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
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.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
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 |
---|---|---|---|---|
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 |
|||
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 |
|
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 |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
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 |
---|---|---|
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 |
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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 |
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Benign intracranial hypertension: correlation of cerebral blood flow with disease severity. | 2001 Apr |
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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
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.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:03:35 GMT 2023
by
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on
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Record UNII |
429ZT169UH
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Record Status |
Validated (UNII)
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Record Version |
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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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SUB00251MIG
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ACTIVE MOIETY |