Basic information
- CAS
1164547-86-7- Standard SMILES
CC(=O)N=c1sc(S(N)(=O)=O)nn1C- InChIKey
FLOSMHQXBMRNHR-UHFFFAOYSA-N- Molecular formula
- C5H8N4O3S2
- Average molar mass
- 236.3 g/mol
- Monoisotopic mass
- 236.00378248
Overview
Methazolamide is a sulfonamide and a member of thiadiazoles.
Names & identifiers
- Preferred name
- Methazolamide
- IUPAC
- N-(3-methyl-5-sulfamoyl-1,3,4-thiadiazol-2-ylidene)acetamide
- English name
- Methazolamide
- Molecular formula
- C5H8N4O3S2
- Molecular weight
- 236.27
Names & synonyms
methazolamide554-57-4MethenamideNeptazaneatNeptazaneNaptazaneMetazolamidaN-(3-methyl-5-sulfamoyl-1,3,4-thiadiazol-2-ylidene)acetamideMethazolamide, (Z)-C5H8N4O3S2Prestwick1_000802N-(3-Methyl-5-Sulfamoyl-1,3,4-Thiadiazol-2(3h)-Ylidene)acetamide
Show more names
CL 8490NeptazaL 584601MethazolamidMathazolamide
Oprea1_161738BRN 0232387DTXSID1023281MFCD00083416L584601NSC-758426Acetamide, N-[5-(aminosulfonyl)-3-methyl-1,3,4-thiadiazol-2(3H)-ylidene]-N-[(2E)-3-Methyl-5-sulfamoyl-2,3-dihydro-1,3,4-thiadiazol-2-ylidene]acetamide
Database identifiers
- CAS
1164547-86-7、554-57-4- PubChem CID
- 4100
- DTXSID
DTXSID1023281- ChEMBL
CHEMBL19- ChEBI
CHEBI:6822- UNII
- DA43GW06P1、W733B0S9SD
Properties
Computed structural properties
- XLogP
- 0.1
- Topological polar surface area
- 139 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 1
- Heavy atoms
- 14
- Formal charge
- 0
- Complexity
- 419
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
LogP0.13
Solubility>35.4 [ug/mL] (The mean of the results at pH 7.4)
Human DrugsPharmaceuticals
Dissociation Constants7.30
Collision Cross Section144.86 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 208 °C · 208 °C (dec.) (lit.)
- Boiling point
- 402 · 402.0±28.0 °C(Predicted)
- Density
- 1.6625 · 1.6625 (rough estimate)
- refractive index
- 1.627 · 1.6270 (estimate)
- storage temp.
- 2 · 2-8°C
- solubility
- 20 mg/mL, · DMSO: soluble20mg/mL, clear
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- 3
- rtecs
- AC6350000
- hs_code
- 2935904000
- risk_code
- 20/21/22-40
- Signal word
- Warning
- Symbol(GHS)
- GHS07,GHS08
- hazard_code
- Xn
- safety_code
- 22-36
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302+H312+H332-H351
- Hazard Classifications
- Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralCarc. 2
- Precautionary statements
- P201-P280-P301+P312-P302+P352+P312-P304+P340+P312-P308+P313
- Hazardous Substances Data
- 554-57-4(Hazardous Substances Data)
Chemistry & industry
Pharmacology
Protein Binding55%
Pharmacodynamics
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.
Mechanism of Action
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.
Biological Half-Life14 hours
Absorption, Distribution and Excretion
Methazolamide is well absorbed from the gastrointestinal tract.
17 to 23 L
Uses & manufacturing
Use ClassificationPharmaceuticals
Applications
DescriptionMethazolamide is a carbonic anhydrase inhibitor (IC50 = 130 nM). It reduces intraocular pressure and cerebrospinal fluid flow in a rat model of glaucoma. Methazolamide reduces electroshock-induced seizures in rats with an ED50 value of 19.2 mg/kg. It also inhibits production of reactive oxygen species (ROS) in a primary cortical neuron (PCN) cellular model of subarachnoid hemorrhage (SAH) and reduces cerebral edema in a mouse model of SAH. Methazolamide is larvicidal, with a larvicidal concentration (LC50) value of 724 ppm, but has no activity when administered in the diet to adult A. aegypti. Formulations containing methazolamide have been used for the treatment of glaucoma.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
Loading…