Mizagliflozin

Mizagliflozin
Legal status
Legal status	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 data
Formula	C28H44N4O8
Molar mass	564.680 g·mol−1
3D 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 SGLT1 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.

[1] 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.

[2] 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.

[3] 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.

[4] 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.

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[2]

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Legal status

Legal status	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 data
Formula	C₂₈H₄₄N₄O₈
Molar mass	564.680 g·mol⁻¹
3D 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