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Details

Stereochemistry ABSOLUTE
Molecular Formula C18H24N6O
Molecular Weight 340.4234
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PEXACERFONT

SMILES

CC[C@@]([H])(C)N=c1[nH]c(C)nc2c(c(C)nn21)-c3ccc(nc3C)OC

InChI

InChIKey=LBWQSAZEYIZZCE-SNVBAGLBSA-N
InChI=1S/C18H24N6O/c1-7-10(2)19-18-22-13(5)21-17-16(12(4)23-24(17)18)14-8-9-15(25-6)20-11(14)3/h8-10H,7H2,1-6H3,(H,19,21,22)/t10-/m1/s1

HIDE SMILES / InChI

Molecular Formula C18H24N6O
Molecular Weight 340.4234
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Pexacerfont is a highly potent and selective CRF1 receptor antagonist that displays no agonist properties. It is specific for CRF1 receptors and has more than 1,000- fold less affinity for CRF2 receptors, and more than 100- fold less affinity for the CRF-binding protein. In extensive preclinical studies, pexacerfont has been shown to inhibit specific binding of CRF to rat, dog, monkey, and human CRF1 receptors. The functional anxiolytic effects of CRF1 receptor occupancy were demonstrated in two rodent models of anxiety, situational anxiety and elevated plus maze paradigms. Pexacerfont did not demonstrate efficacy compared to placebo for the treatment of generalized anxiety disorder in human. The bogus taste tests suggested some protective effect of pexacerfont against eating after a laboratory stressor. Pexacerfont had been in phase II clinical trials for the treatment of irritable bowel syndrome and depression depression.

Approval Year

PubMed

PubMed

TitleDatePubMed
Do corticotropin releasing factor-1 receptors influence colonic transit and bowel function in women with irritable bowel syndrome?
2009 Jun
Multicenter, randomized, double-blind, active comparator and placebo-controlled trial of a corticotropin-releasing factor receptor-1 antagonist in generalized anxiety disorder.
2010 May
In vitro and in vivo metabolism and pharmacokinetics of BMS-562086, a potent and orally bioavailable corticotropin-releasing factor-1 receptor antagonist.
2012 Jun
Metabolic and toxicological considerations for the latest drugs used to treat irritable bowel syndrome.
2013 Apr
Behavioral, biological, and chemical perspectives on targeting CRF(1) receptor antagonists to treat alcoholism.
2013 Mar 1
A simplified and completely automated workflow for regulated LC-MS/MS bioanalysis using cap-piercing direct sampling and evaporation-free solid phase extraction.
2013 Mar 15
The corticotropin releasing hormone-1 (CRH1) receptor antagonist pexacerfont in alcohol dependence: a randomized controlled experimental medicine study.
2015 Mar 13
Effect of the CRF1-receptor antagonist pexacerfont on stress-induced eating and food craving.
2016 Dec
The CRF1 Antagonist Verucerfont in Anxious Alcohol-Dependent Women: Translation of Neuroendocrine, But not of Anti-Craving Effects.
2016 Nov
Medical Therapies in the Pipeline for Irritable Bowel Syndrome.
2017 Sep
Toxicity of Pexacerfont, a Corticotropin-Releasing Factor Type 1 Receptor Antagonist, in Rats and Dogs.
2019 Mar/Apr
Patents

Sample Use Guides

100 mg/day (after a 1 week loading dose of 300 mg/day)
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Sat Jun 26 09:07:55 UTC 2021
Edited
by admin
on Sat Jun 26 09:07:55 UTC 2021
Record UNII
LF1VBG4ZUK
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PEXACERFONT
INN   USAN  
USAN   INN  
Official Name English
DPC-A69448
Common Name English
BMS-562086
Code English
N-((2R)-BUTAN-2-YL)-8-(6-METHOXY-2-METHYLPYRIDIN-3-YL)-2,7-DIMETHYLPYRAZOLO(1,5-A)(1,3,5)TRIAZIN-4-AMINE
Systematic Name English
PEXACERFONT [USAN]
Common Name English
PEXACERFONT [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C28197
Created by admin on Sat Jun 26 09:07:55 UTC 2021 , Edited by admin on Sat Jun 26 09:07:55 UTC 2021
Code System Code Type Description
INN
8883
Created by admin on Sat Jun 26 09:07:55 UTC 2021 , Edited by admin on Sat Jun 26 09:07:55 UTC 2021
PRIMARY
FDA UNII
LF1VBG4ZUK
Created by admin on Sat Jun 26 09:07:55 UTC 2021 , Edited by admin on Sat Jun 26 09:07:55 UTC 2021
PRIMARY
PUBCHEM
9884366
Created by admin on Sat Jun 26 09:07:55 UTC 2021 , Edited by admin on Sat Jun 26 09:07:55 UTC 2021
PRIMARY
ChEMBL
CHEMBL482950
Created by admin on Sat Jun 26 09:07:55 UTC 2021 , Edited by admin on Sat Jun 26 09:07:55 UTC 2021
PRIMARY
DRUG BANK
DB12572
Created by admin on Sat Jun 26 09:07:55 UTC 2021 , Edited by admin on Sat Jun 26 09:07:55 UTC 2021
PRIMARY
CAS
459856-18-9
Created by admin on Sat Jun 26 09:07:55 UTC 2021 , Edited by admin on Sat Jun 26 09:07:55 UTC 2021
PRIMARY
MESH
C542342
Created by admin on Sat Jun 26 09:07:55 UTC 2021 , Edited by admin on Sat Jun 26 09:07:55 UTC 2021
PRIMARY
WIKIPEDIA
PEXACERFONT
Created by admin on Sat Jun 26 09:07:55 UTC 2021 , Edited by admin on Sat Jun 26 09:07:55 UTC 2021
PRIMARY
NCI_THESAURUS
C76508
Created by admin on Sat Jun 26 09:07:55 UTC 2021 , Edited by admin on Sat Jun 26 09:07:55 UTC 2021
PRIMARY
EPA CompTox
459856-18-9
Created by admin on Sat Jun 26 09:07:55 UTC 2021 , Edited by admin on Sat Jun 26 09:07:55 UTC 2021
PRIMARY
Related Record Type Details
BINDER->LIGAND
BINDING
TARGET -> INHIBITOR
IC50
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
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METABOLITE -> PARENT
IN VITRO
METABOLITE -> PARENT
IN VITRO
METABOLITE -> PARENT
IN VITRO
Related Record Type Details
ACTIVE MOIETY