Avenciguat

Avenciguat
Clinical data
Other names	BI 685509
Legal status
Legal status	Investigational;
Identifiers
	IUPAC name 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;
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;
	SMILES CCOC1=C(C=NN1C2=CC=CC(=N2)C3=CC=CC(=C3OCC4=C(C5=C(CN(CC5)C6CCOCC6)C=C4)C)C)C(=O)O;
	InChI InChI=1S/C34H38N4O5/c1-4-42-33-29(34(39)40)19-35-38(33)31-10-6-9-30(36-31)28-8-5-7-22(2)32(28)43-21-25-12-11-24-20-37(16-13-27(24)23(25)3)26-14-17-41-18-15-26/h5-12,19,26H,4,13-18,20-21H2,1-3H3,(H,39,40); Key:KWNFFNFBUMFTHK-UHFFFAOYSA-N;

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]

References

^ 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.

[1] 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.

[2] 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.

[3] 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.

[4] 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.

[5] 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.

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