VIBEGRON

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C26H28N4O3
Molecular Weight	444.5255
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]1(CC[C@@H](CC2=CC=C(NC(=O)[C@@H]3CCC4=NC=CC(=O)N34)C=C2)N1)[C@H](O)C5=CC=CC=C5

InChI

InChIKey=DJXRIQMCROIRCZ-XOEOCAAJSA-N

InChI=1S/C26H28N4O3/c31-24-14-15-27-23-13-12-22(30(23)24)26(33)29-19-8-6-17(7-9-19)16-20-10-11-21(28-20)25(32)18-4-2-1-3-5-18/h1-9,14-15,20-22,25,28,32H,10-13,16H2,(H,29,33)/t20-,21+,22-,25+/m0/s1

HIDE SMILES / InChI

Description
Sources: https://urovant.com/pipeline/ | https://www.ncbi.nlm.nih.gov/pubmed/30411311 | https://www.kyorin-gr.co.jp/en/news/docs/57a20666168a4c90f3519957b2d2f928028651b5.pdf | https://www.ncbi.nlm.nih.gov/pubmed/27965369

Vibegron is a selective beta 3 adrenergic receptor (β3AR) agonist that is being developed in Japan jointly by Kyorin Pharmaceutical Co., Ltd and Kissei Pharmaceutical Co., Ltd and in other regions worldwide (except in several other Asian countries) by Urovant Sciences for the treatment of overactive bladder (OAB). Vibegron potently activates human b3AR and increases cAMP levels, with an EC50 of 1.1 nM. Based on results from Japanese phase III trials, vibegron received approval in Japan in September 2018 for this indication. Vibegron, an active ingredient of Beova® Tablets, is a novel once-daily oral treatment for overactive bladder (OAB), acts selectively on the bladder's β3-adrenergic receptor, relaxes the bladder and enhances the urine collection, and consequently improves the symptoms of urgency, urinary frequency and urge urinary incontinence associated with OAB.

Originator

Approval Year

PubMed

Title	Date	PubMed
Discovery of Vibegron: A Potent and Selective β3 Adrenergic Receptor Agonist for the Treatment of Overactive Bladder.	2016 Jan 28	26709102
Pharmacological Characterization of a Novel Beta 3 Adrenergic Agonist, Vibegron: Evaluation of Antimuscarinic Receptor Selectivity for Combination Therapy for Overactive Bladder.	2017 Feb	27965369
Vibegron: First Global Approval.	2018 Nov	30411311

Patents

Sample Use Guides

In Vivo Use Guide

Overactive bladder: vibegron 75 milligrams (mg) orally once daily for 24 weeks.

Route of Administration: Oral

In Vitro Use Guide

Vibegron potently activates human b3AR and increases cAMP levels, with an EC50 of 1.1 nM and 87% activation relative to isoproterenol. Vibegron is also highly selective over b1AR and b2AR versus b3AR across multiple species, demonstrating >9000-fold selectivity for activation of b3AR over b1AR or b2AR in cell based in vitro functional assays. A small serum shift was observed in the presence of 40% human serum (EC501.7 nM).

Name

Type

Language

VIBEGRON

Official Name

English

GEMTESA

Brand Name

English

(6S)-N-[4-({(2S,5R)-5-[(R)-Hydroxyphenylmethyl]pyrrolidin-2-yl}methyl)phenyl]-4-oxo-4,6,7,8-tetrahydropyrrolo[1,2-a]pyrimidine-6-carboxamide

Systematic Name

English

Vibegron [WHO-DD]

Common Name

English

PYRROLO(1,2-A)PYRIMIDINE-6-CARBOXAMIDE, 4,6,7,8-TETRAHYDRO-N-(4-(((2S,5R)-5-((R)-HYDROXYPHENYLMETHYL)-2-PYRROLIDINYL)METHYL)PHENYL)-4-OXO-, (6S)-

Systematic Name

English

VIBEGRON [USAN]

Common Name

English

KRP-114V

Code

English

(6S)-N-(4-(((2S,5R)-5-((R)-HYDROXY(PHENYL)METHYL)PYRROLIDIN-2-YL(METHYL)PHENYL)-4-OXO-4,6,7,8-TETRAHYDROPYRROLO(1,2-A)PYRIMIDINE-

Common Name

English

VIBEGRON [JAN]

Common Name

English

vibegron [INN]

Common Name

English

VIBEGRON [ORANGE BOOK]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C48149