Identification

Logo pink
Are you a
new drug developer?
Contact us to learn more about our customized products and solutions.
Name
Dapagliflozin
Accession Number
DB06292
Type
Small Molecule
Groups
Approved
Description

Dapagliflozin is a sodium-glucose cotransporter 2 inhibitor indicated for managing diabetes mellitus type 21. When combined with diet and exercise in adults, dapagliflozin helps to improve glycemic control by inhibiting glucose resorption in the proximal tubule of the nephron and causing glycosuria1. Dapagliflozin was approved by the FDA on Jan 08, 20143.

Structure
Thumb
Synonyms
  • (2S,3R,4R,5S,6R)-2-(4-Chloro-3-(4-ethoxybenzyl)phenyl)-6- (hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
  • Dapagliflozin
  • Dapagliflozina
External IDs
BMS 512148 / BMS-512148
Product Ingredients
IngredientUNIICASInChI Key
Dapagliflozin propanediol monohydrate887K2391VH960404-48-2GOADIQFWSVMMRJ-UPGAGZFNSA-N
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
EdistrideTablet, film coated10 mgOralAstra Zeneca Ab2015-11-09Not applicableEu
EdistrideTablet, film coated5 mgOralAstra Zeneca Ab2015-11-09Not applicableEu
EdistrideTablet, film coated10 mgOralAstra Zeneca Ab2015-11-09Not applicableEu
EdistrideTablet, film coated5 mgOralAstra Zeneca Ab2015-11-09Not applicableEu
EdistrideTablet, film coated10 mgOralAstra Zeneca Ab2015-11-09Not applicableEu
EdistrideTablet, film coated5 mgOralAstra Zeneca Ab2015-11-09Not applicableEu
EdistrideTablet, film coated10 mgOralAstra Zeneca Ab2015-11-09Not applicableEu
EdistrideTablet, film coated5 mgOralAstra Zeneca Ab2015-11-09Not applicableEu
EdistrideTablet, film coated10 mgOralAstra Zeneca Ab2015-11-09Not applicableEu
EdistrideTablet, film coated5 mgOralAstra Zeneca Ab2015-11-09Not applicableEu
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

    Learn more
  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

    Learn more
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
QternDapagliflozin (10 mg) + Saxagliptin (5 mg)TabletOralAstra ZenecaNot applicableNot applicableCanada
QternDapagliflozin (5 mg) + Saxagliptin (5 mg)TabletOralAstra ZenecaNot applicableNot applicableCanada
QternDapagliflozin (5 mg/1) + Saxagliptin hydrochloride (5 mg/1)Tablet, film coatedOralAstraZeneca Pharmaceuticals LP2017-12-04Not applicableUs
QternDapagliflozin (10 mg/1) + Saxagliptin hydrochloride (5 mg/1)Tablet, film coatedOralAstraZeneca Pharmaceuticals LP2017-12-04Not applicableUs
XigduoDapagliflozin propanediol monohydrate (5 mg) + Metformin hydrochloride (1000 mg)Tablet, film coatedOralAstra Zeneca Ab2014-01-16Not applicableEu
XigduoDapagliflozin propanediol monohydrate (5 mg) + Metformin hydrochloride (850 mg)Tablet, film coatedOralAstra Zeneca Ab2014-01-16Not applicableEu
XigduoDapagliflozin propanediol monohydrate (5 mg) + Metformin hydrochloride (850 mg)Tablet, film coatedOralAstra Zeneca Ab2014-01-16Not applicableEu
XigduoDapagliflozin propanediol monohydrate (5 mg) + Metformin hydrochloride (1000 mg)Tablet, film coatedOralAstra Zeneca Ab2014-01-16Not applicableEu
XigduoDapagliflozin propanediol monohydrate (5 mg) + Metformin hydrochloride (850 mg)Tablet, film coatedOralAstra Zeneca Ab2014-01-16Not applicableEu
XigduoDapagliflozin propanediol monohydrate (5 mg) + Metformin hydrochloride (1000 mg)Tablet, film coatedOralAstra Zeneca Ab2014-01-16Not applicableEu
Categories
UNII
1ULL0QJ8UC
CAS number
461432-26-8
Weight
Average: 408.873
Monoisotopic: 408.133966239
Chemical Formula
C21H25ClO6
InChI Key
JVHXJTBJCFBINQ-ADAARDCZSA-N
InChI
InChI=1S/C21H25ClO6/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/h3-8,10,17-21,23-26H,2,9,11H2,1H3/t17-,18-,19+,20-,21+/m1/s1
IUPAC Name
(2S,3R,4R,5S,6R)-2-{4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl}-6-(hydroxymethyl)oxane-3,4,5-triol
SMILES
CCOC1=CC=C(CC2=C(Cl)C=CC(=C2)[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C=C1

Pharmacology

Indication

Dapagliflozin is indicated to improve glycemic control in adult patients with type 2 diabetes mellitus along with diet and exerciseLabel,1,2.

Associated Conditions
Pharmacodynamics

Dapagliflozin inhibits the sodium-glucose contransporter 2(SGLT2) which is primarily located in the proximal tubule of the nephron1. SGLT2 facilitates 90% of glucose resorption in the kidneys and so its inhibition allows for glucose to be excreted in the urine1. This excretion allows for better glycemic control and potentially weight loss in patients with type 2 diabetes mellitus1.

Mechanism of action

Dapagliflozin inhibits the sodium-glucose contransporter 2(SGLT2) which is primarily located in the proximal tubule of the nephron1. SGLT2 facilitates 90% of glucose resorption in the kidneys and so its inhibition allows for glucose to be excreted in the urine1. This excretion allows for better glycemic control and potentially weight loss in patients with type 2 diabetes mellitus1.

TargetActionsOrganism
ASodium/glucose cotransporter 2
antagonist
inhibitor
Humans
Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

Learn more
Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

Learn more
Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

Learn more
Absorption

Oral dapagliflozin reaches a maximum concentration within 1 hour of administration when patients have been fasting1. When patients have consumed a high fat meal, the time to maximum concentration increases to 2 hours and the maximum concentration decreases by half though a dose adjustment is not necessaryLabel. Oral dapagliflozin is 78% bioavailableLabel.

Volume of distribution

118L2.

Protein binding

91%Label,1,2.

Metabolism

Dapagliflozin is primarily glucuronidated to become the inactive 3-O-glucuronide metabolite(60.7%)Label,1,2. Dapagliflozin also produces another minor glucuronidated metabolite(5.4%), a de-ethylated metabolite(<5%), and a hydroxylated metabolite(<5%)1. Metabolism of dapagliflozin is mediated by cytochrome p-450(CYP)1A1, CYP1A2, CYP2A6, CYP2C9, CYP2D6, CYP3A4, uridine diphosphate glucuronyltransferase(UGT)1A9, UGT2B4, and UGT2B72. Glucuronidation to the major metabolite is mediated by UGT1A9Label,2.

Route of elimination

75.2% of dapagliflozin is recovered in the urine with 1.6% of the dose unchanged by metabolism1. 21% of the dose is excreted in the feces with 15% of the dose unchanged by metabolismLabel.

Half life

13.8h1.

Clearance

Oral plasma clearance was 4.9 mL/min/kg, and renal clearance was 5.6 mL/min1.

Toxicity

Age, gender, race, and body weight do not affect dapagliflozin dosing requirementsLabel,2. Although age does not affect dosing requirements, safety has not been established in pediatric populations and patients at an especially advanced age may be more susceptible to adverse effectsLabel. Animal studies in pregnancy showed no fetal toxicity in the first trimester but exposure later in pregnancy was associated with renal pelvic dilatation and maternal toxicity at much higher doses than the maximum recommended human doseLabel. Due to this data, dapagliflozin is not recommended in the second and third trimester of pregnancyLabel. Dapagliflozin is excreted in milk from rats, though this may not necessarily be the case in humansLabel. Children under 2 years old who are exposed to dapagliflozin may be at risk of improper kidney developmentLabel. Dapagliflozin is not recommended in patients with a creatinine clearance below 45mL/min and is contraindicated in patients with creatinine clearance below 30mL/minLabel. Dose adjustments are not necessary in patients with hepatic impairment at any stage, although the risk and benefit to the patient must be assessed as there is limited data on dapagliflozin use in this populationLabel.

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
(R)-warfarinThe metabolism of (R)-warfarin can be decreased when combined with Dapagliflozin.
1-(2-Phenylethyl)-4-phenyl-4-acetoxypiperidineThe metabolism of Dapagliflozin can be decreased when combined with 1-(2-Phenylethyl)-4-phenyl-4-acetoxypiperidine.
2,4-thiazolidinedioneDapagliflozin may increase the hypoglycemic activities of 2,4-thiazolidinedione.
4-MethoxyamphetamineThe metabolism of Dapagliflozin can be decreased when combined with 4-Methoxyamphetamine.
5-(2-methylpiperazine-1-sulfonyl)isoquinolineThe therapeutic efficacy of Dapagliflozin can be increased when used in combination with 5-(2-methylpiperazine-1-sulfonyl)isoquinoline.
5-methoxy-N,N-dimethyltryptamineThe metabolism of 5-methoxy-N,N-dimethyltryptamine can be decreased when combined with Dapagliflozin.
6-O-benzylguanineThe metabolism of 6-O-benzylguanine can be decreased when combined with Dapagliflozin.
7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline may increase the orthostatic hypotensive activities of Dapagliflozin.
8-azaguanineThe metabolism of 8-azaguanine can be decreased when combined with Dapagliflozin.
8-chlorotheophyllineThe metabolism of 8-chlorotheophylline can be decreased when combined with Dapagliflozin.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

    Learn more
  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

    Learn more
  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

    Learn more
  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

    Learn more
Food Interactions
Not Available

References

General References
  1. Obermeier M, Yao M, Khanna A, Koplowitz B, Zhu M, Li W, Komoroski B, Kasichayanula S, Discenza L, Washburn W, Meng W, Ellsworth BA, Whaley JM, Humphreys WG: In vitro characterization and pharmacokinetics of dapagliflozin (BMS-512148), a potent sodium-glucose cotransporter type II inhibitor, in animals and humans. Drug Metab Dispos. 2010 Mar;38(3):405-14. doi: 10.1124/dmd.109.029165. Epub 2009 Dec 8. [PubMed:19996149]
  2. Kasichayanula S, Liu X, Lacreta F, Griffen SC, Boulton DW: Clinical pharmacokinetics and pharmacodynamics of dapagliflozin, a selective inhibitor of sodium-glucose co-transporter type 2. Clin Pharmacokinet. 2014 Jan;53(1):17-27. doi: 10.1007/s40262-013-0104-3. [PubMed:24105299]
  3. FDA Drug Approval Package: Dapagliflozin [Link]
External Links
KEGG Drug
D08897
PubChem Compound
9887712
PubChem Substance
175427068
ChemSpider
8063384
BindingDB
50448923
ChEBI
85078
ChEMBL
CHEMBL429910
Drugs.com
Drugs.com Drug Page
Wikipedia
Dapagliflozin
ATC Codes
A10BK01 — DapagliflozinA10BD15 — Metformin and dapagliflozinA10BD21 — Saxagliptin and dapagliflozinA10BD25 — Metformin, saxagliptin and dapagliflozin
AHFS Codes
  • 68:20.18 — Sodium-glucose Cotransporter 2 (SGLT2) Inhibitors
FDA label
Download (1.22 MB)
MSDS
Download (62.4 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1Active Not RecruitingTreatmentType 2 Diabetes Mellitus2
1CompletedNot AvailableDiabetes Mellitus (DM) / Healthy Male and Female Subjects1
1CompletedNot AvailableType 2 Diabetes Mellitus9
1CompletedBasic ScienceBioequivalence / Fixed Dose Combination Tablets / Healthy Male and Female Subjects1
1CompletedBasic ScienceHealthy Volunteers4
1CompletedBasic ScienceType 1 Insulin-Dependent Diabetes Mellitus1
1CompletedBasic ScienceType 2 Diabetes Mellitus3
1CompletedHealth Services ResearchType2 Diabetes1
1CompletedTreatmentHealthy Volunteers2
1CompletedTreatmentType 1 Insulin-Dependent Diabetes Mellitus1
1CompletedTreatmentType 2 Diabetes Mellitus7
1CompletedTreatmentType1diabetes1
1RecruitingTreatmentHealthy Subjects in Fasted and Fed State1
1RecruitingTreatmentType1 Diabetes Mellitus1
1TerminatedNot AvailableType 2 Diabetes Mellitus1
1TerminatedDiagnosticDiabetes, NOS1
1, 2RecruitingTreatmentAlzheimer's Disease (AD)1
2Active Not RecruitingPreventionChronic Kidney Disease (CKD) / Proteinuria1
2CompletedBasic SciencePhysical Activity1
2CompletedBasic ScienceType 2 Diabetes Mellitus1
2CompletedBasic ScienceObese experiencing rapid weight loss1
2CompletedPreventionBMI >30 kg/m2 / Prediabetic State1
2CompletedTreatmentAsymptomatic Hyperuricemia1
2CompletedTreatmentBMI >30 kg/m21
2CompletedTreatmentT2 Diabetes and Fatty Liver Disease (Non-alcoholic Origin)1
2CompletedTreatmentType 1 Insulin-Dependent Diabetes Mellitus1
2CompletedTreatmentType 2 Diabetes Mellitus4
2RecruitingBasic ScienceMetabolically Healthy Controls / Type 2 Diabetes Mellitus1
2RecruitingPreventionType 1 Insulin-Dependent Diabetes Mellitus1
2RecruitingTreatmentGlucose, Low Blood / Type2 Diabetes Mellitus1
2RecruitingTreatmentHypoglycemia / Hypoglycemia Unawareness / Type 1 Insulin-Dependent Diabetes Mellitus1
2TerminatedBasic ScienceObese experiencing rapid weight loss1
2, 3CompletedTreatmentType 2 Diabetes Mellitus2
2, 3CompletedTreatmentType 2 Diabetes Mellitus, CKD and Albuminuria / Type 2 Diabetes Mellitus, CKD3 and Albuminuria1
2, 3RecruitingTreatmentObesity, Morbid / Pre-Diabetic / Type 2 Diabetes Mellitus1
2, 3RecruitingTreatmentType 1 Insulin-Dependent Diabetes Mellitus1
3Active Not RecruitingTreatmentChronic Kidney Disease (CKD)1
3Active Not RecruitingTreatmentType 2 Diabetes Mellitus3
3CompletedTreatmentCardiovascular Disease (CVD) / High Blood Pressure (Hypertension) / Inadequate Glycaemic Control / Type 2 Diabetes Mellitus1
3CompletedTreatmentCardiovascular Disease (CVD) / Inadequate Glycaemic Control / Type 2 Diabetes Mellitus1
3CompletedTreatmentChronic Heart Failure With Reduced Ejection Fraction (HFrEF)1
3CompletedTreatmentDiabetes Mellitus (DM)3
3CompletedTreatmentDiabetes Mellitus (DM) / Type 1 Insulin-Dependent Diabetes Mellitus1
3CompletedTreatmentDiabetes Mellitus, Non-Insulin-Dependent / High Risk for Cardiovascular Event1
3CompletedTreatmentDiabetes Prevention in Women After GDM Who Are at High-risk1
3CompletedTreatmentHigh Blood Sugar / Type 2 Diabetes Mellitus1
3CompletedTreatmentHigh Blood Sugar / Type2 Diabetes1
3CompletedTreatmentHigh HbA1c Level / Inadequate Glycaemic Control / Type 2 Diabetes Mellitus1
3CompletedTreatmentInadequate Glycaemic Control / Type 2 Diabetes Mellitus / Type2 Diabetes Mellitus1
3CompletedTreatmentType 1 Insulin-Dependent Diabetes Mellitus3
3CompletedTreatmentType 2 Diabetes Mellitus25
3Not Yet RecruitingBasic ScienceType 1 Insulin-Dependent Diabetes Mellitus1
3Not Yet RecruitingOtherType 1 Insulin-Dependent Diabetes Mellitus1
3Not Yet RecruitingTreatmentCVD / Myocardial Infarction / Pre-Diabetic / Type 2 Diabetes Mellitus1
3Not Yet RecruitingTreatmentType 2 Diabetes Mellitus1
3Not Yet RecruitingTreatmentType2 Diabetes Mellitus1
3RecruitingTreatmentBMI >30 kg/m2 / Polycystic Ovaries Syndrome1
3RecruitingTreatmentBMI >30 kg/m2 / Type 2 Diabetes Mellitus1
3RecruitingTreatmentHeart Failure With Preserved Ejection Fraction (HFpEF)2
3RecruitingTreatmentHeart Failure With Reduced Ejection Fraction (HFrEF)1
3RecruitingTreatmentNonalcoholic Steatohepatitis1
3RecruitingTreatmentStable Coronary Artery Disease / Type2 Diabetes Mellitus1
3RecruitingTreatmentType 1 Insulin-Dependent Diabetes Mellitus1
3RecruitingTreatmentType 2 Diabetes Mellitus2
3SuspendedTreatmentType 2 Diabetes Mellitus1
4Active Not RecruitingBasic ScienceSkeletal Muscle Insulin Sensitivity / Type 2 Diabetes Mellitus1
4Active Not RecruitingTreatmentCardiovascular Disease (CVD) / Type2 Diabetes1
4Active Not RecruitingTreatmentChronic Heart Failure With Reduced Ejection Fraction (HFrEF)1
4Active Not RecruitingTreatmentPre-Diabetic / Prehypertension1
4Active Not RecruitingTreatmentType 2 Diabetes Mellitus3
4CompletedBasic ScienceHigh Cholesterol / Type 2 Diabetes Mellitus1
4CompletedBasic ScienceType 2 Diabetes Mellitus1
4CompletedPreventionDiabetic Nephropathies / Type 2 Diabetes Mellitus1
4CompletedTreatmentBlood Pressures / BMI >30 kg/m2 / Cardiac Hypertrophy / High Blood Pressure (Hypertension) / Microalbuminuria / Type 2 Diabetes Mellitus / Vascular Stiffness1
4CompletedTreatmentCarotid Artery Diseases / Coronary Artery Disease / Type 2 Diabetes Mellitus1
4CompletedTreatmentDiabetes Mellitus (DM)2
4CompletedTreatmentDiabetes Mellitus (DM) / Heart Failure1
4CompletedTreatmentGlomerulosclerosis, Focal Segmental1
4CompletedTreatmentHyperglycemia Steroid-induced1
4CompletedTreatmentImpaired Fasting Glucose (IFG) / Impaired Glucose Tolerance (IGT) / Pre-Diabetic1
4CompletedTreatmentInadequate Glycaemic Control / Type 2 Diabetes Mellitus / Type2 Diabetes Mellitus1
4CompletedTreatmentIschaemic Heart Diseases / Type 2 Diabetes Mellitus1
4CompletedTreatmentLeft Ventricular Hypertrophy / Type 2 Diabetes Mellitus1
4CompletedTreatmentMetabolic Syndromes1
4CompletedTreatmentType 2 Diabetes Mellitus11
4Enrolling by InvitationTreatmentHigh Blood Pressure (Hypertension)1
4Not Yet RecruitingNot AvailableDiabetes Mellitus (DM) / Hypoglycemic Episodes1
4Not Yet RecruitingBasic ScienceType 2 Diabetes Mellitus1
4Not Yet RecruitingTreatmentCoronary Disease With Diabetes Mellitus1
4Not Yet RecruitingTreatmentEvaluate Ketogenic Stress1
4Not Yet RecruitingTreatmentOral Antidiabetics / Type 2 Diabetes Mellitus1
4Not Yet RecruitingTreatmentType 2 Diabetes Mellitus8
4RecruitingBasic ScienceDiabetes Mellitus (DM) / Heart Failure1
4RecruitingBasic ScienceHepatic Glucose Metabolism1
4RecruitingBasic SciencePrediabetic State / Substrate Oxidation1
4RecruitingBasic ScienceType 2 Diabetes Mellitus2
4RecruitingScreeningMyocardial Fibrosis / Myocardial Inflammation / Type 2 Diabetes Mellitus1
4RecruitingTreatmentBMI >30 kg/m21
4RecruitingTreatmentBMI >30 kg/m2 / Type 2 Diabetes Mellitus1
4RecruitingTreatmentCardiovascular Disease (CVD) / Type 2 Diabetes Mellitus1
4RecruitingTreatmentChronic Heart Failure With Preserved Systolic Function1
4RecruitingTreatmentDiabetes Mellitus (DM)1
4RecruitingTreatmentEndothelial Function / Type 2 Diabetes Mellitus1
4RecruitingTreatmentFasting Glucose / Glucose Excursion / Glycemic Control1
4RecruitingTreatmentHigh Blood Pressure (Hypertension) / Type 2 Diabetes Mellitus1
4RecruitingTreatmentKetonemia / Type 2 Diabetes Mellitus1
4RecruitingTreatmentKidney Function Tests / Type 2 Diabetes Mellitus1
4RecruitingTreatmentSteatosis, Liver / Type2 Diabetes1
4RecruitingTreatmentType 2 Diabetes Mellitus11
4RecruitingTreatmentType2 Diabetes1
4TerminatedBasic ScienceType 2 Diabetes Mellitus1
4Unknown StatusTreatmentType 2 Diabetes Mellitus1
4WithdrawnTreatmentType 2 Diabetes Mellitus2
Not AvailableActive Not RecruitingNot AvailableType 2 Diabetes Mellitus1
Not AvailableCompletedNot AvailableCardiovascular Disease (CVD) / Type 2 Diabetes Mellitus1
Not AvailableCompletedNot AvailableType 2 Diabetes Mellitus3
Not AvailableCompletedBasic ScienceInsulin Sensitivity / Multiple Mitochondrial Dysfunctions Syndrome1
Not AvailableCompletedBasic ScienceType 2 Diabetes Mellitus1
Not AvailableCompletedTreatmentType 2 Diabetes Mellitus1
Not AvailableRecruitingNot AvailableType2 Diabetes1
Not AvailableRecruitingOtherArterial Hypertension / Body Weight Changes / Type 2 Diabetes Mellitus1
Not AvailableRecruitingOtherType 2 Diabetes Mellitus1
Not AvailableRecruitingTreatmentBMI >30 kg/m2 / Cognitive Impairments / Type 2 Diabetes Mellitus1
Not AvailableRecruitingTreatmentImpaired Fasting Glucose (IFG) / Impaired Glucose Tolerance (IGT) / Type 2 Diabetes Mellitus1
Not AvailableTerminatedNot AvailableType 2 Diabetes Mellitus1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
Tablet, film coatedOral10 mg
Tablet, film coatedOral5 mg
Tablet, film coatedOral10 mg/1
Tablet, film coatedOral5 mg/1
TabletOral
TabletOral
Tablet, film coatedOral
Tablet, film coated, extended releaseOral
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US8216180No2012-07-102028-01-12Us
US8439864No2013-05-142028-03-25Us
US6667061Yes2003-12-232020-11-25Us
US6495164No2002-12-172020-05-25Us
US6872700No2005-03-292020-01-14Us
US6956026No2005-10-182018-01-07Us
US7741269No2010-06-222018-01-07Us
US9238076No2016-01-192024-04-15Us
US8906851No2014-12-092026-08-18Us
US7612176No2009-11-032025-04-13Us
US8431685No2013-04-302025-04-13Us
US8461105No2013-06-112025-04-13Us
US8329648No2012-12-112026-08-18Us
US7456254No2008-11-252025-06-30Us
US7563871No2009-07-212024-04-15Us
US6824822No2004-11-302022-10-09Us
US6479065No2002-11-122020-08-10Us
US7223440No2007-05-292021-08-31Us
USRE44186No2013-04-302023-07-31Us
US8628799No2014-01-142025-07-13Us
US8685934No2014-04-012030-05-26Us
US8501698No2013-08-062027-06-20Us
US6414126No2002-07-022020-10-04Us
US6515117No2003-02-042020-10-04Us
US6936590No2005-08-302020-10-04Us
US9198925No2015-12-012020-10-04Us
US7919598No2011-04-052029-12-16Us
US8361972No2013-01-292028-03-21Us
US8716251No2014-05-062028-03-21Us
US7851502No2010-12-142028-08-19Us
US8221786No2012-07-172028-03-21Us
US9616028No2017-04-112030-11-12Us
US9320853No2016-04-262028-03-25Us
US8827963No2014-09-092029-02-04Us
US8712615No2014-04-292030-01-18Us
US8998876No2015-04-072030-01-07Us
US8758292No2014-06-242027-11-12Us
US8690837No2014-04-082029-05-19Us
US8721615No2014-05-132030-01-18Us
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

    Learn more

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)65[MSDS]
boiling point (°C)609[MSDS]
logP2.7[MSDS]
Predicted Properties
PropertyValueSource
Water Solubility0.173 mg/mLALOGPS
logP2.52ALOGPS
logP2.11ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)12.57ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area99.38 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity104.93 m3·mol-1ChemAxon
Polarizability42.36 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Carbohydrates and carbohydrate conjugates
Direct Parent
Phenolic glycosides
Alternative Parents
Diphenylmethanes / Hexoses / C-glycosyl compounds / Phenoxy compounds / Phenol ethers / Alkyl aryl ethers / Chlorobenzenes / Aryl chlorides / Oxanes / Secondary alcohols
show 6 more
Substituents
Phenolic glycoside / Diphenylmethane / Hexose monosaccharide / C-glycosyl compound / Phenoxy compound / Phenol ether / Alkyl aryl ether / Chlorobenzene / Halobenzene / Aryl chloride
show 17 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
aromatic ether, organochlorine compound, C-glycosyl compound (CHEBI:85078)

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
Inhibitor
General Function
Low-affinity glucose:sodium symporter activity
Specific Function
Sodium-dependent glucose transporter. Has a Na(+) to glucose coupling ratio of 1:1.Efficient substrate transport in mammalian kidney is provided by the concerted action of a low affinity high capac...
Gene Name
SLC5A2
Uniprot ID
P31639
Uniprot Name
Sodium/glucose cotransporter 2
Molecular Weight
72895.995 Da
References
  1. Obermeier M, Yao M, Khanna A, Koplowitz B, Zhu M, Li W, Komoroski B, Kasichayanula S, Discenza L, Washburn W, Meng W, Ellsworth BA, Whaley JM, Humphreys WG: In vitro characterization and pharmacokinetics of dapagliflozin (BMS-512148), a potent sodium-glucose cotransporter type II inhibitor, in animals and humans. Drug Metab Dispos. 2010 Mar;38(3):405-14. doi: 10.1124/dmd.109.029165. Epub 2009 Dec 8. [PubMed:19996149]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Vitamin d 24-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A1
Uniprot ID
P04798
Uniprot Name
Cytochrome P450 1A1
Molecular Weight
58164.815 Da
References
  1. Kasichayanula S, Liu X, Lacreta F, Griffen SC, Boulton DW: Clinical pharmacokinetics and pharmacodynamics of dapagliflozin, a selective inhibitor of sodium-glucose co-transporter type 2. Clin Pharmacokinet. 2014 Jan;53(1):17-27. doi: 10.1007/s40262-013-0104-3. [PubMed:24105299]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
References
  1. Kasichayanula S, Liu X, Lacreta F, Griffen SC, Boulton DW: Clinical pharmacokinetics and pharmacodynamics of dapagliflozin, a selective inhibitor of sodium-glucose co-transporter type 2. Clin Pharmacokinet. 2014 Jan;53(1):17-27. doi: 10.1007/s40262-013-0104-3. [PubMed:24105299]
  2. Forxiga Assessment report [File]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Const...
Gene Name
CYP2A6
Uniprot ID
P11509
Uniprot Name
Cytochrome P450 2A6
Molecular Weight
56501.005 Da
References
  1. Kasichayanula S, Liu X, Lacreta F, Griffen SC, Boulton DW: Clinical pharmacokinetics and pharmacodynamics of dapagliflozin, a selective inhibitor of sodium-glucose co-transporter type 2. Clin Pharmacokinet. 2014 Jan;53(1):17-27. doi: 10.1007/s40262-013-0104-3. [PubMed:24105299]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Kasichayanula S, Liu X, Lacreta F, Griffen SC, Boulton DW: Clinical pharmacokinetics and pharmacodynamics of dapagliflozin, a selective inhibitor of sodium-glucose co-transporter type 2. Clin Pharmacokinet. 2014 Jan;53(1):17-27. doi: 10.1007/s40262-013-0104-3. [PubMed:24105299]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Kasichayanula S, Liu X, Lacreta F, Griffen SC, Boulton DW: Clinical pharmacokinetics and pharmacodynamics of dapagliflozin, a selective inhibitor of sodium-glucose co-transporter type 2. Clin Pharmacokinet. 2014 Jan;53(1):17-27. doi: 10.1007/s40262-013-0104-3. [PubMed:24105299]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Kasichayanula S, Liu X, Lacreta F, Griffen SC, Boulton DW: Clinical pharmacokinetics and pharmacodynamics of dapagliflozin, a selective inhibitor of sodium-glucose co-transporter type 2. Clin Pharmacokinet. 2014 Jan;53(1):17-27. doi: 10.1007/s40262-013-0104-3. [PubMed:24105299]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Retinoic acid binding
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols. Isoform 2 lacks trans...
Gene Name
UGT1A9
Uniprot ID
O60656
Uniprot Name
UDP-glucuronosyltransferase 1-9
Molecular Weight
59940.495 Da
References
  1. Kasichayanula S, Liu X, Lacreta F, Griffen SC, Boulton DW: Clinical pharmacokinetics and pharmacodynamics of dapagliflozin, a selective inhibitor of sodium-glucose co-transporter type 2. Clin Pharmacokinet. 2014 Jan;53(1):17-27. doi: 10.1007/s40262-013-0104-3. [PubMed:24105299]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Glucuronosyltransferase activity
Specific Function
UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme is active on polyhydroxylated estrogens (such as...
Gene Name
UGT2B4
Uniprot ID
P06133
Uniprot Name
UDP-glucuronosyltransferase 2B4
Molecular Weight
60512.035 Da
References
  1. Kasichayanula S, Liu X, Lacreta F, Griffen SC, Boulton DW: Clinical pharmacokinetics and pharmacodynamics of dapagliflozin, a selective inhibitor of sodium-glucose co-transporter type 2. Clin Pharmacokinet. 2014 Jan;53(1):17-27. doi: 10.1007/s40262-013-0104-3. [PubMed:24105299]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Glucuronosyltransferase activity
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.Its unique specificity for 3,4-catechol estrogens and estriol su...
Gene Name
UGT2B7
Uniprot ID
P16662
Uniprot Name
UDP-glucuronosyltransferase 2B7
Molecular Weight
60694.12 Da
References
  1. Kasichayanula S, Liu X, Lacreta F, Griffen SC, Boulton DW: Clinical pharmacokinetics and pharmacodynamics of dapagliflozin, a selective inhibitor of sodium-glucose co-transporter type 2. Clin Pharmacokinet. 2014 Jan;53(1):17-27. doi: 10.1007/s40262-013-0104-3. [PubMed:24105299]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Kasichayanula S, Liu X, Lacreta F, Griffen SC, Boulton DW: Clinical pharmacokinetics and pharmacodynamics of dapagliflozin, a selective inhibitor of sodium-glucose co-transporter type 2. Clin Pharmacokinet. 2014 Jan;53(1):17-27. doi: 10.1007/s40262-013-0104-3. [PubMed:24105299]

Drug created on March 19, 2008 10:22 / Updated on November 11, 2019 06:56