SERLOPITANT

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Search structure


Synonyms	MK-0594 Serlopitant VPD-737 Vpd-737
Status
Molecule Category	Free-form
UNII	277V92K32B


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

Structure


InChI Key	FLNYCRJBCNNHRH-OIYLJQICSA-N
Smiles	C[C@@H](O[C@H]1CC[C@@H]2CN(C3=CC(=O)CC3)C[C@H]2[C@@H]1c1ccc(F)cc1)c1cc(C(F)(F)F)cc(C(F)(F)F)c1
InChI	InChI=1S/C29H28F7NO2/c1-16(19-10-20(28(31,32)33)12-21(11-19)29(34,35)36)39-26-9-4-18-14-37(23-7-8-24(38)13-23)15-25(18)27(26)17-2-5-22(30)6-3-17/h2-3,5-6,10-13,16,18,25-27H,4,7-9,14-15H2,1H3/t16-,18-,25-,26+,27+/m1/s1

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C29H28F7NO2
Molecular Weight	555.53
AlogP	7.68
Hydrogen Bond Acceptor	3.0
Hydrogen Bond Donor	0.0
Number of Rotational Bond	5.0
Polar Surface Area	29.54
Molecular species	NEUTRAL
Aromatic Rings	2.0
Heavy Atoms	39.0

Bioactivity

Mechanism of Action	Action	Reference
Neurokinin 1 receptor antagonist	ANTAGONIST	PubMed Other


Protein: Neurokinin 1 receptor Description: Substance-P receptor Organism : Homo sapiens P25103 ENSG00000115353

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2C Cytochrome P450 2C19	-	29000	-	-	-
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2C Cytochrome P450 2C8	-	58000	-	-	-
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2C Cytochrome P450 2C9	-	30000	-	-	-
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2D Cytochrome P450 2D6	-	35000	-	-	-
Enzyme Cytochrome P450 Cytochrome P450 family 3 Cytochrome P450 family 3A Cytochrome P450 3A4	-	39000	-	-	-
Membrane receptor Family A G protein-coupled receptor Peptide receptor (family A GPCR) Short peptide receptor (family A GPCR) Neurokinin receptor	-	0-10	-	2	5

Assay Description	Organism	Bioactivity	Reference
Displacement of [125I]substance P human recombinant NK1 receptor expressed in CHO cells in absence of human serum albumin	Homo sapiens	0.06 nM
Displacement of [125I]substance P human recombinant NK1 receptor expressed in CHO cells in presence of human serum albumin	Homo sapiens	9.5 nM
Binding affinity to human NK2 receptor	Homo sapiens	2.4 nM
Binding affinity to human NK3 receptor	Homo sapiens	2.4 nM
Toxicity in iv dosed gerbils plasma assessed as inhibition of GR-73632-induced foot tapping after 1 hr	Gerbillinae	6.5 nM
Toxicity in iv dosed gerbils plasma assessed as inhibition of GR-73632-induced foot tapping after 24 hrs	Gerbillinae	6.0 nM
Antagonist activity at NK1 receptor in iv dosed gerbil brain assessed as inhibition of GR73632-induced foot tapping after 1 hr	Gerbillinae	7.7 nM
Antagonist activity at NK1 receptor in iv dosed gerbil plasma assessed as inhibition of GR73632-induced foot tapping after 1 hr	Gerbillinae	6.5 nM
Antagonist activity at human NK1 receptor expressed in CHO cells assessed as inhibition of IP1 generation measuring remaining substance P at 100 nM	Homo sapiens	5.0 %
Displacement of [125I]substance P from human NK1 receptor expressed in CHO cells in presence of human serum	Homo sapiens	9.5 nM
Displacement of [125I]substance P from human NK1 receptor expressed in CHO cells	Homo sapiens	0.06 nM

Cross References

Resources	Reference
ChEMBL	CHEMBL447955
DrugBank	DB12973
FDA SRS	277V92K32B
Guide to Pharmacology	9280
PubChem	23653789
SureChEMBL	SCHEMBL3183159

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).