IPRAGLIFLOZIN L-PROLINE

Possibly Marketed Outside US

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C21H21FO5S.C5H9NO2
Molecular Weight	519.582
Optical Activity	UNSPECIFIED
Defined Stereocenters	6 / 6
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

OC(=O)[C@@H]1CCCN1.OC[C@H]2O[C@H]([C@H](O)[C@@H](O)[C@@H]2O)C3=CC=C(F)C(CC4=CC5=C(S4)C=CC=C5)=C3

InChI

InChIKey=TUVGWWULBZIUBS-FVYIYGEMSA-N

InChI=1S/C21H21FO5S.C5H9NO2/c22-15-6-5-12(21-20(26)19(25)18(24)16(10-23)27-21)7-13(15)9-14-8-11-3-1-2-4-17(11)28-14;7-5(8)4-2-1-3-6-4/h1-8,16,18-21,23-26H,9-10H2;4,6H,1-3H2,(H,7,8)/t16-,18-,19+,20-,21+;4-/m10/s1

HIDE SMILES / InChI

Description

Ipragliflozin L-proline is a sodium-glucose cotransporter 2 (SGLT2) inhibitor. It was developed and marketed as Suglat® by Astellas cooperating with Kotobuki Pharmaceutical and Merck Sharp & Dohme, and approved by Pharmaceuticals and Medical Devices Agency of Japan (PMDA) on Jan 17, 2014. It is indicated for the treatment of type 2 diabetes.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Sodium/glucose cotransporter 2 25	Inhibitor 8,297		7.38 nM [IC50]
Sodium/glucose cotransporter 2 25	Inhibitor 8,297		7.38 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Type 2 diabetes mellitus 259
Type 2 diabetes mellitus 259	Primary		Approved 8,429	SUGLAT

C_max

Value	Dose	Analyte	Population
17.89 ng/mL	1 mg single, oral	IPRAGLIFLOZIN plasma	Homo sapiens
53.72 ng/mL	3 mg single, oral	IPRAGLIFLOZIN plasma	Homo sapiens
174.34 ng/mL	10 mg single, oral	IPRAGLIFLOZIN plasma	Homo sapiens
523.63 ng/mL	30 mg single, oral	IPRAGLIFLOZIN plasma	Homo sapiens
1392.39 ng/mL	100 mg single, oral	IPRAGLIFLOZIN plasma	Homo sapiens
3421.41 ng/mL	300 mg single, oral	IPRAGLIFLOZIN plasma	Homo sapiens
398.05 ng/mL	20 mg 1 times / day steady-state, oral	IPRAGLIFLOZIN plasma	Homo sapiens
975.53 ng/mL	50 mg 1 times / day steady-state, oral	IPRAGLIFLOZIN plasma	Homo sapiens
1731.61 ng/mL	100 mg 1 times / day steady-state, oral	IPRAGLIFLOZIN plasma	Homo sapiens
1174.67 ng/mL	50 mg single, oral	IPRAGLIFLOZIN plasma	Homo sapiens
1464.17 ng/mL	50 mg single, oral	IPRAGLIFLOZIN plasma	Homo sapiens
976.32 ng/mL	50 mg single, oral	IPRAGLIFLOZIN plasma	Homo sapiens
1260.674 ng/mL	100 mg 1 times / day multiple, oral	IPRAGLIFLOZIN plasma	Homo sapiens
1690.752 ng/mL	100 mg 1 times / day multiple, oral	IPRAGLIFLOZIN plasma	Homo sapiens
1491.293 ng/mL	100 mg 1 times / day multiple, oral	IPRAGLIFLOZIN plasma	Homo sapiens
1975.718 ng/mL	100 mg 1 times / day multiple, oral	IPRAGLIFLOZIN plasma	Homo sapiens
1592.925 ng/mL	100 mg 1 times / day steady-state, oral	IPRAGLIFLOZIN plasma	Homo sapiens
1676.536 ng/mL	100 mg 1 times / day steady-state, oral	IPRAGLIFLOZIN plasma	Homo sapiens
1584.996 ng/mL	100 mg 1 times / day steady-state, oral	IPRAGLIFLOZIN plasma	Homo sapiens
2124.083 ng/mL	100 mg 1 times / day steady-state, oral	IPRAGLIFLOZIN plasma	Homo sapiens
1044.74 mg/mL	50 mg single, oral	IPRAGLIFLOZIN plasma	Homo sapiens
1088.77 mg/mL	50 mg single, oral	IPRAGLIFLOZIN plasma	Homo sapiens
1160.97 mg/mL	50 mg single, oral	IPRAGLIFLOZIN plasma	Homo sapiens
1277.19 ng/mL	100 mg single, oral	IPRAGLIFLOZIN plasma	Homo sapiens
1456.05 ng/mL	100 mg single, oral	IPRAGLIFLOZIN plasma	Homo sapiens
1625.63 ng/mL	100 mg single, oral	IPRAGLIFLOZIN plasma	Homo sapiens
1448.14 ng/mL	100 mg single, oral	IPRAGLIFLOZIN plasma	Homo sapiens
1576.08 ng/mL	100 mg single, oral	IPRAGLIFLOZIN plasma	Homo sapiens
1397.58 ng/mL	100 mg single, oral	IPRAGLIFLOZIN plasma	Homo sapiens
1761.06 ng/mL	100 mg single, oral	IPRAGLIFLOZIN plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
58.94 ng × h/mL	1 mg single, oral	IPRAGLIFLOZIN plasma	Homo sapiens
244.64 ng × h/mL	3 mg single, oral	IPRAGLIFLOZIN plasma	Homo sapiens
855.06 ng × h/mL	10 mg single, oral	IPRAGLIFLOZIN plasma	Homo sapiens
2895.83 ng × h/mL	30 mg single, oral	IPRAGLIFLOZIN plasma	Homo sapiens
9696.47 ng × h/mL	100 mg single, oral	IPRAGLIFLOZIN plasma	Homo sapiens
27298.54 ng × h/mL	300 mg single, oral	IPRAGLIFLOZIN plasma	Homo sapiens
1894.04 ng × h/mL	20 mg 1 times / day steady-state, oral	IPRAGLIFLOZIN plasma	Homo sapiens
4693.11 ng × h/mL	50 mg 1 times / day steady-state, oral	IPRAGLIFLOZIN plasma	Homo sapiens
9113.99 ng × h/mL	100 mg 1 times / day steady-state, oral	IPRAGLIFLOZIN plasma	Homo sapiens
5238.53 ng × h/mL	50 mg single, oral	IPRAGLIFLOZIN plasma	Homo sapiens
5490.74 ng × h/mL	50 mg single, oral	IPRAGLIFLOZIN plasma	Homo sapiens
5291.35 ng × h/mL	50 mg single, oral	IPRAGLIFLOZIN plasma	Homo sapiens
8519.799 ng × h/mL	100 mg 1 times / day multiple, oral	IPRAGLIFLOZIN plasma	Homo sapiens
9844.079 ng × h/mL	100 mg 1 times / day multiple, oral	IPRAGLIFLOZIN plasma	Homo sapiens
10325.042 ng × h/mL	100 mg 1 times / day multiple, oral	IPRAGLIFLOZIN plasma	Homo sapiens
13772.018 ng × h/mL	100 mg 1 times / day multiple, oral	IPRAGLIFLOZIN plasma	Homo sapiens
8231.224 ng × h/mL	100 mg 1 times / day steady-state, oral	IPRAGLIFLOZIN plasma	Homo sapiens
9582.693 ng × h/mL	100 mg 1 times / day steady-state, oral	IPRAGLIFLOZIN plasma	Homo sapiens
10050.118 ng × h/mL	100 mg 1 times / day steady-state, oral	IPRAGLIFLOZIN plasma	Homo sapiens
14027.041 ng × h/mL	100 mg 1 times / day steady-state, oral	IPRAGLIFLOZIN plasma	Homo sapiens
4821.35 ng × h/mL	50 mg single, oral	IPRAGLIFLOZIN plasma	Homo sapiens
4482.28 ng × h/mL	50 mg single, oral	IPRAGLIFLOZIN plasma	Homo sapiens
5947.6 ng × h/mL	50 mg single, oral	IPRAGLIFLOZIN plasma	Homo sapiens
7325.78 ng × h/mL	100 mg single, oral	IPRAGLIFLOZIN plasma	Homo sapiens
8240.8 ng × h/mL	100 mg single, oral	IPRAGLIFLOZIN plasma	Homo sapiens
10506.14 ng × h/mL	100 mg single, oral	IPRAGLIFLOZIN plasma	Homo sapiens
12103.73 ng × h/mL	100 mg single, oral	IPRAGLIFLOZIN plasma	Homo sapiens
12687.14 ng × h/mL	100 mg single, oral	IPRAGLIFLOZIN plasma	Homo sapiens
9103.55 ng × h/mL	100 mg single, oral	IPRAGLIFLOZIN plasma	Homo sapiens
11814.32 ng × h/mL	100 mg single, oral	IPRAGLIFLOZIN plasma	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
4.35 h	1 mg single, oral	IPRAGLIFLOZIN plasma	Homo sapiens
10.01 h	3 mg single, oral	IPRAGLIFLOZIN plasma	Homo sapiens
13.34 h	10 mg single, oral	IPRAGLIFLOZIN plasma	Homo sapiens
12.43 h	30 mg single, oral	IPRAGLIFLOZIN plasma	Homo sapiens
11.71 h	100 mg single, oral	IPRAGLIFLOZIN plasma	Homo sapiens
10.34 h	300 mg single, oral	IPRAGLIFLOZIN plasma	Homo sapiens
13.93 h	20 mg 1 times / day steady-state, oral	IPRAGLIFLOZIN plasma	Homo sapiens
11.24 h	50 mg 1 times / day steady-state, oral	IPRAGLIFLOZIN plasma	Homo sapiens
15.36 h	100 mg 1 times / day steady-state, oral	IPRAGLIFLOZIN plasma	Homo sapiens
13.67 h	50 mg single, oral	IPRAGLIFLOZIN plasma	Homo sapiens
16.9 h	50 mg single, oral	IPRAGLIFLOZIN plasma	Homo sapiens
17 h	50 mg single, oral	IPRAGLIFLOZIN plasma	Homo sapiens
15.046 h	100 mg 1 times / day multiple, oral	IPRAGLIFLOZIN plasma	Homo sapiens
17.93 h	100 mg 1 times / day multiple, oral	IPRAGLIFLOZIN plasma	Homo sapiens
15.234 h	100 mg 1 times / day multiple, oral	IPRAGLIFLOZIN plasma	Homo sapiens
15.568 h	100 mg 1 times / day multiple, oral	IPRAGLIFLOZIN plasma	Homo sapiens
16.717 h	100 mg 1 times / day steady-state, oral	IPRAGLIFLOZIN plasma	Homo sapiens
23.654 h	100 mg 1 times / day steady-state, oral	IPRAGLIFLOZIN plasma	Homo sapiens
16.798 h	100 mg 1 times / day steady-state, oral	IPRAGLIFLOZIN plasma	Homo sapiens
20.292 h	100 mg 1 times / day steady-state, oral	IPRAGLIFLOZIN plasma	Homo sapiens
14.97 h	50 mg single, oral	IPRAGLIFLOZIN plasma	Homo sapiens
15.37 h	50 mg single, oral	IPRAGLIFLOZIN plasma	Homo sapiens
17.08 h	50 mg single, oral	IPRAGLIFLOZIN plasma	Homo sapiens
15.18 h	100 mg single, oral	IPRAGLIFLOZIN plasma	Homo sapiens
19.16 h	100 mg single, oral	IPRAGLIFLOZIN plasma	Homo sapiens
20.56 h	100 mg single, oral	IPRAGLIFLOZIN plasma	Homo sapiens
20.76 h	100 mg single, oral	IPRAGLIFLOZIN plasma	Homo sapiens
21.22 h	100 mg single, oral	IPRAGLIFLOZIN plasma	Homo sapiens
16.18 h	100 mg single, oral	IPRAGLIFLOZIN plasma	Homo sapiens
15.78 h	100 mg single, oral	IPRAGLIFLOZIN plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
3.5%			IPRAGLIFLOZIN plasma	Homo sapiens

PubMed

Show entries

Title	Date	PubMed
Safety, pharmacokinetic, and pharmacodynamic profiles of ipragliflozin (ASP1941), a novel and selective inhibitor of sodium-dependent glucose co-transporter 2, in patients with type 2 diabetes mellitus.	2011 Dec	21854192
Effect of Ipragliflozin (ASP1941), a novel selective sodium-dependent glucose co-transporter 2 inhibitor, on urinary glucose excretion in healthy subjects.	2011 Dec 1	21877761
Inhibition of the sodium glucose co-transporter-2: its beneficial action and potential combination therapy for type 2 diabetes mellitus.	2013 May	23331516
Active- and placebo-controlled dose-finding study to assess the efficacy, safety, and tolerability of multiple doses of ipragliflozin in patients with type 2 diabetes mellitus.	2013 May-Jun	23276620

Showing 1 to 4 of 4 entries

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Patents

Sample Use Guides

In Vivo Use Guide

The usual adult dosage is 50 mg of ipragliflozin orally administered once daily before or after breakfast. The dose may be increased up to 100 mg once daily with careful monitoring of the patient’s clinical course in the case of inadequate efficacy.

Route of Administration: Oral

In Vitro Use Guide

The inhibitory effect of ipragliflozin on SGLT2 and SGLT1 as measured by sodiumdependent 14C-methyl-α-D-glucopyranoside (14C-AMG) uptake was evaluated in human SGLT2- or SGLT1-expressing CHO cells. As a result, IC50 values were 7.38 and 1880 nmol/L, respectively.

Show entries

Name

Type

Language

IPRAGLIFLOZIN L-PROLINE

Common Name

English

IPRAGLIFLOZIN L-PROLINE [JAN]

Common Name

English

Ipragliflozin l-proline [WHO-DD]

Common Name

English

L-PROLINE, COMPD. WITH (1S)-1,5-ANHYDRO-1-C-(3-(BENZO(B)THIEN-2-YLMETHYL)-4-FLUOROPHENYL)-D-GLUCITOL (1:1)

Common Name

English

IPRAGLIFLOZIN L-PROLINE [MI]

Common Name

English

Showing 1 to 5 of 5 entries

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Show entries

Code System

Code

Type

Description

EPA CompTox

DTXSID20241771

PRIMARY

MERCK INDEX

m11865

PRIMARY

SMS_ID

100000166620

PRIMARY

FDA UNII

M6N3GK48A4

PRIMARY

CAS

951382-34-6

PRIMARY

Showing 1 to 5 of 7 entries

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PARENT (SALT/SOLVATE)


					3N2N8OOR7X

IPRAGLIFLOZIN

PARENT (SALT/SOLVATE)


					9DLQ4CIU6V

PROLINE

SUBSTANCE RECORD


					M6N3GK48A4

IPRAGLIFLOZIN L-PROLINE

SMILES

InChI

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Funbound

PubMed

Patents

Sample Use Guides

C_max

T_1/2

F_unbound