Ipragliflozin

Summary

Ipragliflozin (CHEMBL2018096) is an approved small molecule (ATC A10BK05) targeting SLC5A1 and SLC5A2; indicated across 3 conditions including diabetes mellitus and type 1 diabetes mellitus.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• ATC class: A10BK05
• Targets: 2 (SLC5A1, SLC5A2)
• Indications: 3 conditions
• Clinical trials: 27
• Chemistry: 404.5 Da · C21H21FO5S

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL2018096
Name	Ipragliflozin
Type	Small molecule
Max phase	4
FDA approved	no
PubChem CID	10453870
ATC	A10BK05
Molecular formula	C21H21FO5S
Molecular weight	404.5
InChIKey	AHFWIQIYAXSLBA-RQXATKFSSA-N

SMILES: C1=CC=C2C(=C1)C=C(S2)CC3=C(C=CC(=C3)[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)F

IUPAC name: (2S,3R,4R,5S,6R)-2-[3-(1-benzothiophen-2-ylmethyl)-4-fluorophenyl]-6-(hydroxymethyl)oxane-3,4,5-triol

Also known as: ASP-1941, Ipragliflozin, Ipragliflozina, Ipragliflozine, IPRAGLIFLOZIN, ipragliflozin

Patent coverage: 777 distinct patent families (2,101 SureChEMBL compound mentions), from 3 matched compound structure(s). One matched structure accounts for 1,771 (84%) of the total. Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Primary targets (GtoPdb curated mechanism): the Cancer dependency column is the DepMap CRISPR fitness signal (% of screened cell lines dependent on the target).

Gene	Target	Action	pAffinity	Cancer dependency	UniProt
SLC5A1	Sodium/glucose cotransporter 1	Inhibition	5.73	0%	P13866
SLC5A2	Sodium/glucose cotransporter 2	Inhibition	8.13	0.2%	P31639

Broader ChEMBL bioactivity targets: 5 (assay-derived). Sample: Muscarinic acetylcholine receptor M1, Alpha-1A adrenergic receptor, Sodium-dependent dopamine transporter, Sodium/glucose cotransporter 2, Sodium/glucose cotransporter 1.

Bioactivity

ChEMBL activities: 8 potent at pChembl ≥ 5 of 10 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
SLC5A2	8.13	IC50	7.4	nM	CHEMBL_ACT_10857446
SLC5A2	8.13	IC50	7.4	nM	CHEMBL_ACT_18728724
SLC5A2	8.13	IC50	7.38	nM	CHEMBL_ACT_19001167
SLC5A2	8.13	EC50	7.4	nM	CHEMBL_ACT_19005394
SLC5A2	8.08	IC50	8.4	nM	CHEMBL_ACT_18665718
SLC5A1	5.73	IC50	1876	nM	CHEMBL_ACT_19001158
SLC5A1	5.72	EC50	1900	nM	CHEMBL_ACT_19005393
SLC6A3	5.11	AC50	7690	nM	CHEMBL_ACT_25124869

Target pathways

Aggregated over 2 target gene(s): SLC5A1, SLC5A2.

Top Reactome pathways

11 total, by targets touching each:

Pathway	Targets	Genes
Disease	2	SLC5A1, SLC5A2
Cellular hexose transport	2	SLC5A1, SLC5A2
Transport of small molecules	2	SLC5A1, SLC5A2
SLC-mediated transmembrane transport	2	SLC5A1, SLC5A2
SLC transporter disorders	2	SLC5A1, SLC5A2
Disorders of transmembrane transporters	2	SLC5A1, SLC5A2
Defective SLC5A1 causes congenital glucose/galactose malabsorption (GGM)	1	SLC5A1
Defective SLC5A2 causes renal glucosuria (GLYS1)	1	SLC5A2
Intestinal absorption	1	SLC5A1
Digestion and absorption	1	SLC5A1
Intestinal hexose absorption	1	SLC5A1

Dominant GO biological processes

GO term	Targets
alpha-glucoside transport	2
sodium ion transport	2
renal D-glucose absorption	2
D-glucose import across plasma membrane	2
sodium ion import across plasma membrane	2
D-glucose transmembrane transport	2
monoatomic ion transport	2
transmembrane transport	2
intestinal D-glucose absorption	1
pentose transmembrane transport	1
fucose transmembrane transport	1
galactose transmembrane transport	1
myo-inositol transport	1
transepithelial water transport	1
intestinal hexose absorption	1

Indications & clinical

Indications

3 indications (1 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

Indication	Trial phase	MONDO	EFO
diabetes mellitus	4	MONDO:0005015	EFO:0000400
type 1 diabetes mellitus	3	MONDO:0005147	MONDO:0005147
type 2 diabetes mellitus	3	MONDO:0005148	MONDO:0005148

Clinical trials

Total trials: 27.

Phase distribution

Phase	Trials
PHASE3	14
PHASE4	6
PHASE2	3
PHASE1	2
Not specified	2

Top trials by phase / activity

NCT	Phase	Status	Title
NCT02175784	PHASE4	COMPLETED	A Study to Assess the Efficacy and Safety of Ipragliflozin in Combination With Insulin in Subjects With Type 2 Diabetes Mellitus
NCT02291874	PHASE4	COMPLETED	Post-Marketing Study to Evaluate the Long-term Safety, Tolerability, and Efficacy of Ipragliflozin in Combination With GLP-1 Receptor Agonists in Japanese Patients With Type 2 Diabetes Mellitus (T2DM)
NCT02791035	PHASE4	COMPLETED	Correlation Between Change of HbA1c, Urinary Glucose Excretion and Other Factors in Patients Treated With Ipragliflozin
NCT02847091	PHASE4	COMPLETED	Study of Ipragliflozin in Patients With Type 2 Diabetes Mellitus Receiving Insulin Therapy
NCT02875821	PHASE4	COMPLETED	Effects of Ipragliflozin on Excessive Fat in Type 2 Diabetes Patients With Non-alcoholic Fatty Liver Disease Treated With Metformin and Pioglitazone
NCT03118713	PHASE4	TERMINATED	A Study to Evaluate the Renal Protective Effect (Urine Albumin-to-Creatinine Ratio (UACR)), Efficacy and Safety of Ipragliflozin in Type 2 Diabetes Mellitus Patients With Albuminuria
NCT01054092	PHASE3	COMPLETED	A Study to Assess the Long-term Safety and Efficacy of ASP1941 in Japanese Diabetic Patients
NCT01057628	PHASE3	COMPLETED	A Study to Assess the Efficacy and Safety of ASP1941 in Japanese Type 2 Diabetes Patients
NCT01135433	PHASE3	COMPLETED	A Study to Assess the Efficacy and Safety of ASP1941 in Combination With Metformin in Type 2 Diabetic Patients
NCT01225081	PHASE3	COMPLETED	A Study to Assess the Efficacy and Safety of ASP1941 in Combination With Pioglitazone in Type 2 Diabetic Patients
NCT01242202	PHASE3	COMPLETED	A Study to Assess the Safety and Efficacy of ASP1941 in Combination With α-glucosidase Inhibitor in Type 2 Diabetic Patients
NCT01242215	PHASE3	COMPLETED	A Study to Assess the Efficacy and Safety of ASP1941 in Combination With Sulfonylurea in Type 2 Diabetic Patients
NCT01242228	PHASE3	COMPLETED	A Study to Assess the Safety and Efficacy of ASP1941 in Combination With Dipeptidyl Peptidase-4 (DPP-4) Inhibitor in Type 2 Diabetic Patients
NCT01316107	PHASE3	COMPLETED	A Study to Assess Safety and Efficacy of ASP1941 in Combination With Nateglinide in Type 2 Diabetic Patients
NCT01672762	PHASE3	COMPLETED	A Study to Evaluate Long-term Safety and Efficacy of ASP1941 in Diabetes Patients
NCT02564211	PHASE3	COMPLETED	Ipragliflozin Add-on Long-term Study in Japanese Participants With Type 2 Diabetes Mellitus on Sitagliptin (MK-0431J-849)
NCT02577003	PHASE3	COMPLETED	Double-blind Ipragliflozin Add-on Study in Japanese Participants With Type 2 Diabetes Mellitus Who Have Inadequate Glycemic Control on Sitagliptin (MK-0431J-843)
NCT02577016	PHASE3	COMPLETED	Double-blind Sitagliptin Add-on Study in Japanese Participants With Type 2 Diabetes Mellitus Who Have Inadequate Glycemic Control on Ipragliflozin (MK-0431J-842)
NCT02897219	PHASE3	COMPLETED	A Study of ASP1941 in Combination With Insulin in Patients With Type 1 Diabetes Mellitus
NCT03076112	PHASE3	COMPLETED	Efficacy of Ipragliflozin Compared With Sitagliptin in Uncontrolled Type 2 Diabetes With Sulfonylurea and Metformin
NCT00621868	PHASE2	COMPLETED	A Study of ASP1941 in Participants With Type 2 Diabetes Mellitus
NCT01071850	PHASE2	COMPLETED	A Study to Evaluate the Effect of ASP1941 in Adult Patients With Type 2 Diabetes Mellitus
NCT01117584	PHASE2	COMPLETED	A Study to Evaluate the Effect of ASP1941 in Combination With Metformin in Adult Patients With Type 2 Diabetes Mellitus
NCT01611415	PHASE1	COMPLETED	Drug to Drug Interaction Study With Ipragliflozin and Furosemide
NCT01611428	PHASE1	COMPLETED	Absolute Bioavailability Study With Ipragliflozin
NCT02317484	Not specified	COMPLETED	Investigation for Clinical Efficacy and Safety of Ipragliflozin 50mg and 100mg on Type II Diabetes
NCT02479399	Not specified	COMPLETED	Specified Drug Use Results Survey of Ipragliflozin Treatment in type2 Diabetes Patients

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No PharmGKB pharmacogenomic data curated for this drug.

Related molecules

Related molecules

Molecules sharing ≥1 of this drug’s curated primary targets, merged from two biobtree sources and ranked by shared-target count, then clinical phase: ChEMBL clinical-stage candidates (development phase ≥2) and PubChem drug-class bioactivity (approved / known drugs acting on the target). Deduplicated by drug name; the drug’s own salt forms are excluded. Note: for a drug with few primary targets a shared-target match can reflect off-target / promiscuous binding rather than the same therapeutic mechanism — the phase ordering surfaces bona-fide therapeutics first.

16 molecules share ≥1 primary target. Top 16 by shared-target count:

Molecule	Source	Status	Shared targets
BEXAGLIFLOZIN	ChEMBL + PubChem	Phase 4 (approved)	SLC5A1, SLC5A2
Canagliflozin	ChEMBL + PubChem	Phase 4 (approved)	SLC5A1, SLC5A2
EMPAGLIFLOZIN	ChEMBL + PubChem	Phase 4 (approved)	SLC5A1, SLC5A2
ERTUGLIFLOZIN	ChEMBL + PubChem	Phase 4 (approved)	SLC5A1, SLC5A2
SOTAGLIFLOZIN	ChEMBL + PubChem	Phase 4 (approved)	SLC5A1, SLC5A2
DAPAGLIFLOZIN	ChEMBL	Phase 4 (approved)	SLC5A1, SLC5A2
TOFOGLIFLOZIN	ChEMBL	Phase 4 (approved)	SLC5A1, SLC5A2
ENAVOGLIFLOZIN	ChEMBL	Phase 3	SLC5A1, SLC5A2
HENAGLIFLOZIN	ChEMBL	Phase 3	SLC5A1, SLC5A2
LICOGLIFLOZIN	ChEMBL	Phase 2	SLC5A1, SLC5A2
LUSEOGLIFLOZIN	ChEMBL	Phase 2	SLC5A1, SLC5A2
REMOGLIFLOZIN ETABONATE	ChEMBL	Phase 2	SLC5A1, SLC5A2
SERGLIFLOZIN ETABONATE	ChEMBL	Phase 2	SLC5A1, SLC5A2
MIZAGLIFLOZIN	ChEMBL	Phase 2	SLC5A1
YM-543 FREE ACID	ChEMBL	Phase 2	SLC5A2
Phlorizin	PubChem	Approved	SLC5A1