DAPAGLIFLOZIN PROPANEDIOL ANHYDROUS

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C21H25ClO6.C3H8O2
Molecular Weight	484.967
Optical Activity	UNSPECIFIED
Defined Stereocenters	6 / 6
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of DAPAGLIFLOZIN PROPANEDIOL ANHYDROUS

SMILES

C[C@H](O)CO.CCOC1=CC=C(CC2=C(Cl)C=CC(=C2)[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)C=C1

InChI

InChIKey=VYOCLVRXZCRBML-XMODHJQGSA-N

InChI=1S/C21H25ClO6.C3H8O2/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;1-3(5)2-4/h3-8,10,17-21,23-26H,2,9,11H2,1H3;3-5H,2H2,1H3/t17-,18-,19+,20-,21+;3-/m10/s1

HIDE SMILES / InChI

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 25	Inhibitor 8,504		1.16 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Type 2 diabetes mellitus 262	Primary		Approved 8,583	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 2,252 substrate 1,946	inhibitor 2,438 substrate 1,193	inhibitor 2,507 substrate 1,388

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP 110 CYP1A2 2,153 CYP2A6 879 CYP2B6 926 CYP2C19 2,057 CYP2C8 1,057 OAT1 725 OAT3 747 OATP1B1 1,079 OATP1B3 961 OCT2 779 P-gp 1,741	CYP 303 CYP1A1 389 CYP1A2 1,197 CYP2A6 626 CYP2E1 729 CYP3A5 446 OAT1 395 OAT3 391 OATP1B1 503 OATP1B3 435 OCT2 434 P-gp 2,052 UGT1A9 423	CYP1A2 832 CYP2B6 669 CYP3A4/5 133 PXR 10

Drug as perpetrator

Show entries

Target	Modality	Activity
CYP1A2 2,333	inhibitor 4,027	no [IC50 >45 uM]
CYP2A6 911	inhibitor 4,027	no [IC50 >45 uM]
CYP2B6 1,160	inhibitor 4,027	no [IC50 >45 uM]
CYP2C19 2,141	inhibitor 4,027	no [IC50 >45 uM]
CYP2D6 2,546	inhibitor 4,027	no [IC50 >45 uM]

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Drug as victim

Show entries

Target	Modality	Activity	Clinical evidence
CYP 303	substrate 4,014	minor
OAT1 395	substrate 4,014	no
OATP1B1 503	substrate 4,014	no
OATP1B3 435	substrate 4,014	no
OCT2 434	substrate 4,014	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

Show entries

Title	Date	PubMed
Molecule of the month. Dapagliflozin.	2007 Dec	18301798
Dapagliflozin, a selective SGLT2 inhibitor, improves glucose homeostasis in normal and diabetic rats.	2008 Jun	18356408
Discovery of dapagliflozin: a potent, selective renal sodium-dependent glucose cotransporter 2 (SGLT2) inhibitor for the treatment of type 2 diabetes.	2008 Mar 13	18260618
Inhibition of renal glucose reabsorption: a novel strategy for achieving glucose control in type 2 diabetes mellitus.	2008 Sep	18996802
Gateways to clinical trials.	2009 Dec	20140276

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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

Show entries

Name

Type

Language

(2S,3R,4R,5S,6R)-2-(4-CHLORO-3-(4-ETHOXYBENZYL)PHENYL)-6-(HYDROXYMETHYL)TETRAHYDRO- 2H-PYRAN-3,4,5-TRIOL, (2S)-PROPANE-1,2-DIOL (1:1)

Preferred Name

English

DAPAGLIFLOZIN PROPANEDIOL ANHYDROUS

Common Name

English

D-GLUCITOL, 1,5-ANHYDRO-1-C-(4-CHLORO-3-((4-ETHOXYPHENYL)METHYL)PHENYL)-, (1S)-, COMPD. WITH (2S)-1,2-PROPANEDIOL (1:1)

Common Name

English

DAPAGLIFLOZIN S-PROPYLENE GLYCOL

Common Name

English

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Code System

Code

Type

Description

FDA UNII

4AKF24FA4C

PRIMARY

CAS

1700615-16-2

NON-SPECIFIC STEREOCHEMISTRY

CAS

1971128-01-4

PRIMARY

PUBCHEM

25032145

PRIMARY

SMS_ID

100000172075

PRIMARY

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ACTIVE MOIETY


					1ULL0QJ8UC

Dapagliflozin

SUBSTANCE RECORD


					4AKF24FA4C

DAPAGLIFLOZIN PROPANEDIOL ANHYDROUS

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