Riociguat
[4,6-Diamino-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]pyrimidin-5-yl]methylcarbamic acid methyl ester
CAS: 625115-55-1
Molecular Formula: C20H19FN8O2
Riociguat - Names and Identifiers
Riociguat - Physico-chemical Properties
| Molecular Formula | C20H19FN8O2 |
| Molar Mass | 422.42 |
| Density | 1.51 |
| Melting Point | 247-251°C (dec.) |
| Boling Point | 567.2±50.0 °C(Predicted) |
| Solubility | DMSO |
| Appearance | Solid |
| Color | Off-White to Orange |
| pKa | 1.51±0.50(Predicted) |
| Storage Condition | Refrigerator |
| In vitro study | The concentration-dependent stimulation of recombinant sGC from 0.1 to 100 μm by BAY 63-2521 exhibited a 2-to 73-fold effect by a NO-independent but heme-dependent mechanism. Riociguat inhibits platelet function in washed platelets without affecting platelet function in whole blood, and has no direct effect on the contraction and relaxation of cardiomyocytes. |
| In vivo study | In chronically treated hypoxic mice and MTC-injected rats, Riociguat (10 mg/kg/d, p.o.) partial reversal of pulmonary hypertension, right ventricular hypertrophy, and structural remodeling of the pulmonary vasculature. |
Riociguat - Preparation solution concentration reference
| 1mg | 5mg | 10mg | |
|---|---|---|---|
| 1 mM | 2.367 ml | 11.837 ml | 23.673 ml |
| 5 mM | 0.473 ml | 2.367 ml | 4.735 ml |
| 10 mM | 0.237 ml | 1.184 ml | 2.367 ml |
| 5 mM | 0.047 ml | 0.237 ml | 0.473 ml |
Last Update：2024-01-02 23:10:35
Riociguat - Reference Information
| Introduction | riociguat is a soluble guanylate cyclase activator developed by Bayer, it can significantly improve the patient's exercise tolerance, hemodynamic parameters, cardiac function, prolong the time to clinical deterioration (PATENT Study), and can also effectively treat CTEPH(CHEST study). On Oct 8, 2013, the US FDA approved the use of roxobin for the treatment of Chronic Thromboembolic Pulmonary Hypertension and Pulmonary Hypertension. Currently, it has not been listed in China and is sold in the United States by the Haoeyou Pharmacy, a subsidiary of California Health com Group, as the market is in its infancy, sales growth is slower. |
| pharmacological action | liosiguar is an important signal transduction enzyme, which can be treated by nitric oxide (NO). Activation catalyzes the conversion of guanosine triphosphate (GTP) to the second messenger cyclic guanosine phosphate (cGMP). Soluble guanylate cyclase is the only known NO receptor. NO-sGC-cGMP damage to signaling pathways is thought to be responsible for cardiovascular, pulmonary, endothelial, renal and hepatic diseases. NO synthesis in patients with pulmonary hypertension is insufficient. Although NO donor drugs are effective, but the half-life is short. riociguat can directly activate sGC, and can also stably bind NO-sGC, thus up-regulating the second messenger cGMP. |
| clinical evaluation | in the clinical trial, 261 patients with chronic thromboembolic pulmonary hypertension (CTEPH) were divided into two groups: the primary clinical endpoint was the six-minute walk distance (6MWD), with a mean 6MWD increase of 46 meters in the riociguat group compared with the placebo group after 16 weeks of treatment. The 443 PAH patients were divided into riociguat and placebo groups, and after 12 weeks of treatment, the riociguat group had an average 6MWD increase of 36 m compared to the placebo group. The black box warning suggests that the drug is embryotoxic and is contraindicated in pregnant patients. The approval of Adempas was based on two global Phase III studies, CHEST-1 and PATENT-1, which were published in the New England Journal of Medicine on 25 July, 2013;369:330-40; 2013;369:319-29). Sales of the drug are expected to reach $0.679 billion in, according to an analysis released by Thomson Reuters, and will also be available to the Swiss companies bosentan,Tracleer and Gilead. The drug ambelisentan (Letairis, amborisentan) poses a potential threat. |
| synthesis method | the key to the synthesis of liosi is the synthesis of three heterocycles. Compounds 1 and 2 directly close the pyrazole ring to obtain 3,3 and 4 and then close the pyridine ring to obtain the ethyl ester on 5,5 is amidated by ammonia gas and then dehydrated with trifluoroacetic anhydride to obtain a cyano group, the latter was treated with sodium methoxide and ammonium chloride to give amidine 6. The two nitrogen atoms on amidine 6 act as a nucleophile, and the two cyano groups in compound 7 act as an electrophile to directly close the pyrimidine ring to give 8. In 8, the 5-position amino group of pyrimidine has strong nucleophilicity, and is directly reacted with methyl chloroformate and then methylated to obtain liomicai. Figure 1 is a schematic diagram of the chemical reaction of the man-made rioxisopipe. |
| patent case | US7173037 (available until 25-Apr -2023),US6743798 (available until 16-Jul -2019). |
| biological activity | Riociguat (BAY 63-2521) is a soluble, for the treatment of pulmonary hypertension. |
| Target | Value |
Last Update：2024-04-09 21:01:54
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