Identification
- Name
- Riociguat
- Accession Number
- DB08931
- Description
Riociguat is a soluble guanylate cyclase (sGC) agonist approved in the USA, Europe and several other regions for patients with group I PAH (pulmonary arterial hypertension) in WHO FC II or III; and for the treatment of patients with inoperable CTEPH (chronic thromboembolic pulmonary hypertension), or persistent/recurrent PH (pulmonary hypertension) after pulmonary endarterectomy in WHO FC II or III. Riociguat is marketed under the brand Adempas® by Bayer HealthCare Pharmaceuticals. Treatment with riociguat costs USD $7,500 for 30 days of treatment.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Riociguat (DB08931)
- Weight
- Average: 422.4157
Monoisotopic: 422.161500097 - Chemical Formula
- C20H19FN8O2
- Synonyms
- Methyl N-[4,6-Diamino-2-[1-[(2-fluorophenyl)methyl]-1H-pyrazolo[3,4-b]pyridin-3-yl]-5-pyrimidinyl]-N-methyl-carbaminate
- Riociguat
- Riociguatum
- External IDs
- BAY 41-2272
- BAY 63-2521
Pharmacology
- Indication
Riociguat is indicated for the treatment of adults with persistent/recurrent chronic thromboembolic pulmonary hypertension (CTEPH), (WHO Group 4) after surgical treatment, or inoperable CTEPH, to improve exercise capacity and WHO functional class. Riociguat is indicated for the treatment of adults with pulmonary arterial hypertension (PAH), (WHO Group 1), to improve exercise capacity, WHO functional class and to delay clinical worsening. Efficacy was shown in patients on Riociguat monotherapy or in combination with endothelin receptor antagonists or prostanoids. Studies establishing effectiveness included predominately patients with WHO functional class II–III and etiologies of idiopathic or heritable PAH (61%) or PAH associated with connective tissue diseases (25%).
- Associated Conditions
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- Pharmacodynamics
- Not Available
- Mechanism of action
Riociguat is a stimulator of soluble guanylate cyclase (sGC), an enzyme in the cardiopulmonary system and the receptor for nitric oxide (NO). When NO binds to sGC, the enzyme catalyzes synthesis of the signaling molecule cyclic guanosine monophosphate (cGMP). Intracellular cGMP plays an important role in regulating processes that influence vascular tone, proliferation, fibrosis and inflammation. Pulmonary hypertension is associated with endothelial dysfunction, impaired synthesis of nitric oxide and insufficient stimulation of the NO-sGC-cGMP pathway.
Riociguat has a dual mode of action. It sensitizes sGC to endogenous NO by stabilizing the NO-sGC binding. Riociguat also directly stimulates sGC via a different binding site, independently of NO. Riociguat stimulates the NO-sGC-cGMP pathway and leads to increased generation of cGMP with subsequent vasodilation.
Target Actions Organism AGuanylate cyclase soluble subunit alpha-2 agoniststimulatorHumans - Absorption
The pharmacokinetics of riociguant are dose proportional from 0.5 mg to 2.5 mg. The absolute bioavailability is approximately 94%. After oral administration, peak plasma concentrations were achieved within 1.5 hours. Food does not affect the bioavailability of riociguat.
- Volume of distribution
Volume of distribution at steady state = 30 L
- Protein binding
95% with serum albumin and alpha-1–acidic glycoprotein being the main binding components.
- Metabolism
The active metabolite (M1) of riociguat is 1/3 to 1/10 as potent as riociguat.
- Route of elimination
Riociguat is eliminated in the urine (40%) and feces (53%), largely as metabolites.
- Half-life
About 12 hours in patients and 7 hours in healthy subjects.
- Clearance
- Not Available
- Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More- Toxicity
EMBRYO-FETAL TOXICITY Do not administer Riociguat to a pregnant female because it may cause fetal harm. Females of reproductive potential: Exclude pregnancy before the start of treatment, monthly during treatment, and 1 month after stopping treatment. Prevent pregnancy during treatment and for one month after stopping treatment by using acceptable methods of contraception. For all female patients, Riociguat is available only through a restricted program called the Adempas Risk Evaluation and Mitigation Strategy.
- Affected organisms
- Humans and other mammals
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Unlock Additional DataAbametapir The serum concentration of Riociguat can be increased when it is combined with Abametapir. Abatacept The metabolism of Riociguat can be increased when combined with Abatacept. Abemaciclib Abemaciclib may decrease the excretion rate of Riociguat which could result in a higher serum level. Abiraterone The metabolism of Riociguat can be decreased when combined with Abiraterone. Acebutolol Acebutolol may increase the hypotensive activities of Riociguat. Aceclofenac The therapeutic efficacy of Riociguat can be decreased when used in combination with Aceclofenac. Acemetacin The therapeutic efficacy of Riociguat can be decreased when used in combination with Acemetacin. Acetylsalicylic acid Acetylsalicylic acid may decrease the antihypertensive activities of Riociguat. Adalimumab The metabolism of Riociguat can be increased when combined with Adalimumab. Afatinib Afatinib may decrease the excretion rate of Riociguat which could result in a higher serum level. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- Avoid St. John's Wort. This herb induces the CYP3A4 metabolism of riociguat and may reduce its serum concentration.
- Take separate from antacids. Take at least 1 hour before or after antacids. Aluminum or magnesium hydroxide antacids may reduce riociguat absorption.
- Take with or without food.
Products
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataAdempas Tablet, film coated 1.5 mg Oral Bayer Ag 2014-03-27 Not applicable EU 
Adempas Tablet, film coated 2.5 mg/1 Oral Bayer HealthCare Pharmaceuticals Inc. 2013-10-08 Not applicable US 
Adempas Tablet, film coated 2 mg Oral Bayer Ag 2014-03-27 Not applicable EU Adempas Tablet 2.5 mg Oral Bayer 2013-09-25 Not applicable Canada 
Adempas Tablet, film coated 1 mg Oral Bayer Ag 2014-03-27 Not applicable EU Adempas Tablet, film coated 1 mg Oral Bayer Ag 2014-03-27 Not applicable EU Adempas Tablet, film coated 1 mg/1 Oral Bayer HealthCare Pharmaceuticals Inc. 2013-10-08 Not applicable US Adempas Tablet 1 mg Oral Bayer 2013-09-25 Not applicable Canada Adempas Tablet, film coated 1.5 mg Oral Bayer Ag 2014-03-27 Not applicable EU Adempas Tablet, film coated 2.5 mg Oral Bayer Ag 2014-03-27 Not applicable EU Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
Categories
- ATC Codes
- C02KX05 — Riociguat
- Drug Categories
- Antihypertensive Agents
- Antihypertensives for Pulmonary Arterial Hypertension
- BCRP/ABCG2 Substrates
- Cytochrome P-450 CYP2C8 Substrates
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Substrates
- Enzyme Activators
- Guanylate Cyclase
- Guanylate Cyclase Stimulators
- Hypotensive Agents
- Soluble Guanylate Cyclase Stimulator
- Vasodilating Agents
- Chemical TaxonomyProvided by Classyfire
- 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.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Pyrazolopyridines
- Sub Class
- 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 show 6 more
- Substituents
- Amine / Aminopyrimidine / Aromatic heteropolycyclic compound / Aryl fluoride / Aryl halide / Azacycle / Azole / Benzenoid / Carbamic acid ester / Carbonic acid derivative show 20 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- organofluorine compound, carbamate ester, aminopyrimidine, pyrazolopyridine (CHEBI:76018)
Chemical Identifiers
- UNII
- RU3FE2Y4XI
- CAS number
- 625115-55-1
- InChI Key
- WXXSNCNJFUAIDG-UHFFFAOYSA-N
- InChI
- 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)
- IUPAC Name
- methyl N-(4,6-diamino-2-{1-[(2-fluorophenyl)methyl]-1H-pyrazolo[3,4-b]pyridin-3-yl}pyrimidin-5-yl)-N-methylcarbamate
- SMILES
- COC(=O)N(C)C1=C(N)N=C(N=C1N)C1=NN(CC2=C(F)C=CC=C2)C2=C1C=CC=N2
References
- Synthesis Reference
"Patent Link":http://www.google.com/patents/US7173037
- General References
- Soeiro-Pereira PV, Falcai A, Kubo CA, Oliveira-Junior EB, Marques OC, Antunes E, Condino-Neto A: BAY 41-2272, a soluble guanylate cyclase agonist, activates human mononuclear phagocytes. Br J Pharmacol. 2012 Jul;166(5):1617-30. doi: 10.1111/j.1476-5381.2011.01764.x. [PubMed:22044316]
- Hambly N, Granton J: Riociguat for the treatment of pulmonary hypertension. Expert Rev Respir Med. 2015;9(6):679-95. doi: 10.1586/17476348.2015.1106316. Epub 2015 Nov 24. [PubMed:26599488]
- Humbert M, Ghofrani HA: The molecular targets of approved treatments for pulmonary arterial hypertension. Thorax. 2016 Jan;71(1):73-83. doi: 10.1136/thoraxjnl-2015-207170. Epub 2015 Jul 28. [PubMed:26219978]
- Conole D, Scott LJ: Riociguat: first global approval. Drugs. 2013 Nov;73(17):1967-75. doi: 10.1007/s40265-013-0149-5. [PubMed:24218053]
- Khaybullina D, Patel A, Zerilli T: Riociguat (adempas): a novel agent for the treatment of pulmonary arterial hypertension and chronic thromboembolic pulmonary hypertension. P T. 2014 Nov;39(11):749-58. [PubMed:25395817]
- External Links
- KEGG Drug
- D09572
- PubChem Compound
- 11304743
- PubChem Substance
- 310264904
- ChemSpider
- 9479719
- 1439816
- ChEBI
- 76018
- ChEMBL
- CHEMBL2107834
- ZINC
- ZINC000003819392
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- PDRhealth
- PDRhealth Drug Page
- Wikipedia
- Riociguat
- AHFS Codes
- 48:48.00 — Vasodilating Agents
- FDA label
- Download (1.55 MB)
- MSDS
- Download (246 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Other Altitude Sickness / Pulmonary Hypertension (PH) 1 4 Completed Treatment Pulmonary Arterial Hypertension (PAH) 1 4 Completed Treatment Pulmonary Hypertension (PH) 1 4 Recruiting Treatment Pulmonary Hypertension (PH) 2 4 Unknown Status Treatment Sarcoidosis 1 3 Active Not Recruiting Treatment Pulmonary Hypertension (PH) 1 3 Completed Treatment Pulmonary Hypertension (PH) 5 3 Recruiting Treatment Pulmonary Arterial Hypertension (PAH) 1 2 Active Not Recruiting Treatment Left Ventricular Dysfunction / Pulmonary Hypertension (PH) 1 2 Active Not Recruiting Treatment Pulmonary Hypertension (PH) 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet Oral 0.5 mg Tablet Oral 1 mg Tablet Oral 1.5 mg Tablet Oral 2 mg Tablet Oral 2.5 mg Tablet, film coated Oral .5 mg/1 Tablet, film coated Oral 0.5 mg Tablet, film coated Oral 1 mg/1 Tablet, film coated Oral 1 mg Tablet, film coated Oral 1.5 mg/1 Tablet, film coated Oral 1.5 mg Tablet, film coated Oral 2 mg/1 Tablet, film coated Oral 2 mg Tablet, film coated Oral 2.5 mg/1 Tablet, film coated Oral 2.5 mg Tablet, coated 0.5 mg Tablet Tablet, coated 1 mg Tablet, coated 1.5 mg Tablet, coated 2 mg Tablet, coated 2.5 mg - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region Unlock Additional DataUS7173037 No 2007-02-06 2023-04-25 US US6743798 No 2004-06-01 2019-07-16 US US10662188 No 2014-02-18 2034-02-18 US Additional Data Available- Filed On
Properties
- State
- Solid
- Experimental Properties
Property Value Source water solubility 4 mg/L at 25°C FDA label - Predicted Properties
Property Value Source Water Solubility 0.0682 mg/mL ALOGPS logP 2.27 ALOGPS logP 2.69 ChemAxon logS -3.8 ALOGPS pKa (Strongest Acidic) 18.9 ChemAxon pKa (Strongest Basic) 3.5 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 8 ChemAxon Hydrogen Donor Count 2 ChemAxon Polar Surface Area 138.07 Å2 ChemAxon Rotatable Bond Count 5 ChemAxon Refractivity 135.25 m3·mol-1 ChemAxon Polarizability 41.9 Å3 ChemAxon Number of Rings 4 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter No ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- AgonistStimulator
- General Function
- Heme binding
- Specific Function
- Has guanylyl cyclase on binding to the beta-1 subunit.Isoform 2 acts as a negative regulator of guanylyl cyclase activity as it forms non-functional heterodimers with the beta subunits.
- Gene Name
- GUCY1A2
- Uniprot ID
- P33402
- Uniprot Name
- Guanylate cyclase soluble subunit alpha-2
- Molecular Weight
- 81749.185 Da
References
- Soeiro-Pereira PV, Falcai A, Kubo CA, Oliveira-Junior EB, Marques OC, Antunes E, Condino-Neto A: BAY 41-2272, a soluble guanylate cyclase agonist, activates human mononuclear phagocytes. Br J Pharmacol. 2012 Jul;166(5):1617-30. doi: 10.1111/j.1476-5381.2011.01764.x. [PubMed:22044316]
- Humbert M, Ghofrani HA: The molecular targets of approved treatments for pulmonary arterial hypertension. Thorax. 2016 Jan;71(1):73-83. doi: 10.1136/thoraxjnl-2015-207170. Epub 2015 Jul 28. [PubMed:26219978]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Substrate
- General Function
- Vitamin d 24-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP1A1
- Uniprot ID
- P04798
- Uniprot Name
- Cytochrome P450 1A1
- Molecular Weight
- 58164.815 Da
References
- Khaybullina D, Patel A, Zerilli T: Riociguat (adempas): a novel agent for the treatment of pulmonary arterial hypertension and chronic thromboembolic pulmonary hypertension. P T. 2014 Nov;39(11):749-58. [PubMed:25395817]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Vitamin d3 25-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- Khaybullina D, Patel A, Zerilli T: Riociguat (adempas): a novel agent for the treatment of pulmonary arterial hypertension and chronic thromboembolic pulmonary hypertension. P T. 2014 Nov;39(11):749-58. [PubMed:25395817]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Steroid hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP2C8
- Uniprot ID
- P10632
- Uniprot Name
- Cytochrome P450 2C8
- Molecular Weight
- 55824.275 Da
References
- Khaybullina D, Patel A, Zerilli T: Riociguat (adempas): a novel agent for the treatment of pulmonary arterial hypertension and chronic thromboembolic pulmonary hypertension. P T. 2014 Nov;39(11):749-58. [PubMed:25395817]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Steroid hydroxylase activity
- Specific Function
- This enzyme metabolizes arachidonic acid predominantly via a NADPH-dependent olefin epoxidation to all four regioisomeric cis-epoxyeicosatrienoic acids. One of the predominant enzymes responsible f...
- Gene Name
- CYP2J2
- Uniprot ID
- P51589
- Uniprot Name
- Cytochrome P450 2J2
- Molecular Weight
- 57610.165 Da
References
- Khaybullina D, Patel A, Zerilli T: Riociguat (adempas): a novel agent for the treatment of pulmonary arterial hypertension and chronic thromboembolic pulmonary hypertension. P T. 2014 Nov;39(11):749-58. [PubMed:25395817]
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Toxic substance binding
- Specific Function
- Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
- Gene Name
- ALB
- Uniprot ID
- P02768
- Uniprot Name
- Serum albumin
- Molecular Weight
- 69365.94 Da
References
- Khaybullina D, Patel A, Zerilli T: Riociguat (adempas): a novel agent for the treatment of pulmonary arterial hypertension and chronic thromboembolic pulmonary hypertension. P T. 2014 Nov;39(11):749-58. [PubMed:25395817]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Not Available
- Specific Function
- Functions as transport protein in the blood stream. Binds various ligands in the interior of its beta-barrel domain. Also binds synthetic drugs and influences their distribution and availability in...
- Gene Name
- ORM1
- Uniprot ID
- P02763
- Uniprot Name
- Alpha-1-acid glycoprotein 1
- Molecular Weight
- 23511.38 Da
References
- Khaybullina D, Patel A, Zerilli T: Riociguat (adempas): a novel agent for the treatment of pulmonary arterial hypertension and chronic thromboembolic pulmonary hypertension. P T. 2014 Nov;39(11):749-58. [PubMed:25395817]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Substrate
- General Function
- Xenobiotic-transporting atpase activity
- Specific Function
- High-capacity urate exporter functioning in both renal and extrarenal urate excretion. Plays a role in porphyrin homeostasis as it is able to mediates the export of protoporhyrin IX (PPIX) both fro...
- Gene Name
- ABCG2
- Uniprot ID
- Q9UNQ0
- Uniprot Name
- ATP-binding cassette sub-family G member 2
- Molecular Weight
- 72313.47 Da
References
- Khaybullina D, Patel A, Zerilli T: Riociguat (adempas): a novel agent for the treatment of pulmonary arterial hypertension and chronic thromboembolic pulmonary hypertension. P T. 2014 Nov;39(11):749-58. [PubMed:25395817]
Drug created on November 13, 2013 16:07 / Updated on October 21, 2020 01:55
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