Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00597)
Name
Riociguat
Synonyms    Click to Show/Hide the Synonyms of This API
Riociguat; 625115-55-1; Adempas; BAY 63-2521; Riociguat (BAY 63-2521); UNII-RU3FE2Y4XI; RU3FE2Y4XI; Methyl (4,6-diamino-2-(1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl)pyrimidin-5-yl)(methyl)carbamate; BAY-63-2521; CHEBI:76018; Methyl N-(4,6-diamino-2-{1-((2-fluorophenyl)methyl)-1H-pyrazolo(3,4-b)pyridin-3-yl}pyrimidin-5-yl)-N-methylcarbamate; Methyl 4,6-diamino-2-(1-(2-fluorobenzyl)-1H-pyrazolo(3,4-b)pyridin-3-yl)-5-pyrimidinyl(methyl)carbamate; riociguatum; Riociguate; Riociguat [USAN:INN:JAN]; Riocguat-d3; Methyl 4,6-diamino-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-5-pyrimidinyl(methyl)carbamate; methyl N-(4,6-diamino-2-{1-[(2-fluorophenyl)methyl]-1H-pyrazolo[3,4-b]pyridin-3-yl}pyrimidin-5-yl)-N-methylcarbamate; Adempas (TN); BAY 632521; Bay 63-2521,Riociguat; N-[4,6-Diamino-2-[1-[(2-fluorophenyl)methyl]-1H-pyrazolo[3,4-b]pyridin-3-yl]-5-pyrimidinyl]-N-methylcarbamic acid methyl ester; Riociguat (JAN/USAN/INN); SCHEMBL245457; GTPL5257; CHEMBL2107834; C20H19FN8O2; DTXSID50978109; QCR-167; BCP04750; BCP23980; EX-A2023; ZINC3819392; Riociguat,CAS:625115-55-1; CR0020; MFCD19443708; AKOS015900718; AKOS032950011; ACN-036668; BAY-632521; BCP9000382; CCG-268912; CS-0584; DB08931; PB25734; NCGC00379065-03; NCGC00379065-04; NCGC00379065-05; [4,6-Diamino-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]pyrimidin-5-yl]methylcarbamic acid methyl ester; AC-27647; AK172141; AS-19299; HY-14779; BCP0726000023; AB0033159; DB-073136; FT-0760451; A11549; BAY 63-2521;BAY 632521; D09572; Q-4478; BAY 63-2521; BAY 632521; 115R551; Q2154494; 1304478-72-5; BAY 63-2521-d3; BAY 632521-d3; Methyl [4,6-diamino-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]pyrimidin-5-yl]methylcarbamate-d3; Carbamic acid, (4,6-diamino-2-(1-((2-fluorophenyl)methyl)-1H-pyrazolo(3,4-b)pyridin-3-yl)-5-pyrimidinyl)methyl-, methyl ester; Carbamic acid, N-(4,6-diamino-2-(1-((2-fluorophenyl)methyl)-1H-pyrazolo(3,4-b)pyridin-3-yl)-5-pyrimidinyl)-N-methyl-, methyl ester; Methyl (4-amino-2-{1-[(2-fluorophenyl)methyl]-1H-pyrazolo[3,4-b]pyridin-3-yl}-6-imino-1,6-dihydropyrimidin-5-yl)methylcarbamate; methyl {4,6-diamino-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]pyrimidin-5-yl}methylcarbamate; methyl 4,6-diamino-2-(1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl)pyrimidin-5-yl(methyl)carbamate; Methyl N-[4,6-Diamino-2-[1-[(2-fluorophenyl)methyl]-1H-pyrazolo[3,4-b]pyridin-3-yl]-5-pyrimidinyl]-N-methyl-carbaminate; methyl N-[4,6-diamino-2-[1-[(2-fluorophenyl)methyl]pyrazolo[3,4-b]pyridin-3-yl]pyrimidin-5-yl]-N-methylcarbamate
Clinical Status
Approved
Disease Indication Pulmonary hypertension ICD-11: BB01 [1]
PubChem CID
11304743
Formula
C20H19FN8O2
Canonical SMILES
CN(C1=C(N=C(N=C1N)C2=NN(C3=C2C=CC=N3)CC4=CC=CC=C4F)N)C(=O)OC
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)
InChIKey
WXXSNCNJFUAIDG-UHFFFAOYSA-N
   Click to Show/Hide the Molecular Data (Structure/Property) of This API
Structure
<iframe style="width: 300px; height: 300px;" frameborder="0" src="https://embed.molview.org/v1/?mode=balls&cid=11304743"></iframe>
3D MOL 2D MOL
Physicochemical Properties Molecular Weight 422.4 Topological Polar Surface Area 138
XlogP 1.6 Complexity 618
Heavy Atom Count 31 Rotatable Bond Count 5
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 9
Full List of Drug Formulations (DFMs) Containing This API
          Riociguat 2 mg tablet Click to Show/Hide the Full List of Formulation(s):          1 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Lactose monohydrate; Sodium lauryl sulfate; Magnesium stearate; Ferric oxide red; Ferric oxide yellow; Propylene glycol; Titanium dioxide; Cellulose, microcrystalline; Crospovidone (15 mpa.s at 5%); Hydroxypropyl cellulose (type h); Hypromelloses
                   Dosage Form Oral Tablet
                   Company Bayer HealthCare
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [2]
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [3]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
          Riociguat 2.5 mg tablet Click to Show/Hide the Full List of Formulation(s):          1 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Lactose monohydrate; Sodium lauryl sulfate; Magnesium stearate; Ferric oxide red; Ferric oxide yellow; Propylene glycol; Titanium dioxide; Cellulose, microcrystalline; Crospovidone (15 mpa.s at 5%); Hydroxypropyl cellulose (type h); Hypromelloses
                   Dosage Form Oral Tablet
                   Company Bayer HealthCare
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [2]
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [3]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
          Riociguat 1 mg tablet Click to Show/Hide the Full List of Formulation(s):          1 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Lactose monohydrate; Sodium lauryl sulfate; Magnesium stearate; Ferric oxide yellow; Propylene glycol; Titanium dioxide; Cellulose, microcrystalline; Crospovidone (15 mpa.s at 5%); Hydroxypropyl cellulose (type h); Hypromelloses
                   Dosage Form Oral Tablet
                   Company Bayer HealthCare
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [2]
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [3]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
          Riociguat 1.5 mg tablet Click to Show/Hide the Full List of Formulation(s):          1 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Lactose monohydrate; Sodium lauryl sulfate; Magnesium stearate; Ferric oxide yellow; Propylene glycol; Titanium dioxide; Cellulose, microcrystalline; Crospovidone (15 mpa.s at 5%); Hydroxypropyl cellulose (type h); Hypromelloses
                   Dosage Form Oral Tablet
                   Company Bayer HealthCare
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [2]
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [3]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
          Riociguat 0.5 mg tablet Click to Show/Hide the Full List of Formulation(s):          1 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Lactose monohydrate; Sodium lauryl sulfate; Magnesium stearate; Propylene glycol; Titanium dioxide; Cellulose, microcrystalline; Crospovidone (15 mpa.s at 5%); Hydroxypropyl cellulose (type h); Hypromelloses
                   Dosage Form Oral Tablet
                   Company Bayer HealthCare
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [2]
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [3]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
References
1 FDA label for approved riociguat from the official website of the U.S. Food and Drug Administration.
2 Bacterial metabolism rescues the inhibition of intestinal drug absorption by food and drug additives. Proc Natl Acad Sci U S A. 2020 Jul 7;117(27):16009-16018.
3 Pharmaceutical excipients inhibit cytochrome P450 activity in cell free systems and after systemic administration. Eur J Pharm Biopharm. 2008 Sep;70(1):279-88.
4 Effects of commonly used excipients on the expression of CYP3A4 in colon and liver cells. Pharm Res. 2010 Aug;27(8):1703-12.

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