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

Structure Search

SMILES

OC(=O)[C@@H]1CCCN1.OC(=O)[C@@H]2CCCN2.CCOC3=CC=C(CC4=CC(=CC=C4Cl)[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

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

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

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/202293s003lbl.pdf | https://www.ncbi.nlm.nih.gov/pubmed/27042132

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 Target ID: CHEMBL3884 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/202293s003lbl.pdf \| https://www.ncbi.nlm.nih.gov/pubmed/23657801	Inhibitor 8504		1.16 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Type 2 diabetes mellitus 262 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/202293s003lbl.pdf	Primary		Approved 8583	FARXIGA Approved Use FARXIGA (dapagliflozin) is indicated as an adjunct to diet and exercise to improve glycemic control in adults with type 2 diabetes mellitus Launch Date 2014

C_max

Value	Dose	Analyte	Population
118 ng/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT01525238	10 mg single, oral dose: 10 mg route of administration: oral experiment type: single co-administered:	DAPAGLIFLOZIN plasma	Homo sapiens population: unhealthy age: Children sex: food status:
154 ng/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT01525238	10 mg single, oral dose: 10 mg route of administration: oral experiment type: single co-administered:	DAPAGLIFLOZIN 3-O-GLUCURONIDE plasma	Homo sapiens population: unhealthy age: Children sex: food status:
24.8 ng/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT01525238	2.5 mg single, oral dose: 2.5 mg route of administration: oral experiment type: single co-administered:	DAPAGLIFLOZIN plasma	Homo sapiens population: unhealthy age: Children sex: food status:
24.6 ng/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT01525238	2.5 mg single, oral dose: 2.5 mg route of administration: oral experiment type: single co-administered:	DAPAGLIFLOZIN 3-O-GLUCURONIDE plasma	Homo sapiens population: unhealthy age: Children sex: food status:
48.4 ng/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT01525238	5 mg single, oral dose: 5 mg route of administration: oral experiment type: single co-administered:	DAPAGLIFLOZIN plasma	Homo sapiens population: unhealthy age: Children sex: food status:
49 ng/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT01525238	5 mg single, oral dose: 5 mg route of administration: oral experiment type: single co-administered:	DAPAGLIFLOZIN 3-O-GLUCURONIDE plasma	Homo sapiens population: unhealthy age: Children sex: food status:
116 ng/mL REVIEW https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/202293Orig1s000ClinPharmR.pdf	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	DAPAGLIFLOZIN plasma	Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: FASTED
119 ng/mL REVIEW https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/202293Orig1s000ClinPharmR.pdf	10 mg 1 times / day steady-state, oral dose: 10 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	DAPAGLIFLOZIN plasma	Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: FASTED

AUC

Value	Dose	Analyte	Population
427 ng*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT01525238	10 mg single, oral dose: 10 mg route of administration: oral experiment type: single co-administered:	DAPAGLIFLOZIN plasma	Homo sapiens population: unhealthy age: Children sex: food status:
418 ng*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT01525238	10 mg single, oral dose: 10 mg route of administration: oral experiment type: single co-administered:	DAPAGLIFLOZIN plasma	Homo sapiens population: unhealthy age: Children sex: food status:
658 ng*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT01525238	10 mg single, oral dose: 10 mg route of administration: oral experiment type: single co-administered:	DAPAGLIFLOZIN 3-O-GLUCURONIDE plasma	Homo sapiens population: unhealthy age: Children sex: food status:
612 ng*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT01525238	10 mg single, oral dose: 10 mg route of administration: oral experiment type: single co-administered:	DAPAGLIFLOZIN 3-O-GLUCURONIDE plasma	Homo sapiens population: unhealthy age: Children sex: food status:
101 ng*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT01525238	2.5 mg single, oral dose: 2.5 mg route of administration: oral experiment type: single co-administered:	DAPAGLIFLOZIN plasma	Homo sapiens population: unhealthy age: Children sex: food status:
92.3 ng*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT01525238	2.5 mg single, oral dose: 2.5 mg route of administration: oral experiment type: single co-administered:	DAPAGLIFLOZIN plasma	Homo sapiens population: unhealthy age: Children sex: food status:
105 ng*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT01525238	2.5 mg single, oral dose: 2.5 mg route of administration: oral experiment type: single co-administered:	DAPAGLIFLOZIN 3-O-GLUCURONIDE plasma	Homo sapiens population: unhealthy age: Children sex: food status:
95.8 ng*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT01525238	2.5 mg single, oral dose: 2.5 mg route of administration: oral experiment type: single co-administered:	DAPAGLIFLOZIN 3-O-GLUCURONIDE plasma	Homo sapiens population: unhealthy age: Children sex: food status:
199 ng*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT01525238	5 mg single, oral dose: 5 mg route of administration: oral experiment type: single co-administered:	DAPAGLIFLOZIN plasma	Homo sapiens population: unhealthy age: Children sex: food status:
189 ng*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT01525238	5 mg single, oral dose: 5 mg route of administration: oral experiment type: single co-administered:	DAPAGLIFLOZIN plasma	Homo sapiens population: unhealthy age: Children sex: food status:
232 ng*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT01525238	5 mg single, oral dose: 5 mg route of administration: oral experiment type: single co-administered:	DAPAGLIFLOZIN 3-O-GLUCURONIDE plasma	Homo sapiens population: unhealthy age: Children sex: food status:
208 ng*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT01525238	5 mg single, oral dose: 5 mg route of administration: oral experiment type: single co-administered:	DAPAGLIFLOZIN 3-O-GLUCURONIDE plasma	Homo sapiens population: unhealthy age: Children sex: food status:
368 ng × h/mL REVIEW https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/202293Orig1s000ClinPharmR.pdf	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	DAPAGLIFLOZIN plasma	Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: FASTED
506 ng × h/mL REVIEW https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/202293Orig1s000ClinPharmR.pdf	10 mg 1 times / day steady-state, oral dose: 10 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	DAPAGLIFLOZIN plasma	Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
3 h REVIEW https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/202293Orig1s000ClinPharmR.pdf	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:		DAPAGLIFLOZIN plasma	Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: FASTED
15.77 h REVIEW https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/202293Orig1s000ClinPharmR.pdf	10 mg 1 times / day steady-state, oral dose: 10 mg route of administration: Oral experiment type: STEADY-STATE co-administered:		DAPAGLIFLOZIN plasma	Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: FASTED

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252 substrate 1946	inhibitor 2438 substrate 1193	inhibitor 2507 substrate 1388

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP 110 CYP1A2 2153 CYP2A6 879 CYP2B6 926 CYP2C19 2057 CYP2C8 1057 OAT1 725 OAT3 747 OATP1B1 1079 OATP1B3 961 OCT2 779 P-gp 1741	CYP 303 CYP1A1 389 CYP1A2 1197 CYP2A6 626 CYP2E1 729 CYP3A5 446 OAT1 395 OAT3 391 OATP1B1 503 OATP1B3 435 OCT2 434 P-gp 2052 UGT1A9 423	CYP1A2 832 CYP2B6 669 CYP3A4/5 133 PXR 10

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
CYP1A2 2333	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/202293Orig1s000ClinPharmR.pdf Page: 63.0	no [IC50 >45 uM]
CYP2A6 911	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/202293Orig1s000ClinPharmR.pdf Page: 63.0	no [IC50 >45 uM]
CYP2B6 1160	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/202293Orig1s000ClinPharmR.pdf Page: 63.0	no [IC50 >45 uM]
CYP2C19 2141	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/202293Orig1s000ClinPharmR.pdf Page: 63.0	no [IC50 >45 uM]
CYP2D6 2546	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/202293Orig1s000ClinPharmR.pdf Page: 63.0	no [IC50 >45 uM]
CYP2C8 1117	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/202293Orig1s000ClinPharmR.pdf Page: 63, 67	no [IC50 >45 uM]	no (co-administration study) Comment: no clinically meaningful drug-drug interaction observed in the all the DDI studies conducted Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/202293Orig1s000ClinPharmR.pdf Page: 63, 67
CYP2C9 2497	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/202293Orig1s000ClinPharmR.pdf Page: 63, 67	no [IC50 >45 uM]	no (co-administration study) Comment: no clinically meaningful drug-drug interaction observed in the all the DDI studies conducted Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/202293Orig1s000ClinPharmR.pdf Page: 63, 67
CYP3A4 2633	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/202293Orig1s000ClinPharmR.pdf Page: 63, 67	no [IC50 >45 uM]	no (co-administration study) Comment: no clinically meaningful drug-drug interaction observed in the all the DDI studies conducted Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/202293Orig1s000ClinPharmR.pdf Page: 63, 67
P-gp 1932	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/202293Orig1s000ClinPharmR.pdf Page: 64, 67	no [IC50 >57.6 uM]	no (co-administration study) Comment: dapagliflozin does not demonstrate any ability to inhibit P-gp mediated efflux of digoxin Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/202293Orig1s000ClinPharmR.pdf Page: 64, 67
CYP1A2 2333	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/202293Orig1s000ClinPharmR.pdf Page: 63.0	no
CYP2B6 1160	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/202293Orig1s000ClinPharmR.pdf Page: 63.0	no
CYP3A4/5 357	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/202293Orig1s000ClinPharmR.pdf Page: 63.0	no
OAT1 730	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/202293Orig1s000ClinPharmR.pdf Page: 64.0	no
PXR 51	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/202293Orig1s000ClinPharmR.pdf Page: 63.0	no
OCT2 782	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/202293Orig1s000ClinPharmR.pdf Page: 64, 67	no	no (co-administration study) Comment: no clinically meaningful drug-drug interaction observed in the all the DDI studies conducted Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/202293Orig1s000ClinPharmR.pdf Page: 64, 67
CYP 150	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/202293Orig1s000PharmR.pdf Page: 91.0	weak [IC50 >45 uM]
OAT3 749	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/202293Orig1s000ClinPharmR.pdf Page: 64, 67	yes [IC50 33 uM]	no (co-administration study) Comment: no clinically meaningful drug-drug interaction observed in the all the DDI studies conducted Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/202293Orig1s000ClinPharmR.pdf Page: 64, 67
OATP1B1 1095	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/202293Orig1s000PharmR.pdf Page: 29.0	yes [IC50 69 uM]
OATP1B3 970	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/202293Orig1s000PharmR.pdf Page: 29.0	yes [IC50 8 uM]

Drug as victim

Target	Modality	Activity	Clinical evidence
CYP 303	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/202293Orig1s000PharmR.pdf Page: 67.0	minor
OAT1 395	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/202293Orig1s000PharmR.pdf Page: 29.0	no
OATP1B1 503	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/202293Orig1s000PharmR.pdf Page: 29.0	no
OATP1B3 435	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/202293Orig1s000PharmR.pdf Page: 29.0	no
OCT2 434	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/202293Orig1s000PharmR.pdf Page: 29.0	no	no (co-administration study) Comment: no clinically meaningful drug-drug interaction observed in the all the DDI studies conducted from clinical pharmacology review p67 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/202293Orig1s000PharmR.pdf Page: 29.0
P-gp 2052	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/202293Orig1s000PharmR.pdf Page: 68.0	weak
CYP1A2 1197	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/202293Orig1s000ClinPharmR.pdf Page: 63.0	yes
CYP2A6 626	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/202293Orig1s000ClinPharmR.pdf Page: 63.0	yes
CYP2D6 1388	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/202293Orig1s000ClinPharmR.pdf Page: 63.0	yes
CYP2E1 729	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/202293Orig1s000ClinPharmR.pdf Page: 63.0	yes
CYP3A5 446	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/202293Orig1s000ClinPharmR.pdf Page: 63.0	yes
CYP1A1 389	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/202293Orig1s000ClinPharmR.pdf Page: 63, 65	yes	no (co-administration study) Comment: no clinically meaningful drug-drug interaction observed in the all the DDI studies conducted Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/202293Orig1s000ClinPharmR.pdf Page: 63, 65
CYP2C9 1193	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/202293Orig1s000ClinPharmR.pdf Page: 63, 65	yes	no (co-administration study) Comment: no clinically meaningful drug-drug interaction observed in the all the DDI studies conducted Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/202293Orig1s000ClinPharmR.pdf Page: 63, 65
CYP3A4 1946	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/202293Orig1s000ClinPharmR.pdf Page: 63, 65	yes	no (co-administration study) Comment: no clinically meaningful drug-drug interaction observed in the all the DDI studies conducted Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/202293Orig1s000ClinPharmR.pdf Page: 63, 65
OAT3 391	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/202293Orig1s000PharmR.pdf Page: 29.0	yes	no (co-administration study) Comment: no clinically meaningful drug-drug interaction observed in the all the DDI studies conducted from clinical pharmacology review p67 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/202293Orig1s000PharmR.pdf Page: 29.0
UGT1A9 423	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/202293Orig1s000ClinPharmR.pdf Page: 65.0	yes	unlikely (co-administration study) Comment: coadministration of mefenamic acid showed slight increase in dapagliflozin exposure; the increase in exposure does not warrant any dose adjustment Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/202293Orig1s000ClinPharmR.pdf Page: 65.0

Sourcing

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
ZINC	ZINC000003819138	http://zinc15.docking.org/substances/ZINC000003819138

PubMed

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
Sodium-glucose cotransport inhibition with dapagliflozin in type 2 diabetes.	2009 Apr	19114612
Gateways to clinical trials.	2009 Dec	20140276
Dapagliflozin, an oral sodium glucose cotransporter type 2 inhibitor for the treatment of type 2 diabetes mellitus.	2009 Dec	19943222
Dapagliflozin for the treatment of type 2 diabetes.	2009 Jul	19584379
Renal sodium-glucose transport: role in diabetes mellitus and potential clinical implications.	2009 Jun	19357717
Gateways to clinical trials.	2009 Mar	19455266
Diabetes treatment.	2009 Mar	19246581
Dapagliflozin: an emerging treatment option in type 2 diabetes.	2009 Mar	19243283
Dapagliflozin, a novel, selective SGLT2 inhibitor, improved glycemic control over 2 weeks in patients with type 2 diabetes mellitus.	2009 May	19129749
Dapagliflozin, a novel SGLT2 inhibitor, induces dose-dependent glucosuria in healthy subjects.	2009 May	19129748
(5-Bromo-2-chloro-phen-yl)(4-ethoxy-phen-yl)methanone.	2009 Nov 14	21578801
Gateways to clinical trials.	2009 Oct	19967103
Dapagliflozin: where does it fit in the treatment of type 2 diabetes?	2009 Oct	19735212
A study of dapagliflozin in patients with type 2 diabetes receiving high doses of insulin plus insulin sensitizers: applicability of a novel insulin-independent treatment.	2009 Sep	19528367
Dapagliflozin: BMS 512148; BMS-512148.	2010	20509715
Synthesis of pyridazine and thiazole analogs as SGLT2 inhibitors.	2010 Aug 15	20637636
A novel strategy for the treatment of diabetes mellitus - sodium glucose co-transport inhibitors.	2010 Dec	22558567
Quantitative PCR tissue expression profiling of the human SGLT2 gene and related family members.	2010 Dec	22127746
Dapagliflozin: a sodium glucose cotransporter 2 inhibitor in development for type 2 diabetes.	2010 Dec	22127745
Validated LC-MS/MS methods for the determination of dapagliflozin, a sodium-glucose co-transporter 2 inhibitor in normal and ZDF rat plasma.	2010 Dec	21110743
Dapagliflozin: more than just another oral glucose-lowering agent?	2010 Dec	21105857
(5-Bromo-2-methyl-phen-yl)(4-eth-oxy-phen-yl)methanone.	2010 Jul 17	21588347
Gateways to clinical trials.	2010 Jul-Aug	20852754
Dapagliflozin treatment in patients with different stages of type 2 diabetes mellitus: effects on glycaemic control and body weight.	2010 Jun	20518806
Neuropathy, retinopathy, and glucose-lowering treatments.	2010 Jun	20508223
Effect of dapagliflozin in patients with type 2 diabetes who have inadequate glycaemic control with metformin: a randomised, double-blind, placebo-controlled trial.	2010 Jun 26	20609968
Dapagliflozin, an SGLT2 inhibitor, for diabetes.	2010 Jun 26	20609956
In vitro characterization and pharmacokinetics of dapagliflozin (BMS-512148), a potent sodium-glucose cotransporter type II inhibitor, in animals and humans.	2010 Mar	19996149
Sodium-glucose co-transport inhibitors: progress and therapeutic potential in type 2 diabetes mellitus.	2010 Mar 5	20205482
The novel sodium glucose transporter 2 inhibitor dapagliflozin sustains pancreatic function and preserves islet morphology in obese, diabetic rats.	2010 Nov	20880347
Diabetes: Dapagliflozin: an insulin-independent, therapeutic option for type 2 diabetes mellitus.	2010 Oct	21080534
Dapagliflozin monotherapy in type 2 diabetic patients with inadequate glycemic control by diet and exercise: a randomized, double-blind, placebo-controlled, phase 3 trial.	2010 Oct	20566676
Gateways to clinical trials.	2010 Sep	21069103
Discovery of non-glucoside SGLT2 inhibitors.	2011 Apr 15	21398124
Discovery of a clinical candidate from the structurally unique dioxa-bicyclo[3.2.1]octane class of sodium-dependent glucose cotransporter 2 inhibitors.	2011 Apr 28	21449606
Discovery of novel N-β-D-xylosylindole derivatives as sodium-dependent glucose cotransporter 2 (SGLT2) inhibitors for the management of hyperglycemia in diabetes.	2011 Jan 13	21128592

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 Created by `admin` on `Wed Apr 02 15:44:55 GMT 2025` Edited by `admin` on `Wed Apr 02 15:44:55 GMT 2025`
Record UNII	Q54R5GG9QQ
Record Status	`Validated (UNII)`
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Name

Type

Language

Dapagliflozin L-prolinate

Preferred Name

English

Dapagliflozin diproline

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

Code System Code Type Description

SMS_ID

300000045110

Created by admin on Wed Apr 02 15:44:55 GMT 2025 , Edited by admin on Wed Apr 02 15:44:55 GMT 2025

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FDA UNII

Q54R5GG9QQ

Created by admin on Wed Apr 02 15:44:55 GMT 2025 , Edited by admin on Wed Apr 02 15:44:55 GMT 2025

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PUBCHEM

25032144

Created by admin on Wed Apr 02 15:44:55 GMT 2025 , Edited by admin on Wed Apr 02 15:44:55 GMT 2025

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CAS

960404-62-0

Created by admin on Wed Apr 02 15:44:55 GMT 2025 , Edited by admin on Wed Apr 02 15:44:55 GMT 2025

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Related Record Type Details


					1ULL0QJ8UC

Dapagliflozin

PARENT -> SALT/SOLVATE

Amount:


					9DLQ4CIU6V

Proline

PARENT -> SALT/SOLVATE

Amount:

Details

SMILES

InChI

DescriptionSources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/202293s003lbl.pdf | https://www.ncbi.nlm.nih.gov/pubmed/27042132

Originator

Approval Year

Targets

Conditions

Approved Use

Launch Date

Cmax

AUC

T1/2

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Sourcing

PubMed

Patents

Sample Use Guides

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/202293s003lbl.pdf | https://www.ncbi.nlm.nih.gov/pubmed/27042132

C_max

T_1/2

Drug as perpetrator