Riociguat

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Riociguat are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the Riociguat?

The molecule Riociguat presents a molecular formula of C20H19FN8O2 and its IUPAC name is methyl N-[4,6-diamino-2-[1-[(2-fluorophenyl)methyl]pyrazolo[3,4-b]pyridin-3-yl]pyrimidin-5-yl]-N-methylcarbamate.

Riociguat is a molecule that acts as a potent stimulator of soluble guanylate cyclase (sGC). This enzyme belongs in many tissues, including vascular smooth muscle and platelets, and is responsible for the production of cyclic guanosine monophosphate (cGMP). cGMP is a key regulator of many cellular processes, and its production is increased in response to various stimuli, including nitric oxide (NO) and certain hormones. Riociguat is structurally similar to NO, and binds to and activates sGC in a similar manner..

Riociguat has a variety of effects on the body, depending on the tissue in which it is active. In vascular smooth muscle, it causes relaxation and vasodilation. This effect is mediated by the production of cGMP, which leads to the opening of potassium channels and the subsequent decrease in intracellular calcium levels. This in turn leads to smooth muscle relaxation. In platelets, riociguat inhibits aggregation in response to various stimuli, including collagen and thrombin. This effect is also mediated by cGMP..

Riociguat has a number of potential therapeutic applications. It is currently being investigated as a treatment for pulmonary arterial hypertension (PAH). PAH is a condition characterized by high blood pressure in the arteries of the lungs, and can lead to heart failure and death. Riociguat has been shown to be effective in reducing pulmonary artery pressure and has been approved for use in Europe and Canada. It is also being studied as a treatment for erectile dysfunction and other cardiovascular conditions..

3D structure

Cartesian coordinates

Geometry of Riociguat in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

Riociguat WXXSNCNJFUAIDG-UHFFFAOYSA-N chemical compound 2D structure molecule svg
Riociguat

 

Molecule descriptors

 
IUPAC namemethyl N-[4,6-diamino-2-[1-[(2-fluorophenyl)methyl]pyrazolo[3,4-b]pyridin-3-yl]pyrimidin-5-yl]-N-methylcarbamate
InChI codeInChI=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)
InChI KeyWXXSNCNJFUAIDG-UHFFFAOYSA-N
SMILESCOC(=O)N(C)c1c(N)nc(-c2nn(Cc3ccccc3F)c3ncccc23)nc1N

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • 115R551
  • 1304478-72-5
  • 625115-55-1
  • AC-27647
  • AMY4218
  • AS-19299
  • Adempas
  • BAY 63-2521
  • 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
  • BAY 63-2521; BAY 632521
  • BAY 63-2521;BAY 632521
  • BAY 632521
  • BAY-63-2521
  • BAY-632521
  • BCP04750
  • BCP0726000023
  • BCP23980
  • BCP9000382
  • Bay 63-2521,Riociguat
  • CCG-268912
  • CS-0584
  • 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
  • D09572
  • DB-073136
  • DB08931
  • EX-A2023
  • FT-0760451
  • GTPL5257
  • GZO
  • HY-14779
  • METHYL N-(4,6-DIAMINO-2-(1-((2-FLUOROPHENYL)METHYL)-1H-PYRAZOLO(3,4-B)PYRIDIN-3-YL)PYRIMIDIN-5-YL)-N-METHYLCARBAMATE
  • MFCD19443708
  • Methyl (4,6-diamino-2-(1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl)pyrimidin-5-yl)(methyl)carbamate
  • Methyl 4,6-diamino-2-(1-(2-fluorobenzyl)-1H-pyrazolo(3,4-b)pyridin-3-yl)-5-pyrimidinyl(methyl)carbamate
  • 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
  • Methyl N-[4,6-Diamino-2-[1-[(2-fluorophenyl)methyl]-1H-pyrazolo[3,4-b]pyridin-3-yl]-5-pyrimidinyl]-N-methyl-carbaminate
  • N-[4,6-Diamino-2-[1-[(2-fluorophenyl)methyl]-1H-pyrazolo[3,4-b]pyridin-3-yl]-5-pyrimidinyl]-N-methylcarbamic acid methyl ester
  • NCGC00379065-03
  • NCGC00379065-04
  • NCGC00379065-05
  • PB25734
  • Q2154494
  • RU3FE2Y4XI
  • Riocguat-d3
  • Riociguat
  • Riociguat (BAY 63-2521)
  • Riociguat (JAN/USAN/INN)
  • Riociguat,CAS:625115-55-1
  • Riociguate
  • [4,6-Diamino-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]pyrimidin-5-yl]methylcarbamic acid methyl ester
  • methyl N-(4,6-diamino-2-{1-[(2-fluorophenyl)methyl]-1H-pyrazolo[3,4-b]pyridin-3-yl}pyrimidin-5-yl)-N-methylcarbamate
  • methyl N-[4,6-diamino-2-[1-[(2-fluorophenyl)methyl]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]pyrimidin-5-yl}methylcarbamate
  • methyl ~{N}-[4,6-bis(azanyl)-2-[1-[(2-fluorophenyl)methyl]pyrazolo[3,4-b]pyridin-3-yl]pyrimidin-5-yl]-~{N}-methyl-carbamate
  • riociguatum
  • s8135

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC3819392
  • UNII-RU3FE2Y4XI
  • AKOS015900718
  • AKOS032950011
  • DTXSID50978109
  • CHEMBL2107834
  • CHEBI:76018
  • SCHEMBL245457

Physico-Chemical properties

IUPAC namemethyl N-[4,6-diamino-2-[1-[(2-fluorophenyl)methyl]pyrazolo[3,4-b]pyridin-3-yl]pyrimidin-5-yl]-N-methylcarbamate
Molecular formulaC20H19FN8O2
Molecular weight422.416
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity113.76
LogP3.6
Topological polar surface area138.1

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.