Balcinrenone

Balcinrenone
Clinical data
Other names	AZD9977; AZD-9977
Legal status
Legal status	Investigational;
Identifiers
	IUPAC name 2-[(3S)-7-Fluoro-4-(3-oxo-4H-1,4-benzoxazine-6-carbonyl)-2,3-dihydro-1,4-benzoxazin-3-yl]-N-methylacetamide;
CAS Number	1850385-64-6;
PubChem CID	118599727;
DrugBank	DB15418;
ChemSpider	75531296;
UNII	6C9UKZ0CYE;
KEGG	D13184;
ChEMBL	ChEMBL3916929;
Chemical and physical data
Formula	C20H18FN3O5
Molar mass	399.378 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CNC(=O)C[C@H]1COC2=C(N1C(=O)C3=CC4=C(C=C3)OCC(=O)N4)C=CC(=C2)F;
	InChI InChI=1S/C20H18FN3O5/c1-22-18(25)8-13-9-28-17-7-12(21)3-4-15(17)24(13)20(27)11-2-5-16-14(6-11)23-19(26)10-29-16/h2-7,13H,8-10H2,1H3,(H,22,25)(H,23,26)/t13-/m0/s1; Key:MBKYLPOPYYLTNW-ZDUSSCGKSA-N;

Balcinrenone is an experimental selective mineralocorticoid receptor modulator developed by AstraZeneca for heart failure. Compared to mineralocorticoid receptor antagonists, it is hoped to have less effect on electrolytes and therefore a lower risk of hyperkalemia.^[1]^[2]^[3]^[4]^[5]

References

↑ Bamberg, Krister; Johansson, Ulrika; Edman, Karl; William-Olsson, Lena; Myhre, Susanna; Gunnarsson, Anders; Geschwindner, Stefan; Aagaard, Anna; Björnson Granqvist, Anna; Jaisser, Frédéric; Huang, Yufeng; Granberg, Kenneth L.; Jansson-Löfmark, Rasmus; Hartleib-Geschwindner, Judith (23 February 2018). "Preclinical pharmacology of AZD9977: A novel mineralocorticoid receptor modulator separating organ protection from effects on electrolyte excretion". PLOS ONE. 13 (2) e0193380. Bibcode:2018PLoSO..1393380B. doi:10.1371/journal.pone.0193380. PMC 5825103. PMID 29474466.
↑ Bamberg, Krister; William-Olsson, Lena; Johansson, Ulrika; Jansson-Löfmark, Rasmus; Hartleib-Geschwindner, Judith (January 2019). "The selective mineralocorticoid receptor modulator AZD9977 reveals differences in mineralocorticoid effects of aldosterone and fludrocortisone". Journal of the Renin-Angiotensin-Aldosterone System. 20 (1): 147032031982744. doi:10.1177/1470320319827449. PMC 6396052. PMID 30813831.
↑ Whittaker, Andrew; Kragh, Åsa M.; Hartleib-Geschwindner, Judith; Albayaty, Muna; Backlund, Anna; Greasley, Peter J.; Heijer, Maria; Kjaer, Magnus; Forte, Pablo; Unwin, Robert; Wernevik, Linda; Ericsson, Hans (March 2020). "Safety, Tolerability, and Pharmacokinetics of the Mineralocorticoid Receptor Modulator AZD9977 in Healthy Men: A Phase I Multiple Ascending Dose Study". Clinical and Translational Science. 13 (2): 275–283. doi:10.1111/cts.12705. PMC 7070793. PMID 31584739.
↑ Squire, Iain B.; Gabrielsen, Anders; Greasley, Peter J.; Wernevik, Linda; Hartleib-Geschwindner, Judith; Holden, Julie; Johansson, Susanne; Rudvik, Anna; Sánchez, José; Bamberg, Krister; Melin, Johanna; Whittaker, Andrew (October 2022). "Effect of AZD9977 and spironolactone on serum potassium in heart failure with preserved or mildly reduced ejection fraction, and renal impairment: A randomized trial". Clinical and Translational Science. 15 (10): 2493–2504. doi:10.1111/cts.13377. PMC 9579384. PMID 35971596.
↑ Mallia, Carl J.; Le Bars, Joël; Hardy, Simon; Lamacraft, Alex; Harding, Simon; Hose, David; Snow, Lindsay; Poulten, Rebecca C.; Dobson, Benjamin C.; Churchill, Trevor; Gillespie, Paul M. (20 January 2023). "Control of Hydrogen Fluoride Formation and Release during a Large-Scale Nitroarene Reduction in the Manufacture of AZD9977". Organic Process Research & Development. 27 (1): 167–178. doi:10.1021/acs.oprd.2c00323. S2CID 255262346.

[1] Bamberg, Krister; Johansson, Ulrika; Edman, Karl; William-Olsson, Lena; Myhre, Susanna; Gunnarsson, Anders; Geschwindner, Stefan; Aagaard, Anna; Björnson Granqvist, Anna; Jaisser, Frédéric; Huang, Yufeng; Granberg, Kenneth L.; Jansson-Löfmark, Rasmus; Hartleib-Geschwindner, Judith (23 February 2018). "Preclinical pharmacology of AZD9977: A novel mineralocorticoid receptor modulator separating organ protection from effects on electrolyte excretion". PLOS ONE. 13 (2) e0193380. Bibcode:2018PLoSO..1393380B. doi:10.1371/journal.pone.0193380. PMC 5825103. PMID 29474466.

[2] Bamberg, Krister; William-Olsson, Lena; Johansson, Ulrika; Jansson-Löfmark, Rasmus; Hartleib-Geschwindner, Judith (January 2019). "The selective mineralocorticoid receptor modulator AZD9977 reveals differences in mineralocorticoid effects of aldosterone and fludrocortisone". Journal of the Renin-Angiotensin-Aldosterone System. 20 (1): 147032031982744. doi:10.1177/1470320319827449. PMC 6396052. PMID 30813831.

[3] Whittaker, Andrew; Kragh, Åsa M.; Hartleib-Geschwindner, Judith; Albayaty, Muna; Backlund, Anna; Greasley, Peter J.; Heijer, Maria; Kjaer, Magnus; Forte, Pablo; Unwin, Robert; Wernevik, Linda; Ericsson, Hans (March 2020). "Safety, Tolerability, and Pharmacokinetics of the Mineralocorticoid Receptor Modulator AZD9977 in Healthy Men: A Phase I Multiple Ascending Dose Study". Clinical and Translational Science. 13 (2): 275–283. doi:10.1111/cts.12705. PMC 7070793. PMID 31584739.

[4] Squire, Iain B.; Gabrielsen, Anders; Greasley, Peter J.; Wernevik, Linda; Hartleib-Geschwindner, Judith; Holden, Julie; Johansson, Susanne; Rudvik, Anna; Sánchez, José; Bamberg, Krister; Melin, Johanna; Whittaker, Andrew (October 2022). "Effect of AZD9977 and spironolactone on serum potassium in heart failure with preserved or mildly reduced ejection fraction, and renal impairment: A randomized trial". Clinical and Translational Science. 15 (10): 2493–2504. doi:10.1111/cts.13377. PMC 9579384. PMID 35971596.

[5] Mallia, Carl J.; Le Bars, Joël; Hardy, Simon; Lamacraft, Alex; Harding, Simon; Hose, David; Snow, Lindsay; Poulten, Rebecca C.; Dobson, Benjamin C.; Churchill, Trevor; Gillespie, Paul M. (20 January 2023). "Control of Hydrogen Fluoride Formation and Release during a Large-Scale Nitroarene Reduction in the Manufacture of AZD9977". Organic Process Research & Development. 27 (1): 167–178. doi:10.1021/acs.oprd.2c00323. S2CID 255262346.

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References