Avenciguat, 1579514-06-9
BI-685509, 582.7 g/mol, C34H38N4O5
UNII ZA7KTB4PSP
5-ethoxy-1-[6-[3-methyl-2-[[5-methyl-2-(oxan-4-yl)-3,4-dihydro-1H-isoquinolin-6-yl]methoxy]phenyl]pyridin-2-yl]pyrazole-4-carboxylic acid
Avenciguat (BI-685509) is a potent and orally active sGC activator. Avenciguat restores cyclic guanosine monophosphate (cGMP) and improves functionality of nitric oxide (NO) pathways. Avenciguat can be used in research of chronic kidney disease (CKD) and diabetic kidney disease (DKD).
Avenciguat is under investigation in clinical trial NCT05282121 (A Study to Test Whether BI 685509 Alone or in Combination With Empagliflozin Helps People With Liver Cirrhosis Caused by Viral Hepatitis or Non-alcoholic Steatohepatitis (NASH) Who Have High Blood Pressure in the Portal Vein (Main Vessel Going to the Liver)).
Avenciguat (development name BI 685509) is a soluble guanylate cyclase activator developed by Boehringer Ingelheim for kidney disease,[1][2] and cirrhosis.[3][4][5]
SCHEME
Ref
PAPER
Journal of Pharmacology and Experimental Therapeutics (2023), 384(3), 382-39
PATENT
Boehringer Ingelheim International GmbH
WO2014039434
https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2014039434&_cid=P12-M29UB4-37937-1
PATENT
US20230293513
WO2020011804
| Clinical data | |
|---|---|
| Other names | BI 685509 |
| Legal status | |
| Legal status | Investigational |
| Identifiers | |
| showIUPAC name | |
| CAS Number | 1579514-06-9 |
| PubChem CID | 89992620 |
| UNII | ZA7KTB4PSP |
| Chemical and physical data | |
| Formula | C34H38N4O5 |
| Molar mass | 582.701 g·mol−1 |
| 3D model (JSmol) | Interactive image |
| showSMILES | |
| showInChI | |
^ Cherney, David Z. I.; de Zeeuw, Dick; Heerspink, Hiddo J. L.; Cardona, Jose; Desch, Marc; Wenz, Arne; Schulze, Friedrich; Nangaku, Masaomi (August 2023). “Safety, tolerability, pharmacodynamics and pharmacokinetics of the soluble guanylyl cyclase activator BI 685509 in patients with diabetic kidney disease: A randomized trial”. Diabetes, Obesity and Metabolism. 25 (8): 2218–2226. doi:10.1111/dom.15099. PMID 37232058. S2CID 258909393.
^ Reinhart, Glenn A.; Harrison, Paul C.; Lincoln, Kathleen; Chen, Hongxing; Sun, Peng; Hill, Jon; Qian, Hu Sheng; McHugh, Mark C.; Clifford, Holly; Ng, Khing Jow; Wang, Hong; Fowler, Danielle; Gueneva-Boucheva, Kristina; Brenneman, Jehrod B.; Bosanac, Todd; Wong, Diane; Fryer, Ryan M.; Sarko, Chris; Boustany-Kari, Carine M.; Pullen, Steven S. (March 2023). “The Novel, Clinical-Stage Soluble Guanylate Cyclase Activator BI 685509 Protects from Disease Progression in Models of Renal Injury and Disease”. Journal of Pharmacology and Experimental Therapeutics. 384 (3): 382–392. doi:10.1124/jpet.122.001423. PMID 36507845. S2CID 254387173.
^ Lawitz, Eric J.; Reiberger, Thomas; Schattenberg, Jörn M.; Schoelch, Corinna; Coxson, Harvey O.; Wong, Diane; Ertle, Judith (November 2023). “Safety and pharmacokinetics of BI 685509, a soluble guanylyl cyclase activator, in patients with cirrhosis: A randomized Phase Ib study”. Hepatology Communications. 7 (11). doi:10.1097/HC9.0000000000000276. PMC 10615399. PMID 37889522.
^ Jones, Amanda K.; Chen, Hongxing; Ng, Khing Jow; Villalona, Jorge; McHugh, Mark; Zeveleva, Svetlana; Wilks, James; Brilisauer, Klaus; Bretschneider, Tom; Qian, Hu Sheng; Fryer, Ryan M. (July 2023). “Soluble Guanylyl Cyclase Activator BI 685509 Reduces Portal Hypertension and Portosystemic Shunting in a Rat Thioacetamide-Induced Cirrhosis Model”. Journal of Pharmacology and Experimental Therapeutics. 386 (1): 70–79. doi:10.1124/jpet.122.001532. PMID 37230799. S2CID 258909514.
^ Reiberger, Thomas; Berzigotti, Annalisa; Trebicka, Jonel; Ertle, Judith; Gashaw, Isabella; Swallow, Ros; Tomisser, Andrea (24 April 2023). “The rationale and study design of two phase II trials examining the effects of BI 685509, a soluble guanylyl cyclase activator, on clinically significant portal hypertension in patients with compensated cirrhosis”. Trials. 24 (1): 293. doi:10.1186/s13063-023-07291-3. PMC 10123479. PMID 37095557.
////////////Avenciguat, 1579514-06-9, BI 685509,