTC 2019 , Edited by admin on Tue Oct 22 00:46:34 UTC 2019
PRIMARY
HSDB
59-66-5
Created by admin on Tue Oct 22 00:46:34 UTC 2019 , Edited by admin on Tue Oct 22 00:46:34 UTC 2019
PRIMARY
PUBCHEM
1986
Created by admin on Tue Oct 22 00:46:34 UTC 2019 , Edited by admin on Tue Oct 22 00:46:34 UTC 2019
PRIMARY
WHO INTERNATIONAL PHARMACPOEIA
ACETAZOLAMIDE
Created by admin on Tue Oct 22 00:46:34 UTC 2019 , Edited by admin on Tue Oct 22 00:46:34 UTC 2019
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 Oct 22 00:46:34 UTC 2019 , Edited by admin on Tue Oct 22 00:46:34 UTC 2019
PRIMARY
ECHA (EC/EINECS)
200-440-5
Created by admin on Tue Oct 22 00:46:34 UTC 2019 , Edited by admin on Tue Oct 22 00:46:34 UTC 2019
PRIMARY
NCI_THESAURUS
C28809
Created by admin on Tue Oct 22 00:46:34 UTC 2019 , Edited by admin on Tue Oct 22 00:46:34 UTC 2019
PRIMARY
DRUG BANK
DB00819
Created by admin on Tue Oct 22 00:46:34 UTC 2019 , Edited by admin on Tue Oct 22 00:46:34 UTC 2019
PRIMARY
IUPHAR
6792
Created by admin on Tue Oct 22 00:46:34 UTC 2019 , Edited by admin on Tue Oct 22 00:46:34 UTC 2019
PRIMARY
RXCUI
167
Created by admin on Tue Oct 22 00:46:34 UTC 2019 , Edited by admin on Tue Oct 22 00:46:34 UTC 2019
PRIMARY RxNorm
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