Dapagliflozin diproline

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C21H25ClO6.2C5H9NO2
Molecular Weight	639.134
Optical Activity	UNSPECIFIED
Defined Stereocenters	7 / 7
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

OC(=O)[C@@H]1CCCN1.OC(=O)[C@@H]2CCCN2.CCOC3=CC=C(CC4=C(Cl)C=CC(=C4)[C@@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O)C=C3

InChI

InChIKey=SAKQQYWVEGDWOE-UFLUWJSBSA-N

InChI=1S/C21H25ClO6.2C5H9NO2/c1-2-27-15-6-3-12(4-7-15)9-14-10-13(5-8-16(14)22)21-20(26)19(25)18(24)17(11-23)28-21;2*7-5(8)4-2-1-3-6-4/h3-8,10,17-21,23-26H,2,9,11H2,1H3;2*4,6H,1-3H2,(H,7,8)/t17-,18-,19+,20-,21+;2*4-/m100/s1

HIDE SMILES / InChI

Molecular Formula	C21H25ClO6
Molecular Weight	408.873
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	5 / 5
E/Z Centers	0
Optical Activity	UNSPECIFIED

Molecular Formula	C5H9NO2
Molecular Weight	115.1305
Charge	0
Count	MOL RATIO 2 MOL RATIO (average)

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description

Dapagliflozin (trade name Farxiga in the U.S. and Forxiga in the EU and Russia) is a drug of the gliflozin class, developed by Bristol-Myers Squibb in partnership with AstraZeneca. Farxiga is a sodium-glucose cotransporter 2 (SGLT2) inhibitor indicated as an adjunct to diet and exercise to improve glycemic control in adults with type 2 diabetes mellitus.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Sodium/glucose cotransporter 2	Inhibitor		1.16 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Type 2 diabetes mellitus	Primary		Approved	FARXIGA

C_max

Value	Dose	Analyte	Population
118 ng/mL	10 mg single, oral	DAPAGLIFLOZIN plasma	Homo sapiens
154 ng/mL	10 mg single, oral	DAPAGLIFLOZIN 3-O-GLUCURONIDE plasma	Homo sapiens
24.8 ng/mL	2.5 mg single, oral	DAPAGLIFLOZIN plasma	Homo sapiens
24.6 ng/mL	2.5 mg single, oral	DAPAGLIFLOZIN 3-O-GLUCURONIDE plasma	Homo sapiens
48.4 ng/mL	5 mg single, oral	DAPAGLIFLOZIN plasma	Homo sapiens
49 ng/mL	5 mg single, oral	DAPAGLIFLOZIN 3-O-GLUCURONIDE plasma	Homo sapiens
116 ng/mL	10 mg single, oral	DAPAGLIFLOZIN plasma	Homo sapiens
119 ng/mL	10 mg 1 times / day steady-state, oral	DAPAGLIFLOZIN plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
427 ng*h/mL	10 mg single, oral	DAPAGLIFLOZIN plasma	Homo sapiens
418 ng*h/mL	10 mg single, oral	DAPAGLIFLOZIN plasma	Homo sapiens
658 ng*h/mL	10 mg single, oral	DAPAGLIFLOZIN 3-O-GLUCURONIDE plasma	Homo sapiens
612 ng*h/mL	10 mg single, oral	DAPAGLIFLOZIN 3-O-GLUCURONIDE plasma	Homo sapiens
101 ng*h/mL	2.5 mg single, oral	DAPAGLIFLOZIN plasma	Homo sapiens
92.3 ng*h/mL	2.5 mg single, oral	DAPAGLIFLOZIN plasma	Homo sapiens
105 ng*h/mL	2.5 mg single, oral	DAPAGLIFLOZIN 3-O-GLUCURONIDE plasma	Homo sapiens
95.8 ng*h/mL	2.5 mg single, oral	DAPAGLIFLOZIN 3-O-GLUCURONIDE plasma	Homo sapiens
199 ng*h/mL	5 mg single, oral	DAPAGLIFLOZIN plasma	Homo sapiens
189 ng*h/mL	5 mg single, oral	DAPAGLIFLOZIN plasma	Homo sapiens
232 ng*h/mL	5 mg single, oral	DAPAGLIFLOZIN 3-O-GLUCURONIDE plasma	Homo sapiens
208 ng*h/mL	5 mg single, oral	DAPAGLIFLOZIN 3-O-GLUCURONIDE plasma	Homo sapiens
368 ng × h/mL	10 mg single, oral	DAPAGLIFLOZIN plasma	Homo sapiens
506 ng × h/mL	10 mg 1 times / day steady-state, oral	DAPAGLIFLOZIN plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
3 h	10 mg single, oral		DAPAGLIFLOZIN plasma	Homo sapiens
15.77 h	10 mg 1 times / day steady-state, oral		DAPAGLIFLOZIN plasma	Homo sapiens

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor substrate	inhibitor substrate	inhibitor substrate

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP CYP1A2 CYP2A6 CYP2B6 CYP2C19 CYP2C8 OAT1 OAT3 OATP1B1 OATP1B3 OCT2 P-gp	CYP CYP1A1 CYP1A2 CYP2A6 CYP2E1 CYP3A5 OAT1 OAT3 OATP1B1 OATP1B3 OCT2 P-gp UGT1A9	CYP1A2 CYP2B6 CYP3A4/5 PXR

Drug as perpetrator

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Target	Modality	Activity
CYP1A2	inhibitor	no [IC50 >45 uM]
CYP2A6	inhibitor	no [IC50 >45 uM]
CYP2B6	inhibitor	no [IC50 >45 uM]
CYP2C19	inhibitor	no [IC50 >45 uM]
CYP2D6	inhibitor	no [IC50 >45 uM]

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Drug as victim

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Target	Modality	Activity	Clinical evidence
CYP	substrate	minor
OAT1	substrate	no
OATP1B1	substrate	no
OATP1B3	substrate	no
OCT2	substrate	no	no (co-administration study)

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
ChEBI	CHEBI:85078	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:85078
ChemicalBook	CB91011730	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB91011730
eMolecules	32278060	https://www.emolecules.com/cgi-bin/more?vid=32278060
MolPort	MolPort-009-682-875	https://www.molport.com/shop/molecule-link/MolPort-009-682-875
Selleck Chemicals	Dapagliflozin	http://www.selleckchem.com/products/Dapagliflozin.html

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PubMed

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Title	Date	PubMed
Dapagliflozin, a novel, selective SGLT2 inhibitor, improved glycemic control over 2 weeks in patients with type 2 diabetes mellitus.	2009 May	19129749
(5-Bromo-2-chloro-phen-yl)(4-ethoxy-phen-yl)methanone.	2009 Nov 14	21578801
Gateways to clinical trials.	2009 Oct	19967103
A novel strategy for the treatment of diabetes mellitus - sodium glucose co-transport inhibitors.	2010 Dec	22558567
Dapagliflozin treatment in patients with different stages of type 2 diabetes mellitus: effects on glycaemic control and body weight.	2010 Jun	20518806

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Patents

Sample Use Guides

In Vivo Use Guide

The recommended starting dose is 5 mg once daily, taken in the morning, with or without food. Dose can be increased to 10 mg once daily in patients tolerating FARXIGA who require additional glycemic control.

Route of Administration: Oral

In Vitro Use Guide

The IC50 values of dapagliflozin for hSGLT2 and hSGLT1 determined using 1-NBDG were 1.86 nM and 880 nM

Substance Class	Chemical
Record UNII	Q54R5GG9QQ
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

Dapagliflozin diproline

Common Name

English

Dapagliflozin L-prolinate

Common Name

English

Dapagliflozin bis L-proline [WHO-DD]

Common Name

English

Dapagliflozin bis L-proline

Common Name

English

L-Proline, compd. with (1S)-1,5-anhydro-1-C-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-D-glucitol (2:1)

Systematic Name

English

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Code System

Code

Type

Description

FDA UNII

Q54R5GG9QQ

PRIMARY

PUBCHEM

25032144

PRIMARY

CAS

960404-62-0

PRIMARY

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Related Record

Type

Details


					1ULL0QJ8UC

DAPAGLIFLOZIN

PARENT -> SALT/SOLVATE

Amount:


					9DLQ4CIU6V

PROLINE

PARENT -> SALT/SOLVATE

Amount:

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SMILES

InChI

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2

Drug as perpetrator