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Details

Stereochemistry ACHIRAL
Molecular Formula C5H8N4O3S2
Molecular Weight 236.272
Optical Activity NONE
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 No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description
Curator's Comment: Description was created based on several sources, including https://www.drugs.com/pro/methazolamide.html

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
50.0 nM [Ki]
14.0 nM [Ki]
27.0 nM [Ki]
3.4 nM [Ki]
2.1 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Methazolamide

Approved Use

indicated in the treatment of ocular conditions where lowering intraocular pressure is likely to be of therapeutic benefit, such as chronic open-angle glaucoma, secondary glaucoma, and preoperatively in acute angle-closure glaucoma where lowering the intraocular pressure is desired before surgery.

Launch Date

1993
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
2.5 μg/mL
25 mg 2 times / day multiple, oral
dose: 25 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
METHAZOLAMIDE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
5.1 μg/mL
50 mg 2 times / day multiple, oral
dose: 50 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
METHAZOLAMIDE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
10.7 μg/mL
100 mg 2 times / day multiple, oral
dose: 100 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
METHAZOLAMIDE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
1130 μg × min/mL
25 mg 2 times / day multiple, oral
dose: 25 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
METHAZOLAMIDE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
2571 μg × min/mL
50 mg 2 times / day multiple, oral
dose: 50 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
METHAZOLAMIDE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
5418 μg × min/mL
100 mg 2 times / day multiple, oral
dose: 100 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
METHAZOLAMIDE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
14 h
steady-state, oral
METHAZOLAMIDE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
45%
25 mg 2 times / day multiple, oral
dose: 25 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
METHAZOLAMIDE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
100 mg 3 times / day multiple, oral
Highest studied dose
Dose: 100 mg, 3 times / day
Route: oral
Route: multiple
Dose: 100 mg, 3 times / day
Sources:
unhealthy, 67.5 years
n = 24
Health Status: unhealthy
Condition: Glaucoma
Age Group: 67.5 years
Sex: M+F
Population Size: 24
Sources:
Disc. AE: Loss of energy, Fatigue...
AEs leading to
discontinuation/dose reduction:
Loss of energy (2 patients)
Fatigue (2 patients)
Lethargy (2 patients)
Sources:
50 mg 2 times / day multiple, oral
Dose: 50 mg, 2 times / day
Route: oral
Route: multiple
Dose: 50 mg, 2 times / day
Co-administed with::
aspirin(high concentration)
Sources:
unhealthy
Disc. AE: Anorexia, Tachypnea...
AEs

AEs

AESignificanceDosePopulation
Fatigue 2 patients
Disc. AE
100 mg 3 times / day multiple, oral
Highest studied dose
Dose: 100 mg, 3 times / day
Route: oral
Route: multiple
Dose: 100 mg, 3 times / day
Sources:
unhealthy, 67.5 years
n = 24
Health Status: unhealthy
Condition: Glaucoma
Age Group: 67.5 years
Sex: M+F
Population Size: 24
Sources:
Lethargy 2 patients
Disc. AE
100 mg 3 times / day multiple, oral
Highest studied dose
Dose: 100 mg, 3 times / day
Route: oral
Route: multiple
Dose: 100 mg, 3 times / day
Sources:
unhealthy, 67.5 years
n = 24
Health Status: unhealthy
Condition: Glaucoma
Age Group: 67.5 years
Sex: M+F
Population Size: 24
Sources:
Loss of energy 2 patients
Disc. AE
100 mg 3 times / day multiple, oral
Highest studied dose
Dose: 100 mg, 3 times / day
Route: oral
Route: multiple
Dose: 100 mg, 3 times / day
Sources:
unhealthy, 67.5 years
n = 24
Health Status: unhealthy
Condition: Glaucoma
Age Group: 67.5 years
Sex: M+F
Population Size: 24
Sources:
Anorexia Disc. AE
50 mg 2 times / day multiple, oral
Dose: 50 mg, 2 times / day
Route: oral
Route: multiple
Dose: 50 mg, 2 times / day
Co-administed with::
aspirin(high concentration)
Sources:
unhealthy
Coma Disc. AE
50 mg 2 times / day multiple, oral
Dose: 50 mg, 2 times / day
Route: oral
Route: multiple
Dose: 50 mg, 2 times / day
Co-administed with::
aspirin(high concentration)
Sources:
unhealthy
Lethargy Disc. AE
50 mg 2 times / day multiple, oral
Dose: 50 mg, 2 times / day
Route: oral
Route: multiple
Dose: 50 mg, 2 times / day
Co-administed with::
aspirin(high concentration)
Sources:
unhealthy
Tachypnea Disc. AE
50 mg 2 times / day multiple, oral
Dose: 50 mg, 2 times / day
Route: oral
Route: multiple
Dose: 50 mg, 2 times / day
Co-administed with::
aspirin(high concentration)
Sources:
unhealthy
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
no
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Treatment of essential tremor with methazolamide.
1991 Oct
In vitro characterization of the erythrocyte distribution of methazolamide: a model of erythrocyte transport and binding kinetics.
1999 Feb
Simulation of the pharmacokinetic profile of methazolamide in blood: effect of erythrocyte carbonic anhydrase binding on drug disposition.
2002 Apr
Effects of anion and cation inhibitors and carbonic anhydrase inhibitors upon the activity of the gypsy moth (Lepidoptera: Lymantriidae) nucleo-polyhedrovirus.
2002 Apr
Forskolin-induced clearance of the fluorescent dye sulforhodamine from rat parotid intralobular duct lumen: visualization of the secretory function under a confocal laser scanning microscope.
2002 Dec 1
Benefits and risks of pharmacological treatments for essential tremor.
2003
Focal CO2/H+ alters phrenic motor output response to chemical stimulation of cat pre-Botzinger complex in vivo.
2003 Jun
Carbonic anhydrase inhibitors are specific openers of skeletal muscle BK channel of K+-deficient rats.
2004 Apr
Carbonic anhydrase inhibitors. Inhibition of the prokariotic beta and gamma-class enzymes from Archaea with sulfonamides.
2004 Dec 20
Interactions of human organic anion transporters with diuretics.
2004 Mar
Carbonic anhydrase inhibitors: aromatic and heterocyclic sulfonamides incorporating adamantyl moieties with strong anticonvulsant activity.
2004 May 15
Carbonic anhydrase inhibitors. Inhibition of the membrane-bound human and bovine isozymes IV with sulfonamides.
2005 Feb 15
Mechanism of augmented duodenal HCO(3)(-) secretion after elevation of luminal CO(2).
2005 Mar
Functional interaction of carbonic anhydrase and chloride/bicarbonate exchange in human platelets.
2005 Nov
Carbonic anhydrase inhibitors: inhibition of the transmembrane isozyme XIV with sulfonamides.
2005 Sep 1
Expression, purification, kinetic, and structural characterization of an alpha-class carbonic anhydrase from Aedes aegypti (AaCA1).
2006 Aug
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
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
PAT-1 (Slc26a6) is the predominant apical membrane Cl-/HCO3- exchanger in the upper villous epithelium of the murine duodenum.
2007 Apr
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
The development of topically acting carbonic anhydrase inhibitors as antiglaucoma agents.
2008
Acetazolamide reversibly inhibits water conduction by aquaporin-4.
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. 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
Titration calorimetry standards and the precision of isothermal titration calorimetry data.
2009 Jun 18
Carbonic anhydrase inhibitors. Cloning, characterization, and inhibition studies of a new beta-carbonic anhydrase from Mycobacterium tuberculosis.
2009 May 14
Patents

Sample Use Guides

Usual Adult Dose for Glaucoma 50 to 100 mg orally 2 or 3 times a day
Route of Administration: Oral
Methazolamide (0.1 mM) inhibited acid-induced [CO(2)](t) increase in mice.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:13:11 GMT 2023
Edited
by admin
on Fri Dec 15 15:13:11 GMT 2023
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 [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
Acetamide, N-[5-(aminosulfonyl)-3-methyl-1,3,4-thiadiazol-2(3H)-ylidene]-, [N(E)]-
Systematic 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
Methazolamide [WHO-DD]
Common Name English
VVP808
Code English
METHAZOLAMIDE [MI]
Common Name English
NEPTAZANEAT
Common Name English
METHAZOLAMIDE [USP MONOGRAPH]
Common Name English
NSC-758426
Code English
[N(E)]-N-[5-(Aminosulfonyl)-3-methyl-1,3,4-thiadiazol-2(3H)-ylidene]acetamide
Systematic 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
Classification Tree Code System Code
LIVERTOX NBK548664
Created by admin on Fri Dec 15 15:13:11 GMT 2023 , Edited by admin on Fri Dec 15 15:13:11 GMT 2023
NCI_THESAURUS C29577
Created by admin on Fri Dec 15 15:13:11 GMT 2023 , Edited by admin on Fri Dec 15 15:13:11 GMT 2023
WHO-VATC QS01EC05
Created by admin on Fri Dec 15 15:13:11 GMT 2023 , Edited by admin on Fri Dec 15 15:13:11 GMT 2023
WHO-ATC S01EC05
Created by admin on Fri Dec 15 15:13:11 GMT 2023 , Edited by admin on Fri Dec 15 15:13:11 GMT 2023
NCI_THESAURUS C448
Created by admin on Fri Dec 15 15:13:11 GMT 2023 , Edited by admin on Fri Dec 15 15:13:11 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID1023281
Created by admin on Fri Dec 15 15:13:11 GMT 2023 , Edited by admin on Fri Dec 15 15:13:11 GMT 2023
PRIMARY
MESH
D008704
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PRIMARY
EVMPD
SUB08843MIG
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PRIMARY
RS_ITEM_NUM
1406005
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PRIMARY
DAILYMED
W733B0S9SD
Created by admin on Fri Dec 15 15:13:11 GMT 2023 , Edited by admin on Fri Dec 15 15:13:11 GMT 2023
PRIMARY
CHEBI
29202
Created by admin on Fri Dec 15 15:13:11 GMT 2023 , Edited by admin on Fri Dec 15 15:13:11 GMT 2023
PRIMARY
DRUG CENTRAL
1741
Created by admin on Fri Dec 15 15:13:11 GMT 2023 , Edited by admin on Fri Dec 15 15:13:11 GMT 2023
PRIMARY
WIKIPEDIA
METHAZOLAMIDE
Created by admin on Fri Dec 15 15:13:11 GMT 2023 , Edited by admin on Fri Dec 15 15:13:11 GMT 2023
PRIMARY
IUPHAR
6828
Created by admin on Fri Dec 15 15:13:11 GMT 2023 , Edited by admin on Fri Dec 15 15:13:11 GMT 2023
PRIMARY
CAS
2101958-72-7
Created by admin on Fri Dec 15 15:13:11 GMT 2023 , Edited by admin on Fri Dec 15 15:13:11 GMT 2023
ALTERNATIVE
ECHA (EC/EINECS)
209-066-7
Created by admin on Fri Dec 15 15:13:11 GMT 2023 , Edited by admin on Fri Dec 15 15:13:11 GMT 2023
PRIMARY
MERCK INDEX
m7304
Created by admin on Fri Dec 15 15:13:11 GMT 2023 , Edited by admin on Fri Dec 15 15:13:11 GMT 2023
PRIMARY Merck Index
ChEMBL
CHEMBL19
Created by admin on Fri Dec 15 15:13:11 GMT 2023 , Edited by admin on Fri Dec 15 15:13:11 GMT 2023
PRIMARY
INN
882
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PRIMARY
NSC
758426
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PRIMARY
HSDB
3269
Created by admin on Fri Dec 15 15:13:11 GMT 2023 , Edited by admin on Fri Dec 15 15:13:11 GMT 2023
PRIMARY
DRUG BANK
DB00703
Created by admin on Fri Dec 15 15:13:11 GMT 2023 , Edited by admin on Fri Dec 15 15:13:11 GMT 2023
PRIMARY
RXCUI
6826
Created by admin on Fri Dec 15 15:13:11 GMT 2023 , Edited by admin on Fri Dec 15 15:13:11 GMT 2023
PRIMARY RxNorm
LACTMED
Methazolamide
Created by admin on Fri Dec 15 15:13:11 GMT 2023 , Edited by admin on Fri Dec 15 15:13:11 GMT 2023
PRIMARY
CAS
554-57-4
Created by admin on Fri Dec 15 15:13:11 GMT 2023 , Edited by admin on Fri Dec 15 15:13:11 GMT 2023
PRIMARY
SMS_ID
100000081410
Created by admin on Fri Dec 15 15:13:11 GMT 2023 , Edited by admin on Fri Dec 15 15:13:11 GMT 2023
PRIMARY
NCI_THESAURUS
C61318
Created by admin on Fri Dec 15 15:13:11 GMT 2023 , Edited by admin on Fri Dec 15 15:13:11 GMT 2023
PRIMARY
FDA UNII
W733B0S9SD
Created by admin on Fri Dec 15 15:13:11 GMT 2023 , Edited by admin on Fri Dec 15 15:13:11 GMT 2023
PRIMARY
Related Record Type Details
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
TARGET -> INHIBITOR
TARGET -> INHIBITOR
BINDER->LIGAND
BINDING
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