Azosemid
Azosemide
Daten werden ergänzt – lade die Seite später neu, um den aktuellen Stand zu sehen
Grundinformationen
- CAS
27589-33-9- Standard-SMILES
NS(=O)(=O)c1cc(-c2nn[nH]n2)c(NCc2cccs2)cc1Cl- InChIKey
HMEDEBAJARCKCT-UHFFFAOYSA-N- Summenformel
- C12H11ClN6O2S2
- Durchschnittliche Molmasse
- 370,8 g/mol
- Monoisotopische Masse
- 370,00734327
Überblick
Azosemide is a sulfonamide that is benzenesulfonamide which is substituted at positions 2, 4, and 5 by chlorine, (2-thienylmethyl)amino and 1H-tetrazol-5-yl groups, respectively. It is a diuretic that has been used in the management of oedema and hypertension. It has a role as a loop diuretic. It is a member of thiophenes, a sulfonamide, a member of tetrazoles and a member of monochlorobenzenes.
Namen und Bezeichner
- Bevorzugter Name
- Azosemide
- IUPAC
- 2-chloro-5-(2H-tetrazol-5-yl)-4-(thiophen-2-ylmethylamino)benzenesulfonamide
- Lokaler Name
- Azosemid
- Englischer Name
- Azosemide
- Summenformel
- C12H11ClN6O2S2
- Molmasse
- 370.84
Namen und Synonyme
azosemide27589-33-9AzosemidDiartAzosemidaAzosemidumLuretDTXSID7046910MR40VT1L8Z2-Chloro-5-(1H-tetrazol-5-yl)-N(sup 4)-2-thenylsulfanilamideBenzenesulfonamide, 2-chloro-5-(1H-tetrazol-5-yl)-4-((2-thienylmethyl)amino)-5-(4'-chloro-5'-sulfamoyl-2'-thenylaminophenyl)tetrazole
Weitere Namen anzeigen
SK-110ple1053DiurapidAZOSEMIDE HPLCAzosemide USP/EP/BP
DTXCID5026910CHEBI:312482-chloro-5-(2H-1,2,3,4-tetrazol-5-yl)-4-((thiophen-2-ylmethyl)amino)benzene-1-sulfonamide2-chloro-5-(2H-1,2,3,4-tetrazol-5-yl)-4-[(thiophen-2-ylmethyl)amino]benzene-1-sulfonamide5-(4-chloro-5-sulfamyl-2-thienylaminophenyl)tetrazoleRefChem:5606092-Chloro-5-(1H-tetrazol-5-yl)-4-((thien-2-ylmethyl)amino)benzenesulfonamide248-549-7
Datenbank-Bezeichner
- CAS
27589-33-9- PubChem CID
- 2273
Eigenschaften
Berechnete StruktureigenschaftenWird ergänzt
- XLogP
- 1,5
- Polarare Oberfläche (TPSA)
- 163 Ų
- H-Brücken-Donoren
- 3
- H-Brücken-Akzeptoren
- 8
- Frei drehbare Bindungen
- 5
- Schwere Atome
- 23
- Formalladung
- 0
- Komplexität
- 504
Experimentelle und physikochemische Eigenschaften
DrugsPharmaceuticals -> Listed in ZINC15
Melting Point219.5 °C
Physical DescriptionSolid
Physikochemische Eigenschaften
- Schmelzpunkt
- 218 · 218-221°
- Siedepunkt
- 221 °C · 221°C (rough estimate)
- Dichte
- 1.6843 · 1.6843 (rough estimate)
- Brechungsindex
- 1.61 · 1.6100 (estimate)
- storage temp.
- 2 · under inert gas (nitrogen or Argon) at 2–8 °C
- Löslichkeit
- DMSO (Slightly), Methanol (Slightly, Heated)
- Aggregatzustand
- Solid
- pka
- 3.58 · 3.58±0.10(Predicted)
- Farbe
- Crystals
- InChI
- InChI=1S/C12H11ClN6O2S2/c13-9-5-10(15-6-7-2-1-3-22-7)8(12-16-18-19-17-12)4-11(9)23(14,20)21/h1-5,15H,6H2,(H2,14,20,21)(H,16,17,18,19)
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
Sicherheitsdaten
- Toxizität
- LD50 orl-rat: 2545 mg/kg IYKEDH 18,666,87
Chemie und Industrie
Pharmakologische Informationen
Protein Binding> 95% 4% protein binding to 4% human serum albumin at azosemide concentrations of 10-100ug/ml, using equilibrium dialysis.
PharmacodynamicsDiuretic affects upon oral administration match those of furosemide. However, upon intravenous administration azosemide displays 5.5 to 8 times greater effect.
Mechanism of ActionExact mechanism of action is unclear. However, it acts primarily on the loop of Henle, in both the medullary and cortical segments of the thick ascending limb.
Biological Half-LifeTerminal half life 2-3 hours.
Metabolism/MetabolitesConsiderable first pass metabolism which makes parentral administration more effective than oral administration. Eleven metabolites of azosemide were found in rats, but only azosemide and its glucuronide were detected in humans.
MeSH Pharmacological ClassificationAgents that promote the excretion of urine through their effects on kidney function.
Absorption, Distribution and Excretion
Peak plasma concentrations are achieved in 3-4 hours when azosemide is administered to healthy humans in a fasting state. There is an absorption lag time of approximately 1 hour. Oral bioavailability estimated to be 20.4%
Total body clearance 112ml/min. Renal clearance 41.6ml/min. Actively secreted in the renal proximal tubule of humans. This may or may not involve a nonspecific organic acid secretory pathway. There is thus a potential for disease states and other organic acids such as NSAIDs which affect the organic acid transport pathway to affect the efficacy of azosemide.
Poor affinity for human tissue. Small apparent post-pseudodistribution Vd of 0.262 l/kg.
Cellular LocationsMembrane
Zugehörige Reaktionen
10
Notizen zur Verbindung
Wird geladen…