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Vericiguat

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11 API Suppliers, 3 USDMF, 1 NDC API, 10 Listed Suppliers, $ API Reference Price

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3 USDMF
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5 Europe
3 Canada
6 Australia

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1 US Medicaid Prescriptions, 5 Finished Drug Prices, 2 Annual Reports

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2 Annual Reports

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18 US Patents, 3 US Exclusivities

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18 US Patents
3 US Exclusivities

Moehs Vericiguat

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Chemistry

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Also known as: 1350653-20-1, Verquvo, Methyl (4,6-diamino-2-(5-fluoro-1-(2-fluorobenzyl)-1h-pyrazolo[3,4-b]pyridin-3-yl)pyrimidin-5-yl)carbamate, Mk-1242, Vericiguat [inn], Bay-1021189

Molecular Formula

C₁₉H₁₆F₂N₈O₂

Molecular Weight

426.4 g/mol

InChI Key

QZFHIXARHDBPBY-UHFFFAOYSA-N

FDA UNII

LV66ADM269

Vericiguat is a direct stimulator of soluble guanylate cyclase (sGC) used in the management of systolic heart failure to reduce mortality and hospitalizations. A key component of the NO-sGC-cGMP signaling pathway that helps to regulate the cardiovascular system, sGC enzymes are intracellular enzymes found in vascular smooth muscle cells (amongst other cell types) that catalyze the synthesis of cyclic guanosine monophosphate (cGMP) in response to activation by nitric oxide (NO). Cyclic GMP acts as a second messenger, activating a number of downstream signaling cascades that elicit a broad variety of effects, and these diverse cellular effects have implicated deficiencies in its production (primarily due to insufficient NO bioavailability) in the pathogenesis of various cardiovascular diseases. As a direct stimulator of sGC, vericiguat mitigates the need for a functional NO-sGC-cGMP axis and thereby helps to prevent the myocardial and vascular dysfunction associated with decreased sGC activity in heart failure. Vericiguat was approved by the FDA in January 2021 - developed by Merck under the brand name Verquvo - for use in certain patients with systolic heart failure. Although not the first sGC stimulator to be granted FDA approval ([riociguat] was approved in 2013 for use in pulmonary hypertension), vericiguat is unique amongst its peers in that modifications to its structure have dramatically decreased its susceptibility to oxidative metabolism, resulting in a relatively long half-life and allowing for once-daily dosing.

Vericiguat is a Soluble Guanylate Cyclase Stimulator. The mechanism of action of vericiguat is as a Guanylate Cyclase Stimulator.

1 2D Structure

Vericiguat

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

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

2.1.2 InChI

InChI=1S/C19H16F2N8O2/c1-31-19(30)25-14-15(22)26-17(27-16(14)23)13-11-6-10(20)7-24-18(11)29(28-13)8-9-4-2-3-5-12(9)21/h2-7H,8H2,1H3,(H,25,30)(H4,22,23,26,27)

2.1.3 InChI Key

QZFHIXARHDBPBY-UHFFFAOYSA-N

2.1.4 Canonical SMILES

COC(=O)NC1=C(N=C(N=C1N)C2=NN(C3=C2C=C(C=N3)F)CC4=CC=CC=C4F)N

2.2 Other Identifiers

2.2.1 UNII

LV66ADM269

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Bay 1021189

2. Verquvo

2.3.2 Depositor-Supplied Synonyms

1. 1350653-20-1

2. Verquvo

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

4. Mk-1242

5. Vericiguat [inn]

6. Bay-1021189

7. Bay 1021189

8. Vericiguat [usan]

9. Bay1021189

10. Lv66adm269

11. Methyl N-[4,6-diamino-2-[5-fluoro-1-[(2-fluorophenyl)methyl]pyrazolo[3,4-b]pyridin-3-yl]pyrimidin-5-yl]carbamate

12. Methyl (4,6-diamino-2-(5-fluoro-1-((2-fluorophenyl)methyl)-1h-pyrazolo(3,4-b)pyridin-3-yl(pyrimidin-5-yl)carbamate

13. Methyl (4,6-diamino-2-(5-fluoro-1-(2-fluorobenzyl)-1h-pyrazolo(3,4-b)pyridin-3-yl)pyrimidin-5-yl)carbamate

14. Methyl N-(4,6-diamino-2-(5-fluoro-1-(2-fluorobenzyl)-1h-pyrazolo(3,4-b)pyridin-3-yl)pyrimidin-5-yl)carbamate

15. Unii-lv66adm269

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

17. Vericiguatum

18. Vericiguat [jan]

19. Vericiguat [usan:inn]

20. Vericiguat [who-dd]

21. Bay1021189; Verquvo

22. Schembl429958

23. Vericiguat (jan/usan/inn)

24. Chembl4066936

25. Vericiguat [orange Book]

26. Gtpl10010

27. Chebi:142432

28. Dtxsid001318361

29. Bcp18886

30. Ex-a4694

31. Who 9805

32. Mfcd28502029

33. S9693

34. Zinc72318626

35. Cs-6981

36. Db15456

37. Sb16806

38. Ac-36737

39. Hy-16774

40. Bay1021189bay1021189

41. J3.590.750e

42. D11051

43. P14957

44. A887763

45. Q27283201

46. Bay1021189; Bay 1021189; Bay-1021189; Bay10-21189; Bay-10-21189; Bay 10-21189

47. Methyl 4,6-diamino-2-(5-fluoro-1-(2-fluorobenzyl)-1h-pyrazolo[3,4-b]pyridin-3-yl)pyrimidin-5-ylcarbamate

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

2.4 Create Date

2011-12-26

3 Chemical and Physical Properties

Molecular Formula	C₁₉H₁₆F₂N₈O₂
Molecular Weight	426.4 g/mol
XLogP3	1.5
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	10
Rotatable Bond Count	5
Exact Mass	426.13642811 g/mol
Monoisotopic Mass	426.13642811 g/mol
Topological Polar Surface Area	147 Å²
Heavy Atom Count	31
Formal Charge	0
Complexity	622
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 Indication

Vericiguat is indicated in adults with symptomatic, chronic heart failure and an ejection fraction of <45% to reduce the risk of cardiovascular death and heart failure-related hospitalization following a hospitalization for heart failure or need for outpatient intravenous diuretics.

Treatment of symptomatic chronic heart failure

5 Pharmacology and Biochemistry

5.1 Pharmacology

By directly stimulating the increased production of intracellular cyclic guanosine monophosphate (cGMP), vericiguat causes the relaxation of vascular smooth muscle and vasodilation. Vericiguat has a relatively long half-life (~30h) that allows for once-daily dosing. Animal reproduction studies have demonstrated the potential for embryo-fetal toxicity when vericiguat is administered to pregnant females - defects in major vessel and heart formation, as well as spontaneous abortions/resorptions, were observed when vericiguat was administered to pregnant rabbits during organogenesis. The possibility of pregnancy should be excluded prior to beginning therapy with vericiguat, and adequate contraception should be used throughout therapy and for one month following cessation of treatment.

5.2 FDA Pharmacological Classification

5.2.1 Active Moiety

VERICIGUAT

5.2.2 FDA UNII

LV66ADM269

5.2.3 Pharmacological Classes

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

5.3 ATC Code

C01

C - Cardiovascular system

C01 - Cardiac therapy

C01D - Vasodilators used in cardiac diseases

C01DX - Other vasodilators used in cardiac diseases

C01DX22 - Vericiguat

5.4 Absorption, Distribution and Excretion

Absorption

Following the administration of 10mg of vericiguat by mouth once daily, the average steady-state C_max and AUC in patients with heart failure is 350 mcg/L and 6,680 mcgh/L, respectively, with a T_max of 1 hour. The absolute bioavailability of orally-administered vericiguat is approximately 93% when taken with food - co-administration with meals has been shown to reduce pharmacokinetic variability, increase T_max to roughly 4 hours, and increase C_max and AUC by 41% and 44%, respectively.

Route of Elimination

Following the oral administration of radiolabeled vericiguat, approximately 53% of the administered radioactivity was recovered in the urine and 45% in the feces. A human mass balance study found that the portion recovered in the urine comprised approximately 40.8% N-glucuronide metabolite, 7.7% other metabolites, and 9% unchanged parent drug, while virtually the entire portion recovered in the feces comprised unchanged vericiguat.

Volume of Distribution

In healthy subjects the steady-state volume of distribution of vericiguat is approximately 44 liters.

Clearance

Vericiguat is a low-clearance drug, with an observed plasma clearance of 1.6 L/h in healthy volunteers and 1.3 L/h in patients with systolic heart failure.

5.5 Metabolism/Metabolites

Vericiguat is primarily metabolized via phase II conjugation reactions, with CYP-mediated oxidative metabolism comprising a small (<5%) portion of its overall biotransformation. The major inactive metabolite, vericiguat N-glucuronide (M1), is formed by UGT1A9 and, to a lesser extent, UGT1A1. Other identified metabolites include a denbenzylated compound and an M15 metabolite thought to be the result of oxidative metabolism, although these metabolites are poorly characterized.

5.6 Biological Half-Life

In patients with heart failure, the half-life of vericiguat is 30 hours.

5.7 Mechanism of Action

Heart failure (HF) involves, amongst other morphologic and physiologic changes, the impaired synthesis of nitric oxide (NO) and decreased activity of soluble guanylate cyclase (sGC). Functioning normally, NO binds to sGC and stimulates the synthesis of intracellular cyclic guanosine monophosphate (cGMP), a second messenger involved in the maintenance of vascular tone, as well as cardiac contractility and remodeling. Defects in this pathway are thought to contribute to the myocardial and vascular dysfunction associated with heart failure and are therefore a desirable target in its treatment. Vericiguat directly stimulates sGC by binding to a target site on its beta-subunit, bypassing the need for NO-mediated activation, and in doing so causes an increase in the production of intracellular cGMP that results in vascular smooth muscle relaxation and vasodilation.

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