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
Structure for Piretanide (DB02925)
- 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
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Edema •••••••••••• •••••••• •••••• Used in combination to treat Essential arterial hypertension Combination Product in combination with: Ramipril (DB00178) •••••••••••• ••••• ••••• •••••••• •••••••••• ••••••••• ••••••••• •••• ••• ••••••••••• •••••••••• •••••••••• •• ••• •••• •••••••••• •••••• Used in combination to treat Essential arterial hypertension Combination Product in combination with: Ramipril (DB00178) •••••••••••• ••••• •••••••••• ••••••• •••• ••••••••••• •••••• Treatment of High blood pressure (hypertension) •••••••••••• •••••••• •••••••• ••••••• •••••••• •••••• Treatment of High blood pressure (hypertension) •••••••••••• •••••••• •••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism USolute carrier family 12 member 1 inhibitorHumans - 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir Piretanide may increase the excretion rate of Abacavir which could result in a lower serum level and potentially a reduction in efficacy. Acarbose The therapeutic efficacy of Acarbose can be increased when used in combination with Piretanide. Aceclofenac The therapeutic efficacy of Piretanide can be decreased when used in combination with Aceclofenac. Acemetacin The therapeutic efficacy of Piretanide can be decreased when used in combination with Acemetacin. Acetaminophen Piretanide may increase the excretion rate of Acetaminophen which could result in a lower serum level and potentially a reduction in efficacy. - Food Interactions
- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- International/Other Brands
- Arelix / Eurelix / Tauliz
- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image ARELIX ACE Piretanide (6 mg) + Ramipril (5 mg) Tablet Oral 2014-07-01 Not applicable Germany 
PRILACE Piretanide (6 MG) + Ramipril (5 MG) Tablet Oral Sanofi S.R.L. 2014-07-08 Not applicable Italy 
RAMIPRIL HEXAL PL PIR5/6MG Piretanide (6 mg) + Ramipril (5 mg) Tablet Oral 2014-07-01 2021-01-01 Germany RAMIPRIL HEXAL PL PIR5/6MG Piretanide (6 mg) + Ramipril (5 mg) Tablet Oral 2014-07-01 2021-08-01 Germany RAMIPRIL HEXAL PL PIR5/6MG Piretanide (6 mg) + Ramipril (5 mg) Tablet Oral 2014-07-01 2021-05-15 Germany
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
- External Links
- KEGG Drug
- D01634
- PubChem Compound
- 4849
- PubChem Substance
- 46507197
- ChemSpider
- 4683
- BindingDB
- 50240046
- 33770
- ChEBI
- 32015
- ChEMBL
- CHEMBL349803
- ZINC
- ZINC000003812930
- Therapeutic Targets Database
- DNC001127
- Wikipedia
- Piretanide
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet Oral Capsule, extended release Oral 6 mg Tablet 6 MG Tablet 3 MG Tablet Oral 12 MG Tablet Oral 3 MG Tablet Oral 6 MG Tablet Oral 9 MG - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source logP 3.92 BIOBYTE (1995) - Predicted Properties
Property Value Source Water Solubility 0.0914 mg/mL ALOGPS logP 2.2 ALOGPS logP 2.25 Chemaxon logS -3.6 ALOGPS pKa (Strongest Acidic) 4.68 Chemaxon pKa (Strongest Basic) -0.62 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 109.93 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 93.68 m3·mol-1 Chemaxon Polarizability 35.84 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9907 Blood Brain Barrier + 0.6318 Caco-2 permeable - 0.6466 P-glycoprotein substrate Non-substrate 0.5237 P-glycoprotein inhibitor I Non-inhibitor 0.8026 P-glycoprotein inhibitor II Non-inhibitor 0.6635 Renal organic cation transporter Non-inhibitor 0.7657 CYP450 2C9 substrate Non-substrate 0.7067 CYP450 2D6 substrate Non-substrate 0.8032 CYP450 3A4 substrate Non-substrate 0.5997 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Non-inhibitor 0.9026 CYP450 3A4 inhibitor Non-inhibitor 0.8309 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.6747 Ames test Non AMES toxic 0.6433 Carcinogenicity Non-carcinogens 0.6985 Biodegradation Not ready biodegradable 0.9786 Rat acute toxicity 1.8427 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.848 hERG inhibition (predictor II) Inhibitor 0.5391
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 194.6304684 predictedDarkChem Lite v0.1.0 [M-H]- 173.72267 predictedDeepCCS 1.0 (2019) [M+H]+ 193.7365684 predictedDarkChem Lite v0.1.0 [M+H]+ 176.08067 predictedDeepCCS 1.0 (2019) [M+Na]+ 194.8130684 predictedDarkChem Lite v0.1.0 [M+Na]+ 182.82033 predictedDeepCCS 1.0 (2019)
Targets
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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
- 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