vericiguat   Click here for help

GtoPdb Ligand ID: 10010

Synonyms: BAY-1021189 | MK-1242 | Verquvo®
Approved drug
vericiguat is an approved drug (EMA & FDA (2021))
Compound class: Synthetic organic
Comment: Vericiguat is a novel oral soluble guanylate cyclase (sGC) stimulator [4]. It was initially developed for potential to reduce mortality and morbidity associated with chronic heart failure with reduced ejection fraction.
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 9
Hydrogen bond donors 3
Rotatable bonds 6
Topological polar surface area 146.86
Molecular weight 426.14
XLogP 2.36
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES COC(=O)Nc1c(N)nc(nc1N)c1nn(c2c1cc(F)cn2)Cc1ccccc1F
Isomeric SMILES COC(=O)Nc1c(N)nc(nc1N)c1nn(c2c1cc(F)cn2)Cc1ccccc1F
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)
InChI Key QZFHIXARHDBPBY-UHFFFAOYSA-N
No information available.
Summary of Clinical Use Click here for help
Vericiguat was advanced to clinical evaluation, as an oral therapy for chronic heart failure, either with reduced ejection fraction (HFrEF), or preserved EF (HFpEF) [3,6]. 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) [2,5]. EMA approval followed in July 2021.
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT02861534 A Study of Vericiguat in Participants With Heart Failure With Reduced Ejection Fraction (HFrEF) (MK-1242-001) Phase 3 Interventional Merck Sharp & Dohme Corp. 1-2
NCT01951638 Phase IIb Safety and Efficacy Study of Four Dose Regimens of BAY1021189 in Patients With Heart Failure and Preserved Ejection Fraction Suffering From Worsening Chronic Heart Failure (SOCRATES-PRESERVED) Phase 2 Interventional Bayer