VX-702

Investigational

Details

Stereochemistry	ACHIRAL
Molecular Formula	C19H12F4N4O2
Molecular Weight	404.3178
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC(=O)N(C1=CC=C(C(N)=O)C(=N1)C2=CC=C(F)C=C2F)C3=C(F)C=CC=C3F

InChI

InChIKey=FYSRKRZDBHOFAY-UHFFFAOYSA-N

InChI=1S/C19H12F4N4O2/c20-9-4-5-10(14(23)8-9)16-11(18(24)28)6-7-15(26-16)27(19(25)29)17-12(21)2-1-3-13(17)22/h1-8H,(H2,24,28)(H2,25,29)

HIDE SMILES / InChI

Molecular Formula	C19H12F4N4O2
Molecular Weight	404.3178
Charge	0
Count

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17117592
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/19950901

VX-702 is a highly selective inhibitor of p38α MAPK kinase, developed by Vertex Pharmaceuticals Inc in collaboration with Kissei Pharmaceuticals Co. Ltd for potential treatment of inflammation, rheumatoid arthritis and cardiovascular diseases. VX-702 was evaluated in two phase II clinical trials against rheumatoid arthritis, but its development was discontinued by Vertex.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
MAP kinase p38 alpha 35 Target ID: CHEMBL260 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19950901	Inhibitor 8297		3.7 nM [Kd]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Rheumatoid arthritis 316 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19404957	Primary		Phase II 1132	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
130 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19404957/	5 mg 1 times / day steady-state, oral dose: 5 mg route of administration: Oral experiment type: STEADY-STATE co-administered:		VX-702 plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
234.5 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19404957/	10 mg 1 times / day steady-state, oral dose: 10 mg route of administration: Oral experiment type: STEADY-STATE co-administered:		VX-702 plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
2.1887 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19404957/	5 mg 1 times / day steady-state, oral dose: 5 mg route of administration: Oral experiment type: STEADY-STATE co-administered:		VX-702 plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
4.0226 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19404957/	10 mg 1 times / day steady-state, oral dose: 10 mg route of administration: Oral experiment type: STEADY-STATE co-administered:		VX-702 plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	P-gp 1537 rOATs 1 rOCTs 1

Drug as victim

Target	Modality	Activity
P-gp 1537	substrate 3367 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1346987#sid=363677170	no
rOATs 1	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/20170280/	no
rOCTs 1	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/20170280/	no

PubMed

Title	Date	PubMed

Patents

Sample Use Guides

In Vivo Use Guide

In the study of rheumatoid arthritis, VX-702 was administered orally in the doses of 5 and 10 mg b.i.d.

Route of Administration: Oral

In Vitro Use Guide

In an ex vivo blood assay primed with LPS, VX-702 dose-dependently inhibited the production of IL-6, IL-1β and TNFα (IC50 = 59, 122 and 99 ng/ml, respectively).

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:26:28 GMT 2023` Edited by `admin` on `Fri Dec 15 16:26:28 GMT 2023`
Record UNII	527E7SK68P
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

VX-702

Common Name

English

3-PYRIDINECARBOXAMIDE, 6-((AMINOCARBONYL)(2,6-DIFLUOROPHENYL)AMINO)-2-(2,4-DIFLUOROPHENYL)-

Systematic Name

English

6-(CARBAMOYL(2,6-DIFLUOROPHENYL)AMINO)-2-(2,4-DIFLUOROPHENYL)NICOTINAMIDE

Systematic Name

English

6-((AMINOCARBONYL)(2,6-DIFLUOROPHENYL)AMINO)-2-(2,4-DIFLUOROPHENYL)-3-PYRIDINECARBOXAMIDE

Systematic Name

English

Code System Code Type Description

SMS_ID

300000041453