Riociguat - Moligand™, ≥99% , Soluble guanylate cyclase positive allosteric modulator, CAS No.625115-55-1, Soluble guanylate cyclase positive allosteric modulator

CAS: 625115-55-1 Cat. No.: R127750 Molecular Weight: 422.42 EC Number: 641-755-1 PubChem CID: 11304743

GRADE & PURITY Moligand™, ≥99%

Synonyms

AMY4218 | HMS3413M12 | Methyl 4,6-diamino-2-(1-(2-fluorobenzyl)-1H-pyrazolo(3,4-b)pyridin-3-yl)-5-pyrimidinyl(methyl)carbamate | EX-A2023 | MFCD19443708 | FT-0760451 | AKOS015900718 | Riocguat-d3 | RIOCIGUAT [JAN] | methyl N-[4,6-diamino-2-[1-[(2-fluoroph

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Riociguat (BAY 63-2521) is a stimulator of soluble guanylate cyclase (sGC). IC50 value: Target: sGC stimulator

Specifications

Synonyms

AMY4218 | HMS3413M12 | Methyl 4, 6-diamino-2-(1-(2-fluorobenzyl)-1H-pyrazolo(3, 4-b)pyridin-3-yl)-5-pyrimidinyl(methyl)carbamate | EX-A2023 | MFCD19443708 | FT-0760451 | AKOS015900718 | Riocguat-d3 | RIOCIGUAT [JAN] | methyl N-[4, 6-diamino-2-[1-[(2-fluoroph

Specifications & Purity

Moligand™, ≥99%

Biochemical and Physiological Mechanisms

Riociguat (BAY 63-2521; BAY 632521) is a novel drug that is currently in clinical development by Bayer. Riociguat (BAY 63-2521; BAY 632521) is a stimulator of soluble guanylate cyclase (sGC). At the moment Phase III clinical trials investigate the use of

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Action Type

ACTIVATOR, POSITIVE ALLOSTERIC MODULATOR

Mechanism of action

Soluble guanylate cyclase positive allosteric modulator

Purity

≥99%

Product Properties

• ALogP: 1.6

Names and Identifiers

• Pubchem Sid: 504766272
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504766272
• Canonical Smiles: CN(C1=C(N=C(N=C1N)C2=NN(C3=C2C=CC=N3)CC4=CC=CC=C4F)N)C(=O)OC
• IUPAC Name: methyl N-[4,6-diamino-2-[1-[(2-fluorophenyl)methyl]pyrazolo[3,4-b]pyridin-3-yl]pyrimidin-5-yl]-N-methylcarbamate
• InChIKey: WXXSNCNJFUAIDG-UHFFFAOYSA-N
• 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)
• Isomeric SMILES: CN(C1=C(N=C(N=C1N)C2=NN(C3=C2C=CC=N3)CC4=CC=CC=C4F)N)C(=O)OC
• PubChem CID: 11304743
• Molecular Weight: 422.42

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Pyrazolopyridines

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Pyrazolopyridines
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Pyrazolopyridines
• Alternative Parents: Aminopyrimidines and derivatives Fluorobenzenes Pyridines and derivatives Aryl fluorides Imidolactams Pyrazoles Carbamate esters Heteroaromatic compounds Organic carbonic acids and derivatives Azacyclic compounds Hydrocarbon derivatives Carbonyl compounds Organic oxides Organofluorides Organopnictogen compounds Primary amines
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Pyrazolopyridine - Aminopyrimidine - Halobenzene - Fluorobenzene - Aryl fluoride - Aryl halide - Pyridine - Pyrimidine - Benzenoid - Imidolactam - Monocyclic benzene moiety - Carbamic acid ester - Azole - Heteroaromatic compound - Pyrazole - Carbonic acid derivative - Azacycle - Amine - Organofluoride - Organohalogen compound - Organonitrogen compound - Organooxygen compound - Primary amine - Carbonyl group - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Organic oxygen compound - Organic nitrogen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as pyrazolopyridines. These are compounds containing a pyrazolopyridine skeleton, which consists of a pyrazole fused to a pyridine. Pyrazole is 5-membered ring consisting of three carbon atoms and two adjacent nitrogen centers. Pyridine is a 6-membered ring with four carbon and one nitrogen atoms.
• External Descriptors: organofluorine compound - carbamate ester - aminopyrimidine - pyrazolopyridine

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

GUCY1A1 Tclin Guanylate cyclase soluble subunit alpha-1 (0 Activities)

Discover Target: GUCY1A1

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

GUCY1A2 Tclin Guanylate cyclase soluble subunit alpha-2 (0 Activities)

Discover Target: GUCY1A2

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

GUCY1B1 Tclin Guanylate cyclase soluble subunit beta-1 (0 Activities)

Discover Target: GUCY1B1

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

F2 Tclin Thrombin (11687 Activities)

Discover Target: F2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ESR1 Tclin Estrogen receptor alpha (17718 Activities)

Discover Target: ESR1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PGR Tclin Progesterone receptor (8562 Activities)

Discover Target: PGR

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CHRM2 Tclin Muscarinic acetylcholine receptor M2 (10671 Activities)

Discover Target: CHRM2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HTR1A Tclin Serotonin 1a (5-HT1a) receptor (14969 Activities)

Discover Target: HTR1A

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADRA2A Tclin Alpha-2a adrenergic receptor (9450 Activities)

Discover Target: ADRA2A

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

AR Tclin Androgen Receptor (11781 Activities)

Discover Target: AR

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CHRM1 Tclin Muscarinic acetylcholine receptor M1 (12690 Activities)

Discover Target: CHRM1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

MAOA Tclin Monoamine oxidase A (11911 Activities)

Discover Target: MAOA

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

DRD1 Tclin Dopamine D1 receptor (9720 Activities)

Discover Target: DRD1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ACHE Tclin Acetylcholinesterase (18204 Activities)

Discover Target: ACHE

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PTGS1 Tclin Cyclooxygenase-1 (9233 Activities)

Discover Target: PTGS1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SLC6A2 Tclin Norepinephrine transporter (10102 Activities)

Discover Target: SLC6A2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SLC6A4 Tclin Serotonin transporter (12625 Activities)

Discover Target: SLC6A4

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADRA1A Tclin Alpha-1a adrenergic receptor (8359 Activities)

Discover Target: ADRA1A

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

OPRM1 Tclin Mu opioid receptor (19785 Activities)

Discover Target: OPRM1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

DRD3 Tclin Dopamine D3 receptor (14368 Activities)

Discover Target: DRD3

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SLC6A3 Tclin Dopamine transporter (10535 Activities)

Discover Target: SLC6A3

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

KCNH2 Tclin HERG (29587 Activities)

Discover Target: KCNH2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PDE3A Tclin Phosphodiesterase 3A (3309 Activities)

Discover Target: PDE3A

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HTR2B Tclin Serotonin 2b (5-HT2b) receptor (10323 Activities)

Discover Target: HTR2B

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

TBXA2R Tclin Thromboxane A2 receptor (5717 Activities)

Discover Target: TBXA2R

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PDE4A Tclin Phosphodiesterase 4A (1943 Activities)

Discover Target: PDE4A

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADORA3 Tchem Adenosine A3 receptor (15931 Activities)

Discover Target: ADORA3

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HRH3 Tclin Histamine H3 receptor (10389 Activities)

Discover Target: HRH3

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

KDR Tclin Vascular endothelial growth factor receptor 2 (20924 Activities)

Discover Target: KDR

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PRKAA2 Tchem AMP-activated protein kinase, AMPK (12273 Activities)

Discover Target: PRKAA2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

Hdac6 Histone deacetylase 6 (222 Activities)

Discover Target: Hdac6

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Canis familiaris (36305 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Rattus norvegicus (775804 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

rep Replicase polyprotein 1ab (378 Activities)

Discover Target: rep

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Heart (171 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Aorta (2975 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Gucy1a1 Guanylate cyclase soluble subunit alpha-1 (85 Activities)

Discover Target: Gucy1a1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SARS-CoV-2 (38078 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Solubility: DMSO
• Molecular Weight: 422.400 g/mol
• XLogP3: 1.600
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 5
• Exact Mass: 422.162 Da
• Monoisotopic Mass: 422.162 Da
• Topological Polar Surface Area: 138.000 Ų
• Heavy Atom Count: 31
• Formal Charge: 0
• Complexity: 618.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Congyang Ding, Caihui Guo, Lingzhi Fang, Yajing Li, Zhi Wang, Zhanjun Dong.  (2023)  Determination of vericiguat in rat plasma by UPLC-MS/MS and its application to drug interaction.  JOURNAL OF CHROMATOGRAPHY A,      [PMID:37741219] [10.1016/j.chroma.2023.464401]

2. Nourhan M. Amaar, Fathi S. Awad, Wael I. Mortada, A.B. Abdallah.  (2024)  Innovative approaches in electrochemical sensing for the sensitive and selective label-free detection of vericiguat in real blood samples.  MICROCHEMICAL JOURNAL,      [PMID:] [10.1016/j.microc.2024.112488]