METHAZOLAMIDE

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 Search

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
Sources: http://www.drugbank.ca/drugs/DB00703
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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Carbonic anhydrase I 62 Target ID: CHEMBL261 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23965175	Inhibitor 8504	50.0 nM [Ki]
Carbonic anhydrase II 88 Target ID: CHEMBL205 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23965175	Inhibitor 8504	14.0 nM [Ki]
Carbonic anhydrase IX 36 Target ID: CHEMBL3594 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23965175	Inhibitor 8504	27.0 nM [Ki]
Carbonic anhydrase XII 30 Target ID: CHEMBL3242 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23965175	Inhibitor 8504	3.4 nM [Ki]
Carbonic anhydrase VII 35 Target ID: CHEMBL2326 Sources: http://www.drugbank.ca/drugs/DB00703	Inhibitor 8504	2.1 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Glaucoma 57 Sources: https://www.drugs.com/pro/methazolamide.html	Primary		Approved 8583	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

C_max

Value	Dose	Analyte	Population
2.5 μg/mL DRUG LABEL https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=4c9fc6f5-acd4-4fc0-bf4b-c493a08aa3d6&type=display	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 DRUG LABEL https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=4c9fc6f5-acd4-4fc0-bf4b-c493a08aa3d6&type=display	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 DRUG LABEL https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=4c9fc6f5-acd4-4fc0-bf4b-c493a08aa3d6&type=display	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

Value	Dose	Analyte	Population
1130 μg × min/mL DRUG LABEL https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=4c9fc6f5-acd4-4fc0-bf4b-c493a08aa3d6&type=display	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 DRUG LABEL https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=4c9fc6f5-acd4-4fc0-bf4b-c493a08aa3d6&type=display	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 DRUG LABEL https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=4c9fc6f5-acd4-4fc0-bf4b-c493a08aa3d6&type=display	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
14 h DRUG LABEL https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=4c9fc6f5-acd4-4fc0-bf4b-c493a08aa3d6&type=display	steady-state, oral		METHAZOLAMIDE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
45% DRUG LABEL https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=4c9fc6f5-acd4-4fc0-bf4b-c493a08aa3d6&type=display	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

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP2J2 71

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP2J2 71	substrate 4014 Sources: https://dmd.aspetjournals.org/content/38/2/347 Page: 348.0	no

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY560176	https://www.001chemical.com/chem/554-57-4
3B Scientific (Wuhan) Corp	3B1-00324	http://www.3bsc.com/index/pro_info.php?id=20536
3B Scientific (Wuhan) Corp	3B2-5425	http://www.3bsc.com/index/pro_info.php?id=85227
AA Blocks	AA00DENM	http://www.aablocks.com/goods/Goods/detail?id=AA00DENM
Aaron Chemicals	AR00DFFE	http://www.aaronchem.com/554-57-4
abcr GmbH	AB509196	http://www.abcr.com/shop/en/AB509196
AbMole Bioscience	M2840	http://www.abmole.com/products/methazolamide.html
Achemtek	0104-019526	http://www.achemtek.com/554-57-4
AHH Chemical co.,ltd	MT-53566	http://www.ahhchemical.com/product/MT-53566.html
AK Scientific, Inc. (AKSCI)	H773	http://www.aksci.com/item_detail.php?cat=H773
Alfa Chemistry	AP554574-A	https://reagents.alfa-chemistry.com/product/methazolamide-cas-554-57-4-13061.html
Alfa Chemistry	AP554574-B	https://reagents.alfa-chemistry.com/product/methazolamide-cas-554-57-4-13062.html
Ambeed	A120295	https://www.ambeed.com/products/554-57-4.html
Ambinter	Amb17938206	http://www.ambinter.com/reference/17938206
Ambinter	Amb20243176	http://www.ambinter.com/reference/20243176
Ambinter	Amb20665658	http://www.ambinter.com/reference/20665658
Ambinter	Amb21935015	http://www.ambinter.com/reference/21935015
Ambinter	Amb22352755	http://www.ambinter.com/reference/22352755
Angel Pharmatech	AG147138	http://www.angelpharmatech.com/554-57-4.html
Angene	AGN-PC-0SJ4UC	http://www.angenechemical.com/productshow/AGN-PC-0SJ4UC.html
ApexBio Technology	A4364	http://www.apexbt.com/methazolamide.html
Ark Pharm	AK163546	http://www.arkpharminc.com/products/554-57-4.html
Aurora Fine Chemicals LLC	A17.909.366	http://online.aurorafinechemicals.com/info?ID=A17.909.366
Aurum Pharmatech LLC	K-9905	http://www.Aurumpharmatech.com/Product/ProductDetails/K_9905
BioCrick	BCC2318	http://www.biocrick.com/Methazolamide-BCC2318.html
BLD Pharm	BD137689	http://www.bldpharm.com/products/554-57-4.html
BOC Sciences	554-57-4	https://www.bocsci.com/methazolamide-cas-554-57-4-item-84-71480.html
Chem Scene	CS-2658	http://www.chemscene.com/554-57-4.html
ChemMol	49427793	http://www.chemmol.com/chemmol/49427793.html
Chemspace	CSSB00015223641	https://chem-space.com/CSSB00015223641
Chemspace	CSSB00016254742	https://chem-space.com/CSSB00016254742
Chemspace	CSSB00016286996	https://chem-space.com/CSSB00016286996
Clearsynth	CS-O-11690	https://www.clearsynth.com/en/CSO11690.html
Combi-Blocks	QA-3504	http://www.combi-blocks.com/cgi-bin/find.cgi?QA-3504
CSNpharm	CSN11393	https://www.csnpharm.com/products/methazolamide.html
DC Chemicals	DC31747	http://www.dcchemicals.com//product_show-Methazolamide.html
Debye Scientific	DB-052736	http://www.debyesci.com/cas_554-57-4.html
EMD Millipore	215902	http://www.emdbiosciences.com/product/215902
eNovation Chemicals	D630718	https://www.enovationchem.com/ProductDetails.asp?ProductID=D630718
eNovation Chemicals	K35405	https://www.enovationchem.com/ProductDetails.asp?ProductID=K35405
Hairui	HR23832	http://www.hairuichem.com/en/product/554-57-4.html
iChemical	EBD27355	http://www.ichemical.com/products/554-57-4.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
Lab Network	LN00237894	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00237894
LGC Standards	DRE-C14999900	https://www.lgcstandards.com/US/en/p/DRE-C14999900
mcule	MCULE-1665001985	https://mcule.com/MCULE-1665001985/
MedChem Express	HY-B0553	https://www.medchemexpress.com/methazolamide.html
Molcore	MC560176	https://www.molcore.com/product/554-57-4
MolPort	MolPort-001-791-152	https://www.molport.com/shop/molecule-link/MolPort-001-791-152
MolPort	MolPort-019-998-640	https://www.molport.com/shop/molecule-link/MolPort-019-998-640
MuseChem	I013868	https://www.musechem.com/product/I013868.html
Oakwood	181321	http://www.oakwoodchemical.com/ProductsList.aspx?CategoryID=-2&txtSearch=162059&ExtHyperLink=1
OChem	12480	http://www.ocheminc.com/index.php?act=psearch&pid=554M574
Sigma-Aldrich	1406005_USP	https://www.sigmaaldrich.com/catalog/product/usp/1406005?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	37011_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/37011?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	SML0720_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/sml0720?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Smolecule	S535104	http://www.smolecule.com/products/s535104
Smolecule	S793311	https://www.smolecule.com/products/s793311
Synblock Inc	SB17307	http://www.synblock.com/product/554-57-4.html
THE BioTek	bt-275134	https://www.thebiotek.com/product/inhibitors/bt-275134
TimTec	ST081366	http://www.echemstore.com/st081366-methazolamide.html

PubMed

Title	Date	PubMed
Evaluation of the therapeutic potential of carbonic anhydrase inhibitors in two animal models of dystrophin deficient muscular dystrophy.	2009-11-01	19648295
Methazolamide does not impair respiratory work performance in anesthetized rabbits.	2009-09	19553495
Carbonic anhydrase inhibitors. Inhibition studies of a coral secretory isoform by sulfonamides.	2009-07-15	19520577
Carbonic anhydrase inhibitors. Inhibition and homology modeling studies of the fungal beta-carbonic anhydrase from Candida albicans with sulfonamides.	2009-07-01	19450983
Titration calorimetry standards and the precision of isothermal titration calorimetry data.	2009-06-18	19582227
Carbonic anhydrase inhibitors. Cloning, characterization, and inhibition studies of a new beta-carbonic anhydrase from Mycobacterium tuberculosis.	2009-05-14	19338333
Methazolamide and melatonin inhibit mitochondrial cytochrome C release and are neuroprotective in experimental models of ischemic injury.	2009-05	19299628
Molecular cloning, characterization, and inhibition studies of the Rv1284 beta-carbonic anhydrase from Mycobacterium tuberculosis with sulfonamides and a sulfamate.	2009-04-23	19317447
Acetazolamide reversibly inhibits water conduction by aquaporin-4.	2009-04	19114109
Studies on bicarbonate transporters and carbonic anhydrase in porcine nonpigmented ciliary epithelium.	2009-04	19011010
QSAR studies for the inhibition of the transmembrane carbonic anhydrase isozyme XIV with sulfonamides using PRECLAV software.	2009-04	18830873
Design of a carbonic anhydrase IX active-site mimic to screen inhibitors for possible anticancer properties.	2009-02-17	19170619
Carbonic anhydrase inhibitors: inhibition of the beta-class enzyme from the yeast Saccharomyces cerevisiae with sulfonamides and sulfamates.	2009-02-01	19124253
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.	2009-02-01	19119014
Functional coupling of the downregulated in adenoma Cl-/base exchanger DRA and the apical Na+/H+ exchangers NHE2 and NHE3.	2009-02	19056765
CO2 chemosensing in rat oesophagus.	2008-12	18682519
Recent advances in pharmacotherapy of glaucoma.	2008-10	20040958
Inhibitors of cytochrome c release with therapeutic potential for Huntington's disease.	2008-09-17	18799679
Rational use of the fixed combination of dorzolamide - timolol in the management of raised intraocular pressure and glaucoma.	2008-06	19668730
Pharmacological impact on loop gain properties to prevent irregular breathing.	2008-03	18441386
Carbonic anhydrase II and alveolar fluid reabsorption during hypercapnia.	2008-01	17690328
The development of topically acting carbonic anhydrase inhibitors as antiglaucoma agents.	2008	18336310
The alpha and beta classes carbonic anhydrases from Helicobacter pylori as novel drug targets.	2008	18336307
Direct non-cyclooxygenase-2 targets of celecoxib and their potential relevance for cancer therapy.	2007-12-03	17955049
Carbonic anhydrase inhibitors: cloning, characterization, and inhibition studies of the cytosolic isozyme III with sulfonamides.	2007-12-01	17826101
Statement on high-altitude illnesses. An Advisory Committee Statement (ACS).	2007-04-01	17520777
Inhibition of hypoxia-induced calcium responses in pulmonary arterial smooth muscle by acetazolamide is independent of carbonic anhydrase inhibition.	2007-04	17209136
PAT-1 (Slc26a6) is the predominant apical membrane Cl-/HCO3- exchanger in the upper villous epithelium of the murine duodenum.	2007-04	17170027
Topical inhibition of nasal carbonic anhydrase affects the CO2 detection threshold in rats.	2007-03	17215338
Carbonic anhydrase inhibition prevents and reverts cardiomyocyte hypertrophy.	2007-02-15	17124262
Carbonic anhydrase inhibitors. DNA cloning, characterization, and inhibition studies of the human secretory isoform VI, a new target for sulfonamide and sulfamate inhibitors.	2007-01-25	17228881
The development of topically acting carbonic anhydrase inhibitors as anti-glaucoma agents.	2007	17504129
Inhibition profiling of human carbonic anhydrase II by high-throughput screening of structurally diverse, biologically active compounds.	2006-10	16858005
Expression, purification, kinetic, and structural characterization of an alpha-class carbonic anhydrase from Aedes aegypti (AaCA1).	2006-08	16920039
The carbonic anhydrase inhibitors methazolamide and acetazolamide have different effects on the hypoxic ventilatory response in the anaesthetized cat.	2006-07-15	16675491
Carbonic anhydrases and mucosal vanilloid receptors help mediate the hyperemic response to luminal CO2 in rat duodenum.	2006-07	16831598
Degradation and effects of the potential mosquito larvicides methazolamide and acetazolamide in sheepshead minnow (Cyprinodon variegatus).	2006-07	16054216
Epithelial carbonic anhydrases facilitate PCO2 and pH regulation in rat duodenal mucosa.	2006-06-15	16556652
Topical dorzolamide for the treatment of cystoid macular edema in patients with retinitis pigmentosa.	2006-05	16546110
[Diuretic therapy in heart failure].	2006-04-25	16634001
Carbonic anhydrase inhibitors: cloning and sulfonamide inhibition studies of a carboxyterminal truncated alpha-carbonic anhydrase from Helicobacter pylori.	2006-04-15	16459077
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.	2006-03-23	16539401
Mirtazapine in the treatment of essential tremor: an open-label, observer-blind study.	2006-03	19412450
Carbonic anhydrase inhibitors ameliorate the symptoms of hypokalaemic periodic paralysis in rats by opening the muscular Ca2+-activated-K+ channels.	2006-01	16368240
Effects of low-dose methazolamide on the control of breathing in cats.	2006	16683729
Carbonic anhydrase inhibitors: inhibition of cytosolic/tumor-associated carbonic anhydrase isozymes I, II, and IX with benzo[b]thiophene 1,1-dioxide sulfonamides.	2005-11-01	16165351
Functional interaction of carbonic anhydrase and chloride/bicarbonate exchange in human platelets.	2005-11	16236600
Carbonic anhydrase inhibitors: inhibition of the transmembrane isozyme XIV with sulfonamides.	2005-09-01	16039848
Carbonic anhydrase in the adult mosquito midgut.	2005-09	16109888
Treatment of essential tremor with methazolamide.	1991-10	1921495

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 `Mon Mar 31 17:50:35 GMT 2025` Edited by `admin` on `Mon Mar 31 17:50:35 GMT 2025`
Record UNII	W733B0S9SD
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

METHAZOLAMIDE

Official Name

English

NEPTAZANE

Preferred 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

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