This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Name
Piretanide
Accession Number
DB02925  (EXPT03308)
Type
Small Molecule
Groups
Approved
Description

Piretanide (INN, trade names Arelix, Eurelix, Tauliz) has been synthesized in 1973 at Hoechst AG (Germany) as a loop diuretic compound by using a then-new method for introducing cyclic amine residues in an aromatic nucleus in the presence of other aromatically bonded functional groups.

Structure
Thumb
Synonyms
  • Piretanida
External IDs
HOE 118 / HOE-118 / S 73 4118 / S-73-4118
International/Other Brands
Arelix / Eurelix / Tauliz
Categories
UNII
DQ6KK6GV93
CAS number
55837-27-9
Weight
Average: 362.4
Monoisotopic: 362.093642386
Chemical Formula
C17H18N2O5S
InChI Key
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

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
USolute carrier family 12 member 1
inhibitor
Human
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic AcidPiretanide may increase the hypotensive activities of 1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid.
2,4-thiazolidinedioneThe therapeutic efficacy of 2,4-thiazolidinedione can be increased when used in combination with Piretanide.
AbediterolThe risk or severity of hyperkalemia can be increased when Abediterol is combined with Piretanide.
AcarboseThe therapeutic efficacy of Acarbose can be increased when used in combination with Piretanide.
AceclofenacThe therapeutic efficacy of Piretanide can be decreased when used in combination with Aceclofenac.
AcemetacinThe therapeutic efficacy of Piretanide can be decreased when used in combination with Acemetacin.
AcetohexamideThe therapeutic efficacy of Acetohexamide can be increased when used in combination with Piretanide.
AcetyldigitoxinThe risk or severity of adverse effects can be increased when Piretanide is combined with Acetyldigitoxin.
AcetyldigoxinThe risk or severity of adverse effects can be increased when Piretanide is combined with Acetyldigoxin.
Acetylsalicylic acidThe therapeutic efficacy of Piretanide can be decreased when used in combination with Acetylsalicylic acid.
Food Interactions
Not 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 References
Not Available
External Links
KEGG Drug
D01634
PubChem Compound
4849
PubChem Substance
46507197
ChemSpider
4683
ChEBI
32015
ChEMBL
CHEMBL349803
Therapeutic Targets Database
DNC001127
Wikipedia
Piretanide
ATC Codes
C03CA03 — PiretanideG01AE10 — Combinations of sulfonamides

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-000i-3980000000-dc67e28bf67c9f799108

Taxonomy

Description
This 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.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Diphenylethers
Direct Parent
Diphenylethers
Alternative Parents
Phenylpyrrolidines / Aminobenzenesulfonamides / Diarylethers / Aminobenzoic acids / Benzoic acids / Benzenesulfonyl compounds / Phenoxy compounds / Phenol ethers / Dialkylarylamines / Aniline and substituted anilines
show 11 more
Substituents
Diphenylether / Aminobenzenesulfonamide / 1-phenylpyrrolidine / Diaryl ether / Aminobenzoic acid / Aminobenzoic acid or derivatives / Benzenesulfonamide / Benzoic acid / Benzoic acid or derivatives / Benzenesulfonyl group
show 32 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not 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
Uniprot Name
Solute carrier family 12 member 1
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]

Drug created on June 13, 2005 07:24 / Updated on November 05, 2018 17:48