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

Identification

Summary

Piretanide is a loop diuretic used to manage essential arterial hypertension and edema cardiac, hepatic, and renal origin.

Generic Name
Piretanide
DrugBank Accession Number
DB02925
Background

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.

Type
Small Molecule
Groups
Approved
Structure
Thumb
Weight
Average: 362.4
Monoisotopic: 362.093642386
Chemical Formula
C17H18N2O5S
Synonyms
  • Piretanida
  • Piretanide
External IDs
  • HOE 118
  • HOE-118
  • S 73 4118
  • S-73-4118

Pharmacology

Indication

Not Available

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
USolute carrier family 12 member 1
inhibitor
Humans
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

Adverse Effects
Adverseeffects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbacavirPiretanide may increase the excretion rate of Abacavir which could result in a lower serum level and potentially a reduction in efficacy.
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.
AcetaminophenPiretanide may increase the excretion rate of Acetaminophen which could result in a lower serum level and potentially a reduction in efficacy.
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.
Acetylsalicylic acidAcetylsalicylic acid may decrease the excretion rate of Piretanide which could result in a higher serum level.
AclidiniumPiretanide may increase the excretion rate of Aclidinium which could result in a lower serum level and potentially a reduction in efficacy.
AcrivastinePiretanide may increase the excretion rate of Acrivastine which could result in a lower serum level and potentially a reduction in efficacy.
Interactions
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Food Interactions
Not Available

Products

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International/Other Brands
Arelix / Eurelix / Tauliz

Categories

ATC Codes
C03CA03 — PiretanideG01AE10 — Combinations of sulfonamides
Drug Categories
Chemical TaxonomyProvided by Classyfire
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
1-phenylpyrrolidine / Amine / Amino acid / Amino acid or derivatives / Aminobenzenesulfonamide / Aminobenzoic acid / Aminobenzoic acid or derivatives / Aminosulfonyl compound / Aniline or substituted anilines / Aromatic heteromonocyclic compound
show 32 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
DQ6KK6GV93
CAS number
55837-27-9
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

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
KEGG Drug
D01634
PubChem Compound
4849
PubChem Substance
46507197
ChemSpider
4683
BindingDB
50240046
RxNav
33770
ChEBI
32015
ChEMBL
CHEMBL349803
ZINC
ZINC000003812930
Therapeutic Targets Database
DNC001127
Wikipedia
Piretanide

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
TabletOral
Capsule, extended releaseOral6 mg
Tablet6 MG
Tablet3 MG
TabletOral12 MG
TabletOral3 MG
TabletOral6 MG
TabletOral9 MG
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

Targets

Drugtargets2
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Kind
Protein
Organism
Humans
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. [Article]

Drug created at June 13, 2005 13:24 / Updated at June 08, 2021 11:32