Piretanid

Piretanide

HCID 4849CAS 55837-27-9

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Grundinformationen

Standard-SMILES: NS(=O)(=O)c1cc(C(=O)O)cc(N2CCCC2)c1Oc1ccccc1
InChIKey: UJEWTUDSLQGTOA-UHFFFAOYSA-N
Summenformel: C17H18N2O5S
Durchschnittliche Molmasse: 362,4 g/mol
Monoisotopische Masse: 362,09364285

Namen und Bezeichner

Bevorzugter Name: Piretanide
IUPAC: 4-phenoxy-3-pyrrolidin-1-yl-5-sulfamoylbenzoic acid
Lokaler Name: Piretanid
Englischer Name: Piretanide
Summenformel: C17H18N2O5S
Molmasse: 362.4

Namen und Synonyme

piretanide55837-27-94-phenoxy-3-(pyrrolidin-1-yl)-5-sulfamoylbenzoic acidHOE 118Arlix4-phenoxy-3-pyrrolidin-1-yl-5-sulfamoylbenzoic acidPiretanidumHoe-118PiretanidaDTXSID2023488S 73 4118DQ6KK6GV93

Weitere Namen anzeigen

DiuMaxTaulizEurelixS 734118

Benzoic acid, 3-(aminosulfonyl)-4-phenoxy-5-(1-pyrrolidinyl)-S-73-4118DTXCID703488S-734118RefChem:863638C03CA03259-852-9Arelix

Datenbank-Bezeichner

CAS: 55837-27-9
PubChem CID: 4849
DTXSID: DTXSID2023488
ChEMBL: CHEMBL349803
ChEBI: CHEBI:32015
UNII: DQ6KK6GV93
EC Number: 259-852-9
Nikkaji: J3.520C

Eigenschaften

Berechnete Struktureigenschaften

XLogP: 2,2
Polarare Oberfläche (TPSA): 118 Å²
H-Brücken-Donoren: 2
H-Brücken-Akzeptoren: 7
Frei drehbare Bindungen: 5
Schwere Atome: 25
Formalladung: 0
Komplexität: 564

Experimentelle und physikochemische Eigenschaften

LogP3.92

Physikochemische Eigenschaften

Schmelzpunkt: 225 · 225-227°
Siedepunkt: 253 °C · 253°C (rough estimate)
Dichte: 1.3049 · 1.3049 (rough estimate)
Brechungsindex: 1.651 · 1.6510 (estimate)
storage temp.: 2 · 2-8°C
Löslichkeit: Very slightly soluble in water, sparingly soluble in anhydrous ethanol. It shows polymorphism (5.9).
pka: 10.22 · 10.22±0.60(Predicted)
Aggregatzustand: Solid
Farbe: Pale-yellow platelets from MeOH (aq)
Major Application: pharmaceutical (small molecule)
InChI: 1S/C17H18N2O5S/c18-25(22,23)15-11-12(17(20)21)10-14(19-8-4-5-9-19)16(15)24-13-6-2-1-3-7-13/h1-3,6-7,10-11H,4-5,8-9H2,(H,20,21)(H2,18,22,23)
InChIKey: UJEWTUDSLQGTOA-UHFFFAOYSA-N
SMILES: [S](=O)(=O)(N)c1c(c(cc(c1)C(=O)O)N3CCCC3)Oc2ccccc2
CAS Datenbank: 55837 · 55837-27-9(CAS DataBase Reference)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

This chemical does not meet GHS hazard criteria for 33.3% (1 of 3) of reports.

H412 (66.7%): Harmful to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

P273, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 3 reports by companies from 2 notifications to the ECHA C&L Inventory.；Reported as not meeting GHS hazard criteria per 1 of 3 reports by companies.；There is 1 notification provided by 2 of 3 reports by companies with hazard statement code(s).；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Gefahrenhinweise

Hazard Classes and CategoriesAquatic Chronic 3 (66.7%)

Sicherheitsdaten

wgk: WGK 3
Toxizität: LD50 in rats, mice (mg/kg): 5601, 3672 orally (Merkel)
Speicherklasse: 11 - Combustible Solids

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 2 Einträge

C - Cardiovascular system；C03 - Diuretics；C03C - High-ceiling diuretics；C03CA - Sulfonamides, plain；C03CA03 - Piretanide

QC - Cardiovascular system；QC03 - Diuretics；QC03C - High-ceiling diuretics；QC03CA - Sulfonamides, plain；QC03CA03 - Piretanide

MeSH Pharmacological Classification · 2 Einträge

Agents that promote the excretion of urine through their effects on kidney function.

Agents that inhibit SODIUM-POTASSIUM-CHLORIDE SYMPORTERS which are concentrated in the thick ascending limb at the junction of the LOOP OF HENLE and KIDNEY TUBULES, DISTAL. They act as DIURETICS. Excess use is associated with HYPOKALEMIA and HYPERGLYCEMIA.