Compound Detail

CHEMBL2107834

RIOCIGUAT

💊 Approved Drug

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💊 Approved Drug

COC(=O)N(C)c1c(N)nc(-c2nn(Cc3ccccc3F)c3ncccc23)nc1N

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL2107834
Name	RIOCIGUAT
Phase	Approved
Structure Type	MOL
InChI Key	WXXSNCNJFUAIDG-UHFFFAOYSA-N
Therapeutic	✓ Yes

Known Names

Adempas BAY 63-2521 BAY-63-2521 Riociguat

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

422.4

MW (Da)

2.44

ALogP

HBA

HBD

138.1

PSA (Å²)

0.51

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	2013
Availability	Prescription
Chirality	Achiral

Routes of Administration

Oral

Flags

Black Box Warning First in Class

USAN Stem	-ciguat
USAN Year	2012

Extended Properties

Molecular Formula	C20H19FN8O2
MW	422.42
Aromatic Rings	4
Heavy Atoms	31
NP-Likeness	-1.62

Mechanism of Action

Mechanism	Action Type	Target	Direct	Efficacy
Soluble guanylate cyclase positive allosteric modulator	POSITIVE ALLOSTERIC MODULATOR	Soluble guanylate cyclase	✓	✓

Indications

Familial Primary Pulmonary Hypertension Hypertension Hypertension, Pulmonary Hypertension, Pulmonary Anemia, Sickle Cell Coronary Disease Cystic Fibrosis Ischemic Stroke Raynaud Disease Scleroderma, Localized Scleroderma, Systemic Ulcer HIV Infections

ATC Classification

C02KX05

riociguat

Level 1: CARDIOVASCULAR SYSTEM

Level 2: ANTIHYPERTENSIVES

Drug Warnings

Black Box Warning

teratogenicity

Country: United States

Activity Summary

EC50 3 meas. best 6.75

IC50 2 meas. best 6.92

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Aorta CHEMBL4651286	IC50	6.92	6.92	120.0	1
Unchecked CHEMBL612545	IC50	6.92	6.92	120.0	1
Aorta CHEMBL613606	EC50	6.75	6.75	180.0	1
Heart CHEMBL613629	EC50	6.57	6.57	270.0	1
Unchecked CHEMBL612545	EC50	6.52	6.52	300.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
CL	3.333	mL.min-1.kg-1	Rattus norvegicus
CL	5.0	mL.min-1.kg-1	Canis lupus familiaris
CL	21.67	mL.min-1.kg-1	Rattus norvegicus
F	79.0	%	Canis lupus familiaris
F	46.0	%	Rattus norvegicus
T1/2	2.4	hr	Canis lupus familiaris
T1/2	1.4	hr	Rattus norvegicus
T1/2	5.0	hr	Homo sapiens
Tmax	0.5	hr	Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Unchecked	IC50	=	120.0	nM	6.92	Activation of rabbit sGC assessed as induction of preconstricted aortic ring rel...	33314936
Aorta	IC50	=	120.0	nM	6.92	Relaxation of pre-contracted rabbit aorta	36155354
Aorta	EC50	=	180.0	nM	6.75	Vasodilating activity in Sprague-Dawley rat aortic rings assessed as reduction i...	32914624
Heart	EC50	=	270.0	nM	6.57	Cardioprotective activity in Langendorff perfused Sprague-Dawley rat heart asses...	30995566
Unchecked	EC50	=	300.0	nM	6.52	Stimulatory activity at sGC in Sprague-Dawley rat thoracic aorta assessed as inh...	30995566

Literature References

PubMed	DOI	Target Context	# Activities
32914624	10.1021/acs.jmedchem.0c01132	Unchecked	10
32914624	10.1021/acs.jmedchem.0c01132	Rattus norvegicus	6
28557445	10.1021/acs.jmedchem.7b00449	Canis familiaris	4
28557445	10.1021/acs.jmedchem.7b00449	Rattus norvegicus	4
39058542	10.1021/acs.jmedchem.4c01364	Rattus norvegicus	4
-	10.6019/CHEMBL4495565	SARS-CoV-2	4
32914624	10.1021/acs.jmedchem.0c01132	AMP-activated protein kinase, AMPK	4
39058542	10.1021/acs.jmedchem.4c01364	Unchecked	3
37468498	10.1038/s41467-023-40064-9	Thromboxane A2 receptor	2
37468498	10.1038/s41467-023-40064-9	Muscarinic acetylcholine receptor M1	2
37468498	10.1038/s41467-023-40064-9	Prostaglandin G/H synthase 1	2
33314936	10.1021/acs.jmedchem.0c01093	ADMET	2
-	10.6019/CHEMBL4808148	Histone deacetylase 6	2
32914624	10.1021/acs.jmedchem.0c01132	Aorta	2
-	10.6019/CHEMBL4495564	Replicase polyprotein 1ab	2
37468498	10.1038/s41467-023-40064-9	Alpha-1A adrenergic receptor	2
30995566	10.1016/j.ejmech.2019.04.014	Unchecked	2
33314936	10.1021/acs.jmedchem.0c01093	Unchecked	1
-	10.21203/rs.3.rs-23951/v1	SARS-CoV-2	1
28557445	10.1021/acs.jmedchem.7b00449	ADMET	1

Data from ChEMBL 36 via Core Engine