Identification
NameRiociguat
Accession NumberDB08931
TypeSmall Molecule
GroupsApproved
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.

Structure
Thumb
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 / UNII-RU3FE2Y4XI
Product Ingredients Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AdempasTablet, film coated0.5 mgOralBayer Pharma Ag2014-03-27Not applicableEu
AdempasTablet0.5 mgOralBayer2013-09-25Not applicableCanada
AdempasTablet, film coated1.5 mgOralBayer Pharma Ag2014-03-27Not applicableEu
AdempasTablet, film coated2.5 mgOralBayer Pharma Ag2014-03-27Not applicableEu
AdempasTablet, film coated1 mgOralBayer Pharma Ag2014-03-27Not applicableEu
AdempasTablet2 mgOralBayer2013-09-25Not applicableCanada
AdempasTablet, film coated2 mgOralBayer Pharma Ag2014-03-27Not applicableEu
AdempasTablet, film coated1.5 mg/1OralBayer2013-10-08Not applicableUs
AdempasTablet, film coated1.5 mgOralBayer Pharma Ag2014-03-27Not applicableEu
AdempasTablet, film coated2 mgOralBayer Pharma Ag2014-03-27Not applicableEu
AdempasTablet, film coated0.5 mgOralBayer Pharma Ag2014-03-27Not applicableEu
AdempasTablet, film coated2.5 mgOralBayer Pharma Ag2014-03-27Not applicableEu
AdempasTablet, film coated1 mgOralBayer Pharma Ag2014-03-27Not applicableEu
AdempasTablet, film coated1 mgOralBayer Pharma Ag2014-03-27Not applicableEu
AdempasTablet1 mgOralBayer2013-09-25Not applicableCanada
AdempasTablet, film coated1.5 mgOralBayer Pharma Ag2014-03-27Not applicableEu
AdempasTablet, film coated.5 mg/1OralBayer2013-10-08Not applicableUs
AdempasTablet2.5 mgOralBayer2013-09-25Not applicableCanada
AdempasTablet, film coated2 mgOralBayer Pharma Ag2014-03-27Not applicableEu
AdempasTablet, film coated2 mg/1OralBayer2013-10-08Not applicableUs
AdempasTablet, film coated0.5 mgOralBayer Pharma Ag2014-03-27Not applicableEu
AdempasTablet, film coated2.5 mgOralBayer Pharma Ag2014-03-27Not applicableEu
AdempasTablet, film coated2 mgOralBayer Pharma Ag2014-03-27Not applicableEu
AdempasTablet, film coated1 mg/1OralBayer2013-10-08Not applicableUs
AdempasTablet, film coated1 mgOralBayer Pharma Ag2014-03-27Not applicableEu
AdempasTablet, film coated1.5 mgOralBayer Pharma Ag2014-03-27Not applicableEu
AdempasTablet1.5 mgOralBayer2013-09-25Not applicableCanada
AdempasTablet, film coated0.5 mgOralBayer Pharma Ag2014-03-27Not applicableEu
AdempasTablet, film coated2.5 mgOralBayer Pharma Ag2014-03-27Not applicableEu
AdempasTablet, film coated2.5 mg/1OralBayer2013-10-08Not applicableUs
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
Categories
UNIIRU3FE2Y4XI
CAS number625115-55-1
WeightAverage: 422.4157
Monoisotopic: 422.161500097
Chemical FormulaC20H19FN8O2
InChI KeyWXXSNCNJFUAIDG-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
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%).

Structured Indications
PharmacodynamicsNot 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.

TargetKindPharmacological actionActionsOrganismUniProt ID
Guanylate cyclase soluble subunit alpha-2Proteinyes
agonist
stimulator
HumanP33402 details
Related Articles
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.

ClearanceNot Available
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
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions
DrugInteractionDrug group
1,10-PhenanthrolineThe serum concentration of Riociguat can be increased when it is combined with 1,10-Phenanthroline.Experimental
3,4-DichloroisocoumarinThe serum concentration of Riociguat can be increased when it is combined with 3,4-Dichloroisocoumarin.Experimental
4-(2-Aminoethyl)Benzenesulfonyl FluorideThe serum concentration of Riociguat can be increased when it is combined with 4-(2-AMINOETHYL)BENZENESULFONYL FLUORIDE.Experimental
7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline7,8-DICHLORO-1,2,3,4-TETRAHYDROISOQUINOLINE may increase the hypotensive activities of Riociguat.Experimental
AbirateroneThe serum concentration of Riociguat can be increased when it is combined with Abiraterone.Approved
AcebutololThe risk or severity of adverse effects can be increased when Acebutolol is combined with Riociguat.Approved
AcetazolamideThe risk or severity of adverse effects can be increased when Riociguat is combined with Acetazolamide.Approved, Vet Approved
AldesleukinThe risk or severity of adverse effects can be increased when Aldesleukin is combined with Riociguat.Approved
AlfuzosinAlfuzosin may increase the hypotensive activities of Riociguat.Approved, Investigational
AliskirenThe risk or severity of adverse effects can be increased when Riociguat is combined with Aliskiren.Approved, Investigational
AlogliptinThe serum concentration of Riociguat can be increased when it is combined with Alogliptin.Approved
Alpha-1-proteinase inhibitorThe serum concentration of Riociguat can be increased when it is combined with Alpha-1-proteinase inhibitor.Approved
AlprenololAlprenolol may increase the hypotensive activities of Riociguat.Approved, Withdrawn
Aluminum hydroxideThe serum concentration of Riociguat can be decreased when it is combined with Aluminum hydroxide.Approved
AmbrisentanAmbrisentan may increase the hypotensive activities of Riociguat.Approved, Investigational
Ambroxol acefyllinateAmbroxol acefyllinate may increase the hypotensive activities of Riociguat.Experimental
AmifostineRiociguat may increase the hypotensive activities of Amifostine.Approved, Investigational
AmilorideThe risk or severity of adverse effects can be increased when Amiloride is combined with Riociguat.Approved
AminophyllineAminophylline may increase the hypotensive activities of Riociguat.Approved
AmiodaroneThe metabolism of Riociguat can be decreased when combined with Amiodarone.Approved, Investigational
AmlodipineThe risk or severity of adverse effects can be increased when Amlodipine is combined with Riociguat.Approved
AmobarbitalAmobarbital may increase the hypotensive activities of Riociguat.Approved, Illicit
Amphotericin BThe risk or severity of adverse effects can be increased when Riociguat is combined with Amphotericin B.Approved, Investigational
AmprenavirThe serum concentration of Riociguat can be increased when it is combined with Amprenavir.Approved
Amyl NitriteAmyl Nitrite may increase the hypotensive activities of Riociguat.Approved
AnagrelideAnagrelide may increase the hypotensive activities of Riociguat.Approved
Antithrombin III humanThe serum concentration of Riociguat can be increased when it is combined with Antithrombin III human.Approved
ApixabanThe serum concentration of Riociguat can be increased when it is combined with Apixaban.Approved
ApomorphineThe risk or severity of adverse effects can be increased when Riociguat is combined with Apomorphine.Approved, Investigational
ApraclonidineThe risk or severity of adverse effects can be increased when Apraclonidine is combined with Riociguat.Approved
ApremilastApremilast may increase the hypotensive activities of Riociguat.Approved, Investigational
AprepitantThe serum concentration of Riociguat can be increased when it is combined with Aprepitant.Approved, Investigational
AprotininThe serum concentration of Riociguat can be increased when it is combined with Aprotinin.Approved, Withdrawn
ArgatrobanThe serum concentration of Riociguat can be increased when it is combined with Argatroban.Approved, Investigational
AripiprazoleAripiprazole may increase the hypotensive activities of Riociguat.Approved, Investigational
ArotinololThe risk or severity of adverse effects can be increased when Riociguat is combined with Arotinolol.Approved
Arsenic trioxideThe risk or severity of adverse effects can be increased when Riociguat is combined with Arsenic trioxide.Approved, Investigational
AsunaprevirThe serum concentration of Riociguat can be increased when it is combined with Asunaprevir.Approved, Investigational
AtazanavirThe serum concentration of Riociguat can be increased when it is combined with Atazanavir.Approved, Investigational
AtenololThe risk or severity of adverse effects can be increased when Atenolol is combined with Riociguat.Approved
AtomoxetineThe metabolism of Riociguat can be decreased when combined with Atomoxetine.Approved
Azilsartan medoxomilThe risk or severity of adverse effects can be increased when Azilsartan medoxomil is combined with Riociguat.Approved
BarbexacloneBarbexaclone may increase the hypotensive activities of Riociguat.Experimental
BarbitalBarbital may increase the hypotensive activities of Riociguat.Illicit
BarnidipineThe risk or severity of adverse effects can be increased when Riociguat is combined with Barnidipine.Approved
BatimastatThe serum concentration of Riociguat can be increased when it is combined with Batimastat.Experimental
BenazeprilThe serum concentration of Riociguat can be increased when it is combined with Benazepril.Approved, Investigational
BendroflumethiazideThe risk or severity of adverse effects can be increased when Bendroflumethiazide is combined with Riociguat.Approved
BenmoxinBenmoxin may increase the hypotensive activities of Riociguat.Withdrawn
BenzamidineThe serum concentration of Riociguat can be increased when it is combined with Benzamidine.Experimental
BepridilBepridil may increase the hypotensive activities of Riociguat.Approved, Withdrawn
BetaxololThe risk or severity of adverse effects can be increased when Betaxolol is combined with Riociguat.Approved
BethanidineBethanidine may increase the hypotensive activities of Riociguat.Approved
BexaroteneThe serum concentration of Riociguat can be decreased when it is combined with Bexarotene.Approved, Investigational
BimatoprostBimatoprost may increase the hypotensive activities of Riociguat.Approved, Investigational
Bismuth SubcitrateThe serum concentration of Riociguat can be decreased when it is combined with Bismuth Subcitrate.Approved
BisoprololThe risk or severity of adverse effects can be increased when Bisoprolol is combined with Riociguat.Approved
BivalirudinThe serum concentration of Riociguat can be increased when it is combined with Bivalirudin.Approved, Investigational
BoceprevirThe serum concentration of Riociguat can be increased when it is combined with Boceprevir.Withdrawn
BortezomibThe metabolism of Riociguat can be decreased when combined with Bortezomib.Approved, Investigational
BosentanThe serum concentration of Riociguat can be decreased when it is combined with Bosentan.Approved, Investigational
BretyliumThe risk or severity of adverse effects can be increased when Bretylium is combined with Riociguat.Approved
BrimonidineBrimonidine may increase the antihypertensive activities of Riociguat.Approved
BrimonidineThe risk or severity of adverse effects can be increased when Brimonidine is combined with Riociguat.Approved
BromocriptineThe risk or severity of adverse effects can be increased when Riociguat is combined with Bromocriptine.Approved, Investigational
BumetanideThe risk or severity of adverse effects can be increased when Bumetanide is combined with Riociguat.Approved
BupivacaineThe risk or severity of adverse effects can be increased when Riociguat is combined with Bupivacaine.Approved, Investigational
BupranololBupranolol may increase the hypotensive activities of Riociguat.Approved
Calcium CarbonateThe serum concentration of Riociguat can be decreased when it is combined with Calcium carbonate.Approved
CanagliflozinThe risk or severity of adverse effects can be increased when Canagliflozin is combined with Riociguat.Approved
CandesartanThe risk or severity of adverse effects can be increased when Candesartan is combined with Riociguat.Approved
CandoxatrilThe serum concentration of Riociguat can be increased when it is combined with Candoxatril.Experimental
CandoxatrilatThe serum concentration of Riociguat can be increased when it is combined with Candoxatrilat.Experimental
CaptoprilThe serum concentration of Riociguat can be increased when it is combined with Captopril.Approved
CarbamazepineThe metabolism of Riociguat can be increased when combined with Carbamazepine.Approved, Investigational
CarbetocinThe risk or severity of adverse effects can be increased when Riociguat is combined with Carbetocin.Approved
CaroxazoneCaroxazone may increase the hypotensive activities of Riociguat.Withdrawn
CarteololThe risk or severity of adverse effects can be increased when Carteolol is combined with Riociguat.Approved
CarvedilolThe risk or severity of adverse effects can be increased when Carvedilol is combined with Riociguat.Approved, Investigational
CelecoxibThe metabolism of Riociguat can be decreased when combined with Celecoxib.Approved, Investigational
CeliprololCeliprolol may increase the hypotensive activities of Riociguat.Approved, Investigational
CeritinibThe serum concentration of Riociguat can be increased when it is combined with Ceritinib.Approved
ChlorothiazideThe risk or severity of adverse effects can be increased when Chlorothiazide is combined with Riociguat.Approved, Vet Approved
ChlorpromazineThe risk or severity of adverse effects can be increased when Riociguat is combined with Chlorpromazine.Approved, Vet Approved
ChlorthalidoneThe risk or severity of adverse effects can be increased when Chlorthalidone is combined with Riociguat.Approved
ChymostatinThe serum concentration of Riociguat can be increased when it is combined with Chymostatin.Experimental
CilastatinThe serum concentration of Riociguat can be increased when it is combined with Cilastatin.Approved
CilazaprilThe serum concentration of Riociguat can be increased when it is combined with Cilazapril.Approved
CilnidipineThe risk or severity of adverse effects can be increased when Riociguat is combined with Cilnidipine.Approved
CilostazolCilostazol may increase the hypotensive activities of Riociguat.Approved
ClarithromycinThe metabolism of Riociguat can be decreased when combined with Clarithromycin.Approved
ClemastineThe metabolism of Riociguat can be decreased when combined with Clemastine.Approved
ClevidipineThe risk or severity of adverse effects can be increased when Clevidipine is combined with Riociguat.Approved
ClofarabineThe risk or severity of adverse effects can be increased when Riociguat is combined with Clofarabine.Approved, Investigational
ClomipramineThe risk or severity of adverse effects can be increased when Riociguat is combined with Clomipramine.Approved, Vet Approved
ClonidineThe risk or severity of adverse effects can be increased when Clonidine is combined with Riociguat.Approved
ClopidogrelThe metabolism of Riociguat can be decreased when combined with Clopidogrel.Approved, Nutraceutical
ClotrimazoleThe metabolism of Riociguat can be decreased when combined with Clotrimazole.Approved, Vet Approved
ClozapineThe risk or severity of adverse effects can be increased when Riociguat is combined with Clozapine.Approved
CobicistatThe serum concentration of Riociguat can be increased when it is combined with Cobicistat.Approved
ConivaptanThe serum concentration of Riociguat can be increased when it is combined with Conivaptan.Approved, Investigational
CrizotinibThe metabolism of Riociguat can be decreased when combined with Crizotinib.Approved
CryptenamineCryptenamine may increase the hypotensive activities of Riociguat.Approved
CyclosporineThe metabolism of Riociguat can be decreased when combined with Cyclosporine.Approved, Investigational, Vet Approved
CyclothiazideCyclothiazide may increase the hypotensive activities of Riociguat.Approved
Dabigatran etexilateThe serum concentration of Riociguat can be increased when it is combined with Dabigatran etexilate.Approved
DabrafenibThe serum concentration of Riociguat can be decreased when it is combined with Dabrafenib.Approved
DapagliflozinThe risk or severity of adverse effects can be increased when Dapagliflozin is combined with Riociguat.Approved
DarexabanThe serum concentration of Riociguat can be increased when it is combined with Ym150.Investigational
DarunavirThe serum concentration of Riociguat can be increased when it is combined with Darunavir.Approved
DasatinibThe serum concentration of Riociguat can be increased when it is combined with Dasatinib.Approved, Investigational
DebrisoquinDebrisoquin may increase the hypotensive activities of Riociguat.Approved
DeferasiroxThe serum concentration of Riociguat can be decreased when it is combined with Deferasirox.Approved, Investigational
DelavirdineThe metabolism of Riociguat can be decreased when combined with Delavirdine.Approved
DeserpidineDeserpidine may increase the hypotensive activities of Riociguat.Approved
DesfluraneThe risk or severity of adverse effects can be increased when Riociguat is combined with Desflurane.Approved
DexamethasoneThe serum concentration of Riociguat can be decreased when it is combined with Dexamethasone.Approved, Investigational, Vet Approved
DexlansoprazoleThe serum concentration of Riociguat can be decreased when it is combined with TAK-390MR.Approved
DexmedetomidineThe risk or severity of adverse effects can be increased when Dexmedetomidine is combined with Riociguat.Approved, Vet Approved
DiazoxideDiazoxide may increase the hypotensive activities of Riociguat.Approved
DiclofenamideThe risk or severity of adverse effects can be increased when Diclofenamide is combined with Riociguat.Approved
DihydralazineRiociguat may increase the hypotensive activities of Dihydralazine.Investigational
DihydroergotamineThe metabolism of Riociguat can be decreased when combined with Dihydroergotamine.Approved
DiltiazemThe risk or severity of adverse effects can be increased when Diltiazem is combined with Riociguat.Approved
DinutuximabThe risk or severity of adverse effects can be increased when Riociguat is combined with Dinutuximab.Approved
DipyridamoleDipyridamole may increase the hypotensive activities of Riociguat.Approved
DorzolamideDorzolamide may increase the hypotensive activities of Riociguat.Approved
DoxazosinThe risk or severity of adverse effects can be increased when Doxazosin is combined with Riociguat.Approved
DoxofyllineDoxofylline may increase the hypotensive activities of Riociguat.Approved
DoxycyclineThe metabolism of Riociguat can be decreased when combined with Doxycycline.Approved, Investigational, Vet Approved
DronedaroneThe metabolism of Riociguat can be decreased when combined with Dronedarone.Approved
DuloxetineRiociguat may increase the orthostatic hypotensive activities of Duloxetine.Approved
DyphyllineDyphylline may increase the hypotensive activities of Riociguat.Approved
EcabetThe serum concentration of Riociguat can be increased when it is combined with Ecabet.Approved, Investigational
EdoxabanThe serum concentration of Riociguat can be increased when it is combined with Edoxaban.Approved
EfavirenzThe serum concentration of Riociguat can be decreased when it is combined with Efavirenz.Approved, Investigational
EfonidipineEfonidipine may increase the hypotensive activities of Riociguat.Approved
ElafinThe serum concentration of Riociguat can be increased when it is combined with Elafin.Investigational
EltrombopagThe serum concentration of Riociguat can be increased when it is combined with Eltrombopag.Approved
EmpagliflozinThe risk or severity of adverse effects can be increased when Riociguat is combined with Empagliflozin.Approved
EnalaprilThe serum concentration of Riociguat can be increased when it is combined with Enalapril.Approved, Vet Approved
EnalaprilatThe serum concentration of Riociguat can be increased when it is combined with Enalaprilat.Approved
EnalkirenThe serum concentration of Riociguat can be increased when it is combined with Enalkiren.Experimental
EnzalutamideThe serum concentration of Riociguat can be decreased when it is combined with Enzalutamide.Approved
EplerenoneThe risk or severity of adverse effects can be increased when Eplerenone is combined with Riociguat.Approved
EpoprostenolEpoprostenol may increase the hypotensive activities of Riociguat.Approved
EprosartanThe risk or severity of adverse effects can be increased when Eprosartan is combined with Riociguat.Approved
Erythrityl TetranitrateErythrityl Tetranitrate may increase the hypotensive activities of Riociguat.Approved
ErythromycinThe metabolism of Riociguat can be decreased when combined with Erythromycin.Approved, Vet Approved
Eslicarbazepine acetateThe serum concentration of Riociguat can be decreased when it is combined with Eslicarbazepine acetate.Approved
EsmololThe risk or severity of adverse effects can be increased when Esmolol is combined with Riociguat.Approved
EsomeprazoleThe serum concentration of Riociguat can be decreased when it is combined with Esomeprazole.Approved, Investigational
Etacrynic acidThe risk or severity of adverse effects can be increased when Etacrynic acid is combined with Riociguat.Approved
EtravirineThe serum concentration of Riociguat can be decreased when it is combined with Etravirine.Approved
FaldaprevirThe serum concentration of Riociguat can be increased when it is combined with Bi201335.Investigational
FelodipineThe risk or severity of adverse effects can be increased when Felodipine is combined with Riociguat.Approved, Investigational
FenoldopamFenoldopam may increase the hypotensive activities of Riociguat.Approved
FimasartanThe risk or severity of adverse effects can be increased when Riociguat is combined with Fimasartan.Approved
FluconazoleThe metabolism of Riociguat can be decreased when combined with Fluconazole.Approved
FluvoxamineThe metabolism of Riociguat can be decreased when combined with Fluvoxamine.Approved, Investigational
FosamprenavirThe serum concentration of Riociguat can be increased when it is combined with Fosamprenavir.Approved
FosaprepitantThe serum concentration of Riociguat can be increased when it is combined with Fosaprepitant.Approved
FosinoprilThe serum concentration of Riociguat can be increased when it is combined with Fosinopril.Approved
FosphenytoinThe metabolism of Riociguat can be increased when combined with Fosphenytoin.Approved
FurazolidoneFurazolidone may increase the hypotensive activities of Riociguat.Approved, Vet Approved
FurosemideThe risk or severity of adverse effects can be increased when Furosemide is combined with Riociguat.Approved, Vet Approved
Fusidic AcidThe serum concentration of Riociguat can be increased when it is combined with Fusidic Acid.Approved
GabexateThe serum concentration of Riociguat can be increased when it is combined with Gabexate.Investigational
GeldanamycinThe serum concentration of Riociguat can be increased when it is combined with Geldanamycin.Experimental
GemfibrozilThe metabolism of Riociguat can be decreased when combined with Gemfibrozil.Approved
GM6001The serum concentration of Riociguat can be increased when it is combined with GM6001.Experimental
GuanabenzGuanabenz may increase the hypotensive activities of Riociguat.Approved
GuanadrelGuanadrel may increase the hypotensive activities of Riociguat.Approved
GuanethidineGuanethidine may increase the hypotensive activities of Riociguat.Approved
GuanfacineThe risk or severity of adverse effects can be increased when Guanfacine is combined with Riociguat.Approved, Investigational
HalothaneThe risk or severity of adverse effects can be increased when Riociguat is combined with Halothane.Approved, Vet Approved
HexamethoniumHexamethonium may increase the hypotensive activities of Riociguat.Experimental
HexobarbitalHexobarbital may increase the hypotensive activities of Riociguat.Approved
HydracarbazineHydracarbazine may increase the hypotensive activities of Riociguat.Experimental
HydralazineThe risk or severity of adverse effects can be increased when Hydralazine is combined with Riociguat.Approved
HydrochlorothiazideThe risk or severity of adverse effects can be increased when Hydrochlorothiazide is combined with Riociguat.Approved, Vet Approved
HydroflumethiazideHydroflumethiazide may increase the hypotensive activities of Riociguat.Approved
IbudilastIbudilast may increase the hypotensive activities of Riociguat.Approved, Investigational
IdelalisibThe serum concentration of Riociguat can be increased when it is combined with Idelalisib.Approved
IdraparinuxThe serum concentration of Riociguat can be increased when it is combined with idraparinux.Investigational
IloprostIloprost may increase the hypotensive activities of Riociguat.Approved, Investigational
ImatinibThe metabolism of Riociguat can be decreased when combined with Imatinib.Approved
ImidaprilThe serum concentration of Riociguat can be increased when it is combined with Imidapril.Investigational
ImipramineThe risk or severity of adverse effects can be increased when Riociguat is combined with Imipramine.Approved
IndapamideThe risk or severity of adverse effects can be increased when Indapamide is combined with Riociguat.Approved
IndenololIndenolol may increase the hypotensive activities of Riociguat.Withdrawn
IndinavirThe serum concentration of Riociguat can be increased when it is combined with Indinavir.Approved
IndoraminIndoramin may increase the hypotensive activities of Riociguat.Withdrawn
IproclozideIproclozide may increase the hypotensive activities of Riociguat.Withdrawn
IproniazidIproniazid may increase the hypotensive activities of Riociguat.Withdrawn
IrbesartanThe risk or severity of adverse effects can be increased when Irbesartan is combined with Riociguat.Approved, Investigational
IsavuconazoniumThe metabolism of Riociguat can be decreased when combined with Isavuconazonium.Approved, Investigational
IsocarboxazidIsocarboxazid may increase the hypotensive activities of Riociguat.Approved
IsofluraneThe risk or severity of adverse effects can be increased when Riociguat is combined with Isoflurane.Approved, Vet Approved
IsoflurophateThe serum concentration of Riociguat can be increased when it is combined with Isoflurophate.Approved, Withdrawn
Isosorbide DinitrateIsosorbide Dinitrate may increase the hypotensive activities of Riociguat.Approved
Isosorbide MononitrateIsosorbide Mononitrate may increase the hypotensive activities of Riociguat.Approved
IsoxsuprineThe risk or severity of adverse effects can be increased when Riociguat is combined with Isoxsuprine.Approved, Withdrawn
IsradipineThe risk or severity of adverse effects can be increased when Isradipine is combined with Riociguat.Approved
ItraconazoleThe serum concentration of Riociguat can be increased when it is combined with Itraconazole.Approved, Investigational
IvacaftorThe serum concentration of Riociguat can be increased when it is combined with Ivacaftor.Approved
IxazomibThe serum concentration of Riociguat can be increased when it is combined with Ixazomib.Approved
KetanserinRiociguat may increase the hypotensive activities of Ketanserin.Investigational
KetoconazoleThe serum concentration of Riociguat can be increased when it is combined with Ketoconazole.Approved, Investigational
KetoconazoleThe metabolism of Riociguat can be decreased when combined with Ketoconazole.Approved, Investigational
LabetalolThe risk or severity of adverse effects can be increased when Labetalol is combined with Riociguat.Approved
LacidipineLacidipine may increase the hypotensive activities of Riociguat.Approved
LansoprazoleThe serum concentration of Riociguat can be decreased when it is combined with Lansoprazole.Approved, Investigational
LapatinibThe metabolism of Riociguat can be decreased when combined with Lapatinib.Approved, Investigational
LatanoprostLatanoprost may increase the hypotensive activities of Riociguat.Approved, Investigational
LepirudinThe serum concentration of Riociguat can be increased when it is combined with Lepirudin.Approved
LercanidipineLercanidipine may increase the hypotensive activities of Riociguat.Approved, Investigational
LevobunololThe risk or severity of adverse effects can be increased when Levobunolol is combined with Riociguat.Approved
LevobupivacaineThe risk or severity of adverse effects can be increased when Riociguat is combined with Levobupivacaine.Approved
LevodopaRiociguat may increase the orthostatic hypotensive activities of Levodopa.Approved
LevosimendanThe risk or severity of adverse effects can be increased when Riociguat is combined with Levosimendan.Approved, Investigational
LinagliptinThe serum concentration of Riociguat can be increased when it is combined with Linagliptin.Approved
LisinoprilThe serum concentration of Riociguat can be increased when it is combined with Lisinopril.Approved, Investigational
LofexidineLofexidine may increase the hypotensive activities of Riociguat.Approved, Investigational
LopinavirThe serum concentration of Riociguat can be increased when it is combined with Lopinavir.Approved
LosartanThe risk or severity of adverse effects can be increased when Losartan is combined with Riociguat.Approved
LovastatinThe metabolism of Riociguat can be decreased when combined with Lovastatin.Approved, Investigational
LuliconazoleThe serum concentration of Riociguat can be increased when it is combined with Luliconazole.Approved
LumacaftorThe serum concentration of Riociguat can be increased when it is combined with Lumacaftor.Approved
MacitentanRiociguat may increase the hypotensive activities of Macitentan.Approved
MagaldrateThe serum concentration of Riociguat can be decreased when it is combined with Magaldrate.Withdrawn
Magnesium carbonateThe serum concentration of Riociguat can be decreased when it is combined with Magnesium carbonate.Approved
Magnesium HydroxideThe serum concentration of Riociguat can be decreased when it is combined with Magnesium hydroxide.Approved
Magnesium oxideThe serum concentration of Riociguat can be decreased when it is combined with Magnesium oxide.Approved
Magnesium TrisilicateThe serum concentration of Riociguat can be decreased when it is combined with Magnesium Trisilicate.Approved
ManidipineManidipine may increase the hypotensive activities of Riociguat.Approved
MannitolThe risk or severity of adverse effects can be increased when Mannitol is combined with Riociguat.Approved, Investigational
MebanazineMebanazine may increase the hypotensive activities of Riociguat.Withdrawn
MecamylamineThe risk or severity of adverse effects can be increased when Mecamylamine is combined with Riociguat.Approved
MethazolamideThe risk or severity of adverse effects can be increased when Methazolamide is combined with Riociguat.Approved
MethohexitalMethohexital may increase the hypotensive activities of Riociguat.Approved
MethyclothiazideThe risk or severity of adverse effects can be increased when Methyclothiazide is combined with Riociguat.Approved
MethyldopaThe risk or severity of adverse effects can be increased when Methyldopa is combined with Riociguat.Approved
Methylene blueMethylene blue may increase the hypotensive activities of Riociguat.Investigational
MethylphenidateMethylphenidate may decrease the antihypertensive activities of Riociguat.Approved, Investigational
MethylphenobarbitalMethylphenobarbital may increase the hypotensive activities of Riociguat.Approved
MetipranololThe risk or severity of adverse effects can be increased when Metipranolol is combined with Riociguat.Approved
MetolazoneThe risk or severity of adverse effects can be increased when Metolazone is combined with Riociguat.Approved
MetoprololThe risk or severity of adverse effects can be increased when Metoprolol is combined with Riociguat.Approved, Investigational
MetyrosineRiociguat may increase the hypotensive activities of Metyrosine.Approved
MibefradilMibefradil may increase the hypotensive activities of Riociguat.Withdrawn
MifepristoneThe serum concentration of Riociguat can be increased when it is combined with Mifepristone.Approved, Investigational
MilrinoneMilrinone may increase the hypotensive activities of Riociguat.Approved
MinaprineMinaprine may increase the hypotensive activities of Riociguat.Approved
MinoxidilThe risk or severity of adverse effects can be increased when Minoxidil is combined with Riociguat.Approved
MitotaneThe serum concentration of Riociguat can be decreased when it is combined with Mitotane.Approved
MoclobemideMoclobemide may increase the hypotensive activities of Riociguat.Approved
ModafinilThe serum concentration of Riociguat can be decreased when it is combined with Modafinil.Approved, Investigational
MoexiprilThe serum concentration of Riociguat can be increased when it is combined with Moexipril.Approved
MolsidomineMolsidomine may increase the hypotensive activities of Riociguat.Approved
MorphineThe risk or severity of adverse effects can be increased when Riociguat is combined with Morphine.Approved, Investigational
MoxonidineMoxonidine may increase the hypotensive activities of Riociguat.Approved
N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-ProlineThe serum concentration of Riociguat can be increased when it is combined with N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-Proline.Experimental
NabiloneThe risk or severity of adverse effects can be increased when Riociguat is combined with Nabilone.Approved, Investigational
NadololThe risk or severity of adverse effects can be increased when Nadolol is combined with Riociguat.Approved
NafamostatThe serum concentration of Riociguat can be increased when it is combined with Nafamostat.Approved, Investigational
NafcillinThe serum concentration of Riociguat can be decreased when it is combined with Nafcillin.Approved
NaftopidilRiociguat may increase the hypotensive activities of Naftopidil.Investigational
NebivololThe risk or severity of adverse effects can be increased when Nebivolol is combined with Riociguat.Approved, Investigational
NefazodoneThe metabolism of Riociguat can be decreased when combined with Nefazodone.Approved, Withdrawn
NelfinavirThe serum concentration of Riociguat can be increased when it is combined with Nelfinavir.Approved
NesiritideThe risk or severity of adverse effects can be increased when Nesiritide is combined with Riociguat.Approved, Investigational
NetupitantThe serum concentration of Riociguat can be increased when it is combined with Netupitant.Approved
NevirapineThe metabolism of Riociguat can be increased when combined with Nevirapine.Approved
NialamideNialamide may increase the hypotensive activities of Riociguat.Withdrawn
NicardipineThe risk or severity of adverse effects can be increased when Nicardipine is combined with Riociguat.Approved
NicorandilNicorandil may increase the hypotensive activities of Riociguat.Approved
NifedipineThe risk or severity of adverse effects can be increased when Nifedipine is combined with Riociguat.Approved
NiguldipineNiguldipine may increase the hypotensive activities of Riociguat.Experimental
NilotinibThe metabolism of Riociguat can be decreased when combined with Nilotinib.Approved, Investigational
NilvadipineNilvadipine may increase the hypotensive activities of Riociguat.Approved
NimodipineThe risk or severity of adverse effects can be increased when Nimodipine is combined with Riociguat.Approved
NisoldipineThe risk or severity of adverse effects can be increased when Nisoldipine is combined with Riociguat.Approved
NitrendipineNitrendipine may increase the hypotensive activities of Riociguat.Approved
Nitric OxideThe risk or severity of adverse effects can be increased when Riociguat is combined with Nitric Oxide.Approved
NitroaspirinThe serum concentration of Riociguat can be increased when it is combined with Nitroaspirin.Investigational
NitroglycerinNitroglycerin may increase the hypotensive activities of Riociguat.Approved, Investigational
NitroprussideThe risk or severity of adverse effects can be increased when Nitroprusside is combined with Riociguat.Approved
ObinutuzumabRiociguat may increase the hypotensive activities of Obinutuzumab.Approved
OctamoxinOctamoxin may increase the hypotensive activities of Riociguat.Withdrawn
OlaparibThe metabolism of Riociguat can be decreased when combined with Olaparib.Approved
OlmesartanThe risk or severity of adverse effects can be increased when Olmesartan is combined with Riociguat.Approved, Investigational
OmapatrilatThe serum concentration of Riociguat can be increased when it is combined with Omapatrilat.Investigational
OmeprazoleThe serum concentration of Riociguat can be decreased when it is combined with Omeprazole.Approved, Investigational, Vet Approved
OsimertinibThe serum concentration of Riociguat can be increased when it is combined with Osimertinib.Approved
OtamixabanThe serum concentration of Riociguat can be increased when it is combined with Otamixaban.Investigational
OxprenololOxprenolol may increase the hypotensive activities of Riociguat.Approved
PaclitaxelThe risk or severity of adverse effects can be increased when Riociguat is combined with Paclitaxel.Approved, Vet Approved
PalbociclibThe serum concentration of Riociguat can be increased when it is combined with Palbociclib.Approved
PantoprazoleThe serum concentration of Riociguat can be decreased when it is combined with Pantoprazole.Approved
PapaverineThe risk or severity of adverse effects can be increased when Papaverine is combined with Riociguat.Approved
PargylinePargyline may increase the hypotensive activities of Riociguat.Approved
PenbutololThe risk or severity of adverse effects can be increased when Penbutolol is combined with Riociguat.Approved, Investigational
PentobarbitalThe metabolism of Riociguat can be increased when combined with Pentobarbital.Approved, Vet Approved
PentoliniumPentolinium may increase the hypotensive activities of Riociguat.Approved
PentoxifyllinePentoxifylline may increase the hypotensive activities of Riociguat.Approved, Investigational
PerindoprilThe serum concentration of Riociguat can be increased when it is combined with Perindopril.Approved
PhenelzinePhenelzine may increase the hypotensive activities of Riociguat.Approved
PheniprazinePheniprazine may increase the hypotensive activities of Riociguat.Withdrawn
PhenobarbitalThe metabolism of Riociguat can be increased when combined with Phenobarbital.Approved
PhenoxybenzaminePhenoxybenzamine may increase the hypotensive activities of Riociguat.Approved
PhenoxypropazinePhenoxypropazine may increase the hypotensive activities of Riociguat.Withdrawn
PhentolaminePhentolamine may increase the hypotensive activities of Riociguat.Approved
PhenytoinThe metabolism of Riociguat can be increased when combined with Phenytoin.Approved, Vet Approved
PhosphoramidonThe serum concentration of Riociguat can be increased when it is combined with Phosphoramidon.Experimental
PinacidilPinacidil may increase the hypotensive activities of Riociguat.Withdrawn
PindololThe risk or severity of adverse effects can be increased when Pindolol is combined with Riociguat.Approved
PioglitazoneThe metabolism of Riociguat can be decreased when combined with Pioglitazone.Approved, Investigational
PipamperoneThe risk or severity of adverse effects can be increased when Riociguat is combined with Pipamperone.Approved
PirlindolePirlindole may increase the hypotensive activities of Riociguat.Approved
PivhydrazinePivhydrazine may increase the hypotensive activities of Riociguat.Withdrawn
PolythiazidePolythiazide may increase the hypotensive activities of Riociguat.Approved
PosaconazoleThe metabolism of Riociguat can be decreased when combined with Posaconazole.Approved, Investigational, Vet Approved
PramipexoleThe risk or severity of adverse effects can be increased when Riociguat is combined with Pramipexole.Approved, Investigational
PrazosinThe risk or severity of adverse effects can be increased when Prazosin is combined with Riociguat.Approved
PrimidoneThe metabolism of Riociguat can be increased when combined with Primidone.Approved, Vet Approved
PrinomastatThe serum concentration of Riociguat can be increased when it is combined with Prinomastat.Investigational
PropofolThe risk or severity of adverse effects can be increased when Riociguat is combined with Propofol.Approved, Investigational, Vet Approved
PropranololThe risk or severity of adverse effects can be increased when Propranolol is combined with Riociguat.Approved, Investigational
QuetiapineThe risk or severity of adverse effects can be increased when Quetiapine is combined with Riociguat.Approved
QuinaprilThe serum concentration of Riociguat can be increased when it is combined with Quinapril.Approved, Investigational
QuinineQuinine may increase the hypotensive activities of Riociguat.Approved
RabeprazoleThe serum concentration of Riociguat can be decreased when it is combined with Rabeprazole.Approved, Investigational
RacecadotrilThe serum concentration of Riociguat can be increased when it is combined with Racecadotril.Investigational
RamiprilThe serum concentration of Riociguat can be increased when it is combined with Ramipril.Approved
RanolazineThe metabolism of Riociguat can be decreased when combined with Ranolazine.Approved, Investigational
RasagilineRasagiline may increase the hypotensive activities of Riociguat.Approved
RemifentanilThe risk or severity of adverse effects can be increased when Riociguat is combined with Remifentanil.Approved
RemikirenThe serum concentration of Riociguat can be increased when it is combined with Remikiren.Approved
RescinnamineRescinnamine may increase the hypotensive activities of Riociguat.Approved
ReserpineThe risk or severity of adverse effects can be increased when Reserpine is combined with Riociguat.Approved
RifabutinThe metabolism of Riociguat can be increased when combined with Rifabutin.Approved
RifampicinThe metabolism of Riociguat can be increased when combined with Rifampicin.Approved
RifapentineThe metabolism of Riociguat can be increased when combined with Rifapentine.Approved
RilmenidineRiociguat may increase the hypotensive activities of Rilmenidine.Investigational
RisperidoneRiociguat may increase the hypotensive activities of Risperidone.Approved, Investigational
RitonavirThe serum concentration of Riociguat can be increased when it is combined with Ritonavir.Approved, Investigational
RituximabRiociguat may increase the hypotensive activities of Rituximab.Approved
RivaroxabanThe serum concentration of Riociguat can be increased when it is combined with Rivaroxaban.Approved
RoflumilastRoflumilast may increase the hypotensive activities of Riociguat.Approved
RolapitantThe serum concentration of Riociguat can be increased when it is combined with Rolapitant.Approved
RopiniroleThe risk or severity of adverse effects can be increased when Riociguat is combined with Ropinirole.Approved, Investigational
RopivacaineThe risk or severity of adverse effects can be increased when Riociguat is combined with Ropivacaine.Approved
RosiglitazoneThe metabolism of Riociguat can be decreased when combined with Rosiglitazone.Approved, Investigational
RotigotineThe risk or severity of adverse effects can be increased when Riociguat is combined with Rotigotine.Approved
SacubitrilThe risk or severity of adverse effects can be increased when Riociguat is combined with Sacubitril.Approved
SafrazineSafrazine may increase the hypotensive activities of Riociguat.Withdrawn
SaprisartanSaprisartan may increase the hypotensive activities of Riociguat.Experimental
SaquinavirThe serum concentration of Riociguat can be increased when it is combined with Saquinavir.Approved, Investigational
SaxagliptinThe serum concentration of Riociguat can be increased when it is combined with Saxagliptin.Approved
SecobarbitalThe metabolism of Riociguat can be increased when combined with Secobarbital.Approved, Vet Approved
SelegilineSelegiline may increase the hypotensive activities of Riociguat.Approved, Investigational, Vet Approved
SelexipagSelexipag may increase the hypotensive activities of Riociguat.Approved
SevofluraneThe risk or severity of adverse effects can be increased when Riociguat is combined with Sevoflurane.Approved, Vet Approved
SildenafilSildenafil may increase the hypotensive activities of Riociguat.Approved, Investigational
SiltuximabThe serum concentration of Riociguat can be decreased when it is combined with Siltuximab.Approved
SimeprevirThe serum concentration of Riociguat can be increased when it is combined with Simeprevir.Approved
SitagliptinThe serum concentration of Riociguat can be increased when it is combined with Sitagliptin.Approved, Investigational
SitaxentanSitaxentan may increase the hypotensive activities of Riociguat.Approved, Investigational, Withdrawn
Sodium NitriteThe risk or severity of adverse effects can be increased when Riociguat is combined with Sodium Nitrite.Approved
SotalolThe risk or severity of adverse effects can be increased when Sotalol is combined with Riociguat.Approved
SpiraprilThe serum concentration of Riociguat can be increased when it is combined with Spirapril.Approved
SpironolactoneThe risk or severity of adverse effects can be increased when Spironolactone is combined with Riociguat.Approved
St. John's WortThe serum concentration of Riociguat can be decreased when it is combined with St. John's Wort.Nutraceutical
StiripentolThe serum concentration of Riociguat can be increased when it is combined with Stiripentol.Approved
StreptokinaseThe risk or severity of adverse effects can be increased when Riociguat is combined with Streptokinase.Approved
SufentanilThe risk or severity of adverse effects can be increased when Riociguat is combined with Sufentanil.Approved, Investigational
SulfamethoxazoleThe metabolism of Riociguat can be decreased when combined with Sulfamethoxazole.Approved
SulfisoxazoleThe metabolism of Riociguat can be decreased when combined with Sulfisoxazole.Approved, Vet Approved
TadalafilTadalafil may increase the hypotensive activities of Riociguat.Approved, Investigational
TamoxifenThe metabolism of Riociguat can be decreased when combined with Tamoxifen.Approved
TamsulosinThe risk or severity of adverse effects can be increased when Riociguat is combined with Tamsulosin.Approved, Investigational
TelaprevirThe serum concentration of Riociguat can be increased when it is combined with Telaprevir.Withdrawn
TelithromycinThe metabolism of Riociguat can be decreased when combined with Telithromycin.Approved
TelmisartanThe risk or severity of adverse effects can be increased when Telmisartan is combined with Riociguat.Approved, Investigational
TemocaprilThe serum concentration of Riociguat can be increased when it is combined with Temocapril.Experimental, Investigational
TerazosinThe risk or severity of adverse effects can be increased when Terazosin is combined with Riociguat.Approved
TeriflunomideThe serum concentration of Riociguat can be increased when it is combined with Teriflunomide.Approved
TerlipressinTerlipressin may increase the hypotensive activities of Riociguat.Approved, Investigational
ThalidomideThe risk or severity of adverse effects can be increased when Riociguat is combined with Thalidomide.Approved, Investigational, Withdrawn
TheophyllineTheophylline may increase the hypotensive activities of Riociguat.Approved
ThiamylalThiamylal may increase the hypotensive activities of Riociguat.Approved, Vet Approved
ThiopentalThiopental may increase the hypotensive activities of Riociguat.Approved, Vet Approved
ThioridazineThe risk or severity of adverse effects can be increased when Riociguat is combined with Thioridazine.Withdrawn
ThiorphanThe serum concentration of Riociguat can be increased when it is combined with Thiorphan.Experimental
TiboloneTibolone may increase the hypotensive activities of Riociguat.Approved
TiclopidineThe metabolism of Riociguat can be decreased when combined with Ticlopidine.Approved
TicrynafenTicrynafen may increase the hypotensive activities of Riociguat.Withdrawn
TimololThe risk or severity of adverse effects can be increased when Timolol is combined with Riociguat.Approved
TipranavirThe serum concentration of Riociguat can be increased when it is combined with Tipranavir.Approved, Investigational
TizanidineThe risk or severity of adverse effects can be increased when Tizanidine is combined with Riociguat.Approved
TocilizumabThe serum concentration of Riociguat can be decreased when it is combined with Tocilizumab.Approved
TolazolineTolazoline may increase the hypotensive activities of Riociguat.Approved, Vet Approved
TolcaponeThe risk or severity of adverse effects can be increased when Riociguat is combined with Tolcapone.Approved, Withdrawn
ToloxatoneToloxatone may increase the hypotensive activities of Riociguat.Approved
TorasemideThe risk or severity of adverse effects can be increased when Torasemide is combined with Riociguat.Approved
TrandolaprilThe serum concentration of Riociguat can be increased when it is combined with Trandolapril.Approved
Trans-2-PhenylcyclopropylamineTrans-2-Phenylcyclopropylamine may increase the hypotensive activities of Riociguat.Experimental
TranylcypromineTranylcypromine may increase the hypotensive activities of Riociguat.Approved
TravoprostTravoprost may increase the hypotensive activities of Riociguat.Approved
TreprostinilTreprostinil may increase the hypotensive activities of Riociguat.Approved, Investigational
TretinoinThe risk or severity of adverse effects can be increased when Riociguat is combined with Tretinoin.Approved, Investigational, Nutraceutical
TriamtereneThe risk or severity of adverse effects can be increased when Triamterene is combined with Riociguat.Approved
TrichlormethiazideTrichlormethiazide may increase the hypotensive activities of Riociguat.Approved, Vet Approved
TrimazosinTrimazosin may increase the hypotensive activities of Riociguat.Experimental
TrimethaphanTrimethaphan may increase the hypotensive activities of Riociguat.Approved
TrimethoprimThe metabolism of Riociguat can be decreased when combined with Trimethoprim.Approved, Vet Approved
UbenimexThe serum concentration of Riociguat can be increased when it is combined with Ubenimex.Experimental
UdenafilUdenafil may increase the hypotensive activities of Riociguat.Approved, Investigational
UlinastatinThe serum concentration of Riociguat can be increased when it is combined with Ulinastatin.Investigational
UnoprostoneUnoprostone may increase the hypotensive activities of Riociguat.Approved
ValsartanThe risk or severity of adverse effects can be increased when Valsartan is combined with Riociguat.Approved, Investigational
VardenafilVardenafil may increase the hypotensive activities of Riociguat.Approved
VenlafaxineThe metabolism of Riociguat can be decreased when combined with Venlafaxine.Approved
VerapamilThe risk or severity of adverse effects can be increased when Verapamil is combined with Riociguat.Approved
VildagliptinThe serum concentration of Riociguat can be increased when it is combined with Vildagliptin.Approved, Investigational
VinpocetineRiociguat may increase the hypotensive activities of Vinpocetine.Investigational
VoriconazoleThe metabolism of Riociguat can be decreased when combined with Voriconazole.Approved, Investigational
XimelagatranThe serum concentration of Riociguat can be increased when it is combined with Ximelagatran.Approved, Investigational, Withdrawn
XylometazolineXylometazoline may increase the hypotensive activities of Riociguat.Approved
YohimbineYohimbine may decrease the antihypertensive activities of Riociguat.Approved, Vet Approved
ZiprasidoneThe metabolism of Riociguat can be decreased when combined with Ziprasidone.Approved
Food InteractionsNot Available
References
Synthesis Reference

"Patent Link":http://www.google.com/patents/US7173037

General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. Conole D, Scott LJ: Riociguat: first global approval. Drugs. 2013 Nov;73(17):1967-75. doi: 10.1007/s40265-013-0149-5. [PubMed:24218053 ]
  5. 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
ATC CodesC02KX05 — Riociguat
AHFS Codes
  • 24:12.92
PDB EntriesNot Available
FDA labelDownload (1.55 MB)
MSDSDownload (246 KB)
Clinical Trials
Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedNot AvailableDrug Interactions1
1CompletedNot AvailableHealthy Volunteers1
1CompletedNot AvailablePharmacology, Clinical1
1CompletedOtherHIV-DDI1
1CompletedTreatmentPharmacology, Clinical1
1CompletedTreatmentPulmonary Disease, Chronic Obstructive / Pulmonary Hypertension (PH)1
1CompletedTreatmentPulmonary Hypertension (PH)1
2Active Not RecruitingTreatmentPulmonary Hypertension (PH)1
2Active Not RecruitingTreatmentPulmonary Hypertension (PH) / Ventricular Dysfunction, Left1
2Active Not RecruitingTreatmentScleroderma, Systemic1
2CompletedNot AvailableRaynaud's Disease1
2CompletedTreatmentPulmonary Hypertension (PH)2
2Not Yet RecruitingTreatmentChronic Thromboembolic Pulmonary Hypertension1
2RecruitingTreatmentCystic Fibrosis (CF)1
2RecruitingTreatmentDigital Ulcers / Scleroderma1
2RecruitingTreatmentHeart Failure With Normal Ejection Fraction / Pulmonary Hypertension (PH)1
2RecruitingTreatmentSickle Cell Disorders1
2TerminatedTreatmentIdiopathic Interstitial Pneumonias / Hypertension,Pulmonary1
2TerminatedTreatmentPulmonary Hypertension (PH) / Ventricular Dysfunction, Left2
2WithdrawnTreatmentCoronary Artery Disease1
3Active Not RecruitingTreatmentPulmonary Hypertension (PH)2
3CompletedTreatmentPulmonary Hypertension (PH)3
3RecruitingTreatmentPulmonary Hypertension (PH)1
4CompletedNot AvailableAltitude Sickness / Pulmonary Hypertension (PH)1
4CompletedTreatmentPulmonary / Pulmonary Hypertension (PH)1
4RecruitingTreatmentPulmonary Arterial Hypertension (PAH)1
4RecruitingTreatmentPulmonary Hypertension (PH)1
4RecruitingTreatmentSarcoidosis1
Not AvailableActive Not RecruitingNot AvailablePulmonary Hypertension (PH)1
Not AvailableCompletedNot AvailablePulmonary Hypertension (PH)1
Not AvailableNo Longer AvailableNot AvailablePulmonary Hypertension (PH)1
Not AvailableRecruitingNot AvailablePulmonary Hypertension (PH)2
Not AvailableRecruitingDiagnosticChronic Thromboembolic Pulmonary Hypertension / Sleep Disordered Breathing (SDB)1
Not AvailableRecruitingTreatmentChronic Thromboembolic Pulmonary Hypertension1
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage forms
FormRouteStrength
TabletOral0.5 mg
TabletOral1 mg
TabletOral1.5 mg
TabletOral2 mg
TabletOral2.5 mg
Tablet, film coatedOral.5 mg/1
Tablet, film coatedOral0.5 mg
Tablet, film coatedOral1 mg/1
Tablet, film coatedOral1 mg
Tablet, film coatedOral1.5 mg
Tablet, film coatedOral1.5 mg/1
Tablet, film coatedOral2 mg/1
Tablet, film coatedOral2 mg
Tablet, film coatedOral2.5 mg
Tablet, film coatedOral2.5 mg/1
PricesNot Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US7173037 No2003-04-252023-04-25Us
US6743798 No1999-07-162019-07-16Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
water solubility4 mg/L at 25°CFDA label
Predicted Properties
PropertyValueSource
Water Solubility0.0682 mg/mLALOGPS
logP2.27ALOGPS
logP2.69ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)18.9ChemAxon
pKa (Strongest Basic)3.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area138.07 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity135.25 m3·mol-1ChemAxon
Polarizability41.9 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET featuresNot Available
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyrazolopyridines
Sub ClassNot Available
Direct ParentPyrazolopyridines
Alternative ParentsAminopyrimidines and derivatives / Fluorobenzenes / Pyridines and derivatives / Aryl fluorides / Imidolactams / Pyrazoles / Carbamate esters / Heteroaromatic compounds / Organic carbonic acids and derivatives / Azacyclic compounds
SubstituentsPyrazolopyridine / Aminopyrimidine / Halobenzene / Fluorobenzene / Aryl fluoride / Aryl halide / Pyridine / Pyrimidine / Benzenoid / Imidolactam
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptorsorganofluorine compound, carbamate ester, aminopyrimidine, pyrazolopyridine (CHEBI:76018 )

Targets

Kind
Protein
Organism
Human
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
  1. 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 ]
  2. 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
Human
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 unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP1A1
Uniprot ID:
P04798
Uniprot Name:
Cytochrome P450 1A1
Molecular Weight:
58164.815 Da
References
  1. 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
Human
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 reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Uniprot Name:
Cytochrome P450 3A4
Molecular Weight:
57342.67 Da
References
  1. 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
Human
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 unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme...
Gene Name:
CYP2C8
Uniprot ID:
P10632
Uniprot Name:
Cytochrome P450 2C8
Molecular Weight:
55824.275 Da
References
  1. 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
Human
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 for the epoxidation of endogenous cardiac arachidonic acid pools.
Gene Name:
CYP2J2
Uniprot ID:
P51589
Uniprot Name:
Cytochrome P450 2J2
Molecular Weight:
57610.165 Da
References
  1. 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
Human
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 colloidal osmotic pressure of blood. Major zinc transporter in plasma, typically binds about 80% of all plasma zinc.
Gene Name:
ALB
Uniprot ID:
P02768
Uniprot Name:
Serum albumin
Molecular Weight:
69365.94 Da
References
  1. 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
Human
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 the body. Appears to function in modulating the activity of the immune system during the acute-phase reaction.
Gene Name:
ORM1
Uniprot ID:
P02763
Uniprot Name:
Alpha-1-acid glycoprotein 1
Molecular Weight:
23511.38 Da
References
  1. 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
Human
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 from mitochondria to cytosol and from cytosol to extracellular space, and cellular export of hemin, and heme. Xenobiotic transporter that may play an important role in the exclusion of xenobiotics from t...
Gene Name:
ABCG2
Uniprot ID:
Q9UNQ0
Uniprot Name:
ATP-binding cassette sub-family G member 2
Molecular Weight:
72313.47 Da
References
  1. 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 September 01, 2017 12:00