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
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
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 Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL205 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11430635 |
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Target ID: CHEMBL3729 Sources: https://www.ncbi.nlm.nih.gov/pubmed/?term=18336310 |
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Target ID: CHEMBL3242 Sources: https://www.ncbi.nlm.nih.gov/pubmed/?term=18336310 |
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Target ID: CHEMBL261 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11430635 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Palliative | DIAMOX Approved UseFor 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 Date1953 |
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Preventing | DIAMOX Approved UseFor 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 Date1953 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
776 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27300254 |
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 |
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1313 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27300254 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
52130 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27300254 |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27300254 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
42.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27300254 |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27300254 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
5% |
unknown, oral |
ACETAZOLAMIDE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse 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... |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
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
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
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OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
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Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical 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
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
weak |
PubMed
Title | Date | PubMed |
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Renal failure associated with acetazolamide therapy for glaucoma. | 1975 Apr |
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[Salicylism and glaucoma: reciprocal augmentation of the toxicity of acetazolamide and acetylsalicylic acid]. | 1999 Feb |
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Acetazolamide-responsive periodic ataxia induced by amiodarone. | 1999 Mar |
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Acetazolamide-induced Gerstmann syndrome. | 1999 Oct-Nov |
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Acetazolamide and enalapril combination offers complete protection from nitric oxide-deficient stroke in stroke-prone spontaneously hypertensive rats. | 2000 Jun |
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Cerebellar Ataxia. | 2000 May |
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Management strategies for refractory localization-related seizures. | 2001 |
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[Therapeutic use of potassium citrate]. | 2001 |
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Herpes simplex virus bullous keratitis misdiagnosed as a case of pseudophakic bullous keratopathy with secondary glaucoma: an unusual presentation. | 2001 |
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Diuretic therapy for newborn infants with posthemorrhagic ventricular dilatation. | 2001 |
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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 |
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[A case of potassium-sensitive periodic paralysis with cardiac dysrhythmia controlled with imipramine and acetazolamide]. | 2001 Apr |
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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 |
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Benign intracranial hypertension: correlation of cerebral blood flow with disease severity. | 2001 Apr |
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Calcification in the planula and polyp of the hydroid Hydractinia symbiolongicarpus (Cnidaria, Hydrozoa). | 2001 Aug |
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Acetazolamide poisoning in a toddler. | 2001 Aug |
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Grossly false applanation tonometry associated with interface fluid in susceptible LASIK patients. | 2001 Aug |
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Evaluation of blood flow in the cerebral microcirculation: analysis of the refill kinetics during ultrasound contrast agent infusion. | 2001 Aug |
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[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 |
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Minocycline and Pseudotumor cerebri: The well-known but well-kept secret. | 2001 Aug |
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Cerebrovascular reserve in patients with carotid occlusive disease assessed by stable xenon-enhanced ct cerebral blood flow and transcranial Doppler. | 2001 Aug |
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Carbonic anhydrase isozyme distribution and characterization in metabolic fiber types of the dorsal levator muscle of the blue crab, Callinectes sapidus. | 2001 Aug 1 |
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Beta-adrenergic blocker therapy and the trabecular meshwork. | 2001 Feb |
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Effect of familial hypertension on glomerular hemodynamics and tubulo-glomerular feedback after uninephrectomy. | 2001 Feb |
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Indapamide, a thiazide-like diuretic, decreases bone resorption in vitro. | 2001 Feb |
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Long-term follow-up of asymptomatic patients with major artery occlusion: rate of symptomatic change and evaluation of cerebral hemodynamics. | 2001 Feb |
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In vivo evidence for K(Ca) channel opening properties of acetazolamide in the human vasculature. | 2001 Jan |
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Theta rhythm of hippocampal CA1 neuron activity: gating by GABAergic synaptic depolarization. | 2001 Jan |
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Pharmacological prevention of acute mountain sickness. Same ascent rates must be used to assess effectiveness of different doses of acetazolamide. | 2001 Jan 6 |
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Pharmacological prevention of acute mountain sickness. Many climbers and trekkers find acetazolamide 500 mg/day to be useful. | 2001 Jan 6 |
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Preferential acetazolamide-induced vasodilation based on vessel size and organ: confirmation of peripheral vasodilation with use of colored microspheres. | 2001 Jul |
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Liquid and ion transport by fetal airway and lung epithelia of mice deficient in sodium-potassium-2-chloride transporter. | 2001 Jul |
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Cerebral vasoreactivity and internal carotid artery flow help to identify patients at risk for hyperperfusion after carotid endarterectomy. | 2001 Jul |
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Reliable measurement of mouse intraocular pressure by a servo-null micropipette system. | 2001 Jul |
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High-altitude illness. | 2001 Jul 12 |
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Extracellular carbonic anhydrase in the dogfish, Squalus acanthias: a role in CO2 excretion. | 2001 Jul-Aug |
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Medical support on a Himalayan expedition. | 2001 Jun |
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Acetazolamide in women with catamenial epilepsy. | 2001 Jun |
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Langerhans' cell histiocytosis presenting as intracranial hypertension. | 2001 Jun |
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Serous macular detachments in a patient with IgM paraproteinemia: an optical coherence tomography study. | 2001 Jun |
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Correlation of optic nerve head tomography with visual field sensitivity in papilledema. | 2001 Jun |
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Pharmacological enhancement of synaptic efficacy, spatial learning, and memory through carbonic anhydrase activation in rats. | 2001 Jun |
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Hypokalaemic periodic paralysis type 2 caused by mutations at codon 672 in the muscle sodium channel gene SCN4A. | 2001 Jun |
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Model of ionic transport for bovine ciliary epithelium: effects of acetazolamide and HCO. | 2001 Jun |
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Sporadic late onset paroxysmal cerebellar ataxia in four unrelated patients: a new disease? | 2001 Mar |
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Characterization of carbonic anhydrase from Neisseria gonorrhoeae. | 2001 Mar |
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Revisiting the question, "is the acetazolamide test valid for quantitative assessment of maximal cerebral autoregulatory vasodilation?". | 2001 May |
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Identification and localization of acid-base transporters in the conjunctival epithelium. | 2001 May |
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 Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25937211
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.
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C448
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NCI_THESAURUS |
C29577
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100000085045
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429ZT169UH
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DBSALT000539
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m1322
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31163
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91406
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DTXSID00162031
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CHEMBL20
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13290219
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SUB00251MIG
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C61622
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1424-27-7
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429ZT169UH
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ACTIVE MOIETY
SUBSTANCE RECORD