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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 of MK-0686

SMILES

COC(=O)C1=C(C=CC=C1Cl)C2=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

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.

Approval Year

PubMed

PubMed

TitleDatePubMed
CYP2C75-involved autoinduction of metabolism in rhesus monkeys of methyl 3-chloro-3'-fluoro-4'-{(1R)-1-[({1-[(trifluoroacetyl)amino]cyclopropyl}carbonyl)amino]ethyl}-1,1'-biphenyl-2-carboxylate (MK-0686), a bradykinin B1 receptor antagonist.
2008 Jun
Patents

Patents

Sample Use Guides

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 Mon Mar 31 18:28:44 GMT 2025
Edited
by admin
on Mon Mar 31 18:28:44 GMT 2025
Record UNII
M310323W0U
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MK0686
Preferred Name English
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
Code System Code Type Description
FDA UNII
M310323W0U
Created by admin on Mon Mar 31 18:28:44 GMT 2025 , Edited by admin on Mon Mar 31 18:28:44 GMT 2025
PRIMARY
CAS
578727-68-1
Created by admin on Mon Mar 31 18:28:44 GMT 2025 , Edited by admin on Mon Mar 31 18:28:44 GMT 2025
PRIMARY
DRUG BANK
DB12563
Created by admin on Mon Mar 31 18:28:44 GMT 2025 , Edited by admin on Mon Mar 31 18:28:44 GMT 2025
PRIMARY
SMS_ID
100000174919
Created by admin on Mon Mar 31 18:28:44 GMT 2025 , Edited by admin on Mon Mar 31 18:28:44 GMT 2025
PRIMARY
EPA CompTox
DTXSID20206587
Created by admin on Mon Mar 31 18:28:44 GMT 2025 , Edited by admin on Mon Mar 31 18:28:44 GMT 2025
PRIMARY
PUBCHEM
16102897
Created by admin on Mon Mar 31 18:28:44 GMT 2025 , Edited by admin on Mon Mar 31 18:28:44 GMT 2025
PRIMARY
ChEMBL
CHEMBL232943
Created by admin on Mon Mar 31 18:28:44 GMT 2025 , Edited by admin on Mon Mar 31 18:28:44 GMT 2025
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
Ki
BINDER->LIGAND
BINDING
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ACTIVE MOIETY