Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR1427)
Drug Name
Riociguat
Synonyms
Riociguat; Riociguat (BAY 63-2521); riociguatum; 625115-55-1; BAY 63-2521; BAY 632521; CHEBI:76018; Adempas; RU3FE2Y4XI; 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}pyrimidin-5-yl)-N-methylcarbamate; N-[4,6-Diamino-2-[1-[(2-fluorophenyl)methyl]-1H-pyrazolo[3,4-b]pyridin-3-yl]-5-pyrimidinyl]-N-methylcarbamic acid methyl ester; UNII-RU3FE2Y4XI
Indication Pulmonary hypertension [ICD11: BB01] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 422.4 Topological Polar Surface Area 138
Heavy Atom Count 31 Rotatable Bond Count 5
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 9
Cross-matching ID
PubChem CID
11304743
PubChem SID
16393220 ; 23472114 ; 42384129 ; 80225677 ; 87550988 ; 124490312 ; 124759703 ; 126644888 ; 126680174 ; 135263495 ; 136946407 ; 137126926 ; 139526076 ; 144115685 ; 152040137 ; 152255058 ; 152258603 ; 160647437 ; 160682218 ; 164042214 ; 164347391 ; 170501515 ; 172919534 ; 178101941 ; 185997052 ; 198980755 ; 198993771 ; 211536089 ; 223399697 ; 223676750 ; 224002579 ; 226595445 ; 242826663 ; 249737057 ; 249821754 ; 251971381 ; 252155071 ; 252211224 ; 252216203 ; 252316121 ; 252438349 ; 252553251
ChEBI ID
CHEBI:76018
CAS Number
625115-55-1
TTD Drug ID
D04UKC
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
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
Riociguat metabolite M1 DM015779
11690019
Oxidation - N-demethylation 1 [4] , [3]
Riociguat metabolite M10 DM017916 N. A. Oxidation - N-dealkylation 1 [5]
Riociguat metabolite M8 DM017914 N. A. Hydrolysis - Hydrolysis 1 [5]
Riociguat metabolite M4 DM017913 N. A. Conjugation - N-glucuronidation 2 [3]
Riociguat metabolite M9 DM017915 N. A. Oxidation - N-demethylation 2 [5]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR009544 Riociguat Riociguat metabolite M1 Oxidation - N-demethylation CYP1A1 [4], [3]
MR009546 Riociguat Riociguat metabolite M8 Hydrolysis - Hydrolysis Unclear [5]
MR009548 Riociguat Riociguat metabolite M10 Oxidation - N-dealkylation Unclear [5]
MR009545 Riociguat metabolite M1 Riociguat metabolite M4 Conjugation - N-glucuronidation UGT1A1 ... [3]
MR009547 Riociguat metabolite M8 Riociguat metabolite M9 Oxidation - N-demethylation Unclear [5]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 1A1 (CYP1A1) DME0006 Homo sapiens
CP1A1_HUMAN
1.14.14.1
[2]
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[2]
Cytochrome P450 2J2 (CYP2J2) DME0031 Homo sapiens
CP2J2_HUMAN
1.14.14.24
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[3]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[3]
UDP-glucuronosyltransferase 1A9 (UGT1A9) DME0042 Homo sapiens
UD19_HUMAN
2.4.1.17
[3]
⏷ Show the Full List of 7  DME(s)
References
1 Riociguat was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 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.
3 Clinical Pharmacokinetic and Pharmacodynamic Profile of Riociguat
4 Population pharmacokinetics of riociguat and its metabolite in patients with chronic thromboembolic pulmonary hypertension from routine clinical practice
5 In vitroand in vivo investigation of metabolic fate of riociguat by HPLC-Q-TOF/MS/MS and in silico evaluation of the metabolites by ADMET predictor(?)

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