U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of Dapagliflozin diproline

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

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

Bristol-Myers Squibb
145
Curator's Comment: # Bristol-Myers Squibb

Approval Year

2008
174
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
 1.16 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
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
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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:
24.6 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:
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:
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:
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:
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:
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
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
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
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:
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:
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:
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:
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:
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:
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:
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:
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:
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:
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:
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:
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
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
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
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
Doses

Doses

DosePopulationAdverse events​
10 mg single, oral
Highest studied dose
Dose: 10 mg
Route: oral
Route: single
Dose: 10 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/27291448
unhealthy, 14.6 years (range: 11–17)
n = 8
Health Status: unhealthy
Condition: type 2 diabetes mellitus
Age Group: 14.6 years (range: 11–17)
Sex: M+F
Population Size: 8
Sources:
https://pubmed.ncbi.nlm.nih.gov/27291448
Other AEs: Abdominal pain upper, Back pain...
Other AEs:
Abdominal pain upper (12.5%)
Back pain (12.5%)
Nausea (12.5%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/27291448
10 mg 1 times / day steady, oral
Recommended
Dose: 10 mg, 1 times / day
Route: oral
Route: steady
Dose: 10 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/30653152
unhealthy, 23 years
n = 1
Health Status: unhealthy
Condition: type 2 diabetes mellitus
Age Group: 23 years
Sex: F
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/30653152
Disc. AE: Ketoacidosis...
AEs leading to
discontinuation/dose reduction:
Ketoacidosis (1 patient)
Sources:
https://pubmed.ncbi.nlm.nih.gov/30653152
50 mg single, oral
Highest studied dose
Dose: 50 mg
Route: oral
Route: single
Dose: 50 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/21226818
healthy, 24 years (range: 20–45 years years)
n = 8
Health Status: healthy
Age Group: 24 years (range: 20–45 years years)
Sex: M
Population Size: 8
Sources:
https://pubmed.ncbi.nlm.nih.gov/21226818
Sources:
https://pubmed.ncbi.nlm.nih.gov/21226818
20 mg 1 times / day steady, oral
Highest studied dose
Dose: 20 mg, 1 times / day
Route: oral
Route: steady
Dose: 20 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/21226818
unhealthy, 62 years (range: 20 - 70 years)
n = 12
Health Status: unhealthy
Condition: type 2 diabetes mellitus
Age Group: 62 years (range: 20 - 70 years)
Sex: M
Population Size: 12
Sources:
https://pubmed.ncbi.nlm.nih.gov/21226818
Other AEs: Protein urine present...
Other AEs:
Protein urine present (2 patients)
Sources:
https://pubmed.ncbi.nlm.nih.gov/21226818
10 mg 1 times / day steady, oral
Dose: 10 mg, 1 times / day
Route: oral
Route: steady
Dose: 10 mg, 1 times / day
Sources:
https://clinicaltrials.gov/ct2/show/NCT02096705
unhealthy
n = 139
Health Status: unhealthy
Condition: Type 2 Diabetes
Population Size: 139
Sources:
https://clinicaltrials.gov/ct2/show/NCT02096705
Other AEs: Coronary artery disease, Gastritis...
Other AEs:
Coronary artery disease (serious, 1 patient)
Gastritis (serious, 1 patient)
Lung infection (serious, 1 patient)
Acidosis (serious, 1 patient)
Osteoarthritis (serious, 1 patient)
Colorectal cancer (serious, 1 patient)
Syncope (serious, 1 patient)
Ectopic pregnancy (serious, 1 patient)
Calculus ureteric (serious, 1 patient)
Hydronephrosis (serious, 1 patient)
Hyperlipidaemia (below serious, 31 patient)
Sources:
https://clinicaltrials.gov/ct2/show/NCT02096705
10 mg 1 times / day steady, oral
Dose: 10 mg, 1 times / day
Route: oral
Route: steady
Dose: 10 mg, 1 times / day
Sources:
https://clinicaltrials.gov/ct2/show/NCT02113241
unhealthy
n = 12
Health Status: unhealthy
Condition: Metabolic Syndrome
Population Size: 12
Sources:
https://clinicaltrials.gov/ct2/show/NCT02113241
Other AEs: Urinary infection...
Other AEs:
Urinary infection (below serious, 1 patient)
Sources:
https://clinicaltrials.gov/ct2/show/NCT02113241
10 mg 1 times / day steady, oral
Dose: 10 mg, 1 times / day
Route: oral
Route: steady
Dose: 10 mg, 1 times / day
Sources:
https://clinicaltrials.gov/ct2/show/NCT02371187
unhealthy
n = 18
Health Status: unhealthy
Condition: Type 2 Diabetes
Population Size: 18
Sources:
https://clinicaltrials.gov/ct2/show/NCT02371187
Other AEs: Muscle soreness...
Other AEs:
Muscle soreness (below serious, 8 patients)
Sources:
https://clinicaltrials.gov/ct2/show/NCT02371187
10 mg 1 times / day steady, oral
Dose: 10 mg, 1 times / day
Route: oral
Route: steady
Dose: 10 mg, 1 times / day
Sources:
https://clinicaltrials.gov/ct2/show/NCT02613897
unhealthy
n = 22
Health Status: unhealthy
Condition: Type 2 Diabetes
Population Size: 22
Sources:
https://clinicaltrials.gov/ct2/show/NCT02613897
Other AEs: Increased urinary frequency, Vaginal itching...
Other AEs:
Increased urinary frequency (below serious, 3 patients)
Vaginal itching (below serious, 2 patients)
Nausea (below serious, 1 patient)
Dry mouth (below serious, 2 patients)
Urinary tract infection (below serious, 1 patient)
Sources:
https://clinicaltrials.gov/ct2/show/NCT02613897
10 mg 1 times / day steady, oral
Dose: 10 mg, 1 times / day
Route: oral
Route: steady
Dose: 10 mg, 1 times / day
Sources:
https://clinicaltrials.gov/ct2/show/NCT02700334
unhealthy
n = 12
Health Status: unhealthy
Condition: Type 2 Diabetes
Population Size: 12
Sources:
https://clinicaltrials.gov/ct2/show/NCT02700334
Other AEs: Urinary tract infection, Low back pain...
Other AEs:
Urinary tract infection (below serious, 2 patients)
Low back pain (below serious, 1 patient)
Sources:
https://clinicaltrials.gov/ct2/show/NCT02700334
10 mg 1 times / day steady, oral
Dose: 10 mg, 1 times / day
Route: oral
Route: steady
Dose: 10 mg, 1 times / day
Sources:
https://clinicaltrials.gov/ct2/show/NCT03006471
unhealthy
n = 15
Health Status: unhealthy
Condition: PreDiabetes
Population Size: 15
Sources:
https://clinicaltrials.gov/ct2/show/NCT03006471
Other AEs: Vaginal infection, Urinary tract infections...
Other AEs:
Vaginal infection (below serious, 3 patients)
Urinary tract infections (below serious, 2 patients)
Sources:
https://clinicaltrials.gov/ct2/show/NCT03006471
2.5 mg 1 times / day steady, oral
Dose: 2.5 mg, 1 times / day
Route: oral
Route: steady
Dose: 2.5 mg, 1 times / day
Sources:
https://clinicaltrials.gov/ct2/show/NCT00736879
unhealthy
n = 74
Health Status: unhealthy
Condition: Type 2 Diabetes
Population Size: 74
Sources:
https://clinicaltrials.gov/ct2/show/NCT00736879
Other AEs: Uterine leiomyoma, Pneumonia...
Other AEs:
Uterine leiomyoma (serious, 1 patient)
Pneumonia (serious, 1 patient)
Pharyngitis (below serious, 4 patients)
Dizziness (below serious, 5 patients)
Sources:
https://clinicaltrials.gov/ct2/show/NCT00736879
AEs

AEs

AESignificanceDosePopulation
Abdominal pain upper 12.5%
10 mg single, oral
Highest studied dose
Dose: 10 mg
Route: oral
Route: single
Dose: 10 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/27291448
unhealthy, 14.6 years (range: 11–17)
n = 8
Health Status: unhealthy
Condition: type 2 diabetes mellitus
Age Group: 14.6 years (range: 11–17)
Sex: M+F
Population Size: 8
Sources:
https://pubmed.ncbi.nlm.nih.gov/27291448
Back pain 12.5%
10 mg single, oral
Highest studied dose
Dose: 10 mg
Route: oral
Route: single
Dose: 10 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/27291448
unhealthy, 14.6 years (range: 11–17)
n = 8
Health Status: unhealthy
Condition: type 2 diabetes mellitus
Age Group: 14.6 years (range: 11–17)
Sex: M+F
Population Size: 8
Sources:
https://pubmed.ncbi.nlm.nih.gov/27291448
Nausea 12.5%
10 mg single, oral
Highest studied dose
Dose: 10 mg
Route: oral
Route: single
Dose: 10 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/27291448
unhealthy, 14.6 years (range: 11–17)
n = 8
Health Status: unhealthy
Condition: type 2 diabetes mellitus
Age Group: 14.6 years (range: 11–17)
Sex: M+F
Population Size: 8
Sources:
https://pubmed.ncbi.nlm.nih.gov/27291448
Ketoacidosis 1 patient
Disc. AE
10 mg 1 times / day steady, oral
Recommended
Dose: 10 mg, 1 times / day
Route: oral
Route: steady
Dose: 10 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/30653152
unhealthy, 23 years
n = 1
Health Status: unhealthy
Condition: type 2 diabetes mellitus
Age Group: 23 years
Sex: F
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/30653152
Protein urine present 2 patients
20 mg 1 times / day steady, oral
Highest studied dose
Dose: 20 mg, 1 times / day
Route: oral
Route: steady
Dose: 20 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/21226818
unhealthy, 62 years (range: 20 - 70 years)
n = 12
Health Status: unhealthy
Condition: type 2 diabetes mellitus
Age Group: 62 years (range: 20 - 70 years)
Sex: M
Population Size: 12
Sources:
https://pubmed.ncbi.nlm.nih.gov/21226818
Hyperlipidaemia below serious, 31 patient
10 mg 1 times / day steady, oral
Dose: 10 mg, 1 times / day
Route: oral
Route: steady
Dose: 10 mg, 1 times / day
Sources:
https://clinicaltrials.gov/ct2/show/NCT02096705
unhealthy
n = 139
Health Status: unhealthy
Condition: Type 2 Diabetes
Population Size: 139
Sources:
https://clinicaltrials.gov/ct2/show/NCT02096705
Acidosis serious, 1 patient
10 mg 1 times / day steady, oral
Dose: 10 mg, 1 times / day
Route: oral
Route: steady
Dose: 10 mg, 1 times / day
Sources:
https://clinicaltrials.gov/ct2/show/NCT02096705
unhealthy
n = 139
Health Status: unhealthy
Condition: Type 2 Diabetes
Population Size: 139
Sources:
https://clinicaltrials.gov/ct2/show/NCT02096705
Calculus ureteric serious, 1 patient
10 mg 1 times / day steady, oral
Dose: 10 mg, 1 times / day
Route: oral
Route: steady
Dose: 10 mg, 1 times / day
Sources:
https://clinicaltrials.gov/ct2/show/NCT02096705
unhealthy
n = 139
Health Status: unhealthy
Condition: Type 2 Diabetes
Population Size: 139
Sources:
https://clinicaltrials.gov/ct2/show/NCT02096705
Colorectal cancer serious, 1 patient
10 mg 1 times / day steady, oral
Dose: 10 mg, 1 times / day
Route: oral
Route: steady
Dose: 10 mg, 1 times / day
Sources:
https://clinicaltrials.gov/ct2/show/NCT02096705
unhealthy
n = 139
Health Status: unhealthy
Condition: Type 2 Diabetes
Population Size: 139
Sources:
https://clinicaltrials.gov/ct2/show/NCT02096705
Coronary artery disease serious, 1 patient
10 mg 1 times / day steady, oral
Dose: 10 mg, 1 times / day
Route: oral
Route: steady
Dose: 10 mg, 1 times / day
Sources:
https://clinicaltrials.gov/ct2/show/NCT02096705
unhealthy
n = 139
Health Status: unhealthy
Condition: Type 2 Diabetes
Population Size: 139
Sources:
https://clinicaltrials.gov/ct2/show/NCT02096705
Ectopic pregnancy serious, 1 patient
10 mg 1 times / day steady, oral
Dose: 10 mg, 1 times / day
Route: oral
Route: steady
Dose: 10 mg, 1 times / day
Sources:
https://clinicaltrials.gov/ct2/show/NCT02096705
unhealthy
n = 139
Health Status: unhealthy
Condition: Type 2 Diabetes
Population Size: 139
Sources:
https://clinicaltrials.gov/ct2/show/NCT02096705
Gastritis serious, 1 patient
10 mg 1 times / day steady, oral
Dose: 10 mg, 1 times / day
Route: oral
Route: steady
Dose: 10 mg, 1 times / day
Sources:
https://clinicaltrials.gov/ct2/show/NCT02096705
unhealthy
n = 139
Health Status: unhealthy
Condition: Type 2 Diabetes
Population Size: 139
Sources:
https://clinicaltrials.gov/ct2/show/NCT02096705
Hydronephrosis serious, 1 patient
10 mg 1 times / day steady, oral
Dose: 10 mg, 1 times / day
Route: oral
Route: steady
Dose: 10 mg, 1 times / day
Sources:
https://clinicaltrials.gov/ct2/show/NCT02096705
unhealthy
n = 139
Health Status: unhealthy
Condition: Type 2 Diabetes
Population Size: 139
Sources:
https://clinicaltrials.gov/ct2/show/NCT02096705
Lung infection serious, 1 patient
10 mg 1 times / day steady, oral
Dose: 10 mg, 1 times / day
Route: oral
Route: steady
Dose: 10 mg, 1 times / day
Sources:
https://clinicaltrials.gov/ct2/show/NCT02096705
unhealthy
n = 139
Health Status: unhealthy
Condition: Type 2 Diabetes
Population Size: 139
Sources:
https://clinicaltrials.gov/ct2/show/NCT02096705
Osteoarthritis serious, 1 patient
10 mg 1 times / day steady, oral
Dose: 10 mg, 1 times / day
Route: oral
Route: steady
Dose: 10 mg, 1 times / day
Sources:
https://clinicaltrials.gov/ct2/show/NCT02096705
unhealthy
n = 139
Health Status: unhealthy
Condition: Type 2 Diabetes
Population Size: 139
Sources:
https://clinicaltrials.gov/ct2/show/NCT02096705
Syncope serious, 1 patient
10 mg 1 times / day steady, oral
Dose: 10 mg, 1 times / day
Route: oral
Route: steady
Dose: 10 mg, 1 times / day
Sources:
https://clinicaltrials.gov/ct2/show/NCT02096705
unhealthy
n = 139
Health Status: unhealthy
Condition: Type 2 Diabetes
Population Size: 139
Sources:
https://clinicaltrials.gov/ct2/show/NCT02096705
Urinary infection below serious, 1 patient
10 mg 1 times / day steady, oral
Dose: 10 mg, 1 times / day
Route: oral
Route: steady
Dose: 10 mg, 1 times / day
Sources:
https://clinicaltrials.gov/ct2/show/NCT02113241
unhealthy
n = 12
Health Status: unhealthy
Condition: Metabolic Syndrome
Population Size: 12
Sources:
https://clinicaltrials.gov/ct2/show/NCT02113241
Muscle soreness below serious, 8 patients
10 mg 1 times / day steady, oral
Dose: 10 mg, 1 times / day
Route: oral
Route: steady
Dose: 10 mg, 1 times / day
Sources:
https://clinicaltrials.gov/ct2/show/NCT02371187
unhealthy
n = 18
Health Status: unhealthy
Condition: Type 2 Diabetes
Population Size: 18
Sources:
https://clinicaltrials.gov/ct2/show/NCT02371187
Nausea below serious, 1 patient
10 mg 1 times / day steady, oral
Dose: 10 mg, 1 times / day
Route: oral
Route: steady
Dose: 10 mg, 1 times / day
Sources:
https://clinicaltrials.gov/ct2/show/NCT02613897
unhealthy
n = 22
Health Status: unhealthy
Condition: Type 2 Diabetes
Population Size: 22
Sources:
https://clinicaltrials.gov/ct2/show/NCT02613897
Urinary tract infection below serious, 1 patient
10 mg 1 times / day steady, oral
Dose: 10 mg, 1 times / day
Route: oral
Route: steady
Dose: 10 mg, 1 times / day
Sources:
https://clinicaltrials.gov/ct2/show/NCT02613897
unhealthy
n = 22
Health Status: unhealthy
Condition: Type 2 Diabetes
Population Size: 22
Sources:
https://clinicaltrials.gov/ct2/show/NCT02613897
Dry mouth below serious, 2 patients
10 mg 1 times / day steady, oral
Dose: 10 mg, 1 times / day
Route: oral
Route: steady
Dose: 10 mg, 1 times / day
Sources:
https://clinicaltrials.gov/ct2/show/NCT02613897
unhealthy
n = 22
Health Status: unhealthy
Condition: Type 2 Diabetes
Population Size: 22
Sources:
https://clinicaltrials.gov/ct2/show/NCT02613897
Vaginal itching below serious, 2 patients
10 mg 1 times / day steady, oral
Dose: 10 mg, 1 times / day
Route: oral
Route: steady
Dose: 10 mg, 1 times / day
Sources:
https://clinicaltrials.gov/ct2/show/NCT02613897
unhealthy
n = 22
Health Status: unhealthy
Condition: Type 2 Diabetes
Population Size: 22
Sources:
https://clinicaltrials.gov/ct2/show/NCT02613897
Increased urinary frequency below serious, 3 patients
10 mg 1 times / day steady, oral
Dose: 10 mg, 1 times / day
Route: oral
Route: steady
Dose: 10 mg, 1 times / day
Sources:
https://clinicaltrials.gov/ct2/show/NCT02613897
unhealthy
n = 22
Health Status: unhealthy
Condition: Type 2 Diabetes
Population Size: 22
Sources:
https://clinicaltrials.gov/ct2/show/NCT02613897
Low back pain below serious, 1 patient
10 mg 1 times / day steady, oral
Dose: 10 mg, 1 times / day
Route: oral
Route: steady
Dose: 10 mg, 1 times / day
Sources:
https://clinicaltrials.gov/ct2/show/NCT02700334
unhealthy
n = 12
Health Status: unhealthy
Condition: Type 2 Diabetes
Population Size: 12
Sources:
https://clinicaltrials.gov/ct2/show/NCT02700334
Urinary tract infection below serious, 2 patients
10 mg 1 times / day steady, oral
Dose: 10 mg, 1 times / day
Route: oral
Route: steady
Dose: 10 mg, 1 times / day
Sources:
https://clinicaltrials.gov/ct2/show/NCT02700334
unhealthy
n = 12
Health Status: unhealthy
Condition: Type 2 Diabetes
Population Size: 12
Sources:
https://clinicaltrials.gov/ct2/show/NCT02700334
Urinary tract infections below serious, 2 patients
10 mg 1 times / day steady, oral
Dose: 10 mg, 1 times / day
Route: oral
Route: steady
Dose: 10 mg, 1 times / day
Sources:
https://clinicaltrials.gov/ct2/show/NCT03006471
unhealthy
n = 15
Health Status: unhealthy
Condition: PreDiabetes
Population Size: 15
Sources:
https://clinicaltrials.gov/ct2/show/NCT03006471
Vaginal infection below serious, 3 patients
10 mg 1 times / day steady, oral
Dose: 10 mg, 1 times / day
Route: oral
Route: steady
Dose: 10 mg, 1 times / day
Sources:
https://clinicaltrials.gov/ct2/show/NCT03006471
unhealthy
n = 15
Health Status: unhealthy
Condition: PreDiabetes
Population Size: 15
Sources:
https://clinicaltrials.gov/ct2/show/NCT03006471
Pharyngitis below serious, 4 patients
2.5 mg 1 times / day steady, oral
Dose: 2.5 mg, 1 times / day
Route: oral
Route: steady
Dose: 2.5 mg, 1 times / day
Sources:
https://clinicaltrials.gov/ct2/show/NCT00736879
unhealthy
n = 74
Health Status: unhealthy
Condition: Type 2 Diabetes
Population Size: 74
Sources:
https://clinicaltrials.gov/ct2/show/NCT00736879
Dizziness below serious, 5 patients
2.5 mg 1 times / day steady, oral
Dose: 2.5 mg, 1 times / day
Route: oral
Route: steady
Dose: 2.5 mg, 1 times / day
Sources:
https://clinicaltrials.gov/ct2/show/NCT00736879
unhealthy
n = 74
Health Status: unhealthy
Condition: Type 2 Diabetes
Population Size: 74
Sources:
https://clinicaltrials.gov/ct2/show/NCT00736879
Pneumonia serious, 1 patient
2.5 mg 1 times / day steady, oral
Dose: 2.5 mg, 1 times / day
Route: oral
Route: steady
Dose: 2.5 mg, 1 times / day
Sources:
https://clinicaltrials.gov/ct2/show/NCT00736879
unhealthy
n = 74
Health Status: unhealthy
Condition: Type 2 Diabetes
Population Size: 74
Sources:
https://clinicaltrials.gov/ct2/show/NCT00736879
Uterine leiomyoma serious, 1 patient
2.5 mg 1 times / day steady, oral
Dose: 2.5 mg, 1 times / day
Route: oral
Route: steady
Dose: 2.5 mg, 1 times / day
Sources:
https://clinicaltrials.gov/ct2/show/NCT00736879
unhealthy
n = 74
Health Status: unhealthy
Condition: Type 2 Diabetes
Population Size: 74
Sources:
https://clinicaltrials.gov/ct2/show/NCT00736879
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
inhibitor
1587

substrate
1737
inhibitor
1767

substrate
1037
inhibitor
1852

substrate
1217

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP
111

CYP1A2
1524

CYP2A6
707

CYP2B6
810

CYP2C19
1478

CYP2C8
911

OAT1
599

OAT3
642

OATP1B1
788

OATP1B3
706

OCT2
647

P-gp
1461
CYP
270

CYP1A1
349

CYP1A2
1054

CYP2A6
543

CYP2E1
667

CYP3A5
395

OAT1
326

OAT3
339

OATP1B1
406

OATP1B3
350

OCT2
355

P-gp
1537

UGT1A9
380
CYP1A2
701

CYP2B6
547

CYP3A4/5
124

PXR
9
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP1A2
1692
 no [IC50 >45 uM]
CYP2A6
739
 no [IC50 >45 uM]
CYP2B6
1001
 no [IC50 >45 uM]
CYP2C19
1553
 no [IC50 >45 uM]
CYP2D6
1891
 no [IC50 >45 uM]
CYP2C8
965
 no [IC50 >45 uM]
no (co-administration study)
Comment: no clinically meaningful drug-drug interaction observed in the all the DDI studies conducted
Page: 63, 67
CYP2C9
1819
 no [IC50 >45 uM]
no (co-administration study)
Comment: no clinically meaningful drug-drug interaction observed in the all the DDI studies conducted
Page: 63, 67
CYP3A4
1925
 no [IC50 >45 uM]
no (co-administration study)
Comment: no clinically meaningful drug-drug interaction observed in the all the DDI studies conducted
Page: 63, 67
P-gp
1650
 no [IC50 >57.6 uM]
no (co-administration study)
Comment: dapagliflozin does not demonstrate any ability to inhibit P-gp mediated efflux of digoxin
Page: 64, 67
CYP1A2
1692
 no
CYP2B6
1001
 no
CYP3A4/5
335
 no
OAT1
603
 no
PXR
46
 no
OCT2
648
 no
no (co-administration study)
Comment: no clinically meaningful drug-drug interaction observed in the all the DDI studies conducted
Page: 64, 67
CYP
147
 weak [IC50 >45 uM]
OAT3
644
 yes [IC50 33 uM]
no (co-administration study)
Comment: no clinically meaningful drug-drug interaction observed in the all the DDI studies conducted
Page: 64, 67
OATP1B1
803
 yes [IC50 69 uM]
OATP1B3
715
 yes [IC50 8 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP
270
 minor
OAT1
326
 no
OATP1B1
406
 no
OATP1B3
350
 no
OCT2
355
 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
Page: 29.0
P-gp
1537
 weak
CYP1A2
1054
 yes
CYP2A6
543
 yes
CYP2D6
1217
 yes
CYP2E1
667
 yes
CYP3A5
395
 yes
CYP1A1
349
 yes
no (co-administration study)
Comment: no clinically meaningful drug-drug interaction observed in the all the DDI studies conducted
Page: 63, 65
CYP2C9
1037
 yes
no (co-administration study)
Comment: no clinically meaningful drug-drug interaction observed in the all the DDI studies conducted
Page: 63, 65
CYP3A4
1737
 yes
no (co-administration study)
Comment: no clinically meaningful drug-drug interaction observed in the all the DDI studies conducted
Page: 63, 65
OAT3
339
 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
Page: 29.0
UGT1A9
380
 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
Page: 65.0
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:85078
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:85078
ChemicalBook
CB91011730
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB91011730
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
eMolecules
32278060
https://www.emolecules.com/cgi-bin/more?vid=32278060
PubMed

PubMed

TitleDatePubMed
Molecule of the month. Dapagliflozin.
2007 Dec
Dapagliflozin, a selective SGLT2 inhibitor, improves glucose homeostasis in normal and diabetic rats.
2008 Jun
Discovery of dapagliflozin: a potent, selective renal sodium-dependent glucose cotransporter 2 (SGLT2) inhibitor for the treatment of type 2 diabetes.
2008 Mar 13
Inhibition of renal glucose reabsorption: a novel strategy for achieving glucose control in type 2 diabetes mellitus.
2008 Sep
Sodium-glucose cotransport inhibition with dapagliflozin in type 2 diabetes.
2009 Apr
Gateways to clinical trials.
2009 Dec
Dapagliflozin, an oral sodium glucose cotransporter type 2 inhibitor for the treatment of type 2 diabetes mellitus.
2009 Dec
Dapagliflozin for the treatment of type 2 diabetes.
2009 Jul
Renal sodium-glucose transport: role in diabetes mellitus and potential clinical implications.
2009 Jun
Gateways to clinical trials.
2009 Mar
Diabetes treatment.
2009 Mar
Dapagliflozin: an emerging treatment option in type 2 diabetes.
2009 Mar
Dapagliflozin, a novel, selective SGLT2 inhibitor, improved glycemic control over 2 weeks in patients with type 2 diabetes mellitus.
2009 May
Dapagliflozin, a novel SGLT2 inhibitor, induces dose-dependent glucosuria in healthy subjects.
2009 May
(5-Bromo-2-chloro-phen-yl)(4-ethoxy-phen-yl)methanone.
2009 Nov 14
Gateways to clinical trials.
2009 Oct
Dapagliflozin: where does it fit in the treatment of type 2 diabetes?
2009 Oct
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
Dapagliflozin: BMS 512148; BMS-512148.
2010
Synthesis of pyridazine and thiazole analogs as SGLT2 inhibitors.
2010 Aug 15
A novel strategy for the treatment of diabetes mellitus - sodium glucose co-transport inhibitors.
2010 Dec
Quantitative PCR tissue expression profiling of the human SGLT2 gene and related family members.
2010 Dec
Dapagliflozin: a sodium glucose cotransporter 2 inhibitor in development for type 2 diabetes.
2010 Dec
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
Dapagliflozin: more than just another oral glucose-lowering agent?
2010 Dec
(5-Bromo-2-methyl-phen-yl)(4-eth-oxy-phen-yl)methanone.
2010 Jul 17
Gateways to clinical trials.
2010 Jul-Aug
Dapagliflozin treatment in patients with different stages of type 2 diabetes mellitus: effects on glycaemic control and body weight.
2010 Jun
Neuropathy, retinopathy, and glucose-lowering treatments.
2010 Jun
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
Dapagliflozin, an SGLT2 inhibitor, for diabetes.
2010 Jun 26
In vitro characterization and pharmacokinetics of dapagliflozin (BMS-512148), a potent sodium-glucose cotransporter type II inhibitor, in animals and humans.
2010 Mar
Sodium-glucose co-transport inhibitors: progress and therapeutic potential in type 2 diabetes mellitus.
2010 Mar 5
The novel sodium glucose transporter 2 inhibitor dapagliflozin sustains pancreatic function and preserves islet morphology in obese, diabetic rats.
2010 Nov
Diabetes: Dapagliflozin: an insulin-independent, therapeutic option for type 2 diabetes mellitus.
2010 Oct
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
Gateways to clinical trials.
2010 Sep
Discovery of non-glucoside SGLT2 inhibitors.
2011 Apr 15
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
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
Patents

Patents

08394772
5
JP5302900B2
5

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
Curator's Comment: A non-radioactive cell-based method for the screening of SGLT inhibitors using COS-7 cells transiently expressing human SGLT1 (hSGLT1), CHO-K1 cells stably expressing human SGLT2 (hSGLT2), and a novel fluorescent d-glucose analogue 1-NBDG as a substrate was used.
The IC50 values of dapagliflozin for hSGLT2 and hSGLT1 determined using 1-NBDG were 1.86 nM and 880 nM
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
Code System Code Type Description
FDA UNII
Q54R5GG9QQ
Created by admin on Sat Dec 16 19:27:32 GMT 2023 , Edited by admin on Sat Dec 16 19:27:32 GMT 2023
PRIMARY
PUBCHEM
25032144
Created by admin on Sat Dec 16 19:27:32 GMT 2023 , Edited by admin on Sat Dec 16 19:27:32 GMT 2023
PRIMARY
CAS
960404-62-0
Created by admin on Sat Dec 16 19:27:32 GMT 2023 , Edited by admin on Sat Dec 16 19:27:32 GMT 2023
PRIMARY
PARENT (SALT/SOLVATE)
Structure of DAPAGLIFLOZIN
PARENT (SALT/SOLVATE)
Structure of PROLINE
NIH
NCATS
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