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Details

Stereochemistry ACHIRAL
Molecular Formula C20H22ClF2N3O.C4H4O4
Molecular Weight 509.93
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of BEFIRADOL FUMARATE

SMILES

OC(=O)\C=C\C(O)=O.CC1=CC=C(CNCC2(F)CCN(CC2)C(=O)C3=CC=C(F)C(Cl)=C3)N=C1

InChI

InChIKey=HCRQBLXXJOROBP-WLHGVMLRSA-N
InChI=1S/C20H22ClF2N3O.C4H4O4/c1-14-2-4-16(25-11-14)12-24-13-20(23)6-8-26(9-7-20)19(27)15-3-5-18(22)17(21)10-15;5-3(6)1-2-4(7)8/h2-5,10-11,24H,6-9,12-13H2,1H3;1-2H,(H,5,6)(H,7,8)/b;2-1+

HIDE SMILES / InChI

Molecular Formula C4H4O4
Molecular Weight 116.0722
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Molecular Formula C20H22ClF2N3O
Molecular Weight 393.858
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Befiradol (also known as NLX-112) was initially developed by Pierre Fabre as a selective serotonin-1A receptor agonist for the treatment of cancer pain and neuropathic pain. However, these trials were discontinued. In 2013, the development and commercialization rights were licensed to Neurolixis. Neurolixis studied befiradol in Parkinson’s disease (PD) patients that exhibit dyskinesia. Dyskinesia is a side effect that appears after several years of action Levodopa, a drug that remains the gold standard treatment for PD. In 2019, FDA gave a positive response to Neurolixis’s befiradol to be tested in Phase 2 clinical in Parkinson's disease patients suffering from debilitating levodopa-induced dyskinesia.

Approval Year

PubMed

PubMed

TitleDatePubMed
Profound, non-opioid analgesia produced by the high-efficacy 5-HT(1A) agonist F 13640 in the formalin model of tonic nociceptive pain.
2003 Apr
Conformational analysis and crystal structure of {[1-(3-chloro-4-fluorobenzoyl)-4-fluoropiperidin-4yl]methyl}[(5-methylpyridin-2-yl)methyl]amine, fumaric acid salt.
2005 Nov
High-efficacy 5-hydroxytryptamine 1A receptor activation counteracts opioid hyperallodynia and affective conditioning.
2006 Feb
[(3)H]-F13640, a novel, selective and high-efficacy serotonin 5-HT(1A) receptor agonist radioligand.
2010 Oct
Novel pyridylmethylamines as highly selective 5-HT(1A) superagonists.
2010 Oct 14
Patents
Substance Class Chemical
Created
by admin
on Thu Jul 06 20:30:20 UTC 2023
Edited
by admin
on Thu Jul 06 20:30:20 UTC 2023
Record UNII
87C9853CSK
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BEFIRADOL FUMARATE
Common Name English
F-13,640 FUMARATE
Code English
NLX-112 FUMARATE
Code English
METHANONE, (3-CHLORO-4-FLUOROPHENYL)(4-FLUORO-4-((((5-METHYL-2-PYRIDINYL)METHYL)AMINO)METHYL)-1-PIPERIDINYL)-, (2E)-2-BUTENEDIOATE (1:1)
Systematic Name English
F-13640 FUMARATE
Code English
Code System Code Type Description
SMS_ID
100000183125
Created by admin on Thu Jul 06 20:30:20 UTC 2023 , Edited by admin on Thu Jul 06 20:30:20 UTC 2023
PRIMARY
CAS
208110-65-0
Created by admin on Thu Jul 06 20:30:20 UTC 2023 , Edited by admin on Thu Jul 06 20:30:20 UTC 2023
PRIMARY
FDA UNII
87C9853CSK
Created by admin on Thu Jul 06 20:30:20 UTC 2023 , Edited by admin on Thu Jul 06 20:30:20 UTC 2023
PRIMARY
PUBCHEM
10229295
Created by admin on Thu Jul 06 20:30:20 UTC 2023 , Edited by admin on Thu Jul 06 20:30:20 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY