Grundinformationen
- CAS
1164547-86-7- Standard-SMILES
CC(=O)N=c1sc(S(N)(=O)=O)nn1C- InChIKey
FLOSMHQXBMRNHR-UHFFFAOYSA-N- Summenformel
- C5H8N4O3S2
- Durchschnittliche Molmasse
- 236,3 g/mol
- Monoisotopische Masse
- 236,00378248
Überblick
Methazolamide is a sulfonamide and a member of thiadiazoles.
Namen und Bezeichner
- Bevorzugter Name
- Methazolamide
- IUPAC
- N-(3-methyl-5-sulfamoyl-1,3,4-thiadiazol-2-ylidene)acetamide
- Lokaler Name
- Methazolamid
- Englischer Name
- Methazolamide
- Summenformel
- C5H8N4O3S2
- Molmasse
- 236.27
Namen und Synonyme
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
Weitere Namen anzeigen
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
Datenbank-Bezeichner
- CAS
1164547-86-7、554-57-4- PubChem CID
- 4100
- DTXSID
DTXSID1023281- ChEMBL
CHEMBL19- ChEBI
CHEBI:6822
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 0,1
- Polarare Oberfläche (TPSA)
- 139 Ų
- H-Brücken-Donoren
- 1
- H-Brücken-Akzeptoren
- 6
- Frei drehbare Bindungen
- 1
- Schwere Atome
- 14
- Formalladung
- 0
- Komplexität
- 419
Experimentelle und physikochemische Eigenschaften
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]
Physikochemische Eigenschaften
- Schmelzpunkt
- 208 °C · 208 °C (dec.) (lit.)
- Siedepunkt
- 402 · 402.0±28.0 °C(Predicted)
- Dichte
- 1.6625 · 1.6625 (rough estimate)
- Brechungsindex
- 1.627 · 1.6270 (estimate)
- storage temp.
- 2 · 2-8°C
- Löslichkeit
- 20 mg/mL, · DMSO: soluble20mg/mL, clear
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
Sicherheitsdaten
- wgk
- 3
- hs_code
- 2935904000
- RTECS-Nr.
- AC6350000
- risk_code
- 20/21/22-40
- hazard_code
- Xn
- safety_code
- 22-36
- Speicherklasse
- 11 - Combustible Solids
- Giftige Stoffe Daten
- 554-57-4(Hazardous Substances Data)
- Hazard Classifications
- Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralCarc. 2
Chemie und Industrie
Pharmakologische Informationen
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
Verwendung und Herstellung
Use ClassificationPharmaceuticals
Anwendungen
BeschreibungMethazolamide 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.
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