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
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)
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 |
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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 |
---|---|---|---|---|
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 |
|
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 |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 |
|
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 |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 |
|
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 |
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 Health Status: unhealthy Age Group: 21–80 years Sex: M+F 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 |
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 Health Status: unhealthy Age Group: 21–80 years Sex: M+F 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 |
|
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 |
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 |
---|---|---|
Renal failure associated with acetazolamide therapy for glaucoma. | 1975 Apr |
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Cerebellar Ataxia. | 2000 May |
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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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Treatment of typical absence seizures and related epileptic syndromes. | 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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Abolition of pentagastrin-stimulated alkaline tide using the carbonic anhydrase inhibitor acetazolamide. | 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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[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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Acetazolamide treatment for infantile central sleep apnea. | 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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Depolarization of the liver cell membrane by metformin. | 2001 Aug 6 |
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The effect of acetazolamide on the kinetics of four newer beta-lactams in the aqueous humor. | 2001 Feb |
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Renal interstitial atp responses to changes in arterial pressure during alterations in tubuloglomerular feedback activity. | 2001 Feb |
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Indapamide, a thiazide-like diuretic, decreases bone resorption in vitro. | 2001 Feb |
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Low-dose acetazolamide does affect respiratory muscle function in spontaneously breathing anesthetized rabbits. | 2001 Feb |
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Asymmetric subcellular mRNA distribution correlates with carbonic anhydrase activity in Acetabularia acetabulum. | 2001 Feb |
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The spray drying of acetazolamide as method to modify crystal properties and to improve compression behaviour. | 2001 Feb 1 |
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Influence of nitrovasodilators and cyclooxygenase inhibitors on cerebral vasoreactivity in conscious rabbits. | 2001 Feb 2 |
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[Evaluation of time dependency of the acetazolamide effect on cerebral hemodynamics as measured by 99mTc-ECD single-photon emission computed tomography]. | 2001 Jan |
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[Central retinal artery occlusion--etiology, clinical picture, therapeutic possibilities]. | 2001 Jan |
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Quantitative volumetry in patients with carotid disease--effects of acetazolamide. | 2001 Jan |
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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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Uveal effusion after cataract surgery: an echographic study. | 2001 Jan |
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Effects of enzyme and anion transport inhibitors on in vitro incorporation of inorganic carbon and calcium into endolymph and otoliths in salmon Oncorhynchus masou. | 2001 Jan |
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Role of basolateral carbonic anhydrase in proximal tubular fluid and bicarbonate absorption. | 2001 Jan |
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Use of acetazolamide to decrease cerebrospinal fluid production in chronically ventilated patients with ventriculopleural shunts. | 2001 Jan |
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Cardiovascular effects of hypercarbia in rainbow trout (Oncorhynchus mykiss): a role for externally oriented chemoreceptors. | 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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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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Discordance between cerebral oxygen and glucose metabolism, and hemodynamics in a mitochondrial encephalomyopathy, lactic acidosis, and strokelike episode patient. | 2001 Jul |
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Clinical trial of acetazolamide in SCA6, with assessment using the Ataxia Rating Scale and body stabilometry. | 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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Anticonvulsant activity of omeprazole in rats. | 2001 Jul |
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Extracellular carbonic anhydrase in the dogfish, Squalus acanthias: a role in CO2 excretion. | 2001 Jul-Aug |
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Long-term follow-up study on patients with sleep apnea syndrome. | 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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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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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 |
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Remodeling the cellular profile of collecting ducts by chronic carbonic anhydrase inhibition. | 2001 Mar |
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Transient renal tubular acidosis in a neonate following transplacental acetazolamide. | 2001 May |
|
Dilatation of renal artery distal to stenosis demonstrated using acetazolamide Tc-99m MAG3 scintigraphy. | 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
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Record UNII |
O3FX965V0I
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Record Status |
Validated (UNII)
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Classification Tree | Code System | Code | ||
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WHO-VATC |
QS01EC01
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NCI_THESAURUS |
C448
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NDF-RT |
N0000175517
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CFR |
21 CFR 522.44
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NCI_THESAURUS |
C29577
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WHO-ATC |
S01EC01
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NDF-RT |
N0000000235
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WHO-ESSENTIAL MEDICINES LIST |
21.4
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CFR |
21 CFR 520.28
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LIVERTOX |
NBK548664
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145177
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50634
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Acetazolamide
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CHEMBL20
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D000086
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ACETAZOLAMIDE
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59-66-5
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1986
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ACETAZOLAMIDE
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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. | ||
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DTXSID7022544
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200-440-5
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C28809
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PRIMARY | RxNorm |
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TARGET -> INHIBITOR |
Ki
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TRANSPORTER -> INHIBITOR | |||
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TARGET -> INHIBITOR |
Ki
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (TITRATION)
EP
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TRANSPORTER -> INHIBITOR | |||
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TARGET -> INHIBITOR |
Ki
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SALT/SOLVATE -> PARENT | |||
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TARGET -> INHIBITOR |
Ki
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TRANSPORTER -> INHIBITOR | |||
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TARGET -> INHIBITOR |
Ki
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TARGET -> INHIBITOR |
Ki
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BINDER->LIGAND |
BINDING
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SALT/SOLVATE -> PARENT | |||
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TARGET -> INHIBITOR |
Ki
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
UNSPECIFIED IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
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ACTIVE MOIETY |
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Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Volume of Distribution | PHARMACOKINETIC |
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Biological Half-life | PHARMACOKINETIC |
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