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Details

Stereochemistry ACHIRAL
Molecular Formula C4H6N4O3S2
Molecular Weight 222.245
Optical Activity NONE
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

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
DIAMOX
Preventing
DIAMOX

Cmax

ValueDoseCo-administeredAnalytePopulation
1313 ng/mL
15 mg 1 times / day multiple, oral
ACETAZOLAMIDE plasma
Homo sapiens
776 ng/mL
15 mg 1 times / day multiple, oral
ACETAZOLAMIDE blood
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
6735 ng × h/mL
15 mg 1 times / day multiple, oral
ACETAZOLAMIDE plasma
Homo sapiens
52130 ng × h/mL
15 mg 1 times / day multiple, oral
ACETAZOLAMIDE blood
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
13.1 h
15 mg 1 times / day multiple, oral
ACETAZOLAMIDE plasma
Homo sapiens
42.4 h
15 mg 1 times / day multiple, oral
ACETAZOLAMIDE blood
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
5%
unknown, oral
ACETAZOLAMIDE plasma
Homo sapiens

Doses

AEs

Drug as perpetrator​

Drug as victim

PubMed

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.