ContaminantDB: Prucalopride

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

Record Information

Version

1.0

Creation Date

2016-05-22 07:18:41 UTC

Update Date

2016-11-09 01:16:14 UTC

Accession Number

CHEM020669

Identification

Common Name

Prucalopride

Class

Small Molecule

Description

Prucalopride is a dihydrobenzofurancarboxamide derivative from the benzofurane family that selectively stimulates 5-HT4 receptors and thus, it presents enterokinetic properties.[A37348] The high selectivity of prucalopride allowed further development as it prevented the cardiac adverse reactions observed due to non-target effects of precedent therapies.[A40254] Prucalopride was developed by Shire Development LLC and approved for use in Europe in 2009,[A40250] in Canada on December 7, 2011 and by the FDA on December 17, 2018.[L4880]

Contaminant Sources

ToxCast & Tox21 Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
R-093877Prucalopride	ChEMBL
Resotrans	MeSH
Resolor	MeSH
Resotran	MeSH
4-Amino-5-chloro-N-[1-(3-methoxypropyl)piperidin-4-yl]-2,3-dihydro-1-benzofuran-7-carboximidate	Generator
4-Amino-5-chloro-N-(1-(3-methoxypropyl)-4-piperidinyl)-2,3-dihydro-1-benzofuran-7-carboxamide	MeSH

Chemical Formula

C₁₈H₂₆ClN₃O₃

Average Molecular Mass

367.870 g/mol

Monoisotopic Mass

367.166 g/mol

CAS Registry Number

179474-81-8

IUPAC Name

4-amino-5-chloro-N-[1-(3-methoxypropyl)piperidin-4-yl]-2,3-dihydro-1-benzofuran-7-carboxamide

Traditional Name

prucalopride

SMILES

COCCCN1CCC(CC1)NC(=O)C1=C2OCCC2=C(N)C(Cl)=C1

InChI Identifier

InChI=1S/C18H26ClN3O3/c1-24-9-2-6-22-7-3-12(4-8-22)21-18(23)14-11-15(19)16(20)13-5-10-25-17(13)14/h11-12H,2-10,20H2,1H3,(H,21,23)

InChI Key

ZPMNHBXQOOVQJL-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as aminobenzamides. These are organic compounds containing a benzamide moiety with an amine group attached to the benzene ring.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Aminobenzamides

Alternative Parents

Substituents

Aminobenzamide
Coumaran
Alkyl aryl ether
Aryl chloride
Aryl halide
Piperidine
Amino acid or derivatives
Carboxamide group
Secondary carboxylic acid amide
Tertiary aliphatic amine
Tertiary amine
Oxacycle
Carboxylic acid derivative
Dialkyl ether
Ether
Azacycle
Organoheterocyclic compound
Organohalogen compound
Organopnictogen compound
Organic oxygen compound
Amine
Organic nitrogen compound
Hydrocarbon derivative
Organochloride
Organonitrogen compound
Organooxygen compound
Primary amine
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	0.13 g/L	ALOGPS
logP	2.09	ALOGPS
logP	0.74	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	14.64	ChemAxon
pKa (Strongest Basic)	8.98	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	76.82 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	100.67 m³·mol⁻¹	ChemAxon
Polarizability	39.08 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	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-9812000000-f1bd170ac71ec919b417	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014r-0309000000-de7dc5c7c5e8b2bd381c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05fs-4926000000-bc02ec523ae005321132	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00ym-8900000000-261664a7dcbdfbafb0b6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0109000000-463adb3809c2c0b711fa	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-3849000000-c813744bf4a58d6f13da	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-02td-4960000000-57970845cde3ad05051c	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

DB06480

HMDB ID

HMDB0256880

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

Prucalopride

Chemspider ID

2314539

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

Prucalopride (CHEM020669)

Structure for CHEM020669: Prucalopride