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Vibegron

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11 API Suppliers, 5 USDMF, 1 KDMF, 5 NDC API, 8 Listed Suppliers, $ API Reference Price

11 API Suppliers
5 USDMF
1 KDMF
5 NDC API
8 Listed Suppliers
$ API Reference Price

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22 Drugs in Development

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10 Intermediates Suppliers

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1 FDF Dossiers, 1 FDA Orange Book

1 FDF Dossiers
1 FDA Orange Book

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3 DATA COMPILATION #PharmaFlow, 35 NEWS #PharmaBuzz

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3 DATA COMPILATION #PharmaFlow
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1 US Medicaid Prescriptions, 3 Annual Reports

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1 US Medicaid Prescriptions
3 Annual Reports

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9 APIs

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9 APIs

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3 US Patents, 1 US Exclusivities

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3 US Patents
1 US Exclusivities

Porton Vibegron

Synopsis

ACTIVE PHARMA INGREDIENTS

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US Patents

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Health Canada Patents

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Data Compilation #PharmaFlow

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US Medicaid (USD)

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Chemistry

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Also known as: 1190389-15-1, Krp-114v, Gemtesa, Mk-4618, (s)-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-6-carboxamide, M5tse03w5u

Molecular Formula

C₂₆H₂₈N₄O₃

Molecular Weight

444.5 g/mol

InChI Key

DJXRIQMCROIRCZ-XOEOCAAJSA-N

FDA UNII

M5TSE03W5U

Vibegron is a potent, selective beta-3 adrenergic receptor (3) agonist that relaxes the detrusor smooth muscle of the bladder, thereby increasing bladder capacity. Vibegron was first approved in Japan in September 2018 for the treatment of overactive bladder, a condition associated with distressing symptoms of urge urinary incontinence, urgency, and urinary frequency, and reduced quality of life of patients. On December 23, 2020, vibegron was approved for the same indication in adults. It is available as oral tablets under the market name GEMTESA. Vibegron is the second beta-3 adrenergic agonist approved for the treatment of overactive bladder following [mirabegron], which was approved in 2012. Unlike mirabegron, vibegron is less likely to be associated with drug-drug interactions involving the CYP3A4, 2D6, or 2C9 enzymes.

1 2D Structure

Vibegron

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(6S)-N-[4-[[(2S,5R)-5-[(R)-hydroxy(phenyl)methyl]pyrrolidin-2-yl]methyl]phenyl]-4-oxo-7,8-dihydro-6H-pyrrolo[1,2-a]pyrimidine-6-carboxamide

2.1.2 InChI

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

2.1.3 InChI Key

DJXRIQMCROIRCZ-XOEOCAAJSA-N

2.1.4 Canonical SMILES

C1CC(NC1CC2=CC=C(C=C2)NC(=O)C3CCC4=NC=CC(=O)N34)C(C5=CC=CC=C5)O

2.1.5 Isomeric SMILES

C1C[C@@H](N[C@@H]1CC2=CC=C(C=C2)NC(=O)[C@@H]3CCC4=NC=CC(=O)N34)[C@@H](C5=CC=CC=C5)O

2.2 Other Identifiers

2.2.1 UNII

M5TSE03W5U

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Mk-4618

2. N-(4-((5-(hydroxy(phenyl)methyl)pyrrolidin-2-yl)methyl)phenyl)-4-oxo-4,6,7,8-tetrahydropyrrolo(1,2-a)pyrimidine-6-carboxamide

2.3.2 Depositor-Supplied Synonyms

1. 1190389-15-1

2. Krp-114v

3. Gemtesa

4. Mk-4618

5. (s)-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-6-carboxamide

6. M5tse03w5u

7. C26h28n4o3

8. Mk4618

9. (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

10. 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)-

11. Beova

12. 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)-

13. Vibegron [usan]

14. Vibegron [usan:inn]

15. Unii-m5tse03w5u

16. Vibegronum

17. Beova (tn)

18. Mk 4618

19. Vibegron (jan/usan)

20. Vibegron [inn]

21. Vibegron [jan]

22. Vibegron [who-dd]

23. Vibegron [orange Book]

24. Chembl2107826

25. Schembl11985457

26. Gtpl10100

27. Dtxsid40152299

28. Chebi:142418

29. Ex-a3390

30. Bdbm50146154

31. Mfcd28502057

32. At23148

33. Compound 7 [pmid: 26709102]

34. Db14895

35. Hy-19933

36. Cs-0016926

37. D10433

38. A903957

39. Q27283524

40. (6s)-4,6,7,8-tetrahydro-n-[4-[[(2s,5r)-5-[(r)-hydroxyphenylmethyl]-2-pyrrolidinyl]methyl]phenyl]-4-oxo-pyrrolo[1,2-a]pyrimidine-6-carboxamide

41. (6s)-4,6,7,8-tetrahydro-n-[4-[[(2s,5r)-5-[(r)-hydroxyphenylmethyl]-2-pyrrolidinyl]methyl]phenyl]-4-oxopyrrolo[1,2-a]pyrimidine-6-carboxamide

42. (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-

43. (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-6-carboxamide

44. (6s)-n-[4-[[(2s,5r)-5-[(r)-hydroxy(phenyl)methyl]pyrrolidin-2-yl]methyl]phenyl]-4-oxo-7,8-dihydro-6h-pyrrolo[1,2-a]pyrimidine-6-carboxamide

2.4 Create Date

2009-11-30

3 Chemical and Physical Properties

Molecular Formula	C₂₆H₂₈N₄O₃
Molecular Weight	444.5 g/mol
XLogP3	1.8
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	6
Exact Mass	444.21614077 g/mol
Monoisotopic Mass	444.21614077 g/mol
Topological Polar Surface Area	94 Å²
Heavy Atom Count	33
Formal Charge	0
Complexity	782
Isotope Atom Count	0
Defined Atom Stereocenter Count	4
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Vibegron is indicated for the treatment of overactive bladder (OAB) with symptoms of urge urinary incontinence, urgency, and urinary frequency in adults.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Vibegron selectivity for beta-3 adrenergic receptors is >9000 times higher than for 1AR or 2AR. Vibegron improves clinical symptoms of overactive bladder by increasing bladder capacity without affecting bladder contraction. It significantly increases the functional bladder volume in a dose-dependent manner, which results in prolongation of the interval between voids. In clinical studies, vibegron inhibited detrusor bladder contractions in a concentration-dependent manner, reduced voiding pressure, and increased bladder compliance. In Japanese clinical studies comprising patients with overactive bladder, vibegron significantly improved the frequency of micturition, urgency, and urgency incontinence episodes.

5.2 Absorption, Distribution and Excretion

Absorption

The mean T_max is 1-3 hours. Steady-state concentrations are achieved within 7 days of once-daily dosing.

Route of Elimination

In a radiolabeled drug study, approximately 59% of the radiolabeled dose was recovered in feces, in which 54% of that amount was in the unchanged parent drug form. About 20% of the radioactivity was recovered in urine, in which 19% of the amount was in the unchanged form.

Volume of Distribution

The mean apparent volume of distribution is 6304 L. The average blood-to-plasma concentration ratio is 0.9. According to tissue distribution studies in animals, vibegron does not penetrate the blood-brain barrier, suggesting limited potential for CNS toxicity in humans.

Clearance

There is limited information on the clearance rate of vibegron.

5.3 Metabolism/Metabolites

In vitro, CYP3A4 is the main enzyme responsible for the metabolism of vibegron, which plays a minor role in the elimination of vibegron. Two predominant metabolic pathways are oxidation and glucuronidation to form two oxidative metabolites and three glucuronide metabolites. Metabolites have not been fully characterized.

5.4 Biological Half-Life

The terminal plasma half-life ranges from 60 to 70 hours. The effective half-life is 30.8 hours.

5.5 Mechanism of Action

Overactive bladder is characterized by symptoms of urge urinary incontinence, urgency, and urinary frequency. Bladder filling and emptying are regulated by the coordinated communication between sympathetic and parasympathetic systems. Bladder filling occurs via parasympathetic inhibition and the sympathetic hypogastric nerve releasing norepinephrine, which acts on beta-adrenergic receptors responsible for mediating detrusor muscle relaxation. Symptoms of overactive bladder are thought to be caused by the deterioration of the sensory connections between the bladder, spinal cord and brain, leading to changes in the lower urinary tract and abnormal bladder sensations of the urge to void at small bladder volumes. Beta-3 adrenergic receptors (3ARs) are expressed in the kidneys and lower urinary tract, including ureters, urethra, prostate, and bladder. Vibegron is a selective agonist at 3AR. One vibegron binds to the receptor, 3AR is stimulated and undergoes a conformation change and activates adenylyl cyclases (AC), which promotes the formation of cyclic adenosine monophosphate (cAMP). Increased intracellular cAMP concentration leads to the activation of cAMP-dependent protein kinase A (PKA), which subsequently phosphorylates myosin light chains that are responsible for inhibiting the interaction of actin with myosin dependent on calcium calmodulin complex. In clinical trials, vibegron increased cAMP levels in a dose-proportional manner. There is evidence that 3AR agonists may also work via sensory mechanisms without directly affecting detrusor muscle motor function.

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API Reference Price

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