MK-0686

Investigational

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C22H19ClF4N2O4
Molecular Weight	486.844
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC(=O)C1=C(Cl)C=CC=C1C2=CC(F)=C(C=C2)[C@@H](C)NC(=O)C3(CC3)NC(=O)C(F)(F)F

InChI

InChIKey=WZZIQHIQMWJNLU-LLVKDONJSA-N

InChI=1S/C22H19ClF4N2O4/c1-11(28-19(31)21(8-9-21)29-20(32)22(25,26)27)13-7-6-12(10-16(13)24)14-4-3-5-15(23)17(14)18(30)33-2/h3-7,10-11H,8-9H2,1-2H3,(H,28,31)(H,29,32)/t11-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C22H19ClF4N2O4
Molecular Weight	486.844
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18310472 | https://www.ncbi.nlm.nih.gov/pubmed/17228869 | https://clinicaltrials.gov/ct2/show/NCT00296569 | https://clinicaltrials.gov/ct2/show/NCT00533403 | https://clinicaltrials.gov/ct2/show/NCT00282763

MK-0686 is a bradykinin B1 receptor antagonist patented by American multinational pharmaceutical company Merck & Co for the treatment of neuropathic pain and inflammation. MK-0686 demonstrates significantly reduced susceptibility to human P-gp mediated efflux and shows good potential for human CNS penetration based on brain levels in CF-1 mice and monkeys. Additionally, MK-0686 also exhibited good CNS bradykinin B1 receptor occupancy in the transgenic rat expressing the human B1 receptor and showed oral efficacy in reducing CFA-induced hyperalgesia in a humanized mouse. Unfortunately, in phase II clinical trials MK-0686 failed to demonstrate efficacy in phase II clinical trials.

CNS Activity

Originator

Approval Year

PubMed

Title	Date	PubMed

Patents

Sample Use Guides

In Vivo Use Guide

Rhesus monkey: 30 mg/kg/day, 60 mg/kg/day, and 150 mg/kg/day

Route of Administration: Oral

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:28:07 GMT 2023` Edited by `admin` on `Fri Dec 15 16:28:07 GMT 2023`
Record UNII	M310323W0U
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

MK-0686

Code

English

3-CHLORO-3'-FLUORO-4'-((1R)-1-(((1-((TRIFLUOROACETYL)AMINO)CYCLOPROPYL)CARBONYL)AMINO)ETHYL)-(1,1'-BIPHENYL)-2-CARBOXYLIC ACID, METHYL ESTER

Common Name

English

(1,1'-BIPHENYL)-2-CARBOXYLIC ACID, 3-CHLORO-3'-FLUORO-4'-((1R)-1-(((1-((TRIFLUOROACETYL)AMINO)CYCLOPROPYL)CARBONYL)AMINO)ETHYL)-, METHYL ESTER

Common Name

English

MK0686

Code

English

Code System Code Type Description

FDA UNII

M310323W0U