GRAPIPRANT

Details

Stereochemistry	ACHIRAL
Molecular Formula	C26H29N5O3S
Molecular Weight	491.605
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCC1=NC2=C(C=C(C)N=C2C)N1C3=CC=C(CCNC(=O)NS(=O)(=O)C4=CC=C(C)C=C4)C=C3

InChI

InChIKey=HZVLFTCYCLXTGV-UHFFFAOYSA-N

InChI=1S/C26H29N5O3S/c1-5-24-29-25-19(4)28-18(3)16-23(25)31(24)21-10-8-20(9-11-21)14-15-27-26(32)30-35(33,34)22-12-6-17(2)7-13-22/h6-13,16H,5,14-15H2,1-4H3,(H2,27,30,32)

HIDE SMILES / InChI

Molecular Formula	C26H29N5O3S
Molecular Weight	491.605
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.elanco.us/galliprant/pdf/galliprantpi.pdf | https://www.ncbi.nlm.nih.gov/pubmed/28169162

GALLIPRANT® (grapiprant tablets) is a prostaglandin E2 (PGE2) EP4 receptor antagonist; a non-cyclooxygenase (COX) inhibiting, non-steroidal antiinflammatory drug (NSAID) in the piprant class. Grapiprant is indicated for the control of pain and inflammation associated with osteoarthritis in dogs. It is approved for veterinary use, but it is in phase II development in Japan for the treatment of chronic inflammatory pain, including osteoarthritis and rheumatoid arthritis. Grapiprant shows similar in vitro binding affinity (Ki) for the rat and dog EP4 receptor, 20 and 24 nM, respectively.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Prostanoid EP4 receptor 11 Target ID: CHEMBL1836 Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=dbf8c202-38df-468a-9e68-96f0293ba26f \| https://www.ncbi.nlm.nih.gov/pubmed/28169162	Antagonist 2778		13.0 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Osteoarthritis 157 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27027634 http://www.aratana.com/wp-content/uploads/2015/06/at1-001-14-safety-study-30may14-web.pdf http://onlinelibrary.wiley.com/doi/10.1002/vms3.13/pdf	Primary		Approved 8429	GALLIPRANT Approved Use GALLIPRANT (grapiprant tablets) is indicated for the control of pain and inflammation associated with osteoarthritis in dogs Launch Date 2016
Arthritis 89 Sources: http://adisinsight.springer.com/drugs/800029996	Primary		Phase II 1132	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
CJ-023,423, a novel, potent and selective prostaglandin EP4 receptor antagonist with antihyperalgesic properties.	2007 Aug	17495127

Patents

Sample Use Guides

In Vivo Use Guide

Dogs: The dose of GALLIPRANT (grapiprant tablets) is 0.9 mg/lb (2 mg/kg) once daily.

Route of Administration: Oral

In Vitro Use Guide

The EP4 receptor membrane prepared from the EP4-HEK293 cells demonstrated a single affinity site for PGE2 binding with Kd value of 2.3 nM. Grapiprant displaced [3H]- PGE2 (1 nM) binding to dog recombinant EP4 receptor in a concentration-dependent manner with an IC50 value of 35 +/- 3.9 nM and with a Ki value of 24 +/- 2.7 nM.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 17:11:13 GMT 2023` Edited by `admin` on `Sat Dec 16 17:11:13 GMT 2023`
Record UNII	J9F5ZPH7NB
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

GRAPIPRANT

Official Name

English

CJ 023423

Code

English

BENZENESULFONAMIDE, N-(((2-(4-(2-ETHYL-4,6-DIMETHYL-1H-IMIDAZO(4,5-C)PYRIDIN-1-YL)PHENYL)ETHYL)AMINO)CARBONYL)-4-METHYL-

Systematic Name

English

N-(((2-(4-(2-ETHYL-4,6-DIMETHYL-1H-IMIDAZO(4,5-C)PYRIDIN-1-YL)PHENYL)ETHYL)AMINO)CARBONYL)-4-METHYLBENZENESULFONAMIDE

Systematic Name

English

2-ETHYL-4,6-DIMETHYL-1-(4-(2-(((((4-METHYLPHENYL)SULFONYL)AMINO)CARBONYL)AMINO)ETHYL)PHENYL)-1H-IMIDAZO(4,5-C)PYRIDINE

Systematic Name

English

MR-10A7

Code

English

grapiprant [INN]

Common Name

English

CJ-023,423

Common Name

English

GRAPIPRANT [USAN]

Common Name

English

Grapiprant [WHO-DD]

Common Name

English

GRAPIPRANT [MI]

Common Name

English

GRAPIPRANT [GREEN BOOK]

Common Name

English

N-(((2-(4-(2-ETHYL-4,6-DIMETHYL-1H-IMIDAZO(4,5-C)PYRIDIN-1-YL)PHENYL)ETHYL)AMINO)CARBONYL)-4-METHYL-BENZENESULFONAMIDE

Systematic Name

English

RQ-00000007

Code

English

CJ-023

Code

English

RQ-7

Code

English

AAT-007

Code

English

MR10A7

Code

English

CJ-023423

Code

English

Classification Tree Code System Code

CFR

21 CFR 520.1084