Azosemid

Azosemide

HCID 2273CAS 27589-33-9

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Grundinformationen

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
DTXSID: DTXSID7046910
ChEMBL: CHEMBL1097235
ChEBI: CHEBI:31248
UNII: MR40VT1L8Z
EC Number: 248-549-7
Nikkaji: J10.727A

Eigenschaften

Berechnete Struktureigenschaften

XLogP: 1,5
Polarare Oberfläche (TPSA): 163 Å²
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)
InChIKey: HMEDEBAJARCKCT-UHFFFAOYSA-N
SMILES: C1(S(N)(=O)=O)=CC(C2=NNN=N2)=C(NCC2SC=CC=2)C=C1Cl
CAS Datenbank: 27589 · 27589-33-9(CAS DataBase Reference)

Sicherheit und Regulatorisches

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.

Anwendungen

BeschreibungAzosemide is a high-ceiling diuretic similiar in structure and profile to furosemide, albeit somewhat less potent and less bioavailable. It is useful in the treatment of congestive heart failure and similar edematous conditions.

VerwendenDiuretic.

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

Anbieter50 Anbieter

Hebei Zhuanglai Chemical Trading Co Ltd+86-16264648883 · [email protected]

杭州品高化工有限公司0571-87658025 · [email protected]

陕西缔都新材料有限公司029-63373950 17392216152 · [email protected]

河北展药生物科技有限公司15369953316 +8615369953316 · [email protected]

Hebei Yanxi Chemical Co., Ltd.+86-17531190177 · [email protected]

Ergänzende Hinweise · 1 Eintrag

DefinitionChEBI: 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 hyp rtension.