VERUCERFONT

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C22H26N6O2
Molecular Weight	406.4808
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC[C@H](NC1=CC(C)=NC2=C(C(C)=NN12)C3=C(C)C=C(OC)C=C3)C4=NC(C)=NO4

InChI

InChIKey=VKHVAUKFLBBZFJ-SFHVURJKSA-N

InChI=1S/C22H26N6O2/c1-7-18(22-24-15(5)27-30-22)25-19-11-13(3)23-21-20(14(4)26-28(19)21)17-9-8-16(29-6)10-12(17)2/h8-11,18,25H,7H2,1-6H3/t18-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C22H26N6O2
Molecular Weight	406.4808
Charge	0
Count

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

Description
Sources: https://adisinsight.springer.com/drugs/800025784 | https://www.ncbi.nlm.nih.gov/pubmed/27109623

Verucerfont (formerly GSK561679), a corticotropin releasing factor (CRF) receptor 1 antagonist, is being developed by GlaxoSmithKline under the license from Neurocrine Biosciences, for the treatment of post-traumatic stress disorder and congenital adrenal hyperplasia (CAH). Verucerfont is a potent, selective CRF1 receptor antagonist (IC50 for CRF1, CRF2, and CRF-BP ~ 6.1, >1000 and >1000 nM, respectively), and is orally available and brain penetrant. Verucerfont is in phase II clinical trials for the treatment of post-traumatic stress disorder or alcoholism. The compound was also in trials for the treatment of classic congenital adrenal hyperplasia (CAH). However, this research has been discontinued. In 2015, orphan drug designation was received in U.S. for the indication.

CNS Activity

Originator

Approval Year

PubMed

Title	Date	PubMed
Behavioral, biological, and chemical perspectives on targeting CRF(1) receptor antagonists to treat alcoholism.	2013 Mar 1	23294766
The CRF1 Antagonist Verucerfont in Anxious Alcohol-Dependent Women: Translation of Neuroendocrine, But not of Anti-Craving Effects.	2016 Nov	27109623

Patents

Sample Use Guides

In Vivo Use Guide

Posttraumatic stress disorder (PTSD): fixed dose of 350 mg nightly for six weeks.

Route of Administration: Oral

In Vitro Use Guide

Verucerfont is a potent, selective CRF1 receptor antagonist (IC50 for CRF1, CRF2, and CRF-BP ~ 6.1, >1000 and >1000 nM, respectively). Verucerfont is a high affinity ligand with a pK(i) value of 8.2 and a functional CRF(1) antagonist with pIC(50) value of 7.0 in the in vitro CRF ACTH production assay.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 17:35:30 UTC 2023` Edited by `admin` on `Sat Dec 16 17:35:30 UTC 2023`
Record UNII	X60608B091
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

VERUCERFONT

Official Name

English

GSK-561679

Code

English

3-(4-Methoxy-2-methylphenyl)-2,5-dimethyl-N-[(1S)-1-(3-methyl-1,2,4-oxadiazol-5-yl)propyl]pyrazolo[1,5-a]pyrimidin-7-amine

Systematic Name

English

VERUCERFONT [USAN]

Common Name

English

GSK-561679A

Code

English

Verucerfont [WHO-DD]

Common Name

English

PYRAZOLO(1,5-A)PYRIMIDIN-7-AMINE, 3-(4-METHOXY-2-METHYLPHENYL)-2,5-DIMETHYL-N-((1S)-1-(3-METHYL-1,2,4-OXADIAZOL-5-YL)PROPYL)-

Systematic Name

English

verucerfont [INN]

Common Name

English

GSK561679A

Code

English

GSK-561,679

Code

English

NBI-77860

Code

English

Classification Tree Code System Code

FDA ORPHAN DRUG

399713