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Details

Stereochemistry ACHIRAL
Molecular Formula C4H5N4O3S2.Na
Molecular Weight 244.227
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ACETAZOLAMIDE SODIUM

SMILES

[Na+].CC(=O)NC1=NN=C(S1)S([NH-])(=O)=O

InChI

InChIKey=MRSXAJAOWWFZJJ-UHFFFAOYSA-M
InChI=1S/C4H6N4O3S2.Na/c1-2(9)6-3-7-8-4(12-3)13(5,10)11;/h1H3,(H3,5,6,7,9,10,11);/q;+1/p-1

HIDE SMILES / InChI

Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C4H6N4O3S2
Molecular Weight 222.245
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
DIAMOX

Approved Use

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.

Launch Date

1953
Preventing
DIAMOX

Approved Use

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.

Launch Date

1953
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
776 ng/mL
15 mg 1 times / day multiple, oral
dose: 15 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
ACETAZOLAMIDE blood
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
1313 ng/mL
15 mg 1 times / day multiple, oral
dose: 15 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
ACETAZOLAMIDE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
52130 ng × h/mL
15 mg 1 times / day multiple, oral
dose: 15 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
ACETAZOLAMIDE blood
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
6735 ng × h/mL
15 mg 1 times / day multiple, oral
dose: 15 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
ACETAZOLAMIDE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
42.4 h
15 mg 1 times / day multiple, oral
dose: 15 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
ACETAZOLAMIDE blood
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
13.1 h
15 mg 1 times / day multiple, oral
dose: 15 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
ACETAZOLAMIDE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
5%
unknown, oral
ACETAZOLAMIDE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
250 mg 4 times / day multiple, oral
Recommended
Dose: 250 mg, 4 times / day
Route: oral
Route: multiple
Dose: 250 mg, 4 times / day
Sources:
unhealthy, 21–80 years
n = 52
Health Status: unhealthy
Condition: elevated intraocular pressure
Age Group: 21–80 years
Sex: M+F
Population Size: 52
Sources:
Disc. AE: Leukopenia...
AEs leading to
discontinuation/dose reduction:
Leukopenia
Sources:
500 mg 4 times / day multiple, oral
Studied dose
Dose: 500 mg, 4 times / day
Route: oral
Route: multiple
Dose: 500 mg, 4 times / day
Sources:
unhealthy, 70 years
n = 1
Health Status: unhealthy
Condition: Diabetes | Chronic Renal Failure
Age Group: 70 years
Sex: F
Population Size: 1
Sources:
Other AEs: Metabolic acidosis, Coma...
Other AEs:
Metabolic acidosis (grade 3)
Coma
Sources:
AEs

AEs

AESignificanceDosePopulation
Leukopenia Disc. AE
250 mg 4 times / day multiple, oral
Recommended
Dose: 250 mg, 4 times / day
Route: oral
Route: multiple
Dose: 250 mg, 4 times / day
Sources:
unhealthy, 21–80 years
n = 52
Health Status: unhealthy
Condition: elevated intraocular pressure
Age Group: 21–80 years
Sex: M+F
Population Size: 52
Sources:
Coma
500 mg 4 times / day multiple, oral
Studied dose
Dose: 500 mg, 4 times / day
Route: oral
Route: multiple
Dose: 500 mg, 4 times / day
Sources:
unhealthy, 70 years
n = 1
Health Status: unhealthy
Condition: Diabetes | Chronic Renal Failure
Age Group: 70 years
Sex: F
Population Size: 1
Sources:
Metabolic acidosis grade 3
500 mg 4 times / day multiple, oral
Studied dose
Dose: 500 mg, 4 times / day
Route: oral
Route: multiple
Dose: 500 mg, 4 times / day
Sources:
unhealthy, 70 years
n = 1
Health Status: unhealthy
Condition: Diabetes | Chronic Renal Failure
Age Group: 70 years
Sex: F
Population Size: 1
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no [IC50 >10 uM]
no [IC50 >10 uM]
no [IC50 >10 uM]
no [IC50 >10 uM]
no [IC50 >10 uM]
no [IC50 >10 uM]
no [IC50 >133 uM]
no [IC50 >133 uM]
no [IC50 >133 uM]
no [IC50 >133 uM]
no [IC50 >5000 uM]
weak [IC50 425 uM]
weak [IC50 816 uM]
yes [IC50 75 uM]
yes
yes
yes
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
weak
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Management strategies for refractory localization-related seizures.
2001
Herpes simplex virus bullous keratitis misdiagnosed as a case of pseudophakic bullous keratopathy with secondary glaucoma: an unusual presentation.
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
Treatment options for sleep apnoea.
2001
[A case of potassium-sensitive periodic paralysis with cardiac dysrhythmia controlled with imipramine and 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
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
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
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
Indapamide, a thiazide-like diuretic, decreases bone resorption in vitro.
2001 Feb
Low-dose acetazolamide does affect respiratory muscle function in spontaneously breathing anesthetized rabbits.
2001 Feb
Influence of nitrovasodilators and cyclooxygenase inhibitors on cerebral vasoreactivity in conscious rabbits.
2001 Feb 2
[Evaluation of time dependency of the acetazolamide effect on cerebral hemodynamics as measured by 99mTc-ECD single-photon emission computed tomography].
2001 Jan
[Benign intracranial hypertension].
2001 Jan
[Central retinal artery occlusion--etiology, clinical picture, therapeutic possibilities].
2001 Jan
Quantitative volumetry in patients with carotid disease--effects of acetazolamide.
2001 Jan
Preferential acetazolamide-induced vasodilation based on vessel size and organ: confirmation of peripheral vasodilation with use of colored microspheres.
2001 Jul
Idiopathic "benign" intracranial hypertension: case series and review.
2001 Jul
Cerebral vasoreactivity and internal carotid artery flow help to identify patients at risk for hyperperfusion after carotid endarterectomy.
2001 Jul
High-altitude illness.
2001 Jul 12
Extracellular carbonic anhydrase in the dogfish, Squalus acanthias: a role in CO2 excretion.
2001 Jul-Aug
Medical support on a Himalayan expedition.
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
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
Heterosynaptic transformation of GABAergic gating in the hippocampus and effects of carbonic anhydrase inhibition.
2001 Mar
Remodeling the cellular profile of collecting ducts by chronic carbonic anhydrase inhibition.
2001 Mar
Acute mountain sickness score and hypoxemia.
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
Identification and localization of acid-base transporters in the conjunctival epithelium.
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
Patents

Patents

Sample Use Guides

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 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 Fri Dec 15 15:03:35 GMT 2023
Edited
by admin
on Fri Dec 15 15:03:35 GMT 2023
Record UNII
429ZT169UH
Record Status Validated (UNII)
Record Version
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Name Type Language
ACETAZOLAMIDE SODIUM
GREEN BOOK   JAN   MART.   ORANGE BOOK   VANDF   WHO-DD  
Common Name English
ACETAZOLAMIDE SODIUM SALT [MI]
Common Name English
ACETAZOLAMIDE SODIUM [GREEN BOOK]
Common Name English
ACETAZOLAMIDE SODIUM [JAN]
Common Name English
Acetazolamide sodium [WHO-DD]
Common Name English
ACETAZOLAMIDE SODIUM [MART.]
Common Name English
SODIUM ACETAZOLAMIDE
Common Name English
ACETAZOLAMIDE SODIUM [ORANGE BOOK]
Common Name English
N-(5-Sulfamoyl-1,3,4-thiadiazol-2-yl)acetamide monosodium salt
Common Name English
ACETAZOLAMIDE SODIUM [VANDF]
Common Name English
VETAMOX
Brand Name English
ACETAMIDE, N-(5-(AMINOSULFONYL)-1,3,4-THIADIAZOL-2-YL)-, MONOSODIUM SALT
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C448
Created by admin on Fri Dec 15 15:03:35 GMT 2023 , Edited by admin on Fri Dec 15 15:03:35 GMT 2023
NCI_THESAURUS C29577
Created by admin on Fri Dec 15 15:03:35 GMT 2023 , Edited by admin on Fri Dec 15 15:03:35 GMT 2023
Code System Code Type Description
SMS_ID
100000085045
Created by admin on Fri Dec 15 15:03:35 GMT 2023 , Edited by admin on Fri Dec 15 15:03:35 GMT 2023
PRIMARY
DAILYMED
429ZT169UH
Created by admin on Fri Dec 15 15:03:35 GMT 2023 , Edited by admin on Fri Dec 15 15:03:35 GMT 2023
PRIMARY
DRUG BANK
DBSALT000539
Created by admin on Fri Dec 15 15:03:35 GMT 2023 , Edited by admin on Fri Dec 15 15:03:35 GMT 2023
PRIMARY
MERCK INDEX
m1322
Created by admin on Fri Dec 15 15:03:35 GMT 2023 , Edited by admin on Fri Dec 15 15:03:35 GMT 2023
PRIMARY Merck Index
CHEBI
31163
Created by admin on Fri Dec 15 15:03:35 GMT 2023 , Edited by admin on Fri Dec 15 15:03:35 GMT 2023
PRIMARY
RXCUI
91406
Created by admin on Fri Dec 15 15:03:35 GMT 2023 , Edited by admin on Fri Dec 15 15:03:35 GMT 2023
PRIMARY RxNorm
EPA CompTox
DTXSID00162031
Created by admin on Fri Dec 15 15:03:35 GMT 2023 , Edited by admin on Fri Dec 15 15:03:35 GMT 2023
PRIMARY
ChEMBL
CHEMBL20
Created by admin on Fri Dec 15 15:03:35 GMT 2023 , Edited by admin on Fri Dec 15 15:03:35 GMT 2023
PRIMARY
PUBCHEM
13290219
Created by admin on Fri Dec 15 15:03:35 GMT 2023 , Edited by admin on Fri Dec 15 15:03:35 GMT 2023
PRIMARY
EVMPD
SUB00251MIG
Created by admin on Fri Dec 15 15:03:35 GMT 2023 , Edited by admin on Fri Dec 15 15:03:35 GMT 2023
PRIMARY
NCI_THESAURUS
C61622
Created by admin on Fri Dec 15 15:03:35 GMT 2023 , Edited by admin on Fri Dec 15 15:03:35 GMT 2023
PRIMARY
CAS
1424-27-7
Created by admin on Fri Dec 15 15:03:35 GMT 2023 , Edited by admin on Fri Dec 15 15:03:35 GMT 2023
PRIMARY
FDA UNII
429ZT169UH
Created by admin on Fri Dec 15 15:03:35 GMT 2023 , Edited by admin on Fri Dec 15 15:03:35 GMT 2023
PRIMARY
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