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Riociguat

Zhejiang Riociguat

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ACTIVE PHARMA INGREDIENTS

12 API Suppliers, 3 USDMF, 2 EU WC, 2 NDC API, 10 Listed Suppliers, $ API Reference Price

12 API Suppliers
3 USDMF
2 EU WC
2 NDC API
10 Listed Suppliers
$ API Reference Price

FINISHED DOSAGE FORMULATIONS

76 FDF Dossiers, 14 FDA Orange Book, 32 Europe, 10 Canada, 20 Australia

76 FDF Dossiers
14 FDA Orange Book
32 Europe
10 Canada
20 Australia

RELATED EXCIPIENT COMPANIES

1 SPI Pharma, 2 DKSH, 3 Faran Shimi Pharmaceutical, 8 Gangwal Healthcare, 2 Nanjing Well Pharmaceutical, 1 ACG Worldwide, 3 Anhui Sunhere Pharmaceutical Excipients Co.,Ltd, 6 BASF, 10 Corel Pharma Chem, 4 DFE Pharma, 1 Finar, 5 Gangwal Chemicals, 5 Ideal Cures Pvt Ltd, 29 Kerry, 3 Kima Chemical, 6 Lonza Capsugel, 10 Microlex e.U, 1 Novo Excipients, 1 Pharmatrans-Sanaq, 3 Pluviaendo, 2 Prachin Chemical, 1 Qianhao Chemical (Hebei) Co., Ltd, 1 Qualicaps, 9 Roquette, 6 Seppic, 3 Shanghai Shenmei Pharmaceutical Technology Co., Ltd, 9 Sigachi Industries, 2 The Dow Chemical Company, 1 Valens Pharmachem, 2 Vasa Pharmachem

EXCIPIENTS BY APPLICATIONS

45 Coating Systems & Additives, 42 Fillers, Diluents & Binders, 21 Controlled & Modified Release, 20 Direct Compression, 13 Granulation, 12 Thickeners and Stabilizers, 12 Lubricants & Glidants, 11 Co-Processed Excipients, 9 Film Formers & Plasticizers, 6 Disintegrants & Superdisintegrants, 6 Taste Masking, 5 Empty Capsules, 4 Vegetarian Capsules, 4 Coloring Agents, 4 Topical, 3 Chewable & Orodispersible Aids, 3 API Stability Enhancers, 3 Solubilizers, 3 Emulsifying Agents, 2 Rheology Modifiers, 2 Parenteral, 1 Surfactant & Foaming Agents

DIGITAL CONTENT

2 DATA COMPILATION #PharmaFlow, 24 NEWS #PharmaBuzz

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2 DATA COMPILATION #PharmaFlow
24 NEWS #PharmaBuzz

GLOBAL SALES INFORMATION

1 US Medicaid Prescriptions, 27 Finished Drug Prices, 16 Annual Reports

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1 US Medicaid Prescriptions
27 Finished Drug Prices
16 Annual Reports

MARKET PLACE

7 APIs

marketPlace
7 APIs

PATENTS & EXCLUSIVITIES

25 US Patents, 5 Health Canada Patents

patents
25 US Patents
5 Health Canada Patents

REF. STANDARDS & IMPURITIES

2 Others

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2 Others

Zhejiang Riociguat

Synopsis

ACTIVE PHARMA INGREDIENTS

12

API Suppliers

3

USDMF

0

CEP/COS

CEP/COS Certifications

0

JDMF

2

EU WC

0

KDMF

2

NDC API

0

VMF

10

Listed Suppliers

API REF. PRICE (USD/KG)

$

$ 43,291

MARKET PLACE

7

API

0

FDF

0INTERMEDIATES

FINISHED DOSAGE FORMULATIONS

76

FDF Dossiers

14

FDA Orange Book

FDA (Orange Book)

32

Europe

10

Canada

20

Australia

0

South Africa

0

Listed Dossiers

0 DRUGS IN DEVELOPMENT

DRUG PRODUCT COMPOSITIONS

REF. STANDARDS OR IMPURITIES

0

EDQM

0

USP

0

JP

2

Others

PATENTS & EXCLUSIVITIES

25

US Patents

0

US Exclusivities

5

Health Canada Patents

DIGITAL CONTENT

2

Data Compilation #PharmaFlow

0

Stock Recap #PipelineProspector

0

Weekly News Recap #Phispers

24

News #PharmaBuzz

GLOBAL SALES INFORMATION

US Medicaid (USD)

576,981,088

Annual Reports (USD Million)

7,200

Finished Drug Prices

140 RELATED EXCIPIENT COMPANIES

231EXCIPIENTS BY APPLICATIONS

Chemistry

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Also known as: 625115-55-1, Adempas, Bay 63-2521, Riociguat (bay 63-2521), Bay-63-2521, Ru3fe2y4xi

Molecular Formula

C₂₀H₁₉FN₈O₂

Molecular Weight

422.4 g/mol

InChI Key

WXXSNCNJFUAIDG-UHFFFAOYSA-N

FDA UNII

RU3FE2Y4XI

Riociguat

Riociguat is a soluble guanylate cyclase (sGC) agonist approved in the USA, Europe and several other regions for patients with group I PAH (pulmonary arterial hypertension) in WHO FC II or III; and for the treatment of patients with inoperable CTEPH (chronic thromboembolic pulmonary hypertension), or persistent/recurrent PH (pulmonary hypertension) after pulmonary endarterectomy in WHO FC II or III. Riociguat is marketed under the brand Adempas by Bayer HealthCare Pharmaceuticals. Treatment with riociguat costs USD $7,500 for 30 days of treatment.

Riociguat is a Soluble Guanylate Cyclase Stimulator. The mechanism of action of riociguat is as a Guanylate Cyclase Stimulator.

1 2D Structure

Riociguat

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

methyl N-[4,6-diamino-2-[1-[(2-fluorophenyl)methyl]pyrazolo[3,4-b]pyridin-3-yl]pyrimidin-5-yl]-N-methylcarbamate

2.1.2 InChI

InChI=1S/C20H19FN8O2/c1-28(20(30)31-2)15-16(22)25-18(26-17(15)23)14-12-7-5-9-24-19(12)29(27-14)10-11-6-3-4-8-13(11)21/h3-9H,10H2,1-2H3,(H4,22,23,25,26)

2.1.3 InChI Key

WXXSNCNJFUAIDG-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CN(C1=C(N=C(N=C1N)C2=NN(C3=C2C=CC=N3)CC4=CC=CC=C4F)N)C(=O)OC

2.2 Other Identifiers

2.2.1 UNII

RU3FE2Y4XI

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Adempas

2. Bay 63-2521

3. Bay-63-2521

2.3.2 Depositor-Supplied Synonyms

1. 625115-55-1

2. Adempas

3. Bay 63-2521

4. Riociguat (bay 63-2521)

5. Bay-63-2521

6. Ru3fe2y4xi

7. Methyl (4,6-diamino-2-(1-(2-fluorobenzyl)-1h-pyrazolo[3,4-b]pyridin-3-yl)pyrimidin-5-yl)(methyl)carbamate

8. Methyl N-[4,6-diamino-2-[1-[(2-fluorophenyl)methyl]pyrazolo[3,4-b]pyridin-3-yl]pyrimidin-5-yl]-n-methylcarbamate

9. Chebi:76018

10. 1304478-72-5

11. N-[4,6-diamino-2-[1-[(2-fluorophenyl)methyl]-1h-pyrazolo[3,4-b]pyridin-3-yl]-5-pyrimidinyl]-n-methylcarbamic Acid Methyl Ester

12. Methyl N-(4,6-diamino-2-{1-((2-fluorophenyl)methyl)-1h-pyrazolo(3,4-b)pyridin-3-yl}pyrimidin-5-yl)-n-methylcarbamate

13. Methyl N-(4,6-diamino-2-{1-[(2-fluorophenyl)methyl]-1h-pyrazolo[3,4-b]pyridin-3-yl}pyrimidin-5-yl)-n-methylcarbamate

14. Riociguat [inn]

15. Methyl ~{n}-[4,6-bis(azanyl)-2-[1-[(2-fluorophenyl)methyl]pyrazolo[3,4-b]pyridin-3-yl]pyrimidin-5-yl]-~{n}-methyl-carbamate

16. Methyl 4,6-diamino-2-(1-(2-fluorobenzyl)-1h-pyrazolo(3,4-b)pyridin-3-yl)-5-pyrimidinyl(methyl)carbamate

17. Unii-ru3fe2y4xi

18. Riociguatum

19. Riociguate

20. Riociguat [usan:inn:jan]

21. Riocguat-d3

22. Methyl 4,6-diamino-2-[1-(2-fluorobenzyl)-1h-pyrazolo[3,4-b]pyridin-3-yl]-5-pyrimidinyl(methyl)carbamate

23. Methyl N-(4,6-diamino-2-(1-((2-fluorophenyl)methyl)-1h-pyrazolo(3,4-b)pyridin-3-yl)pyrimidin-5-yl)-n-methylcarbamate

24. Adempas (tn)

25. Bay 632521

26. Riociguat [jan]

27. Riociguat [mi]

28. Riociguat [usan]

29. Riociguat [vandf]

30. Riociguat [usp-rs]

31. Riociguat [who-dd]

32. Bay 63-2521,riociguat

33. Riociguat (jan/usan/inn)

34. Schembl245457

35. Gtpl5257

36. Riociguat [orange Book]

37. Chembl2107834

38. Riociguat [ep Monograph]

39. Amy4218

40. Dtxsid50978109

41. Riociguat [usp Monograph]

42. Bcp04750

43. Bcp23980

44. Ex-a2023

45. Zinc3819392

46. Riociguat,cas:625115-55-1

47. Mfcd19443708

48. S8135

49. Akos015900718

50. Akos032950011

51. Bay-632521

52. Bcp9000382

53. Ccg-268912

54. Cs-0584

55. Db08931

56. Pb25734

57. Ncgc00379065-03

58. Ncgc00379065-04

59. Ncgc00379065-05

60. [4,6-diamino-2-[1-(2-fluorobenzyl)-1h-pyrazolo[3,4-b]pyridin-3-yl]pyrimidin-5-yl]methylcarbamic Acid Methyl Ester

61. Ac-27647

62. As-19299

63. Hy-14779

64. Bcp0726000023

65. Db-073136

66. Ft-0760451

67. Bay 63-2521;bay 632521

68. D09572

69. Bay 63-2521; Bay 632521

70. 115r551

71. Q2154494

72. Bay 63-2521-d3; Bay 632521-d3; Methyl [4,6-diamino-2-[1-(2-fluorobenzyl)-1h-pyrazolo[3,4-b]pyridin-3-yl]pyrimidin-5-yl]methylcarbamate-d3

73. Carbamic Acid, (4,6-diamino-2-(1-((2-fluorophenyl)methyl)-1h-pyrazolo(3,4-b)pyridin-3-yl)-5-pyrimidinyl)methyl-, Methyl Ester

74. Carbamic Acid, N-(4,6-diamino-2-(1-((2-fluorophenyl)methyl)-1h-pyrazolo(3,4-b)pyridin-3-yl)-5-pyrimidinyl)-n-methyl-, Methyl Ester

75. Gzo

76. Methyl {4,6-diamino-2-[1-(2-fluorobenzyl)-1h-pyrazolo[3,4-b]pyridin-3-yl]pyrimidin-5-yl}methylcarbamate

77. Methyl N-[4,6-diamino-2-[1-[(2-fluorophenyl)methyl]-1h-pyrazolo[3,4-b]pyridin-3-yl]-5-pyrimidinyl]-n-methyl-carbaminate

2.4 Create Date

2006-10-26

3 Chemical and Physical Properties

Molecular Formula	C₂₀H₁₉FN₈O₂
Molecular Weight	422.4 g/mol
XLogP3	1.6
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	5
Exact Mass	422.16150004 g/mol
Monoisotopic Mass	422.16150004 g/mol
Topological Polar Surface Area	138 Å²
Heavy Atom Count	31
Formal Charge	0
Complexity	618
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
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 Information

1 of 2
Drug Name	Adempas
PubMed Health	Riociguat (By mouth)
Drug Classes	Cardiovascular Agent
Drug Label	Adempas (riociguat) is a tablet for oral administration. Riociguat is methyl 4,6-diamino-2-[1-(2-fluorobenzyl)-1H-pyrazolo [3,4-b]pyridin-3-yl]-5-pyrimidinyl(methyl)carbamate with the following structural formula:C20H19FN8O2Riociguat is a white to ye...
Active Ingredient	Riociguat
Dosage Form	Tablet
Route	Oral
Strength	2.5mg; 1.5mg; 0.5mg; 2mg; 1mg
Market Status	Prescription
Company	Bayer Hlthcare

2 of 2
Drug Name	Adempas
PubMed Health	Riociguat (By mouth)
Drug Classes	Cardiovascular Agent
Drug Label	Adempas (riociguat) is a tablet for oral administration. Riociguat is methyl 4,6-diamino-2-[1-(2-fluorobenzyl)-1H-pyrazolo [3,4-b]pyridin-3-yl]-5-pyrimidinyl(methyl)carbamate with the following structural formula:C20H19FN8O2Riociguat is a white to ye...
Active Ingredient	Riociguat
Dosage Form	Tablet
Route	Oral
Strength	2.5mg; 1.5mg; 0.5mg; 2mg; 1mg
Market Status	Prescription
Company	Bayer Hlthcare

4.2 Drug Indication

Riociguat is indicated for the treatment of adults with persistent/recurrent chronic thromboembolic pulmonary hypertension (CTEPH), (WHO Group 4) after surgical treatment, or inoperable CTEPH, to improve exercise capacity and WHO functional class. Riociguat is indicated for the treatment of adults with pulmonary arterial hypertension (PAH), (WHO Group 1), to improve exercise capacity, WHO functional class and to delay clinical worsening. Efficacy was shown in patients on Riociguat monotherapy or in combination with endothelin receptor antagonists or prostanoids. Studies establishing effectiveness included predominately patients with WHO functional class IIIII and etiologies of idiopathic or heritable PAH (61%) or PAH associated with connective tissue diseases (25%).

FDA Label

Chronic thromboembolic pulmonary hypertension (CTEPH)

Adempas is indicated for the treatment of adult patients with WHO Functional Class (FC) II to III with

- inoperable CTEPH,

- persistent or recurrent CTEPH after surgical treatment,

to improve exercise capacity (see section 5. 1).

Pulmonary arterial hypertension (PAH)

Adempas, as monotherapy or in combination with endothelin receptor antagonists, is indicated for the

treatment of adult patients with pulmonary arterial hypertension (PAH) with WHO Functional Class

(FC) II to III to improve exercise capacity.

Efficacy has been shown in a PAH population including aetiologies of idiopathic or heritable PAH or

PAH associated with connective tissue disease (see section 5. 1).

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Enzyme Activators

Compounds or factors that act on a specific enzyme to increase its activity. (See all compounds classified as Enzyme Activators.)

5.2 FDA Pharmacological Classification

5.2.1 Active Moiety

RIOCIGUAT

5.2.2 FDA UNII

RU3FE2Y4XI

5.2.3 Pharmacological Classes

Soluble Guanylate Cyclase Stimulator [EPC]; Guanylate Cyclase Stimulators [MoA]

5.3 ATC Code

C02KX05

C - Cardiovascular system

C02 - Antihypertensives

C02K - Other antihypertensives

C02KX - Antihypertensives for pulmonary arterial hypertension

C02KX05 - Riociguat

5.4 Absorption, Distribution and Excretion

Absorption

The pharmacokinetics of riociguant are dose proportional from 0.5 mg to 2.5 mg. The absolute bioavailability is approximately 94%. After oral administration, peak plasma concentrations were achieved within 1.5 hours. Food does not affect the bioavailability of riociguat.

Route of Elimination

Riociguat is eliminated in the urine (40%) and feces (53%), largely as metabolites.

Volume of Distribution

Volume of distribution at steady state = 30 L

5.5 Metabolism/Metabolites

The active metabolite (M1) of riociguat is 1/3 to 1/10 as potent as riociguat.

5.6 Biological Half-Life

About 12 hours in patients and 7 hours in healthy subjects.

5.7 Mechanism of Action

Riociguat is a stimulator of soluble guanylate cyclase (sGC), an enzyme in the cardiopulmonary system and the receptor for nitric oxide (NO). When NO binds to sGC, the enzyme catalyzes synthesis of the signaling molecule cyclic guanosine monophosphate (cGMP). Intracellular cGMP plays an important role in regulating processes that influence vascular tone, proliferation, fibrosis and inflammation. Pulmonary hypertension is associated with endothelial dysfunction, impaired synthesis of nitric oxide and insufficient stimulation of the NO-sGC-cGMP pathway. Riociguat has a dual mode of action. It sensitizes sGC to endogenous NO by stabilizing the NO-sGC binding. Riociguat also directly stimulates sGC via a different binding site, independently of NO. Riociguat stimulates the NO-sGC-cGMP pathway and leads to increased generation of cGMP with subsequent vasodilation.

API SUPPLIERS

01

Zhejiang Hengkang Pharmaceutical

China

USDMF, CEP/COS, JDMF, EU-WC, NDC, KDMF, VMF, Others

Zhejiang Hengkang Pharm Group is a dynamic pharmaceutical entity, spanning drug research, large-scale production, and global marketing.

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China

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Zhejiang Hengkang Pharmaceutical

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Metrochem API Private Limited

India

USDMF, CEP/COS, JDMF, EU-WC, NDC, KDMF, VMF, Others

Medlab Asia & Asia Health

Not Confirmed

Metrochem has been delivering customized volume & quality products to customers across the world, taking utmost care of their needs.

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MSN Laboratories

India

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04

MSN Laboratories

India

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05

Alembic Pharmaceuticals Limited

India

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06

PRG Pharma

India

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07

Zhejiang Ausun Pharmaceutical

China

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08

Maiden Group

India

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09

Micro Labs Limited

India

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Hetero Drugs

India

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API Reference Price

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Number of Transactions

Total Quantity (KGS)

Total Value (USD)

Quantity (KGS) & Unit rate (USD/KGS) over time

API Imports and Exports

Importing Country	Total Quantity (KGS)	Average Price (USD/KGS)	Number of Transactions

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FDF Dossiers

01

Bayer AG

Germany

Medlab Asia & Asia Health

Not Confirmed

02

Bayer AG

Germany

Medlab Asia & Asia Health

Not Confirmed

03

Bayer AG

Germany

Medlab Asia & Asia Health

Not Confirmed

04

Bayer AG

Germany

Medlab Asia & Asia Health

Not Confirmed

05

Bayer AG

Germany

Medlab Asia & Asia Health

Not Confirmed

06

Bayer AG

Germany

Medlab Asia & Asia Health

Not Confirmed

07

Bayer AG

Germany

Medlab Asia & Asia Health

Not Confirmed

08

Bayer AG

Germany

Medlab Asia & Asia Health

Not Confirmed

09

Bayer AG

Germany

Medlab Asia & Asia Health

Not Confirmed

10

MSN Laboratories

India

Medlab Asia & Asia Health

Not Confirmed

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