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554-57-4 molecular structure
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N-[(2Z)-3-methyl-5-sulfamoyl-2,3-dihydro-1,3,4-thiadiazol-2-ylidene]acetamide

ChemBase ID: 584
Molecular Formular: C5H8N4O3S2
Molecular Mass: 236.27202
Monoisotopic Mass: 236.00378214
SMILES and InChIs

SMILES:
S(=O)(=O)(N)c1s/c(=N\C(=O)C)/n(n1)C
Canonical SMILES:
CC(=O)/N=c/1\sc(nn1C)S(=O)(=O)N
InChI:
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-
InChIKey:
FLOSMHQXBMRNHR-DAXSKMNVSA-N

Cite this record

CBID:584 http://www.chembase.cn/molecule-584.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
N-[(2Z)-3-methyl-5-sulfamoyl-2,3-dihydro-1,3,4-thiadiazol-2-ylidene]acetamide
N-(3-methyl-5-sulfamoyl-2,3-dihydro-1,3,4-thiadiazol-2-ylidene)acetamide
IUPAC Traditional name
methazolamide
Brand Name
MZM
Methenamide
Naptazane
Neptazane
Neptazaneat
Synonyms
Methazolamide
''N''-(3-Methyl-5-sulfamoyl-3''H''-1,3,4-thiadiazol-2-ylidene) ethanamide
CAS Number
554-57-4
PubChem SID
160964047
46506393
PubChem CID
4100
ATC CODE
S01EC05
CHEMBL
19
Chemspider ID
3958
DrugBank ID
DB00703
KEGG ID
D00655
Unique Ingredient Identifier
W733B0S9SD
Wikipedia Title
Methazolamide
Medline Plus
a601233

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 9.162322  H Acceptors
H Donor LogD (pH = 5.5) -0.5935168 
LogD (pH = 7.4) -0.6000207  Log P -0.59343314 
Molar Refractivity 51.2971 cm3 Polarizability 20.541395 Å3
Polar Surface Area 105.19 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P -0.2  LOG S -2.13 
Solubility (Water) 1.74e+00 g/l 

PROPERTIES

PROPERTIES

Physical Property Pharmacology Properties Bioassay(PubChem)
Solubility
3500 mg/L expand Show data source
Hydrophobicity(logP)
-1.6 expand Show data source
Admin Routes
Oral expand Show data source
Half Life
14 hours expand Show data source
Protein Bound
55% expand Show data source
Legal Status
Rx-only (US) expand Show data source
Pregnancy Category
C (US) expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Wikipedia Wikipedia
DrugBank - DB00703 external link
Item Information
Drug Groups approved
Description A carbonic anhydrase inhibitor that is used as a diuretic and in the treatment of glaucoma. [PubChem]
Indication For treatment of chronic open-angle glaucoma and acute angle-closure glaucoma
Pharmacology 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.
Toxicity Electrolyte imbalance, development of an acidotic state, and central nervous system effects might be expected to occur in the case of an overdose.
Affected Organisms
Humans and other mammals
Absorption Methazolamide is well absorbed from the gastrointestinal tract.
Half Life 14 hours
Protein Binding 55%
Distribution * 17 to 23 L
References
Iyer GR, Bellantone RA, Taft DR: In vitro characterization of the erythrocyte distribution of methazolamide: a model of erythrocyte transport and binding kinetics. J Pharmacokinet Biopharm. 1999 Feb;27(1):45-66. [Pubmed]
Shirato S, Kagaya F, Suzuki Y, Joukou S: Stevens-Johnson syndrome induced by methazolamide treatment. Arch Ophthalmol. 1997 Apr;115(4):550-3. [Pubmed]
Skorobohach BJ, Ward DA, Hendrix DV: Effects of oral administration of methazolamide on intraocular pressure and aqueous humor flow rate in clinically normal dogs. Am J Vet Res. 2003 Feb;64(2):183-7. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com

REFERENCES

REFERENCES

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  • • Iyer GR, Bellantone RA, Taft DR: In vitro characterization of the erythrocyte distribution of methazolamide: a model of erythrocyte transport and binding kinetics. J Pharmacokinet Biopharm. 1999 Feb;27(1):45-66. Pubmed
  • • Shirato S, Kagaya F, Suzuki Y, Joukou S: Stevens-Johnson syndrome induced by methazolamide treatment. Arch Ophthalmol. 1997 Apr;115(4):550-3. Pubmed
  • • Skorobohach BJ, Ward DA, Hendrix DV: Effects of oral administration of methazolamide on intraocular pressure and aqueous humor flow rate in clinically normal dogs. Am J Vet Res. 2003 Feb;64(2):183-7. Pubmed
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