Dapagliflozin is a sodium-glucose cotransporter 2 (SGLT2) inhibitor, and it was the first SLGT2 inhibitor to be approved. indicated for managing diabetes mellitus type 2.³ When combined with diet and exercise in adults, dapagliflozin helps to improve glycemic control by inhibiting glucose reabsorption in the proximal tubule of the nephron and causing glycosuria.¹ Dapagliflozin has been investigated either as monotherapy or as an adjunct treatment with insulin or other oral hypoglycemic agents.⁴

Dapagliflozin was originally approved by the FDA on Jan 08, 2014, to improve glycemic control in adults with type 2 diabetes in conjunction with diet and exercise.¹² It was later approved to reduce the risk of kidney function decline, kidney failure, cardiovascular death, and hospitalization for heart failure in adults with chronic kidney disease in April 2021.¹²

Type

Small Molecule

Groups

Approved, Investigational

Structure

MOL SDF 3D-SDF PDB SMILES InChI

Similar Structures

Structure for Dapagliflozin (DB06292)

Weight: Average: 408.873
Monoisotopic: 408.133966239
Chemical Formula: C₂₁H₂₅ClO₆

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

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Pharmacology

Indication

Dapagliflozin is indicated as an adjunct treatment, alongside diet and exercise, to improve glycemic control in patients ≥10 years of age with type 2 diabetes mellitus.^13,1,2 For patients with chronic kidney disease at risk of progression, dapagliflozin in used to reduce the risk of sustained eGFR decline, end-stage kidney disease, cardiovascular death, and hospitalization for heart failure.⁹ Dapagliflozin is also indicated to either reduce the risk of cardiovascular death, hospitalization for heart failure, and urgent heart failure visit in adults with heart failure or reduce the risk of hospitalization for heart failure in adults with type 2 diabetes mellitus and either established cardiovascular disease or multiple cardiovascular risk factors.⁹ Combination products with dapagliflozin also exist, either as a dapagliflozin-saxagliptin or dapagliflozin-metformin hydrochloride formulation.^7,8 Both are used as an adjunct treatment to diet and exercise to improve glycemic control in adults with type 2 diabetes.^7,8

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Associated Conditions

Indication Type	Indication	Approval Level	Age Group	Patient Characteristics	Dose Form
Prevention of	Cardiovascular mortality	••••••••••••	•••••		••••••
Prevention of	Cardiovascular mortality	••••••••••••	•••••	•••• •••• ••• ••••••••••• •• •••••• •••••••	••••••
Prevention of	End stage renal disease (esrd)	••••••••••••	•••••	•••• •••• ••• ••••••••••• •• •••••• •••••••	••••••
Prevention of	Hospitalizations	••••••••••••	•••••	••••••••••••••• •••• •••••••• •••• • •••••••• ••••••••	••••••
Prevention of	Hospitalizations	••••••••••••	•••••	•••• • •••••••• ••••••••• ••••••••••• •••••••••••••• •••••••	••••••

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Contraindications & Blackbox Warnings

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Pharmacodynamics

Dapagliflozin also reduces sodium reabsorption and increases the delivery of sodium to the distal tubule. This may influence several physiological functions including, but not restricted to, lowering both pre- and afterload of the heart and downregulation of sympathetic activity, and decreased intraglomerular pressure which is believed to be mediated by increased tubuloglomerular feedback.¹⁰

Increases in the amount of glucose excreted in the urine were observed in healthy subjects and in patients with type 2 diabetes mellitus following the administration of dapagliflozin. Dapagliflozin doses of 5 or 10 mg per day in patients with type 2 diabetes mellitus for 12 weeks resulted in excretion of approximately 70 grams of glucose in the urine per day at Week 12. A near-maximum glucose excretion was observed at the dapagliflozin daily dose of 20 mg. This urinary glucose excretion with dapagliflozin also results in increases in urinary volume. After discontinuation of dapagliflozin, on average, the elevation in urinary glucose excretion approaches baseline by about 3 days for the 10 mg dose.¹⁰

Dapagliflozin was not associated with clinically meaningful prolongation of QTc interval at daily doses up to 150 mg (15 times the recommended maximum dose) in a study of healthy subjects. In addition, no clinically meaningful effect on QTc interval was observed following single doses of up to 500 mg (50 times the recommended maximum dose) of dapagliflozin in healthy subjects.¹⁰

Mechanism of action

Dapagliflozin inhibits the sodium-glucose cotransporter 2(SGLT2) which is primarily located in the proximal tubule of the nephron.¹ SGLT2 facilitates 90% of glucose reabsorption in the kidneys and so its inhibition allows for glucose to be excreted in the urine.¹ This excretion allows for better glycemic control and potentially weight loss in patients with type 2 diabetes mellitus.¹

Target	Actions	Organism
ASodium/glucose cotransporter 2	inhibitor	Humans

Absorption

Oral dapagliflozin reaches a maximum concentration within 1 hour of administration when patients have been fasting.¹ Following oral administration of dapagliflozin, the maximum plasma concentration (C_max) is usually attained within 2 hours under fasting state. The C_max and AUC values increase dose proportionally with an increase in dapagliflozin dose in the therapeutic dose range. The absolute oral bioavailability of dapagliflozin following the administration of a 10 mg dose is 78%. Administration of dapagliflozin with a high-fat meal decreases its C_max by up to 50% and prolongs T_max by approximately 1 hour but does not alter AUC as compared with the fasted state. These changes are not considered to be clinically meaningful and dapagliflozin can be administered with or without food.¹⁰

Volume of distribution

The volume of distribution was estimated to be 118L.²

Protein binding

Dapagliflozin is approximately 91% protein bound. Protein binding is not altered in patients with renal or hepatic impairment.¹⁰

Metabolism

Dapagliflozin is primarily glucuronidated to become the inactive 3-O-glucuronide metabolite(60.7%).^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 UGT1A9.²

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Dapagliflozin

Route of elimination

Dapagliflozin and related metabolites are primarily eliminated via the renal pathway. Following a single 50 mg dose of [¹⁴C]-dapagliflozin, 75% and 21% of total radioactivity is excreted in urine and feces, respectively. In urine, less than 2% of the dose is excreted as the parent drug. In feces, approximately 15% of the dose is excreted as the parent drug.¹⁰

Half-life

The mean plasma terminal half-life (t_1/2) for dapagliflozin is approximately 12.9 hours following a single oral dose of 10 mg.¹⁰ In healthy subjects given a single oral dose of 50 mg of dapagliflozin, the mean terminal half-life was 13.8 hours.¹

Clearance

Oral plasma clearance was 4.9 mL/min/kg, and renal clearance was 5.6 mL/min.¹

Adverse Effects

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Toxicity

Age, gender, race, and body weight do not affect dapagliflozin dosing requirements^Label,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 effects^Label. 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 dose^Label. Due to this data, dapagliflozin is not recommended in the second and third trimester of pregnancy^Label. Dapagliflozin is excreted in milk from rats, though this may not necessarily be the case in humans^Label. Children under 2 years old who are exposed to dapagliflozin may be at risk of improper kidney development^Label. Dapagliflozin is not recommended in patients with a creatinine clearance below 45mL/min and is contraindicated in patients with creatinine clearance below 30mL/min^Label. 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 population^Label.

Pathways

Not Available

Pharmacogenomic Effects/ADRs

Not Available

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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.

Drug	Interaction
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Abaloparatide	The risk or severity of adverse effects can be increased when Abaloparatide is combined with Dapagliflozin.
Acarbose	Dapagliflozin may increase the hypoglycemic activities of Acarbose.
Acebutolol	The therapeutic efficacy of Dapagliflozin can be increased when used in combination with Acebutolol.
Acetazolamide	The therapeutic efficacy of Dapagliflozin can be increased when used in combination with Acetazolamide.
Acetohexamide	Dapagliflozin may increase the hypoglycemic activities of Acetohexamide.

Food Interactions

Avoid excessive or chronic alcohol consumption. Binge drinking or drinking alcohol often may predispose patients to ketoacidosis.
Take with or without food.

Products

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Product Ingredients

Ingredient	UNII	CAS	InChI Key
Dapagliflozin propanediol monohydrate	887K2391VH	960404-48-2	GOADIQFWSVMMRJ-UPGAGZFNSA-N

Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Dapagliflozin Viatris	Tablet, film coated	10 mg	Oral	Viatris Limited	2023-04-04	Not applicable
Dapagliflozin Viatris	Tablet, film coated	5 mg	Oral	Viatris Limited	2023-04-04	Not applicable
Dapagliflozin Viatris	Tablet, film coated	5 mg	Oral	Viatris Limited	2023-04-04	Not applicable
Dapagliflozin Viatris	Tablet, film coated	5 mg	Oral	Viatris Limited	2023-04-04	Not applicable
Dapagliflozin Viatris	Tablet, film coated	10 mg	Oral	Viatris Limited	2023-04-04	Not applicable

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Accel-dapagliflozin	Tablet	5 mg	Oral	Accel Pharma Inc	Not applicable	Not applicable
Accel-dapagliflozin	Tablet	10 mg	Oral	Accel Pharma Inc	Not applicable	Not applicable
Ag-dapagliflozin	Tablet	5 mg	Oral	Angita Pharma Inc.	2023-05-15	Not applicable
Ag-dapagliflozin	Tablet	10 mg	Oral	Angita Pharma Inc.	2023-05-15	Not applicable
Apo-dapagliflozin	Tablet	5 mg	Oral	Apotex Corporation	2023-05-16	Not applicable

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
Apo-dapagliflozin-metformin	Dapagliflozin(5 mg) +Metformin hydrochloride(1000 mg)	Tablet	Oral	Apotex Corporation	2023-12-01	Not applicable
Apo-dapagliflozin-metformin	Dapagliflozin(5 mg) +Metformin hydrochloride(850 mg)	Tablet	Oral	Apotex Corporation	2023-12-14	Not applicable
Auro-dapagliflozin / Metformin	Dapagliflozin(5 mg) +Metformin hydrochloride(1000 mg)	Tablet	Oral	Auro Pharma Inc	2023-05-16	Not applicable
Auro-dapagliflozin / Metformin	Dapagliflozin(5 mg) +Metformin hydrochloride(850 mg)	Tablet	Oral	Auro Pharma Inc	2023-05-16	Not applicable
Dapagliflozin and Metformin Hydrochloride	Dapagliflozin propanediol monohydrate(10 mg/1) +Metformin hydrochloride(1000 mg/1)	Tablet, film coated, extended release	Oral	Prasco, Llc	2024-01-03	Not applicable

Chemical Identifiers

UNII: 1ULL0QJ8UC
CAS number: 461432-26-8
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

References

General References

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. [Article]
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. [Article]
Paik J, Blair HA: Correction to: Dapagliflozin: A Review in Type 1 Diabetes. Drugs. 2019 Dec;79(18):2011. doi: 10.1007/s40265-019-01238-2. [Article]
Anderson SL: Dapagliflozin efficacy and safety: a perspective review. Ther Adv Drug Saf. 2014 Dec;5(6):242-54. doi: 10.1177/2042098614551938. [Article]
FDA Drug Approval Package: Dapagliflozin [Link]
FDA Approved Drug Products: Farxiga Dapagliflozin Oral Tablets [Link]
FDA Approved Drug Products: Qtern (dapagliflozin/saxagliptin) tablets for oral use [Link]
FDA Approved Drug Products: Xigduo XR (metformin hydrochloride/dapagliflozin) extended-release tablets for oral use [Link]
FDA Approved Drug Products: FARXIGA® (dapagliflozin) tablets, for oral use (May 2023) [Link]
FDA Approved Drug Products: FARXIGA® (dapagliflozin) tablets, for oral use (September 2023) [Link]
FDA Approved Drug Products: FARXIGA (dapagliflozin) tablets, for oral use [Link]
FDA Approves Treatment for Chronic Kidney Disease [Link]
FDA Approved Drug Products: Farxiga (dapagliflozin) tablets for oral use (June 2024) [Link]

External Links

KEGG Drug: D08897
PubChem Compound: 9887712
PubChem Substance: 175427068
ChemSpider: 8063384
BindingDB: 50448923
RxNav: 1488564
ChEBI: 85078
ChEMBL: CHEMBL429910
ZINC: ZINC000003819138
PDBe Ligand: LE6
Drugs.com: Drugs.com Drug Page
Wikipedia: Dapagliflozin

PDB Entries

8hez

FDA label

Download(1.22 MB)

MSDS

Download(62.4 KB)

Clinical Trials

Clinical Trials Clinical Trial & Rare Diseases Add-on Data Package Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more.Preview package

Phase	Status	Purpose	Conditions	Count	Start Date	Why Stopped	100+ additional columns
Unlock 175K+ rows when you subscribe.View sample data
Not Available	Active Not Recruiting	Not Available	Alport Syndrome	1	somestatus	stop reason	just information to hide
Not Available	Active Not Recruiting	Not Available	Anemia/CKD	1	somestatus	stop reason	just information to hide
Not Available	Active Not Recruiting	Other	Cardiac Failure/Volume Overload	1	somestatus	stop reason	just information to hide
Not Available	Active Not Recruiting	Other	Type 2 Diabetes Mellitus	1	somestatus	stop reason	just information to hide
Not Available	Active Not Recruiting	Prevention	Glycocalyx/Stiffness, Arterial/Urine Albumin (UAlb)	1	somestatus	stop reason	just information to hide

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Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage Forms

Form	Route	Strength
Tablet, film coated	Oral	12.3 MG
Tablet	Oral	10.000 mg
Tablet, film coated	Oral	10 mg/1
Tablet, film coated	Oral	5 mg/1
Tablet	Oral
Tablet	Oral	10 mg
Tablet	Oral	5 mg
Tablet, coated	Oral	10 mg
Tablet, film coated	Oral
Tablet, film coated	Oral	10 mg
Tablet, film coated	Oral	5 mg
Tablet, film coated	Oral
Tablet, coated	Oral
Tablet	Oral
Tablet, film coated, extended release	Oral
Tablet, extended release	Oral
Tablet, film coated, extended release	Oral	10 mg
Tablet, film coated, extended release	Oral	5 mg
Tablet, extended release	Oral	1005.04 mg

Prices

Not Available

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)
US8216180	Yes	2012-07-10	2028-07-12
US8439864	Yes	2013-05-14	2028-09-25
US6667061	Yes	2003-12-23	2020-11-25
US6495164	No	2002-12-17	2020-05-25
US6872700	No	2005-03-29	2020-01-14
US6956026	No	2005-10-18	2018-01-07
US7741269	No	2010-06-22	2018-01-07
US9238076	Yes	2016-01-19	2024-10-15
US8906851	Yes	2014-12-09	2027-02-18
US7612176	Yes	2009-11-03	2025-10-13
US8431685	Yes	2013-04-30	2025-10-13
US8461105	Yes	2013-06-11	2025-10-13
US8329648	Yes	2012-12-11	2027-02-18
US7456254	Yes	2008-11-25	2025-12-30
US7563871	Yes	2009-07-21	2024-10-15
US6824822	Yes	2004-11-30	2023-04-09
US6479065	No	2002-11-12	2020-08-10
US7223440	Yes	2007-05-29	2022-03-03
USRE44186	No	2013-04-30	2023-07-31
US8628799	No	2014-01-14	2025-07-13
US8685934	Yes	2014-04-01	2030-11-26
US8501698	Yes	2013-08-06	2027-12-20
US6414126	No	2002-07-02	2020-10-04
US6515117	Yes	2003-02-04	2026-04-04
US6936590	No	2005-08-30	2020-10-04
US9198925	No	2015-12-01	2020-10-04
US7919598	Yes	2011-04-05	2030-06-16
US8361972	Yes	2013-01-29	2028-09-21
US8716251	Yes	2014-05-06	2028-09-21
US7851502	Yes	2010-12-14	2029-02-19
US8221786	Yes	2012-07-17	2028-09-21
US9616028	Yes	2017-04-11	2031-05-12
US9320853	Yes	2016-04-26	2028-09-25
US8827963	Yes	2014-09-09	2029-08-04
US8712615	No	2014-04-29	2030-01-18
US8998876	Yes	2015-04-07	2030-07-07
US8758292	Yes	2014-06-24	2028-05-12
US8690837	Yes	2014-04-08	2029-11-19
US8721615	Yes	2014-05-13	2030-07-18
US10973836	Yes	2021-04-13	2040-09-09
US11826376	Yes	2023-11-28	2040-01-18
US11903955	Yes	2024-02-20	2040-09-09

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	65	[MSDS]
boiling point (°C)	609	[MSDS]
logP	2.7	[MSDS]

Predicted Properties

Property	Value	Source
Water Solubility	0.173 mg/mL	ALOGPS
logP	2.52	ALOGPS
logP	2.11	Chemaxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	12.57	Chemaxon
pKa (Strongest Basic)	-3	Chemaxon
Physiological Charge	0	Chemaxon
Hydrogen Acceptor Count	6	Chemaxon
Hydrogen Donor Count	4	Chemaxon
Polar Surface Area	99.38 Å²	Chemaxon
Rotatable Bond Count	6	Chemaxon
Refractivity	104.93 m³·mol^-1	Chemaxon
Polarizability	42.88 Å³	Chemaxon
Number of Rings	3	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	Yes	Chemaxon
Ghose Filter	Yes	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	Yes	Chemaxon

Predicted ADMET Features

Not Available

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0a4i-0004900000-37d5265038fa7c24626e
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0a4i-2004900000-6928e6b6d57bec67ba2d
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0a4v-0189200000-93e1a5b8bad4db74540d
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-001i-9106100000-9a396305692d475c12d7
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0a4r-4397100000-1b671b635a693b641833
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-06si-5369100000-47981f8cfa2a05bfee8a
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å²)	Source type	Source
[M-H]-	186.7367	predicted	DeepCCS 1.0 (2019)
[M+H]+	189.13226	predicted	DeepCCS 1.0 (2019)
[M+Na]+	195.51756	predicted	DeepCCS 1.0 (2019)

Targets

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Binding Properties

Property	Measurement	pH	Temperature (°C)	References
EC 50 (nM)	1.1	7.2	22	A30592
EC 50 (nM)	1.1	N/A	N/A	A30593
EC 50 (nM)	2.4	N/A	N/A	A30610
EC 50 (nM)	3	N/A	N/A	A18427
IC 50 (nM)	6.7	N/A	N/A	A30594 /A30595 /A30599
IC 50 (nM)	1.4	N/A	N/A	A30596
IC 50 (nM)	0.49	N/A	N/A	A30597 /A30598 /A30600 /A30601 /A30602 /A30604 /A30608 /A18427
IC 50 (nM)	4	N/A	N/A	A30603
IC 50 (nM)	22	N/A	N/A	A30603
IC 50 (nM)	3	N/A	N/A	A30605
IC 50 (nM)	3100	N/A	N/A	A30606
IC 50 (nM)	1.35	N/A	N/A	A30607
IC 50 (nM)	1.3	N/A	N/A	A30609 /A30611

Details1.Sodium/glucose cotransporter 2

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Inhibitor

General Function: Electrogenic Na(+)-coupled sugar symporter that actively transports D-glucose at the plasma membrane, with a Na(+) to sugar coupling ratio of 1:1 (PubMed:20980548, PubMed:28592437, PubMed:34880493, PubMed:37217492, PubMed:38057552). Transporter activity is driven by a transmembrane Na(+) electrochemical gradient set by the Na(+)/K(+) pump (PubMed:20980548, PubMed:28592437, PubMed:34880493). Unlike SLC5A1/SGLT1, requires the auxiliary protein PDZK1IP1/MAP17 for full transporter activity (PubMed:37217492). Has a primary role in D-glucose reabsorption from glomerular filtrate across the brush border of the early proximal tubules of the kidney (By similarity)
Specific Function: alpha-glucoside transmembrane transporter activity
Gene Name: SLC5A2
Uniprot ID: P31639
Uniprot Name: Sodium/glucose cotransporter 2
Molecular Weight: 72895.995 Da

References

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. [Article]

Enzymes

Details1.UDP-glucuronosyltransferase 1A9

Kind: Protein
Organism: Humans
Pharmacological action: No
Actions: Substrate

General Function: UDP-glucuronosyltransferase (UGT) that catalyzes phase II biotransformation reactions in which lipophilic substrates are conjugated with glucuronic acid to increase the metabolite's water solubility, thereby facilitating excretion into either the urine or bile (PubMed:12181437, PubMed:15470161, PubMed:15472229, PubMed:18004212, PubMed:18052087, PubMed:18674515, PubMed:19545173, PubMed:15231852, PubMed:21422672, PubMed:38211441). Essential for the elimination and detoxification of drugs, xenobiotics and endogenous compounds (PubMed:12181437, PubMed:18004212). Catalyzes the glucuronidation of endogenous estrogen hormones such as estradiol and estrone (PubMed:15472229). Involved in the glucuronidation of arachidonic acid (AA) and AA-derived eicosanoids including 15-HETE, PGB1 and F2-isoprostanes (8-iso-PGF2alpha and 5-epi-5-F2t-IsoP) (PubMed:15231852, PubMed:38211441). Glucuronates the phytochemical ferulic acid efficently at both the phenolic or the carboxylic acid group (PubMed:21422672). Also catalyzes the glucuronidation of the isoflavones genistein, daidzein, glycitein, formononetin, biochanin A and prunetin, which are phytoestrogens with anticancer and cardiovascular properties (PubMed:18052087, PubMed:19545173). Involved in the glucuronidation of the AGTR1 angiotensin receptor antagonist caderastan, a drug which can inhibit the effect of angiotensin II (PubMed:18674515). Involved in the biotransformation of 7-ethyl-10-hydroxycamptothecin (SN-38), the pharmacologically active metabolite of the anticancer drug irinotecan (PubMed:12181437, PubMed:20610558). Also metabolizes mycophenolate, an immunosuppressive agent (PubMed:15470161, PubMed:18004212)
Specific Function: enzyme binding
Gene Name: UGT1A9
Uniprot ID: O60656
Uniprot Name: UDP-glucuronosyltransferase 1A9
Molecular Weight: 59940.495 Da

References

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. [Article]

Details2.UDP-glucuronosyltransferase 2B4

Kind: Protein
Organism: Humans
Pharmacological action: No
Actions: Substrate

General Function: UDP-glucuronosyltransferase (UGT) that catalyzes phase II biotransformation reactions in which lipophilic substrates are conjugated with glucuronic acid to increase the metabolite's water solubility, thereby facilitating excretion into either the urine or bile (PubMed:18719240, PubMed:23288867). Essential for the elimination and detoxification of drugs, xenobiotics and endogenous compounds (PubMed:18719240, PubMed:23288867). Catalyzes the glucuronidation of the endogenous estrogen hormones such as estradiol and estriol (PubMed:18719240, PubMed:23288867)
Specific Function: glucuronosyltransferase activity
Gene Name: UGT2B4
Uniprot ID: P06133
Uniprot Name: UDP-glucuronosyltransferase 2B4
Molecular Weight: 60512.035 Da

References

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. [Article]

Details3.UDP-glucuronosyltransferase 2B7

Kind: Protein
Organism: Humans
Pharmacological action: No
Actions: Substrate

General Function: UDP-glucuronosyltransferase (UGT) that catalyzes phase II biotransformation reactions in which lipophilic substrates are conjugated with glucuronic acid to increase the metabolite's water solubility, thereby facilitating excretion into either the urine or bile (PubMed:10702251, PubMed:15470161, PubMed:15472229, PubMed:17442341, PubMed:18674515, PubMed:18719240, PubMed:19022937, PubMed:23288867, PubMed:23756265, PubMed:26220143, PubMed:15231852, PubMed:21422672, PubMed:38211441). Essential for the elimination and detoxification of drugs, xenobiotics and endogenous compounds (PubMed:15470161, PubMed:18674515, PubMed:23756265). Catalyzes the glucuronidation of endogenous steroid hormones such as androgens (epitestosterone, androsterone) and estrogens (estradiol, epiestradiol, estriol, catechol estrogens) (PubMed:15472229, PubMed:17442341, PubMed:18719240, PubMed:19022937, PubMed:2159463, PubMed:23288867, PubMed:26220143). Also regulates the levels of retinoic acid, a major metabolite of vitamin A involved in apoptosis, cellular growth and differentiation, and embryonic development (PubMed:10702251). Contributes to bile acid (BA) detoxification by catalyzing the glucuronidation of BA substrates, which are natural detergents for dietary lipids absorption (PubMed:23756265). Involved in the glucuronidation of arachidonic acid (AA) and AA-derived eicosanoids including 15-HETE, 20-HETE, PGE2, PGB1 and F2-isoprostanes (8-iso-PGF2alpha and 5-epi-5-F2t-IsoP) (PubMed:15231852, PubMed:38211441). Involved in the glucuronidation of the phytochemical ferulic acid at the phenolic or the carboxylic acid group (PubMed:21422672). Involved in the glucuronidation of the AGTR1 angiotensin receptor antagonist losartan, caderastan and zolarsatan, drugs which can inhibit the effect of angiotensin II (PubMed:18674515). Also metabolizes mycophenolate, an immunosuppressive agent (PubMed:15470161)
Specific Function: glucuronosyltransferase activity
Gene Name: UGT2B7
Uniprot ID: P16662
Uniprot Name: UDP-glucuronosyltransferase 2B7
Molecular Weight: 60720.15 Da

References

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. [Article]

Details4.Cytochrome P450 1A1

Kind: Protein
Organism: Humans
Pharmacological action: No
Actions: Substrate
Curator comments: Based on in vitro data with recombinant CYP isoforms

General Function: A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids, steroid hormones and vitamins (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15041462, PubMed:15805301, PubMed:18577768, PubMed:19965576, PubMed:20972997). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15041462, PubMed:15805301, PubMed:18577768, PubMed:19965576, PubMed:20972997). Catalyzes the hydroxylation of carbon-hydrogen bonds. Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2, as well as D-ring hydroxylated E1 and E2 at the C15-alpha and C16-alpha positions (PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15805301). Displays different regioselectivities for polyunsaturated fatty acids (PUFA) hydroxylation (PubMed:15041462, PubMed:18577768). Catalyzes the epoxidation of double bonds of certain PUFA (PubMed:15041462, PubMed:19965576, PubMed:20972997). Converts arachidonic acid toward epoxyeicosatrienoic acid (EET) regioisomers, 8,9-, 11,12-, and 14,15-EET, that function as lipid mediators in the vascular system (PubMed:20972997). Displays an absolute stereoselectivity in the epoxidation of eicosapentaenoic acid (EPA) producing the 17(R),18(S) enantiomer (PubMed:15041462). May play an important role in all-trans retinoic acid biosynthesis in extrahepatic tissues. Catalyzes two successive oxidative transformation of all-trans retinol to all-trans retinal and then to the active form all-trans retinoic acid (PubMed:10681376). May also participate in eicosanoids metabolism by converting hydroperoxide species into oxo metabolites (lipoxygenase-like reaction, NADPH-independent) (PubMed:21068195)
Specific Function: arachidonate monooxygenase activity
Gene Name: CYP1A1
Uniprot ID: P04798
Uniprot Name: Cytochrome P450 1A1
Molecular Weight: 58164.815 Da

References

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. [Article]

Details5.Cytochrome P450 1A2

Kind: Protein
Organism: Humans
Pharmacological action: No
Actions: Substrate
Curator comments: Based on in vitro data with recombinant CYP isoforms

General Function: A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids, steroid hormones and vitamins (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:19965576, PubMed:9435160). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:19965576, PubMed:9435160). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:11555828, PubMed:12865317). Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2 (PubMed:11555828, PubMed:12865317). Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). May act as a major enzyme for all-trans retinoic acid biosynthesis in the liver. Catalyzes two successive oxidative transformation of all-trans retinol to all-trans retinal and then to the active form all-trans retinoic acid (PubMed:10681376). Primarily catalyzes stereoselective epoxidation of the last double bond of polyunsaturated fatty acids (PUFA), displaying a strong preference for the (R,S) stereoisomer (PubMed:19965576). Catalyzes bisallylic hydroxylation and omega-1 hydroxylation of PUFA (PubMed:9435160). May also participate in eicosanoids metabolism by converting hydroperoxide species into oxo metabolites (lipoxygenase-like reaction, NADPH-independent) (PubMed:21068195). Plays a role in the oxidative metabolism of xenobiotics. Catalyzes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin (PubMed:14725854). Metabolizes caffeine via N3-demethylation (Probable)
Specific Function: caffeine oxidase activity
Gene Name: CYP1A2
Uniprot ID: P05177
Uniprot Name: Cytochrome P450 1A2
Molecular Weight: 58406.915 Da

References

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. [Article]
Forxiga Assessment report [File]

Details6.Cytochrome P450 2A6

Kind: Protein
Organism: Humans
Pharmacological action: No
Actions: Substrate
Curator comments: Based on in vitro data with recombinant CYP isoforms

General 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. Constitutes the major nicotine C-oxidase. Acts as a 1,4-cineole 2-exo-monooxygenase. Possesses low phenacetin O-deethylation activity
Specific Function: arachidonate epoxygenase activity
Gene Name: CYP2A6
Uniprot ID: P11509
Uniprot Name: Cytochrome P450 2A6
Molecular Weight: 56517.005 Da

References

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. [Article]

Details7.Cytochrome P450 2C9

Kind: Protein
Organism: Humans
Pharmacological action: No
Actions: Substrate
Curator comments: Based on in vitro data with recombinant CYP isoforms

General Function: A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids and steroids (PubMed:12865317, PubMed:15766564, PubMed:19965576, PubMed:21576599, PubMed:7574697, PubMed:9435160, PubMed:9866708). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:12865317, PubMed:15766564, PubMed:19965576, PubMed:21576599, PubMed:7574697, PubMed:9435160, PubMed:9866708). Catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) (PubMed:15766564, PubMed:19965576, PubMed:7574697, PubMed:9866708). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). Exhibits low catalytic activity for the formation of catechol estrogens from 17beta-estradiol (E2) and estrone (E1), namely 2-hydroxy E1 and E2 (PubMed:12865317). Catalyzes bisallylic hydroxylation and hydroxylation with double-bond migration of polyunsaturated fatty acids (PUFA) (PubMed:9435160, PubMed:9866708). Also metabolizes plant monoterpenes such as limonene. Oxygenates (R)- and (S)-limonene to produce carveol and perillyl alcohol (PubMed:11950794). Contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan (PubMed:25994031)
Specific Function: (R)-limonene 6-monooxygenase activity
Gene Name: CYP2C9
Uniprot ID: P11712
Uniprot Name: Cytochrome P450 2C9
Molecular Weight: 55627.365 Da

References

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. [Article]

Details8.Cytochrome P450 2D6

Kind: Protein
Organism: Humans
Pharmacological action: No
Actions: Substrate
Curator comments: Based on in vitro data with recombinant CYP isoforms

General Function: A cytochrome P450 monooxygenase involved in the metabolism of fatty acids, steroids and retinoids (PubMed:18698000, PubMed:19965576, PubMed:20972997, PubMed:21289075, PubMed:21576599). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:18698000, PubMed:19965576, PubMed:20972997, PubMed:21289075, PubMed:21576599). Catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) (PubMed:19965576, PubMed:20972997). Metabolizes endocannabinoid arachidonoylethanolamide (anandamide) to 20-hydroxyeicosatetraenoic acid ethanolamide (20-HETE-EA) and 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:18698000, PubMed:21289075). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). Catalyzes the oxidative transformations of all-trans retinol to all-trans retinal, a precursor for the active form all-trans-retinoic acid (PubMed:10681376). Also involved in the oxidative metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants
Specific Function: anandamide 11,12 epoxidase activity
Gene Name: CYP2D6
Uniprot ID: P10635
Uniprot Name: Cytochrome P450 2D6
Molecular Weight: 55768.94 Da

References

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. [Article]

Details9.Cytochrome P450 3A4

Kind: Protein
Organism: Humans
Pharmacological action: No
Actions: Substrate
Curator comments: Based on in vitro data with recombinant CYP isoforms

General Function: A cytochrome P450 monooxygenase involved in the metabolism of sterols, steroid hormones, retinoids and fatty acids (PubMed:10681376, PubMed:11093772, PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:19965576, PubMed:20702771, PubMed:21490593, PubMed:21576599). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:21490593, PubMed:21576599, PubMed:2732228). Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2, as well as D-ring hydroxylated E1 and E2 at the C-16 position (PubMed:11555828, PubMed:12865317, PubMed:14559847). Plays a role in the metabolism of androgens, particularly in oxidative deactivation of testosterone (PubMed:15373842, PubMed:15764715, PubMed:22773874, PubMed:2732228). Metabolizes testosterone to less biologically active 2beta- and 6beta-hydroxytestosterones (PubMed:15373842, PubMed:15764715, PubMed:2732228). Contributes to the formation of hydroxycholesterols (oxysterols), particularly A-ring hydroxylated cholesterol at the C-4beta position, and side chain hydroxylated cholesterol at the C-25 position, likely contributing to cholesterol degradation and bile acid biosynthesis (PubMed:21576599). Catalyzes bisallylic hydroxylation of polyunsaturated fatty acids (PUFA) (PubMed:9435160). Catalyzes the epoxidation of double bonds of PUFA with a preference for the last double bond (PubMed:19965576). Metabolizes endocannabinoid arachidonoylethanolamide (anandamide) to 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:20702771). Plays a role in the metabolism of retinoids. Displays high catalytic activity for oxidation of all-trans-retinol to all-trans-retinal, a rate-limiting step for the biosynthesis of all-trans-retinoic acid (atRA) (PubMed:10681376). Further metabolizes atRA toward 4-hydroxyretinoate and may play a role in hepatic atRA clearance (PubMed:11093772). Responsible for oxidative metabolism of xenobiotics. Acts as a 2-exo-monooxygenase for plant lipid 1,8-cineole (eucalyptol) (PubMed:11159812). Metabolizes the majority of the administered drugs. Catalyzes sulfoxidation of the anthelmintics albendazole and fenbendazole (PubMed:10759686). Hydroxylates antimalarial drug quinine (PubMed:8968357). Acts as a 1,4-cineole 2-exo-monooxygenase (PubMed:11695850). Also involved in vitamin D catabolism and calcium homeostasis. Catalyzes the inactivation of the active hormone calcitriol (1-alpha,25-dihydroxyvitamin D(3)) (PubMed:29461981)
Specific Function: 1,8-cineole 2-exo-monooxygenase activity
Gene Name: CYP3A4
Uniprot ID: P08684
Uniprot Name: Cytochrome P450 3A4
Molecular Weight: 57342.67 Da

References

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. [Article]

Transporters

Details1.ATP-dependent translocase ABCB1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Translocates drugs and phospholipids across the membrane (PubMed:2897240, PubMed:35970996, PubMed:8898203, PubMed:9038218, PubMed:35507548). Catalyzes the flop of phospholipids from the cytoplasmic to the exoplasmic leaflet of the apical membrane. Participates mainly to the flop of phosphatidylcholine, phosphatidylethanolamine, beta-D-glucosylceramides and sphingomyelins (PubMed:8898203). Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells (PubMed:2897240, PubMed:35970996, PubMed:9038218)
Specific Function: ABC-type xenobiotic transporter activity
Gene Name: ABCB1
Uniprot ID: P08183
Uniprot Name: ATP-dependent translocase ABCB1
Molecular Weight: 141477.255 Da

References

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. [Article]

Drug created at March 19, 2008 16:22 / Updated at March 23, 2025 11:45

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Dapagliflozin

Overview

Identification

Structure for Dapagliflozin (DB06292)

Pharmacology

Interactions

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Chemical Identifiers

References

Clinical Trials

Clinical Trial & Rare Diseases Add-on Data Package

Pharmacoeconomics

Properties

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Collision Cross Sections (CCS)

Targets

Binding Properties

References

Enzymes

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Transporters

References

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