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Details

Stereochemistry ABSOLUTE
Molecular Formula C26H28N4O3
Molecular Weight 444.5265
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of VIBEGRON

SMILES

c1ccc(cc1)[C@]([H])([C@@]2([H])CC[C@@]([H])(Cc3ccc(cc3)NC(=O)[C@]4([H])CCc5nccc(=O)n45)N2)O

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
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.

Approval Year

PubMed

PubMed

TitleDatePubMed
Discovery of Vibegron: A Potent and Selective β3 Adrenergic Receptor Agonist for the Treatment of Overactive Bladder.
2016 Jan 28
Pharmacological Characterization of a Novel Beta 3 Adrenergic Agonist, Vibegron: Evaluation of Antimuscarinic Receptor Selectivity for Combination Therapy for Overactive Bladder.
2017 Feb
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment:: The usual oral dosage for adults is 50mg of vibegron once daily after meal. https://www.kyorin-gr.co.jp/en/news/docs/57a20666168a4c90f3519957b2d2f928028651b5.pdf
Overactive bladder: vibegron 75 milligrams (mg) orally once daily for 24 weeks.
Route of Administration: Oral
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
INN   USAN   WHO-DD  
USAN   INN  
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 [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C48149
Created by admin on Sat Jun 26 14:14:52 UTC 2021 , Edited by admin on Sat Jun 26 14:14:52 UTC 2021
Code System Code Type Description
EPA CompTox
1190389-15-1
Created by admin on Sat Jun 26 14:14:52 UTC 2021 , Edited by admin on Sat Jun 26 14:14:52 UTC 2021
PRIMARY
FDA UNII
M5TSE03W5U
Created by admin on Sat Jun 26 14:14:52 UTC 2021 , Edited by admin on Sat Jun 26 14:14:52 UTC 2021
PRIMARY
DRUG BANK
DB14895
Created by admin on Sat Jun 26 14:14:52 UTC 2021 , Edited by admin on Sat Jun 26 14:14:52 UTC 2021
PRIMARY
ChEMBL
CHEMBL2107826
Created by admin on Sat Jun 26 14:14:52 UTC 2021 , Edited by admin on Sat Jun 26 14:14:52 UTC 2021
PRIMARY
INN
9676
Created by admin on Sat Jun 26 14:14:52 UTC 2021 , Edited by admin on Sat Jun 26 14:14:52 UTC 2021
PRIMARY
DRUG CENTRAL
5311
Created by admin on Sat Jun 26 14:14:52 UTC 2021 , Edited by admin on Sat Jun 26 14:14:52 UTC 2021
PRIMARY
CAS
1190389-15-1
Created by admin on Sat Jun 26 14:14:52 UTC 2021 , Edited by admin on Sat Jun 26 14:14:52 UTC 2021
PRIMARY
NCI_THESAURUS
C152872
Created by admin on Sat Jun 26 14:14:52 UTC 2021 , Edited by admin on Sat Jun 26 14:14:52 UTC 2021
PRIMARY
PUBCHEM
44472635
Created by admin on Sat Jun 26 14:14:52 UTC 2021 , Edited by admin on Sat Jun 26 14:14:52 UTC 2021
PRIMARY