ContaminantDB: Piretanide

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-22 03:45:08 UTC

Update Date

2016-11-09 01:15:28 UTC

Accession Number

CHEM016839

Identification

Common Name

Piretanide

Class

Small Molecule

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.

Contaminant Sources

STOFF IDENT Compounds
ToxCast & Tox21 Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Arelix	Kegg
4-Phenoxy-3-pyrrolidin-1-yl-5-sulfamoylbenzoic acid	MeSH
HOE 118	MeSH

Chemical Formula

C₁₇H₁₈N₂O₅S

Average Molecular Mass

362.400 g/mol

Monoisotopic Mass

362.094 g/mol

CAS Registry Number

55837-27-9

IUPAC Name

4-phenoxy-3-(pyrrolidin-1-yl)-5-sulfamoylbenzoic acid

Traditional Name

piretanide

SMILES

NS(=O)(=O)C1=CC(=CC(N2CCCC2)=C1OC1=CC=CC=C1)C(O)=O

InChI Identifier

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)

InChI Key

UJEWTUDSLQGTOA-UHFFFAOYSA-N

Chemical Taxonomy

Description

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

Substituents

Diphenylether
Aminobenzenesulfonamide
1-phenylpyrrolidine
Diaryl ether
Aminobenzoic acid
Aminobenzoic acid or derivatives
Benzenesulfonamide
Benzoic acid
Benzoic acid or derivatives
Benzenesulfonyl group
Tertiary aliphatic/aromatic amine
Benzoyl
Aniline or substituted anilines
Dialkylarylamine
Phenol ether
Phenoxy compound
Organosulfonic acid amide
Aminosulfonyl compound
Pyrrole
Pyrrolidine
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Sulfonyl
Amino acid or derivatives
Tertiary amine
Amino acid
Azacycle
Carboxylic acid derivative
Carboxylic acid
Organoheterocyclic compound
Ether
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Amine
Organosulfur compound
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.091 g/L	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	35.85 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

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-001m-4194000000-625e0ba14afa2ffee540	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-000i-3980000000-dc67e28bf67c9f799108	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-000i-3980000000-dc67e28bf67c9f799108	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0019000000-ff0f88ecfe2c8603f592	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0179000000-33b14175fb0ca1b8c527	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-1390000000-ee1de56f2481858b2ae4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-4009000000-a02bb82a138376f82b62	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-02vj-6459000000-4a209e12057a0ff1f04e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004l-9110000000-c0696e29ff54a56554ef	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB02925

HMDB ID

HMDB0256593

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Piretanide

Chemspider ID

4683

ChEBI ID

Not Available

PubChem Compound ID

Not Available

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Piretanide (CHEM016839)

Structure for CHEM016839: Piretanide