PRUCALOPRIDE

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Search structure


Synonyms	Prucalopride R-093877 R093877 Resolor
Status
Molecule Category	Free-form
ATC	A06AX05
UNII	0A09IUW5TP
EPA CompTox	DTXSID5057670


Active Pharmaceutical Ingredients Bioactive chemicals	Exact Similarity SubStructure	Threshold (%) >= 70

Structure


InChI Key	ZPMNHBXQOOVQJL-UHFFFAOYSA-N
Smiles	COCCCN1CCC(NC(=O)c2cc(Cl)c(N)c3c2OCC3)CC1
InChI	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)

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C18H26ClN3O3
Molecular Weight	367.88
AlogP	2.09
Hydrogen Bond Acceptor	5.0
Hydrogen Bond Donor	2.0
Number of Rotational Bond	6.0
Polar Surface Area	76.82
Molecular species	BASE
Aromatic Rings	1.0
Heavy Atoms	25.0

Bioactivity

Mechanism of Action	Action	Reference
Serotonin 4 (5-HT4) receptor agonist	AGONIST	PubMed


Protein: Serotonin 4 (5-HT4) receptor Description: 5-hydroxytryptamine receptor 4 Organism : Homo sapiens Q13639 ENSG00000164270

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Ion channel Ligand-gated ion channel 5HT3 receptor	-	-	-	3981	-
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Serotonin receptor	5-26	-	-	3-110	-

Assay Description	Organism	Bioactivity	Reference
Tested for agonist activity against 5-hydroxytryptamine 4 receptor	None	7.5 nM
Tested for selectivity for 5-hydroxytryptamine 4 receptor	None	110.0 nM
Binding affinity at 5HT4 receptor	None	2.512 nM
Agonist activity at human 5HT4e receptor expressed in CHO cells assessed as cAMP level after 4 hrs by luciferase reporter gene assay	Homo sapiens	5.2 nM
Agonist activity at rat 5HT4e receptor expressed in HEK293 cells assessed as cAMP level after 30 mins by HTRF assay	Rattus norvegicus	26.0 nM
Agonist activity at recombinant human 5-HT4E receptor expressed in CHO cells assessed as induction of c-AMP accumulation after 4 hrs by luciferase reporter assay	Homo sapiens	5.2 nM
Agonist activity at 5-HT4E receptor (unknown origin)	Homo sapiens	26.0 nM
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging	Homo sapiens	-5.75 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	26.3 %		SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	-0.9272 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	-0.12 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	-0.04 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	-0.12 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	-0.04 %

Related Entries

Cross References

Resources	Reference
ChEBI	135552
ChEMBL	CHEMBL117287
DrugBank	DB06480
DrugCentral	3502
FDA SRS	0A09IUW5TP
Guide to Pharmacology	243
PubChem	3052762
SureChEMBL	SCHEMBL16952
ZINC	ZINC000001891034

CONTENTS

PREMIER has received funding from the Innovative Medicines Initiative 2 Joint Undertaking (JU) under grant agreement No 875508. The JU receives support from the EU’s Horizon 2020 research and innovation programme and the European Federation of Pharmaceutical Industries and Associations (EFPIA). The views reflect only the authors’ perspective and the JU is not responsible for any use that may be made of the information this manuscript contains.

Elements of the website have been developed under projects PREMIER and the Biocenter Finland Drug Discovery and Chemical Biology network. CSC-IT is thanked for providing computational resources. Content of the website is provided without guarantee for correctness. Data has been collected and integrated from multiple public sources, for the largest: FDA, HUGO Gene Nomenclature Committee, ChEMBL, IUPHAR/BPS guide to pharmacology, Reactome, UniProt, and Ensembl. Credit is given to Ensembl for collecting species images (provided under public domain licences such as Wikimedia and NHGRI).