Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C4H4N4O3S2.2Na |
| Molecular Weight | 266.209 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[Na+].[Na+].CC(=O)[N-]C1=NN=C(S1)S([NH-])(=O)=O
InChI
InChIKey=KHMPLEYWJAOPQK-UHFFFAOYSA-M
InChI=1S/C4H5N4O3S2.2Na/c1-2(9)6-3-7-8-4(12-3)13(5,10)11;;/h1H3,(H2-,5,6,7,9,10,11);;/q-1;2*+1/p-1
| 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 |
| Molecular Formula | Na |
| Molecular Weight | 22.98976928 |
| Charge | 1 |
| 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 |
|||
Target ID: CHEMBL3729 Sources: https://www.ncbi.nlm.nih.gov/pubmed/?term=18336310 |
|||
Target ID: CHEMBL3242 Sources: https://www.ncbi.nlm.nih.gov/pubmed/?term=18336310 |
|||
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 |
|---|---|---|---|---|
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 |
|---|---|---|
| Dilatation of renal artery distal to stenosis demonstrated using acetazolamide Tc-99m MAG3 scintigraphy. | 2001-09 |
|
| Quantitative cerebral blood flow imaging in a patient with the Heidenhain variant of Creutzfeldt-Jakob disease. | 2001-09 |
|
| Timolol may inhibit aqueous humor secretion by cAMP-independent action on ciliary epithelial cells. | 2001-09 |
|
| Depolarization of the liver cell membrane by metformin. | 2001-08-06 |
|
| Carbonic anhydrase isozyme distribution and characterization in metabolic fiber types of the dorsal levator muscle of the blue crab, Callinectes sapidus. | 2001-08-01 |
|
| Calcification in the planula and polyp of the hydroid Hydractinia symbiolongicarpus (Cnidaria, Hydrozoa). | 2001-08 |
|
| Acetazolamide poisoning in a toddler. | 2001-08 |
|
| Grossly false applanation tonometry associated with interface fluid in susceptible LASIK patients. | 2001-08 |
|
| Evaluation of blood flow in the cerebral microcirculation: analysis of the refill kinetics during ultrasound contrast agent infusion. | 2001-08 |
|
| [A coronary artery bypass grafting using cardiopulmonary bypass with intraaortic balloon pumping in patient with low cardiac function combined with cerebral vascular disease]. | 2001-08 |
|
| Acetazolamide treatment for infantile central sleep apnea. | 2001-08 |
|
| Physiological and molecular biological characterization of intracellular carbonic anhydrase from the marine diatom Phaeodactylum tricornutum. | 2001-08 |
|
| Minocycline and Pseudotumor cerebri: The well-known but well-kept secret. | 2001-08 |
|
| Cerebrovascular reserve in patients with carotid occlusive disease assessed by stable xenon-enhanced ct cerebral blood flow and transcranial Doppler. | 2001-08 |
|
| Dissolution of poorly crystalline apatite crystals by osteoclasts determined on artificial thin-film apatite. | 2001-08 |
|
| High-altitude illness. | 2001-07-12 |
|
| Preferential acetazolamide-induced vasodilation based on vessel size and organ: confirmation of peripheral vasodilation with use of colored microspheres. | 2001-07 |
|
| Liquid and ion transport by fetal airway and lung epithelia of mice deficient in sodium-potassium-2-chloride transporter. | 2001-07 |
|
| Discordance between cerebral oxygen and glucose metabolism, and hemodynamics in a mitochondrial encephalomyopathy, lactic acidosis, and strokelike episode patient. | 2001-07 |
|
| Anticonvulsant medications. | 2001-07 |
|
| Idiopathic "benign" intracranial hypertension: case series and review. | 2001-07 |
|
| Clinical trial of acetazolamide in SCA6, with assessment using the Ataxia Rating Scale and body stabilometry. | 2001-07 |
|
| Cerebral vasoreactivity and internal carotid artery flow help to identify patients at risk for hyperperfusion after carotid endarterectomy. | 2001-07 |
|
| Reliable measurement of mouse intraocular pressure by a servo-null micropipette system. | 2001-07 |
|
| Anticonvulsant activity of omeprazole in rats. | 2001-07 |
|
| Medical support on a Himalayan expedition. | 2001-06 |
|
| [Mountaineering and altitude sickness]. | 2001-06 |
|
| Indomethacin activates carbonic anhydrase and antagonizes the effect of the specific carbonic anhydrase inhibitor acetazolamide, by a direct mechanism of action. | 2001-06 |
|
| Long-term follow-up study on patients with sleep apnea syndrome. | 2001-06 |
|
| Acetazolamide in women with catamenial epilepsy. | 2001-06 |
|
| Langerhans' cell histiocytosis presenting as intracranial hypertension. | 2001-06 |
|
| Serous macular detachments in a patient with IgM paraproteinemia: an optical coherence tomography study. | 2001-06 |
|
| Correlation of optic nerve head tomography with visual field sensitivity in papilledema. | 2001-06 |
|
| Pharmacological enhancement of synaptic efficacy, spatial learning, and memory through carbonic anhydrase activation in rats. | 2001-06 |
|
| Hypokalaemic periodic paralysis type 2 caused by mutations at codon 672 in the muscle sodium channel gene SCN4A. | 2001-06 |
|
| Model of ionic transport for bovine ciliary epithelium: effects of acetazolamide and HCO. | 2001-06 |
|
| Acute mountain sickness score and hypoxemia. | 2001-05 |
|
| HCO3- potentiates the cAMP-dependent secretory response of the human distal colon through a DIDS-sensitive pathway. | 2001-05 |
|
| Transient renal tubular acidosis in a neonate following transplacental acetazolamide. | 2001-05 |
|
| [A case of potassium-sensitive periodic paralysis with cardiac dysrhythmia controlled with imipramine and acetazolamide]. | 2001-04 |
|
| Abolition of pentagastrin-stimulated alkaline tide using the carbonic anhydrase inhibitor acetazolamide. | 2001-04 |
|
| Sporadic late onset paroxysmal cerebellar ataxia in four unrelated patients: a new disease? | 2001-03 |
|
| Beta-adrenergic blocker therapy and the trabecular meshwork. | 2001-02 |
|
| Extracellular carbonic anhydrase in the dogfish, Squalus acanthias: a role in CO2 excretion. | 2001-01-30 |
|
| 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 |
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 |
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| Record Status |
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