Mizagliflozin : Wikipedia, the free encyclopedia

Mizagliflozin

Chemical compound

Investigational

Identifiers

IUPAC name

2,2-dimethyl-3-[3-[3-methyl-4-[[5-propan-2-yl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1H-pyrazol-4-yl]methyl]phenoxy]propylamino]propanamide

CAS Number

666843-10-3

PubChem CID

10460535

ChemSpider

8635948

UNII

1X96A704XV

ChEMBL

ChEMBL5314923

Chemical and physical dataFormulaC₂₈H₄₄N₄O₈Molar mass564.680 g·mol⁻¹3D model (JSmol)

Interactive image

SMILES

CC1=C(C=CC(=C1)OCCCNCC(C)(C)C(=O)N)CC2=C(NN=C2O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)C(C)C

InChI

InChI=1S/C28H44N4O8/c1-15(2)21-19(25(32-31-21)40-26-24(36)23(35)22(34)20(13-33)39-26)12-17-7-8-18(11-16(17)3)38-10-6-9-30-14-28(4,5)27(29)37/h7-8,11,15,20,22-24,26,30,33-36H,6,9-10,12-14H2,1-5H3,(H2,29,37)(H,31,32)/t20-,22-,23+,24-,26+/m1/s1
Key:LREHMKLEOJAVMQ-TXKDOCKMSA-N

Mizagliflozin is an SGLT2 inhibitor developed as a potential treatment for chronic constipation.^[1]^[2] It progressed as far as Phase II trials in humans but was not approved for medical use, however it has since been investigated for other applications.^[3]^[4]

References

^ Inoue T, Takemura M, Fushimi N, Fujimori Y, Onozato T, Kurooka T, et al. (July 2017). "Mizagliflozin, a novel selective SGLT1 inhibitor, exhibits potential in the amelioration of chronic constipation". European Journal of Pharmacology. 806: 25–31. doi:10.1016/j.ejphar.2017.04.010. PMID 28410751.
^ Fukudo S, Endo Y, Hongo M, Nakajima A, Abe T, Kobayashi H, et al. (September 2018). "Safety and efficacy of the sodium-glucose cotransporter 1 inhibitor mizagliflozin for functional constipation: a randomised, placebo-controlled, double-blind phase 2 trial". The Lancet. Gastroenterology & Hepatology. 3 (9): 603–613. doi:10.1016/S2468-1253(18)30165-1. PMID 30056028.
^ Ishida N, Saito M, Sato S, Tezuka Y, Sanbe A, Taira E, et al. (October 2021). "Mizagliflozin, a selective SGLT1 inhibitor, improves vascular cognitive impairment in a mouse model of small vessel disease". Pharmacology Research & Perspectives. 9 (5): e00869. doi:10.1002/prp2.869. PMC 8480397. PMID 34586752.
^ Tsunokake S, Iwabuchi E, Miki Y, Kanai A, Onodera Y, Sasano H, et al. (October 2023). "SGLT1 as an adverse prognostic factor in invasive ductal carcinoma of the breast". Breast Cancer Research and Treatment. 201 (3): 499–513. doi:10.1007/s10549-023-07024-9. PMID 37439959.