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Identification
NamePiretanide
Accession NumberDB02925  (EXPT03308)
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
Structure
Thumb
SynonymsNot Available
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
ArelixNot Available
PiretanideJAN
Brand mixturesNot Available
SaltsNot Available
Categories
UNIIDQ6KK6GV93
CAS number55837-27-9
WeightAverage: 362.4
Monoisotopic: 362.093642386
Chemical FormulaC17H18N2O5S
InChI KeyInChIKey=UJEWTUDSLQGTOA-UHFFFAOYSA-N
InChI
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)
IUPAC Name
4-phenoxy-3-(pyrrolidin-1-yl)-5-sulfamoylbenzoic acid
SMILES
NS(=O)(=O)C1=CC(=CC(N2CCCC2)=C1OC1=CC=CC=C1)C(O)=O
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as diphenylethers. These are aromatic compounds containing two benzene rings linked to each other through an ether group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassDiphenylethers
Direct ParentDiphenylethers
Alternative Parents
Substituents
  • Diphenylether
  • 1-phenylpyrrolidine
  • Diaryl ether
  • Aminobenzenesulfonamide
  • Benzenesulfonamide
  • Aminobenzoic acid or derivatives
  • Aminobenzoic acid
  • Benzoic acid
  • Benzoic acid or derivatives
  • Substituted aniline
  • Dialkylarylamine
  • Benzoyl
  • Aniline
  • Aminosulfonyl compound
  • Sulfonyl
  • Sulfonic acid derivative
  • Sulfonamide
  • Pyrrolidine
  • Pyrrole
  • Tertiary amine
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9907
Blood Brain Barrier+0.6318
Caco-2 permeable-0.6466
P-glycoprotein substrateNon-substrate0.5237
P-glycoprotein inhibitor INon-inhibitor0.8026
P-glycoprotein inhibitor IINon-inhibitor0.6635
Renal organic cation transporterNon-inhibitor0.7657
CYP450 2C9 substrateNon-substrate0.7067
CYP450 2D6 substrateNon-substrate0.8032
CYP450 3A4 substrateNon-substrate0.5997
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6747
Ames testNon AMES toxic0.6433
CarcinogenicityNon-carcinogens0.6985
BiodegradationNot ready biodegradable0.9786
Rat acute toxicity1.8427 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.848
hERG inhibition (predictor II)Inhibitor0.5391
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
logP3.92BIOBYTE (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.0914 mg/mLALOGPS
logP2.2ALOGPS
logP2.25ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)4.68ChemAxon
pKa (Strongest Basic)-0.62ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area109.93 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity93.68 m3·mol-1ChemAxon
Polarizability35.85 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
References
Synthesis Reference

Yuji Chikaraishi, Yoshihisa Matsuda, Makoto Otsuka, “Amorphous piretanide, piretanide polymorphs, process for their preparation and their use.” U.S. Patent US6096779, issued September, 1993.

US6096779
General ReferencesNot Available
External Links
ATC CodesC03CA03
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Sodium:potassium:chloride symporter activity
Specific Function:
Electrically silent transporter system. Mediates sodium and chloride reabsorption. Plays a vital role in the regulation of ionic balance and cell volume.
Gene Name:
SLC12A1
Uniprot ID:
Q13621
Molecular Weight:
121449.13 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23