Methazolamide

Names

[ CAS No. ]:
554-57-4

[ Name ]:
Methazolamide

[Synonym ]:
N-[(2E)-5-(aminosulfonyl)-3-methyl-1,3,4-thiadiazol-2(3H)-ylidene]acetamide
methazolamide
Methazolamide [BAN:INN:JAN]
Acetamide, N-[(2E)-5-(aminosulfonyl)-3-methyl-1,3,4-thiadiazol-2(3H)-ylidene]-
Methazolamide (JAN/USP)
EINECS 209-066-7
N-(4-Methyl-2-sulfamoyl-D2-1,3,4-thiadiazolin-5-ylidene)acetamide
Metazolamide [DCIT]
Acetamide, N-[(2Z)-5-(aminosulfonyl)-3-methyl-1,3,4-thiadiazol-2(3H)-ylidene]-
5-Acetylamino-4-methyl-D2-1,3,4-thiadiazoline-2-sulfonamide
NEPTAZANE
N1-[5-(aminosulfonyl)-3-methyl-2,3-dihydro-1,3,4-thiadiazol-2-yliden]acetamide
4-27-00-08221 (Beilstein Handbook Reference)
N-[(2Z)-3-Methyl-5-sulfamoyl-1,3,4-thiadiazol-2(3H)-ylidene]acetamide
N-[5-(Aminosulfonyl)-3-methyl-1,3,4-triadiazol-2(3H)-ylidene]acetamide
N-[(2E)-3-Methyl-5-sulfamoyl-1,3,4-thiadiazol-2(3H)-ylidene]acetamide
MFCD00083416
N-(3-methyl-5-sulfamoyl-1,3,4-thiadiazol-2-ylidene)acetamide

Biological Activity

[Description]:

Methazolamide is a carbonic anhydrase inhibitor used to treat glaucoma.Target: Carbonic AnhydraseMethazolamide is a carbonic anhydrase inhibitor with Ki of 50 nM, 14 nM and 36 nM for hCA I, hCA II and bCA IV isoforms, respectively [1]. Methazolamide is of strength equal to acetazolamide, another carbonic anhydrase inhibitor used to treat irregular breathing disorders. However, methazolamide differs from acetazolamide in that it fails to activate Ca2+-dependent potassium channels in skeletal muscles. Methazolamide does not impair respiratory work performance in anesthetized rabbits [2]. Oral administration of methazolamide decreases IOPs and AHFRs in clinically normal dogs, with effectiveness diminishing in the evening [3].

[Related Catalog]:

Signaling Pathways >> Metabolic Enzyme/Protease >> Carbonic Anhydrase

Research Areas >> Others

[References]

[1]. Casini, A., et al., Carbonic anhydrase inhibitors: SAR and X-ray crystallographic study for the interaction of sugar sulfamates/sulfamides with isozymes I, II and IV. Bioorg Med Chem Lett, 2003. 13(5): p. 841-5.

[2]. Kiwull-Schone, H.F., et al., Methazolamide does not impair respiratory work performance in anesthetized rabbits. Am J Physiol Regul Integr Comp Physiol, 2009. 297(3): p. R648-54.

[3]. Skorobohach, B.J., D.A. Ward, and D.V. Hendrix, Effects of oral administration of methazolamide on intraocular pressure and aqueous humor flow rate in clinically normal dogs. Am J Vet Res, 2003. 64(2): p. 183-7.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.8±0.1 g/cm3

[ Boiling Point ]:
402.0±28.0 °C at 760 mmHg

[ Melting Point ]:
208ºC (dec.)

[ Molecular Formula ]:
C₅H₈N₄O₃S₂

[ Molecular Weight ]:
236.272

[ Flash Point ]:
196.9±24.0 °C

[ Exact Mass ]:
236.003784

[ PSA ]:
144.03000

[ LogP ]:
0.13

[ Vapour Pressure ]:
0.0±0.9 mmHg at 25°C

[ Index of Refraction ]:
1.737

[ Storage condition ]:
2-8°C

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: AC6350000

CHEMICAL NAME :: Acetamide, N-(4-methyl-2-sulfamoyl-delta(sup 2)-1,3,4-thiadiazolin-5-ylidene)-

CAS REGISTRY NUMBER :: 554-57-4

BEILSTEIN REFERENCE NO. :: 0232387

LAST UPDATED :: 199612

DATA ITEMS CITED :: 3

MOLECULAR FORMULA :: C5-H8-N4-O3-S2

MOLECULAR WEIGHT :: 236.29

WISWESSER LINE NOTATION :: T5NNYSJ B CUNV1 ESZW

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 2420 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - other changes

REFERENCE :: JMCMAR Journal of Medicinal Chemistry. (American Chemical Soc., Distribution Office Dept. 223, POB POB 57136, West End Stn., Washington, DC 20037) V.6- 1963- Volume(issue)/page/year: 18,351,1975

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >1 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,819,1982 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X7129 No. of Facilities: 10 (estimated) No. of Industries: 1 No. of Occupations: 1 No. of Employees: 197 (estimated) No. of Female Employees: 59 (estimated)

Safety Information

[ Symbol ]:

GHS07, GHS08

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302 + H312 + H332-H351

[ Precautionary Statements ]:
P261-P280-P301 + P312 + P330

[ Hazard Codes ]:
Xn:Harmful

[ Risk Phrases ]:
R20/21/22;R40

[ Safety Phrases ]:
S22-S36

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
AC6350000

[ HS Code ]:
2935009090

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2935009090

[ Summary ]:
2935009090 other sulphonamides VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:6.5% General tariff:35.0%

Articles

Inhibition of hyperactivity and impulsivity by carbonic anhydrase inhibitors in spontaneously hypertensive rats, an animal model of ADHD.

Psychopharmacology 232 , 3763-72, (2015)

Dysregulation of noradrenergic and dopaminergic systems is involved in the pathology of attention deficit hyperactivity disorder (ADHD). Carbonic anhydrase (CA) has been reported to affect monoamine t...

Related Compounds

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