ChemicalBook > CAS DataBase List > vericiguat

vericiguat

Product Name: vericiguat
CAS No.: 1350653-20-1
Chemical Name: vericiguat
Synonyms: Methyl (4,6-diamino-2-(5-fluoro-1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl)pyrimidin-5-yl)carbamate;MK-1242;Vericygua;Vilisigua;vericiguat;BAY1021189;Vericiguat Impurity;Vericiguat (BAY 1021189);Vericiguat, 10 mM in DMSO;Inhibitor,BAY-1021189,BAY 1021189,inhibit,Guanylate Cyclase,Vericiguat
CBNumber: CB83033102
Molecular Formula: C19H16F2N8O2
Formula Weight: 426.38
MOL File: 1350653-20-1.mol

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vericiguat Property

Boiling point:: 535.9±50.0 °C(Predicted)
Density: 1.63±0.1 g/cm3(Predicted)
storage temp.: Store at 0-8 °C
solubility: DMSO:60.0(Max Conc. mg/mL);140.7(Max Conc. mM)
form: A solid
pka: 10.61±0.70(Predicted)
color: Light yellow to brown
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)
InChIKey: QZFHIXARHDBPBY-UHFFFAOYSA-N
SMILES: C(OC)(=O)NC1=C(N)N=C(C2C3=CC(F)=CN=C3N(CC3=CC=CC=C3F)N=2)N=C1N

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H301Toxic if swalloed

H311Toxic in contact with skin

H331Toxic if inhaled

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P310Immediately call a POISON CENTER or doctor/physician.

P330Rinse mouth.

P361Remove/Take off immediately all contaminated clothing.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

ChemScene

Product number: CS-6981
Product name: Vericiguat
Purity: 99.09%
Packaging: 2mg
Price: $90
Updated: 2021/12/16

ChemScene

Product number: CS-6981
Product name: Vericiguat
Purity: 99.09%
Packaging: 5mg
Price: $160
Updated: 2021/12/16

ChemScene

Product number: CS-6981
Product name: Vericiguat
Purity: 99.09%
Packaging: 10mg
Price: $220
Updated: 2021/12/16

ChemScene

Product number: CS-6981
Product name: Vericiguat
Purity: 99.09%
Packaging: 50mg
Price: $650
Updated: 2021/12/16

ChemScene

Product number: CS-6981
Product name: Vericiguat
Purity: 99.09%
Packaging: 100mg
Price: $950
Updated: 2021/12/16

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vericiguat Chemical Properties,Usage,Production

Description

Vericiguat is a novel oral soluble guanylate cyclase (sGC) stimulator.
- Soluble guanylate cyclase (sGC) is an enzyme that is activated by nitric oxide (NO). The activation initiates a signaling cascade which converts guanosine triphosphate (GTP) to cyclic guanosine monophosphate (cGMP). cGMP levels increase & protein kinase G (PKG) is activated, resulting in a decrease of intracellular free Ca++ -> vascular smooth muscle cell relaxation.
- However, individuals with HF have reduced NO levels. Vericiguat, as a sGC stimulator, increases the enzymatic activity of sGC to generate cGMP independently of NO and enhances sGC sensitivity to endogenous NO.
Vericiguat is the 2nd drug in this class and follows riociguat ADEMPAS, which has been approved for treating pulmonary arterial hypertension.
SOCRATES-REDUCED was a phase II dose-finding trial of vericiguat in HF-rEF. The primary endpoint, change in NTproBNP over 12 weeks, was not statistically significant compared to placebo. A secondary exploratory analysis suggested a dose-response relationship in which higher doses of vericiguat were associated with greater reductions in NTproBNP levels.

Uses

Vericiguat is a novel oral soluble guanylate cyclase (sGC) stimulator that enhances the cyclic guanosine monophosphate (GMP) production pathway, by directly stimulating soluble guanylate cyclase activity, as well as sensitizing soluble guanylate cyclase to endogenous NO. It was initially developed for potential to reduce mortality and morbidity associated with chronic heart failure with reduced ejection fraction.

Uses

Vericiguat is used on targeting cyclic guanosine monophosphate in the treatment of heart failure.

Definition

ChEBI: Vericiguat is a pyrazolopyridine that is 5-fluoro-1H-pyrazolo[3,4-b]pyridine in which the amino hydrogen at position 1 has been substituted by a 2-fluorobenzyl group and the hydrogen at position 3 has been substituted by a 4,6-diamino-5-[(methoxycarbonyl)amino]pyrimidin-2-yl group. It is a soluble guanylate cyclase stimulator which is used for treatment of chronic heart failure. It has a role as a soluble guanylate cyclase activator, a vasodilator agent and an antihypertensive agent. It is an aminopyrimidine, a pyrazolopyridine, a carbamate ester and an organofluorine compound.

Mechanism of action

Vericiguat stimulates sGC, which increases cGMP production even when nitric oxide (NO) levels in the body are low. The NO-sGC-cGMP pathway is a key signaling pathway in the cardiovascular system, closely related to vasodilation, blood pressure regulation, and heart function. In patients with heart failure, this pathway may be impaired, resulting in reduced availability of NO, which in turn affects the health of the heart and blood vessels. Vericiguat helps restore the function of this pathway by mimicking the effects of NO, thereby improving the symptoms and quality of life of patients with heart failure.

Clinical Use

Vericiguat was advanced to clinical evaluation, as an oral therapy for chronic heart failure, either with reduced ejection fraction (HFrEF), or preserved EF (HFpEF). In mid-June 2020 Merck announced that the FDA had granted priority review status to vericiguat and based on this. The FDA approved vericiguat in January 2021, to reduce the risk of cardiovascular death, heart failure re-hospitalisation, or the requirement for outpatient intravenous diuretics, in patients with symptomatic chronic heart failure and ejection fraction less than 45%. This approval was based on efficacy data arising from the Phase 3 trial NCT02861534 (a.k.a. the VICTORIA trial).

Synthesis

The synthesis process of Vericiguat is to prepare intermediate 6.11 from the reaction of aniline diazonium salt (6.10) and malononitrile. The obtained dinitrile 6.11 is condensed with intermediate 6.9 in dimethylformamide (DMF) to obtain 6.12 in two steps. Next, amine (6.13) is obtained by catalytic hydrogenation reduction. Finally, methyl chloroformate reacts selectively with the amino group at the C5 position to produce Vericiguat (6) with a yield of 96%.

in vivo

Vericiguat (compound 24) (oral administration; 3 mg/kg, 10 mg/kg; once daily; 21 days) maintains heart and kidney function in a model of hypertension-induced end-organ damage in L-NAME-treated renin transgenic rats. Additionally,Vericiguat-treated group substantially reduces overall mortality when compared to the control group^[1].

Animal Model:	L-NAME-treated renin transgenic rats^[1]
Dosage:	3 mg/kg, 10 mg/kg
Administration:	Oral administration; 3 mg/kg, 10 mg/kg; once daily; 21 days
Result:	Resulted in a significant attenuation of blood pressure increase, however the overall rise of blood pressure increase was not halted in the 3/10 mg/kg treatment groups.Resulted a significant and dose-dependent reduction of heart hypertrophy, in both the right and left ventricle.With respect to kidney damage, Vericiguat? Led to a significant reduction in kidney injury molecule Kim-1 and osteopontin expression which are used as biomarkers for renal injury and dysfunction.Resulted in a significant and dose-dependent increase in survival rates. The rat survival rate was 70% and 90%, respectively in the 3 and 10 mg/kg qd treatment groups. In contrast, the survival rate in the placebo group was only 25% after 21 days.

vericiguat Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from vericiguat manufacturers

ZHENGZHOU JIUYI TIME NEW MATERIALS CO,.LTD

Product: vericiguat 1350653-20-1
Price: US $2.00-5.00/kg
Min. Order: 1kg
Purity: 99%
Supply Ability: 100kg
Release date: 2025-06-18

Shaanxi Dideu New Materials Co. Ltd

Product: vericiguat 1350653-20-1
Price: US $0.00/kg
Min. Order: 1kg
Purity: 98%
Supply Ability: 1000kg
Release date: 2025-06-02

WUHAN FORTUNA CHEMICAL CO., LTD

Product: Vericiguat 1350653-20-1
Price: US $0.00-0.00/g
Min. Order: 1g
Purity: 98%
Supply Ability: 10kg/month
Release date: 2024-05-28

1350653-20-1, vericiguatRelated Search:

vericiguat

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

BAY1021189

Carbamic acid, N-[4,6-diamino-2-[5-fluoro-1-[(2-fluorophenyl)methyl]-1H-pyrazolo[3,4-b]pyridin-3-yl]-5-pyrimidinyl]-, methyl ester

Vericiguat (BAY 1021189)

MK-1242

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

Inhibitor,BAY-1021189,BAY 1021189,inhibit,Guanylate Cyclase,Vericiguat

Vericygua

Vericiguat Impurity

Vericiguat, 10 mM in DMSO

Vilisigua

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

1350653-20-1

C19H16F2N8O2

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