Prucalopride (CED0006996)

Record Information

Version

1.0

Creation Date

2016-05-22 07:18:41 UTC

Update Date

2026-08-20 01:08:22 UTC

Accession Number

CHEM020669

Identification

Common Name

Prucalopride

Class

Small Molecule

Description

Prucalopride is an organic compound with the formula C18H26ClN3O3 and an average molecular weight of 367.87 g/mol. Prucalopride belongs to the benzoic acids and derivatives, a subclass of benzene and substituted derivatives within the organic compounds. It acts as an agonist of the protein target 5-hydroxytryptamine receptor 4 (HTR4). The compound is found in or released from two recorded sources: household cleaning and consumer products, specifically non electric simulated smoking devices, and healthcare, pharmaceuticals and veterinary products, where it is used as a drug for constipation. The recorded route of exposure for this substance is oral.

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

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

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	Yes	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	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-0002-9812000000-f1bd170ac71ec919b417	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014r-0309000000-de7dc5c7c5e8b2bd381c	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-05fs-4926000000-bc02ec523ae005321132	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00ym-8900000000-261664a7dcbdfbafb0b6	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-0109000000-463adb3809c2c0b711fa	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-3849000000-c813744bf4a58d6f13da	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-02td-4960000000-57970845cde3ad05051c	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
606.0	Log mg/kg	[340:1100]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
253	Drugs for constipation	Healthcare, pharmaceuticals & veterinary products	Not Available
559	Non Electric Simulated Smoking Devices	Household cleaning & consumer products	Not Available

Pathways

2 pathways

Prucalopride Action Pathway

Prucalopride Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	D(2) dopamine receptor	P61169	Rat	Predicted (SEA)	125.726
Click to view 3D structure	5-hydroxytryptamine receptor 1A	P08908	Humans	Predicted (SEA)	152.351
Click to view 3D structure	5-hydroxytryptamine receptor 7	P34969	Humans	Predicted (SEA)	112.648
Click to view 3D structure	5-hydroxytryptamine receptor 1D	P28221	Humans	Predicted (SEA)	55.1951
Click to view 3D structure	D(4) dopamine receptor	P21917	Humans	Predicted (SEA)	131.799
Click to view 3D structure	Alpha-1A adrenergic receptor	P35348	Humans	Predicted (SEA)	90.85
Click to view 3D structure	5-hydroxytryptamine receptor 6	P50406	Humans	Predicted (SEA)	109.767
Click to view 3D structure	D(1A) dopamine receptor	P21728	Humans	Predicted (SEA)	95.2874
Click to view 3D structure	Sigma non-opioid intracellular receptor 1	Q99720	Humans	Predicted (SEA)	178.275
Click to view 3D structure	Alpha-2C adrenergic receptor	P18825	Humans	Predicted (SEA)	75.903
Click to view 3D structure	5-hydroxytryptamine receptor 1B	P28222	Humans	Predicted (SEA)	72.9447
Click to view 3D structure	Alpha-2B adrenergic receptor	P18089	Humans	Predicted (SEA)	68.1181
Click to view 3D structure	D(3) dopamine receptor	P19020	Rattus norvegicus	Predicted (SEA)	77.7714
Click to view 3D structure	Beta-2 adrenergic receptor	P07550	Humans	Predicted (SEA)	44.3741
Click to view 3D structure	5-hydroxytryptamine receptor 4	Q13639	Humans	Predicted (SEA)	1.55698
Click to view 3D structure	5-hydroxytryptamine receptor 3A	P46098	Humans	Predicted (SEA)	2.25763
Click to view 3D structure	5-hydroxytryptamine receptor 4	Q62758	Rattus norvegicus	Predicted (SEA)	2.17978
Click to view 3D structure	Voltage-gated inwardly rectifying potassium channel KCNH2	Q12809	Humans	Predicted (SEA)	43.8291
Click to view 3D structure	5-hydroxytryptamine receptor 2C	P28335	Humans	Predicted (SEA)	46.9431
Click to view 3D structure	5-hydroxytryptamine receptor 2A	P28223	Humans	Predicted (SEA)	68.8187
Click to view 3D structure	Alpha-2A adrenergic receptor	P08913	Humans	Predicted (SEA)	31.5289
Click to view 3D structure	5-hydroxytryptamine receptor 2B	P41595	Humans	Predicted (SEA)	49.1229
Click to view 3D structure	5-hydroxytryptamine receptor 4	O70528	Cavia porcellus	Predicted (SEA)	7.31783
Click to view 3D structure	D(3) dopamine receptor	P35462	Humans	Predicted (SEA)	100.893
Click to view 3D structure	D(2) dopamine receptor	P14416	Humans	Predicted (SEA)	149.86