U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C4H6N4O3S2
Molecular Weight 222.2478
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ACETAZOLAMIDE

SMILES

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

-5.18572802E11
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

-5.18572802E11
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
[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
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
[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
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
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
Depolarization of the liver cell membrane by metformin.
2001 Aug 6
Beta-adrenergic blocker therapy and the trabecular meshwork.
2001 Feb
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
Cerebral vasoreactivity and internal carotid artery flow help to identify patients at risk for hyperperfusion after carotid endarterectomy.
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
Medical support on a Himalayan expedition.
2001 Jun
[Mountaineering and altitude sickness].
2001 Jun
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
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
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

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
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 [EP MONOGRAPH]
Common Name English
ACETAZOLAMIDE [HSDB]
Common Name English
PHONURIT
Common Name English
ACETAZOLAMIDE [EP]
Common 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 [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
ACETAZOLAMIDE [USP MONOGRAPH]
Common 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 Fri Jun 25 20:52:48 UTC 2021 , Edited by admin on Fri Jun 25 20:52:48 UTC 2021
NCI_THESAURUS C448
Created by admin on Fri Jun 25 20:52:48 UTC 2021 , Edited by admin on Fri Jun 25 20:52:48 UTC 2021
NDF-RT N0000175517
Created by admin on Fri Jun 25 20:52:48 UTC 2021 , Edited by admin on Fri Jun 25 20:52:48 UTC 2021
CFR 21 CFR 522.44
Created by admin on Fri Jun 25 20:52:47 UTC 2021 , Edited by admin on Fri Jun 25 20:52:47 UTC 2021
NCI_THESAURUS C29577
Created by admin on Fri Jun 25 20:52:48 UTC 2021 , Edited by admin on Fri Jun 25 20:52:48 UTC 2021
WHO-ATC S01EC01
Created by admin on Fri Jun 25 20:52:47 UTC 2021 , Edited by admin on Fri Jun 25 20:52:47 UTC 2021
NDF-RT N0000000235
Created by admin on Fri Jun 25 20:52:48 UTC 2021 , Edited by admin on Fri Jun 25 20:52:48 UTC 2021
WHO-ESSENTIAL MEDICINES LIST 21.4
Created by admin on Fri Jun 25 20:52:48 UTC 2021 , Edited by admin on Fri Jun 25 20:52:48 UTC 2021
CFR 21 CFR 520.28
Created by admin on Fri Jun 25 20:52:47 UTC 2021 , Edited by admin on Fri Jun 25 20:52:47 UTC 2021
LIVERTOX 9
Created by admin on Fri Jun 25 20:52:48 UTC 2021 , Edited by admin on Fri Jun 25 20:52:48 UTC 2021
Code System Code Type Description
LACTMED
Acetazolamide
Created by admin on Fri Jun 25 20:52:48 UTC 2021 , Edited by admin on Fri Jun 25 20:52:48 UTC 2021
PRIMARY
INN
481
Created by admin on Fri Jun 25 20:52:48 UTC 2021 , Edited by admin on Fri Jun 25 20:52:48 UTC 2021
PRIMARY
MERCK INDEX
M1322
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PRIMARY Merck Index
ChEMBL
CHEMBL20
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PRIMARY
FDA UNII
O3FX965V0I
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PRIMARY
EVMPD
SUB05219MIG
Created by admin on Fri Jun 25 20:52:47 UTC 2021 , Edited by admin on Fri Jun 25 20:52:47 UTC 2021
PRIMARY
MESH
D000086
Created by admin on Fri Jun 25 20:52:48 UTC 2021 , Edited by admin on Fri Jun 25 20:52:48 UTC 2021
PRIMARY
WIKIPEDIA
ACETAZOLAMIDE
Created by admin on Fri Jun 25 20:52:48 UTC 2021 , Edited by admin on Fri Jun 25 20:52:48 UTC 2021
PRIMARY
CAS
59-66-5
Created by admin on Fri Jun 25 20:52:47 UTC 2021 , Edited by admin on Fri Jun 25 20:52:47 UTC 2021
PRIMARY
HSDB
3002
Created by admin on Fri Jun 25 20:52:48 UTC 2021 , Edited by admin on Fri Jun 25 20:52:48 UTC 2021
PRIMARY
PUBCHEM
1986
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PRIMARY
USP_CATALOG
1005004
Created by admin on Fri Jun 25 20:52:48 UTC 2021 , Edited by admin on Fri Jun 25 20:52:48 UTC 2021
PRIMARY USP-RS
WHO INTERNATIONAL PHARMACPOEIA
ACETAZOLAMIDE
Created by admin on Fri Jun 25 20:52:48 UTC 2021 , Edited by admin on Fri Jun 25 20:52:48 UTC 2021
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 Fri Jun 25 20:52:48 UTC 2021 , Edited by admin on Fri Jun 25 20:52:48 UTC 2021
PRIMARY
ECHA (EC/EINECS)
200-440-5
Created by admin on Fri Jun 25 20:52:48 UTC 2021 , Edited by admin on Fri Jun 25 20:52:48 UTC 2021
PRIMARY
NCI_THESAURUS
C28809
Created by admin on Fri Jun 25 20:52:48 UTC 2021 , Edited by admin on Fri Jun 25 20:52:48 UTC 2021
PRIMARY
DRUG BANK
DB00819
Created by admin on Fri Jun 25 20:52:47 UTC 2021 , Edited by admin on Fri Jun 25 20:52:47 UTC 2021
PRIMARY
DRUG CENTRAL
56
Created by admin on Fri Jun 25 20:52:48 UTC 2021 , Edited by admin on Fri Jun 25 20:52:48 UTC 2021
PRIMARY
IUPHAR
6792
Created by admin on Fri Jun 25 20:52:48 UTC 2021 , Edited by admin on Fri Jun 25 20:52:48 UTC 2021
PRIMARY
RXCUI
167
Created by admin on Fri Jun 25 20:52:48 UTC 2021 , Edited by admin on Fri Jun 25 20:52:48 UTC 2021
PRIMARY RxNorm