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Substance Name: Piretanide [USAN:INN:BAN:JAN]
RN: 55837-27-9
UNII: DQ6KK6GV93
InChIKey: UJEWTUDSLQGTOA-UHFFFAOYSA-N

Note

  • Potent inhibitor of chloride transport.

Molecular Formula

  • C17-H18-N2-O5-S

Molecular Weight

  • 362.4042
 

Classification Codes

  • Diuretic
  • Diuretics
  • Drug / Therapeutic Agent
  • Membrane Transport Modulators
  • Natriuretic Agents
  • Reproductive Effect
  • Sodium Potassium Chloride Symporter Inhibitors
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Names and Synonyms

Name of Substance

  • Piretanide
  • Piretanide [USAN:INN:BAN:JAN]

Synonyms

  • 3-(Aminosulfonyl)-4-phenoxy-5-(1-pyrrolidinyl)-benzoic acid
  • 4-Phenoxy-3-(1-pyrrolidinyl)-5-sulfamoylbenzoic acid
  • Acide phenoxy-4-(1-pyrrolidinyl)-3-sulfamoyl-5 benzoique
  • Acide phenoxy-4-(1-pyrrolidinyl)-3-sulfamoyl-5 benzoique [French]
  • Arlix
  • BRN 5633965
  • EINECS 259-852-9
  • HOE 118
  • Piretanide
  • Piretanido
  • Piretanido [INN-Spanish]
  • Piretanido [Spanish]
  • Piretanidum
  • Piretanidum [INN-Latin]
  • S 73 4118
  • S 734118
  • Tauliz
  • UNII-DQ6KK6GV93

Systematic Names

  • Benzoic acid, 3-(aminosulfonyl)-4-phenoxy-5-(1-pyrrolidinyl)-
  • Piretanide

Registry Numbers

CAS Registry Number

  • 55837-27-9

FDA UNII

  • DQ6KK6GV93

System Generated Number

  • 0055837279

Structure Descriptors

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

NS(=O)(=O)c1cc(cc(N2CCCC2)c1Oc3ccccc3)C(=O)O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 oral > 1gm/kg (1000mg/kg)   Yakkyoku. Pharmacy. Vol. 35, Pg. 2037, 1984.
guinea pig LD50 oral 93mg/kg (93mg/kg)   Medicamentos de Actualidad. Vol. 18, Pg. 271, 1982.
mouse LD50 intraperitoneal 700mg/kg (700mg/kg) BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Kiso to Rinsho. Clinical Report. Vol. 14, Pg. 4254, 1980.
mouse LD50 intravenous 618mg/kg (618mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: ATAXIA

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Kiso to Rinsho. Clinical Report. Vol. 14, Pg. 4254, 1980.
mouse LD50 oral 2gm/kg (2000mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE

BEHAVIORAL: ATAXIA
Kiso to Rinsho. Clinical Report. Vol. 14, Pg. 4254, 1980.
mouse LD50 subcutaneous 660mg/kg (660mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ATAXIA
Kiso to Rinsho. Clinical Report. Vol. 14, Pg. 4254, 1980.
rabbit LD50 intravenous 178mg/kg (178mg/kg)   Kiso to Rinsho. Clinical Report. Vol. 14, Pg. 4254, 1980.
rabbit LD50 oral 960mg/kg (960mg/kg)   Kiso to Rinsho. Clinical Report. Vol. 14, Pg. 4254, 1980.
rat LD50 intraperitoneal 485mg/kg (485mg/kg) BEHAVIORAL: ATAXIA

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Kiso to Rinsho. Clinical Report. Vol. 14, Pg. 4254, 1980.
rat LD50 intravenous 700mg/kg (700mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: ATAXIA

BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)
Kiso to Rinsho. Clinical Report. Vol. 14, Pg. 4254, 1980.
rat LD50 oral 5601mg/kg (5601mg/kg)   European Journal of Medicinal Chemistry--Chimie Therapeutique. Vol. 11, Pg. 399, 1976.
rat LD50 subcutaneous 1100mg/kg (1100mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ATAXIA
Kiso to Rinsho. Clinical Report. Vol. 14, Pg. 4254, 1980.

Physical Properties

Physical Property Value Units Temp (deg C) Source
log P (octanol-water) 3.92 (none)   EXP
Water Solubility 2.340 mg/L 25 EST
Vapor Pressure 1.07E-11 mm Hg 25 EST
Henry's Law Constant 2.30E-15 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 2.95E-11 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.