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Details

Stereochemistry ACHIRAL
Molecular Formula C5H8N4O3S2
Molecular Weight 236.272
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of METHAZOLAMIDE

SMILES

CN1N=C(S\C1=N\C(C)=O)S(N)(=O)=O

InChI

InChIKey=FLOSMHQXBMRNHR-QPJJXVBHSA-N
InChI=1S/C5H8N4O3S2/c1-3(10)7-4-9(2)8-5(13-4)14(6,11)12/h1-2H3,(H2,6,11,12)/b7-4+

HIDE SMILES / InChI

Molecular Formula C5H8N4O3S2
Molecular Weight 236.272
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description

Methazolamide is topical carbonic anhydrase inhibitor. Methazolamide is indicated for the reduction of elevated intraocular pressure in patients with open-angle glaucoma or ocular hypertension who are insufficiently responsive to beta-blockers. Methazolamide is a sulfonamide derivative; however, it does not have any clinically significant antimicrobial properties. Although methazolamide achieves a high concentration in the cerebrospinal fluid, it is not-considered an effective anticonvulsant. Methazolamide has a weak and transient diuretic effect, therefore use results in an increase in urinary volume, with excretion of sodium, potassium and chloride. Methazolamide is a potent inhibitor of carbonic anhydrase. Inhibition of carbonic anhydrase in the ciliary processes of the eye decreases aqueous humor secretion, presumably by slowing the formation of bicarbonate ions with subsequent reduction in sodium and fluid transport. Methazolamide is used for treatment of chronic open-angle glaucoma and acute angle-closure glaucoma.

CNS Activity

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
Treatment of essential tremor with methazolamide.
1991 Oct
Measuring drug concentrations using pulsatile microdialysis: theory and method development in vitro.
2005 Apr 11
Expression of a novel carbonic anhydrase, CA XIII, in normal and neoplastic colorectal mucosa.
2005 Apr 18
Proton-mediated feedback inhibition of presynaptic calcium channels at the cone photoreceptor synapse.
2005 Apr 20
Carbonic anhydrase inhibitors. Zonisamide is an effective inhibitor of the cytosolic isozyme II and mitochondrial isozyme V: solution and X-ray crystallographic studies.
2005 May 2
Functional interaction of carbonic anhydrase and chloride/bicarbonate exchange in human platelets.
2005 Nov
Effects of low-dose methazolamide on the control of breathing in cats.
2006
Carbonic anhydrase inhibitors: cloning and sulfonamide inhibition studies of a carboxyterminal truncated alpha-carbonic anhydrase from Helicobacter pylori.
2006 Apr 15
Expression, purification, kinetic, and structural characterization of an alpha-class carbonic anhydrase from Aedes aegypti (AaCA1).
2006 Aug
[Diuretic therapy in heart failure].
2006 Jan-Feb
Carbonic anhydrases and mucosal vanilloid receptors help mediate the hyperemic response to luminal CO2 in rat duodenum.
2006 Jul
Degradation and effects of the potential mosquito larvicides methazolamide and acetazolamide in sheepshead minnow (Cyprinodon variegatus).
2006 Jul
The carbonic anhydrase inhibitors methazolamide and acetazolamide have different effects on the hypoxic ventilatory response in the anaesthetized cat.
2006 Jul 15
Epithelial carbonic anhydrases facilitate PCO2 and pH regulation in rat duodenal mucosa.
2006 Jun 15
Mirtazapine in the treatment of essential tremor: an open-label, observer-blind study.
2006 Mar
Carbonic anhydrase inhibitors: DNA cloning and inhibition studies of the alpha-carbonic anhydrase from Helicobacter pylori, a new target for developing sulfonamide and sulfamate gastric drugs.
2006 Mar 23
Topical dorzolamide for the treatment of cystoid macular edema in patients with retinitis pigmentosa.
2006 May
Inhibition profiling of human carbonic anhydrase II by high-throughput screening of structurally diverse, biologically active compounds.
2006 Oct
The development of topically acting carbonic anhydrase inhibitors as anti-glaucoma agents.
2007
Inhibition of hypoxia-induced calcium responses in pulmonary arterial smooth muscle by acetazolamide is independent of carbonic anhydrase inhibition.
2007 Apr
PAT-1 (Slc26a6) is the predominant apical membrane Cl-/HCO3- exchanger in the upper villous epithelium of the murine duodenum.
2007 Apr
Statement on high-altitude illnesses. An Advisory Committee Statement (ACS).
2007 Apr 1
Carbonic anhydrase inhibitors: cloning, characterization, and inhibition studies of the cytosolic isozyme III with sulfonamides.
2007 Dec 1
Direct non-cyclooxygenase-2 targets of celecoxib and their potential relevance for cancer therapy.
2007 Dec 3
Carbonic anhydrase inhibition prevents and reverts cardiomyocyte hypertrophy.
2007 Feb 15
Carbonic anhydrase inhibitors. DNA cloning, characterization, and inhibition studies of the human secretory isoform VI, a new target for sulfonamide and sulfamate inhibitors.
2007 Jan 25
Topical inhibition of nasal carbonic anhydrase affects the CO2 detection threshold in rats.
2007 Mar
The development of topically acting carbonic anhydrase inhibitors as antiglaucoma agents.
2008
The alpha and beta classes carbonic anhydrases from Helicobacter pylori as novel drug targets.
2008
CO2 chemosensing in rat oesophagus.
2008 Dec
Carbonic anhydrase II and alveolar fluid reabsorption during hypercapnia.
2008 Jan
Rational use of the fixed combination of dorzolamide - timolol in the management of raised intraocular pressure and glaucoma.
2008 Jun
Pharmacological impact on loop gain properties to prevent irregular breathing.
2008 Mar
Recent advances in pharmacotherapy of glaucoma.
2008 Oct
Inhibitors of cytochrome c release with therapeutic potential for Huntington's disease.
2008 Sep 17
Acetazolamide reversibly inhibits water conduction by aquaporin-4.
2009 Apr
Studies on bicarbonate transporters and carbonic anhydrase in porcine nonpigmented ciliary epithelium.
2009 Apr
QSAR studies for the inhibition of the transmembrane carbonic anhydrase isozyme XIV with sulfonamides using PRECLAV software.
2009 Apr
Molecular cloning, characterization, and inhibition studies of the Rv1284 beta-carbonic anhydrase from Mycobacterium tuberculosis with sulfonamides and a sulfamate.
2009 Apr 23
Functional coupling of the downregulated in adenoma Cl-/base exchanger DRA and the apical Na+/H+ exchangers NHE2 and NHE3.
2009 Feb
Carbonic anhydrase inhibitors: inhibition of the beta-class enzyme from the yeast Saccharomyces cerevisiae with sulfonamides and sulfamates.
2009 Feb 1
Carbonic anhydrase inhibitors. Comparison of chlorthalidone, indapamide, trichloromethiazide, and furosemide X-ray crystal structures in adducts with isozyme II, when several water molecules make the difference.
2009 Feb 1
Design of a carbonic anhydrase IX active-site mimic to screen inhibitors for possible anticancer properties.
2009 Feb 17
Carbonic anhydrase inhibitors. Inhibition and homology modeling studies of the fungal beta-carbonic anhydrase from Candida albicans with sulfonamides.
2009 Jul 1
Carbonic anhydrase inhibitors. Inhibition studies of a coral secretory isoform by sulfonamides.
2009 Jul 15
Titration calorimetry standards and the precision of isothermal titration calorimetry data.
2009 Jun 18
Methazolamide and melatonin inhibit mitochondrial cytochrome C release and are neuroprotective in experimental models of ischemic injury.
2009 May
Carbonic anhydrase inhibitors. Cloning, characterization, and inhibition studies of a new beta-carbonic anhydrase from Mycobacterium tuberculosis.
2009 May 14
Evaluation of the therapeutic potential of carbonic anhydrase inhibitors in two animal models of dystrophin deficient muscular dystrophy.
2009 Nov 1
Methazolamide does not impair respiratory work performance in anesthetized rabbits.
2009 Sep
Patents

Sample Use Guides

In Vivo Use Guide
Usual Adult Dose for Glaucoma 50 to 100 mg orally 2 or 3 times a day
Route of Administration: Oral
In Vitro Use Guide
Methazolamide (0.1 mM) inhibited acid-induced [CO(2)](t) increase in mice.
Substance Class Chemical
Created
by admin
on Tue Oct 22 00:41:15 UTC 2019
Edited
by admin
on Tue Oct 22 00:41:15 UTC 2019
Record UNII
W733B0S9SD
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
METHAZOLAMIDE
HSDB   INN   JAN   MART.   MI   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD  
INN  
Official Name English
METHAZOLAMIDE [HSDB]
Common Name English
METHAZOLAMIDE [WHO-DD]
Common Name English
METHAZOLAMIDE [INN]
Common Name English
ACETAMIDE, N-(5-(AMINOSULFONYL)-3-METHYL-1,3,4-THIADIAZOL-2(3H)-YLIDENE)-
Systematic Name English
METHAZOLAMIDE [VANDF]
Common Name English
METHAZOLAMIDE [USP-RS]
Common Name English
NEPTAZANE
Brand Name English
N-(4-METHYL-2-SULFAMOYL-.DELTA.(SUP 2)-1,3,4-THIADIAZOLIN-5-YLIDENE)ACETAMIDE
Common Name English
METHAZOLAMIDE [JAN]
Common Name English
VVP808
Code English
METHAZOLAMIDE [MI]
Common Name English
NEPTAZANEAT
Common Name English
METHENAMIDE
Common Name English
VVP-808
Code English
L-584601
Code English
METHAZOLAMIDE [MART.]
Common Name English
METHAZOLAMIDE [ORANGE BOOK]
Common Name English
METHAZOLAMIDE [USP]
Common Name English
Classification Tree Code System Code
LIVERTOX 614
Created by admin on Tue Oct 22 00:41:15 UTC 2019 , Edited by admin on Tue Oct 22 00:41:15 UTC 2019
NCI_THESAURUS C29577
Created by admin on Tue Oct 22 00:41:15 UTC 2019 , Edited by admin on Tue Oct 22 00:41:15 UTC 2019
WHO-VATC QS01EC05
Created by admin on Tue Oct 22 00:41:15 UTC 2019 , Edited by admin on Tue Oct 22 00:41:15 UTC 2019
WHO-ATC S01EC05
Created by admin on Tue Oct 22 00:41:15 UTC 2019 , Edited by admin on Tue Oct 22 00:41:15 UTC 2019
NCI_THESAURUS C448
Created by admin on Tue Oct 22 00:41:15 UTC 2019 , Edited by admin on Tue Oct 22 00:41:15 UTC 2019
Code System Code Type Description
EPA CompTox
554-57-4
Created by admin on Tue Oct 22 00:41:15 UTC 2019 , Edited by admin on Tue Oct 22 00:41:15 UTC 2019
PRIMARY
MESH
D008704
Created by admin on Tue Oct 22 00:41:15 UTC 2019 , Edited by admin on Tue Oct 22 00:41:15 UTC 2019
PRIMARY
EVMPD
SUB08843MIG
Created by admin on Tue Oct 22 00:41:15 UTC 2019 , Edited by admin on Tue Oct 22 00:41:15 UTC 2019
PRIMARY
WIKIPEDIA
METHAZOLAMIDE
Created by admin on Tue Oct 22 00:41:15 UTC 2019 , Edited by admin on Tue Oct 22 00:41:15 UTC 2019
PRIMARY
IUPHAR
6828
Created by admin on Tue Oct 22 00:41:15 UTC 2019 , Edited by admin on Tue Oct 22 00:41:15 UTC 2019
PRIMARY
ECHA (EC/EINECS)
209-066-7
Created by admin on Tue Oct 22 00:41:15 UTC 2019 , Edited by admin on Tue Oct 22 00:41:15 UTC 2019
PRIMARY
MERCK INDEX
M7304
Created by admin on Tue Oct 22 00:41:15 UTC 2019 , Edited by admin on Tue Oct 22 00:41:15 UTC 2019
PRIMARY Merck Index
ChEMBL
CHEMBL19
Created by admin on Tue Oct 22 00:41:15 UTC 2019 , Edited by admin on Tue Oct 22 00:41:15 UTC 2019
PRIMARY
INN
882
Created by admin on Tue Oct 22 00:41:15 UTC 2019 , Edited by admin on Tue Oct 22 00:41:15 UTC 2019
PRIMARY
HSDB
554-57-4
Created by admin on Tue Oct 22 00:41:15 UTC 2019 , Edited by admin on Tue Oct 22 00:41:15 UTC 2019
PRIMARY
DRUG BANK
DB00703
Created by admin on Tue Oct 22 00:41:15 UTC 2019 , Edited by admin on Tue Oct 22 00:41:15 UTC 2019
PRIMARY
RXCUI
6826
Created by admin on Tue Oct 22 00:41:15 UTC 2019 , Edited by admin on Tue Oct 22 00:41:15 UTC 2019
PRIMARY RxNorm
CAS
554-57-4
Created by admin on Tue Oct 22 00:41:15 UTC 2019 , Edited by admin on Tue Oct 22 00:41:15 UTC 2019
PRIMARY
NCI_THESAURUS
C61318
Created by admin on Tue Oct 22 00:41:15 UTC 2019 , Edited by admin on Tue Oct 22 00:41:15 UTC 2019
PRIMARY
LactMed
554-57-4
Created by admin on Tue Oct 22 00:41:15 UTC 2019 , Edited by admin on Tue Oct 22 00:41:15 UTC 2019
PRIMARY
PUBCHEM
4100
Created by admin on Tue Oct 22 00:41:15 UTC 2019 , Edited by admin on Tue Oct 22 00:41:15 UTC 2019
PRIMARY
Related Record Type Details
TRANSPORTER -> INHIBITOR
TARGET -> INHIBITOR
TARGET -> INHIBITOR
BINDER->LIGAND
BINDING
TRANSPORTER -> INHIBITOR
TARGET -> INHIBITOR
TARGET -> INHIBITOR
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC