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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

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

DEVELOPMENTS

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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

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1 FDA Orange Book

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1 US Medicaid Prescriptions, 3 Annual Reports

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1 US Medicaid Prescriptions
3 Annual Reports

MARKET PLACE

9 APIs

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9 APIs

PATENTS & EXCLUSIVITIES

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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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.

API SUPPLIERS

01

Porton Pharma Solutions

China

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Ami Lifesciences Private Limited

India

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Metrochem API Private Limited

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Suanfarma

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05

Medichem S.A

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CPhI India 2024

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HONOUR LAB LTD

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Porton Pharma Solutions Ltd

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GDUFA

DMF Review : N/A

Rev. Date :

Pay. Date :

DMF Number : 40275

Submission : 2024-08-01

Status : Active

Type : II

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Ami Lifesciences Private Ltd

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DMF Review : Complete

Rev. Date : 2024-07-31

Pay. Date : 2024-06-13

DMF Number : 39538

Submission : 2024-03-21

Status : Active

Type : II

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Yangzhou Aurisco Pharmaceutical Co L...

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Honour Lab Ltd

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Msn Organics Private Ltd

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Sumitomo Chemical

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Porton Fine Chemicals Ltd

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VIBEGRON

NDC Package Code : 75877-0008

Start Marketing Date : 2023-05-27

End Marketing Date : 2024-12-31

Dosage Form (Strength) : POWDER (1g/g)

Marketing Category : BULK INGREDIENT

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American Pacific Corporation

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Porton Pharma Solutions

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About the Company : Porton Pharma Solutions Ltd. was founded in 2005, & the company's stock was successfully listed in Shenzhen Stock Exchange in 2014. Our R&D, manufacturing & operation facilities ar...

Porton Pharma Solutions Ltd. was founded in 2005, & the company's stock was successfully listed in Shenzhen Stock Exchange in 2014. Our R&D, manufacturing & operation facilities are located in China, Slovenia, the US, Belgium, Switzerland, Denmark, with more than 6000 employees worldwide. Porton leads the way with its excellent CDMO services, but also supplies APIs & intermediates for the treatment of critical diseases such as HIV/AIDS, diabetes, cancer, & influenza. Our Process Technology Centers & WHO/USFDA/EMA/PDMA/NMPA-inspected Facilities feature state-of-the-art equipment, highly flexible cGMP-compliant production assets.

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Ami Lifesciences Private Limited

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About the Company : Ami Lifesciences, established in 2006, is one of the fastest growing API manufacturing companies in India. Specializing in cardiovascular, anti-diabetic, CNS, and respiratory thera...

Ami Lifesciences, established in 2006, is one of the fastest growing API manufacturing companies in India. Specializing in cardiovascular, anti-diabetic, CNS, and respiratory therapeutic areas, Ami offers a wide range of APIs, intermediates, key starting materials, as well as contract bulk manufacturing services. Ami's manufacturing units in Gujarat and Karnataka feature dedicated clean rooms for APIs and adhere to international standards like EU-GMP, WHO-GMP, PMDA, and COFEPRIS. Ami serves as a reliable partner for contract development and manufacturing, offering generic APIs to global pharma companies across more than 60 countries.

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Metrochem API Private Limited

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Established in 2004, Metrochem API is one of the fastest-growing APIs, pellets & intermediates manufacturers. It has 6 dedicated manufacturing facilities for its 3 core product ...

Established in 2004, Metrochem API is one of the fastest-growing APIs, pellets & intermediates manufacturers. It has 6 dedicated manufacturing facilities for its 3 core product groups and has been approved by ISO 9001-2015, USFDA, WHO GMP, Cofepris & Japanese authorities. Metrochem’s in-depth industry knowledge, & hi-tech & advanced infrastructure, helps it provide quality products to its customers. Note: None of the products will be supplied to the countries where this could conflict with existing patents. Further, any products under patent will be offered for R&D purposes only. However, the final responsibility lies with the buyer

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Suanfarma

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About the Company : Suanfarma founded in 1993, is a B2B life science partner committed to health & innovation by developing, manufacturing, & distributing high-quality APIs for the pharmaceutical indu...

Suanfarma founded in 1993, is a B2B life science partner committed to health & innovation by developing, manufacturing, & distributing high-quality APIs for the pharmaceutical industry innovatively & sustainably. Backed by a robust global network of 12 strategically located local offices, we cater to the needs of over 400 active customers in 70+ countries. At Suanfarma we offer our CDMO capacity for fermentation & chemical synthesis projects, offering a One Stop Shop service with a solid track record, & which allows us to achieve success in the development, scaling, manufacturing, & commercialization of an API, either innovative or generic.

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Medichem S.A

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About the Company : Medichem is an indepently-owned company based in Barcelona. Founded in 1972 and with more than 45 years, Medichem has been engaged in the process development and manufacture of Act...

Medichem is an indepently-owned company based in Barcelona. Founded in 1972 and with more than 45 years, Medichem has been engaged in the process development and manufacture of Active Pharmaceutical Ingredients (APIs), including Highly Potent. In 2016, Medichem merged with Combino Pharm, which is devoted to the development and manufacture (licensing) of Finished Dosage Forms. With this merger, Medichem has become a vertically integrated pharmaceutical company which can offer a complete range of products and services for the pharmaceutical industry with the highest standards of quality, operational excellence and environment respect.

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Beijing Sjar Technology Development

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Shanghai Hope Chem

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Symed Labs

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API Reference Price

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