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Details

Stereochemistry ACHIRAL
Molecular Formula C4H4N4O3S2.2Na
Molecular Weight 266.209
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ACETAZOLAMIDE DISODIUM

SMILES

[Na+].[Na+].CC(=O)[N-]C1=NN=C(S1)S([NH-])(=O)=O

InChI

InChIKey=KHMPLEYWJAOPQK-UHFFFAOYSA-M
InChI=1S/C4H5N4O3S2.2Na/c1-2(9)6-3-7-8-4(12-3)13(5,10)11;;/h1H3,(H2-,5,6,7,9,10,11);;/q-1;2*+1/p-1

HIDE SMILES / InChI
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
[Salicylism and glaucoma: reciprocal augmentation of the toxicity of acetazolamide and acetylsalicylic acid].
1999 Feb
Pseudotumor cerebri secondary to intermediate-dose cytarabine HCl.
1999 May
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
Acetazolamide treatment for infantile central sleep apnea.
2001 Aug
Long-term follow-up of asymptomatic patients with major artery occlusion: rate of symptomatic change and evaluation of cerebral hemodynamics.
2001 Feb
Influence of nitrovasodilators and cyclooxygenase inhibitors on cerebral vasoreactivity in conscious rabbits.
2001 Feb 2
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
Uveal effusion after cataract surgery: an echographic study.
2001 Jan
Role of basolateral carbonic anhydrase in proximal tubular fluid and bicarbonate absorption.
2001 Jan
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
Anticonvulsant medications.
2001 Jul
Idiopathic "benign" intracranial hypertension: case series and review.
2001 Jul
Clinical trial of acetazolamide in SCA6, with assessment using the Ataxia Rating Scale and body stabilometry.
2001 Jul
Anticonvulsant activity of omeprazole in rats.
2001 Jul
High-altitude illness.
2001 Jul 12
Long-term follow-up study on patients with sleep apnea syndrome.
2001 Jun
Correlation of optic nerve head tomography with visual field sensitivity in papilledema.
2001 Jun
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
Transient renal tubular acidosis in a neonate following transplacental acetazolamide.
2001 May
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.
Name Type Language
ACETAZOLAMIDE DISODIUM
Common Name English
ACETAMIDE, N-(5-(AMINOSULFONYL)-1,3,4-THIADIAZOL-2-YL)-, SODIUM SALT (1:2)
Common Name English
Code System Code Type Description
EPA CompTox
DTXSID80227218
Created by admin on Fri Dec 15 15:20:08 GMT 2023 , Edited by admin on Fri Dec 15 15:20:08 GMT 2023
PRIMARY
FDA UNII
8L25HEU6OJ
Created by admin on Fri Dec 15 15:20:08 GMT 2023 , Edited by admin on Fri Dec 15 15:20:08 GMT 2023
PRIMARY
PUBCHEM
71587279
Created by admin on Fri Dec 15 15:20:08 GMT 2023 , Edited by admin on Fri Dec 15 15:20:08 GMT 2023
PRIMARY
CAS
76382-16-6
Created by admin on Fri Dec 15 15:20:08 GMT 2023 , Edited by admin on Fri Dec 15 15:20:08 GMT 2023
PRIMARY