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: 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

NAMES AND DATABASE IDS

Names

• 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

Database IDs

• 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

CALCULATED PROPERTIES

JChem

• Acid pKa: 9.162322
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): -0.5935168
• LogD (pH = 7.4): -0.6000207
• Log P: -0.59343314
• Molar Refractivity: 51.2971 cm^3
• Polarizability: 20.541395 Å^3
• Polar Surface Area: 105.19 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.2
• LOG S: -2.13
• Solubility (Water): 1.74e+00 g/l

PROPERTIES

Physical Property

• Solubility: 3500 mg/L
• Hydrophobicity(logP): -1.6

Pharmacology Properties

• Admin Routes: Oral
• Half Life: 14 hours
• Protein Bound: 55%
• Legal Status: Rx-only (US)
• Pregnancy Category: C (US)

DETAILS

DrugBank - DB00703

• 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

• 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