Details
Stereochemistry | ACHIRAL |
Molecular Formula | C4H6N4O3S2 |
Molecular Weight | 222.245 |
Optical Activity | UNSPECIFIED |
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 | |
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
PubMed
Title | Date | PubMed |
---|---|---|
Renal failure associated with acetazolamide therapy for glaucoma. | 1975 Apr |
|
Management strategies for refractory localization-related seizures. | 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 |
|
Carbonic anhydrase inhibitors for hypercapnic ventilatory failure in chronic obstructive pulmonary disease. | 2001 |
|
Treatment options for sleep apnoea. | 2001 |
|
[A case of potassium-sensitive periodic paralysis with cardiac dysrhythmia controlled with imipramine and acetazolamide]. | 2001 Apr |
|
Abolition of pentagastrin-stimulated alkaline tide using the carbonic anhydrase inhibitor 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 |
|
Benign intracranial hypertension: correlation of cerebral blood flow with disease severity. | 2001 Apr |
|
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 |
|
Grossly false applanation tonometry associated with interface fluid in susceptible LASIK patients. | 2001 Aug |
|
Acetazolamide treatment for infantile central sleep apnea. | 2001 Aug |
|
Physiological and molecular biological characterization of intracellular carbonic anhydrase from the marine diatom Phaeodactylum tricornutum. | 2001 Aug |
|
Cerebrovascular reserve in patients with carotid occlusive disease assessed by stable xenon-enhanced ct cerebral blood flow and transcranial Doppler. | 2001 Aug |
|
Dissolution of poorly crystalline apatite crystals by osteoclasts determined on artificial thin-film apatite. | 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 |
|
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 |
|
Assessment of cerebrovascular reactivity with functional magnetic resonance imaging: comparison of CO(2) and breath holding. | 2001 Jan |
|
[Evaluation of time dependency of the acetazolamide effect on cerebral hemodynamics as measured by 99mTc-ECD single-photon emission computed tomography]. | 2001 Jan |
|
Discordance between cerebral oxygen and glucose metabolism, and hemodynamics in a mitochondrial encephalomyopathy, lactic acidosis, and strokelike episode patient. | 2001 Jul |
|
Anticonvulsant medications. | 2001 Jul |
|
Reliable measurement of mouse intraocular pressure by a servo-null micropipette system. | 2001 Jul |
|
Anticonvulsant activity of omeprazole in rats. | 2001 Jul |
|
High-altitude illness. | 2001 Jul 12 |
|
Extracellular carbonic anhydrase in the dogfish, Squalus acanthias: a role in CO2 excretion. | 2001 Jul-Aug |
|
Indomethacin activates carbonic anhydrase and antagonizes the effect of the specific carbonic anhydrase inhibitor acetazolamide, by a direct mechanism of action. | 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 |
|
Hypokalaemic periodic paralysis type 2 caused by mutations at codon 672 in the muscle sodium channel gene SCN4A. | 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 |
|
Acute mountain sickness score and hypoxemia. | 2001 May |
|
HCO3- potentiates the cAMP-dependent secretory response of the human distal colon through a DIDS-sensitive pathway. | 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 |
|
Correlation of cerebrovascular reserve as measured by acetazolamide-challenged SPECT with angiographic flow patterns and intra- or extracranial arterial stenosis. | 2001 May |
|
Identification and localization of acid-base transporters in the conjunctival epithelium. | 2001 May |
|
Nongenomic effect of testosterone on chloride secretion in cultured rat efferent duct epithelia. | 2001 May |
|
Characterisation of carbonic anhydrase in Plasmodium falciparum. | 2001 May 15 |
|
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 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
Tue Oct 22 00:46:34 UTC 2019
by
admin
on
Tue Oct 22 00:46:34 UTC 2019
|
Record UNII |
O3FX965V0I
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Brand Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Code | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Brand Name | English | ||
|
Systematic Name | English | ||
|
Brand Name | English | ||
|
Code | English | ||
|
Systematic Name | English | ||
|
Common Name | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
WHO-VATC |
QS01EC01
Created by
admin on Tue Oct 22 00:46:34 UTC 2019 , Edited by admin on Tue Oct 22 00:46:34 UTC 2019
|
||
|
NCI_THESAURUS |
C448
Created by
admin on Tue Oct 22 00:46:34 UTC 2019 , Edited by admin on Tue Oct 22 00:46:34 UTC 2019
|
||
|
NDF-RT |
N0000175517
Created by
admin on Tue Oct 22 00:46:34 UTC 2019 , Edited by admin on Tue Oct 22 00:46:34 UTC 2019
|
||
|
CFR |
21 CFR 522.44
Created by
admin on Tue Oct 22 00:46:34 UTC 2019 , Edited by admin on Tue Oct 22 00:46:34 UTC 2019
|
||
|
NCI_THESAURUS |
C29577
Created by
admin on Tue Oct 22 00:46:34 UTC 2019 , Edited by admin on Tue Oct 22 00:46:34 UTC 2019
|
||
|
WHO-ATC |
S01EC01
Created by
admin on Tue Oct 22 00:46:34 UTC 2019 , Edited by admin on Tue Oct 22 00:46:34 UTC 2019
|
||
|
NDF-RT |
N0000000235
Created by
admin on Tue Oct 22 00:46:34 UTC 2019 , Edited by admin on Tue Oct 22 00:46:34 UTC 2019
|
||
|
WHO-ESSENTIAL MEDICINES LIST |
21.4
Created by
admin on Tue Oct 22 00:46:34 UTC 2019 , Edited by admin on Tue Oct 22 00:46:34 UTC 2019
|
||
|
CFR |
21 CFR 520.28
Created by
admin on Tue Oct 22 00:46:34 UTC 2019 , Edited by admin on Tue Oct 22 00:46:34 UTC 2019
|
||
|
LIVERTOX |
9
Created by
admin on Tue Oct 22 00:46:34 UTC 2019 , Edited by admin on Tue Oct 22 00:46:34 UTC 2019
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
481
Created by
admin on Tue Oct 22 00:46:34 UTC 2019 , Edited by admin on Tue Oct 22 00:46:34 UTC 2019
|
PRIMARY | |||
|
M1322
Created by
admin on Tue Oct 22 00:46:34 UTC 2019 , Edited by admin on Tue Oct 22 00:46:34 UTC 2019
|
PRIMARY | Merck Index | ||
|
59-66-5
Created by
admin on Tue Oct 22 00:46:34 UTC 2019 , Edited by admin on Tue Oct 22 00:46:34 UTC 2019
|
PRIMARY | |||
|
CHEMBL20
Created by
admin on Tue Oct 22 00:46:34 UTC 2019 , Edited by admin on Tue Oct 22 00:46:34 UTC 2019
|
PRIMARY | |||
|
SUB05219MIG
Created by
admin on Tue Oct 22 00:46:34 UTC 2019 , Edited by admin on Tue Oct 22 00:46:34 UTC 2019
|
PRIMARY | |||
|
D000086
Created by
admin on Tue Oct 22 00:46:34 UTC 2019 , Edited by admin on Tue Oct 22 00:46:34 UTC 2019
|
PRIMARY | |||
|
ACETAZOLAMIDE
Created by
admin on Tue Oct 22 00:46:34 UTC 2019 , Edited by admin on Tue Oct 22 00:46:34 UTC 2019
|
PRIMARY | |||
|
59-66-5
Created by
admin on Tue Oct 22 00:46:34 UTC 2019 , Edited by admin on Tue Oct 22 00:46:34 UTC 2019
|
PRIMARY | |||
|
59-66-5
Created by
admin on Tue Oct 22 00:46:34 UTC 2019 , Edited by admin on Tue Oct 22 00:46:34 UTC 2019
|
PRIMARY | |||
|
1986
Created by
admin on Tue Oct 22 00:46:34 UTC 2019 , Edited by admin on Tue Oct 22 00:46:34 UTC 2019
|
PRIMARY | |||
|
ACETAZOLAMIDE
Created by
admin on Tue Oct 22 00:46:34 UTC 2019 , Edited by admin on Tue Oct 22 00:46:34 UTC 2019
|
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. | ||
|
59-66-5
Created by
admin on Tue Oct 22 00:46:34 UTC 2019 , Edited by admin on Tue Oct 22 00:46:34 UTC 2019
|
PRIMARY | |||
|
200-440-5
Created by
admin on Tue Oct 22 00:46:34 UTC 2019 , Edited by admin on Tue Oct 22 00:46:34 UTC 2019
|
PRIMARY | |||
|
C28809
Created by
admin on Tue Oct 22 00:46:34 UTC 2019 , Edited by admin on Tue Oct 22 00:46:34 UTC 2019
|
PRIMARY | |||
|
DB00819
Created by
admin on Tue Oct 22 00:46:34 UTC 2019 , Edited by admin on Tue Oct 22 00:46:34 UTC 2019
|
PRIMARY | |||
|
6792
Created by
admin on Tue Oct 22 00:46:34 UTC 2019 , Edited by admin on Tue Oct 22 00:46:34 UTC 2019
|
PRIMARY | |||
|
167
Created by
admin on Tue Oct 22 00:46:34 UTC 2019 , Edited by admin on Tue Oct 22 00:46:34 UTC 2019
|
PRIMARY | RxNorm |
Related Record | Type | Details | ||
---|---|---|---|---|
|
TARGET -> INHIBITOR |
Ki
|
||
|
TARGET -> INHIBITOR |
Ki
|
||
|
BASIS OF STRENGTH->SUBSTANCE |
ASSAY (TITRATION)
EP
|
||
|
TARGET -> INHIBITOR |
Ki
|
||
|
SALT/SOLVATE -> PARENT | |||
|
TRANSPORTER -> INHIBITOR | |||
|
TARGET -> INHIBITOR |
Ki
|
||
|
TRANSPORTER -> INHIBITOR | |||
|
TRANSPORTER -> INHIBITOR | |||
|
TARGET -> INHIBITOR |
Ki
|
||
|
TARGET -> INHIBITOR |
Ki
|
||
|
BINDER->LIGAND |
BINDING
|
||
|
SALT/SOLVATE -> PARENT | |||
|
TARGET -> INHIBITOR |
Ki
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
---|---|---|---|---|---|---|
Volume of Distribution | PHARMACOKINETIC |
|
|
|||
Biological Half-life | PHARMACOKINETIC |
|
|
|||