Empagliflozin

Identification

Summary

Empagliflozin is an SGLT2 inhibitor used to manage type 2 diabetes mellitus.

Brand Names

Glyxambi, Jardiance, Synjardy, Trijardy

Generic Name

Empagliflozin

DrugBank Accession Number

DB09038

Background

Empagliflozin is an inhibitor of sodium-glucose co-transporter-2 (SGLT2), the transporters primarily responsible for the reabsorption of glucose in the kidney.¹⁰ It is used clinically as an adjunct to diet and exercise, often in combination with other drug therapies,^15,16,13 for the management of type 2 diabetes mellitus.¹⁸

The first known inhibitor of SGLTs, phlorizin, was isolated from the bark of apple trees in 1835 and researched extensively into the 20th century, but was ultimately deemed inappropriate for clinical use given its lack of specificity and significant gastrointestinal side effects.¹² Attempts at overcoming these limitations first saw the development of O-glucoside analogs of phlorizin (e.g. remogliflozin etabonate), but these molecules proved relatively pharmacokinetically unstable. The development of C-glucoside phlorizin analogs remedied the issues observed in the previous generation, and led to the FDA approval of canagliflozin in 2013 and both dapagliflozin and empagliflozin in 2014.¹² As the most recently approved of the "flozin" drugs, empagliflozin carries the highest selectivity for SGLT2 over SGLT1 (approximately 2700-fold). Empagliflozin was further approved by the EMA in March 2022 and Health Canada in April 2022, making it the first and only approved treatment in Europe and Canada for adults with symptomatic chronic heart failure regardless of ejection fraction.^22,19

Type

Small Molecule

Groups

Approved

Structure

3D

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MOLSDF3D-SDFPDBSMILESInChI

Similar Structures

Structure for Empagliflozin (DB09038)

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Weight

Average: 450.91
Monoisotopic: 450.1445309

Chemical Formula

C₂₃H₂₇ClO₇

Synonyms

• (1S)-1,5-anhydro-1-(4-chloro-3-{4-[(3S)-tetrahydrofuran-3-yloxy]benzyl}phenyl)-D-glucitol
• 1-chloro-4-(glucopyranos-1-yl)-2-(4-(tetrahydrofuran-3-yloxy)benzyl)benzene
• Empagliflozin
• Empagliflozina
• Empagliflozine
• Empagliflozinum

External IDs

• BI 10773
• BI-10773
• BI10773

Pharmacology

Indication

Empagliflozin is indicated as an adjunct to diet and exercise to improve glycemic control in adult patients with type 2 diabetes. It is also indicated to reduce the risk of cardiovascular death in adult patients with both type 2 diabetes mellitus and established cardiovascular disease.^18,21

Empagliflozin is also available as a combination product with either metformin¹⁶ and linagliptin¹⁵ as an adjunct to diet and exercise in the management of type 2 diabetes mellitus in adults.

An extended-release combination product containing empagliflozin, metformin, and linagliptin was approved by the FDA in January 2020 for the improvement of glycemic control in adults with type 2 diabetes mellitus when used adjunctively with diet and exercise.¹³

Empagliflozin is also approved to reduce the risk of cardiovascular mortality and hospitalization due to heart failure in adult patients with heart failure.¹⁸ In Europe, empagliflozin is indicated in adults for the treatment of symptomatic chronic heart failure with reduced ejection fraction.²¹

Empagliflozin is not approved for use in patients with type 1 diabetes.

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Associated Conditions

• Cardiovascular Mortality
• Hospitalizations
• Symptomatic Congestive Heart Failure
• Type 2 Diabetes Mellitus

Associated Therapies

• Monotherapy

Contraindications & Blackbox Warnings

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Pharmacodynamics

Empagliflozin lowers blood glucose levels by preventing glucose reabsorption in the kidneys, thereby increasing the amount of glucose excreted in the urine.¹⁸ It has a relatively long duration of action requiring only once-daily dosing. Patients should be monitored closely for signs and symptoms of ketoacidosis regardless of blood glucose level as empagliflozin may precipitate diabetic ketoacidosis in the absence of hyperglycemia.¹⁸ As its mechanism of action is contingent on the renal excretion of glucose, empagliflozin may be held in cases of acute kidney injury and/or discontinued in patients who develop chronic renal disease.

The overexcretion of glucose creates a sugar-rich urogenital environment which increases the risk of urogenital infections in both male and female patients - monitor closely for signs and symptoms of developing infection.¹⁸

Mechanism of action

The vast majority of glucose filtered through the glomerulus is reabsorbed within the proximal tubule, primarily via SGLT2 (sodium-glucose linked co-transporter-2) which is responsible for ~90% of the total glucose reabsorption within the kidneys. Na⁺/K⁺-ATPase on the basolateral membrane of proximal tubular cells utilize ATP to actively pump Na+ ions into the interstitium surrounding the tubule, establishing a Na⁺ gradient within the tubular cell. SGLT2 on the apical membrane of these cells then utilize this gradient to facilitate secondary active co-transport of both Na+ and glucose out of the filtrate, thereby reabsorbing glucose back into the blood – inhibiting this co-transport, then, allows for a marked increase in glucosuria and decrease in blood glucose levels.¹⁰ Empagliflozin is a potent inhibitor of renal SGLT2 transporters located in the proximal tubules of the kidneys and works to lower blood glucose levels via an increase in glucosuria.¹⁸

Empagliflozin also appears to exert cardiovascular benefits - specifically in the prevention of heart failure - independent of its blood glucose-lowering effects, though the exact mechanism of this benefit is not precisely understood. Several theories have been posited, including the potential inhibition of Na⁺/H⁺ exchanger (NHE) 1 in the myocardium and NHE3 in the proximal tubule, reduction of pre-load via diuretic/natriuretic effects and reduction of blood pressure, prevention of cardiac fibrosis via suppression of pro-fibrotic markers, and reduction of pro-inflammatory adipokines.¹¹

Target	Actions	Organism
ASodium/glucose cotransporter 2	inhibitor	Humans

Absorption

Following oral administration, peak plasma concentrations are reached in approximately 1.5 hours (T_max). At steady-state, plasma AUC and C_max were 1870 nmol·h/L and 259 nmol/L, respectively, following therapy with empagliflozin 10mg daily and 4740 nmol·h/L and 687 nmol/L, respectively, following therapy with empagliflozin 25mg daily.¹⁸ Administration with food does not significantly affect the absorption of empagliflozin.

Volume of distribution

The estimated apparent steady-state volume of distribution is 73.8 L.¹⁸

Protein binding

Empagliflozin is approximately 86.2% protein-bound in plasma.¹⁸

Metabolism

Empagliflozin undergoes minimal metabolism. It is primarily metabolized via glucuronidation by 5'-diphospho-glucuronosyltransferases 2B7, 1A3, 1A8, and 1A9 to yield three glucuronide metabolites: 2-O-, 3-O-, and 6-O-glucuronide.¹⁸ No metabolite represented more than 10% of total drug-related material.

Hover over products below to view reaction partners

• Empagliflozin
  • Empagliflozin-2-glucuronide
  • Empagliflozin-3-glucuronide
  • Empagliflozin-6-glucuronide

Route of elimination

After oral administration of radiolabeled empagliflozin approximately 41.2% of the administered dose was found eliminated in feces and 54.4% eliminated in urine. The majority of radioactivity in the feces was due to unchanged parent drug while approximately half of the radioactivity in urine was due to unchanged parent drug.¹⁸

Half-life

The apparent terminal elimination half-life was found to be 12.4 h based on population pharmacokinetic analysis.¹⁸

Clearance

Apparent oral clearance was found to be 10.6 L/h based on a population pharmacokinetic analysis.¹⁸

Adverse Effects

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Toxicity

Experience with empagliflozin overdose is limited - employ standard symptomatic and supportive measures, as well as gastric decontamination when appropriate. The use of hemodialysis in empagliflozin overdose has not been studied but is unlikely to be of benefit given the drug's relatively high protein-binding.¹⁸

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.

• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental
• All Drugs

Drug	Interaction
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Acarbose	Empagliflozin may increase the hypoglycemic activities of Acarbose.
Acebutolol	The therapeutic efficacy of Empagliflozin can be increased when used in combination with Acebutolol.
Acetazolamide	Empagliflozin may increase the diuretic activities of Acetazolamide.
Acetohexamide	Empagliflozin may increase the hypoglycemic activities of Acetohexamide.
Acetyl sulfisoxazole	The therapeutic efficacy of Empagliflozin can be increased when used in combination with Acetyl sulfisoxazole.
Acetylsalicylic acid	The risk or severity of hypoglycemia can be increased when Acetylsalicylic acid is combined with Empagliflozin.
Albiglutide	Empagliflozin may increase the hypoglycemic activities of Albiglutide.
Alclometasone	The risk or severity of hyperglycemia can be increased when Alclometasone is combined with Empagliflozin.
Aldesleukin	The risk or severity of adverse effects can be increased when Aldesleukin is combined with Empagliflozin.
Aliskiren	The risk or severity of adverse effects can be increased when Aliskiren is combined with Empagliflozin.

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Food Interactions

• Take with or without food. Co-administration with food slightly alters pharmacokinetics, but not to a clinically significant extent.

Products

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Product Images

Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Jardiance	Tablet, film coated	10 mg	Oral	Boehringer Ingelheim	2020-12-16	Not applicable
Jardiance	Tablet, film coated	25 mg/1	Oral	A-S Medication Solutions	2014-08-01	Not applicable
Jardiance	Tablet, film coated	25 mg	Oral	Boehringer Ingelheim	2020-12-16	Not applicable
Jardiance	Tablet, film coated	25 mg/1	Oral	REMEDYREPACK INC.	2019-11-22	Not applicable
Jardiance	Tablet, film coated	10 mg/1	Oral	Cardinal Health	2014-08-01	Not applicable
Jardiance	Tablet, film coated	25 mg	Oral	Boehringer Ingelheim	2020-12-16	Not applicable
Jardiance	Tablet, film coated	10 mg	Oral	Boehringer Ingelheim	2020-12-16	Not applicable
Jardiance	Tablet, film coated	25 mg	Oral	Boehringer Ingelheim	2020-12-16	Not applicable
Jardiance	Tablet	25 mg	Oral	Boehringer Ingelheim (Canada) Ltd Ltee	2015-08-11	Not applicable
Jardiance	Tablet, film coated	10 mg	Oral	Boehringer Ingelheim	2020-12-16	Not applicable

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
Glyxambi	Empagliflozin (10 mg) + Linagliptin (5 mg)	Tablet, film coated	Oral	Boehringer Ingelheim	2020-12-16	Not applicable
Glyxambi	Empagliflozin (25 mg) + Linagliptin (5 mg)	Tablet, film coated	Oral	Boehringer Ingelheim	2020-12-16	Not applicable
Glyxambi	Empagliflozin (10 mg) + Linagliptin (5 mg)	Tablet, film coated	Oral	Boehringer Ingelheim	2020-12-16	Not applicable
Glyxambi	Empagliflozin (25 mg) + Linagliptin (5 mg)	Tablet, film coated	Oral	Boehringer Ingelheim	2020-12-16	Not applicable
Glyxambi	Empagliflozin (25 mg) + Linagliptin (5 mg)	Tablet, film coated	Oral	Boehringer Ingelheim	2020-12-16	Not applicable
Glyxambi	Empagliflozin (10 mg) + Linagliptin (5 mg)	Tablet, film coated	Oral	Boehringer Ingelheim	2020-12-16	Not applicable
Glyxambi	Empagliflozin (25 mg/1) + Linagliptin (5 mg/1)	Tablet, film coated	Oral	Boehringer Ingelheim Pharmaceuticals, Inc.	2015-01-30	Not applicable
Glyxambi	Empagliflozin (10 mg) + Linagliptin (5 mg)	Tablet, film coated	Oral	Boehringer Ingelheim	2020-12-16	Not applicable
Glyxambi	Empagliflozin (25 mg) + Linagliptin (5 mg)	Tablet, film coated	Oral	Boehringer Ingelheim	2020-12-16	Not applicable
Glyxambi	Empagliflozin (10 mg) + Linagliptin (5 mg)	Tablet, film coated	Oral	Boehringer Ingelheim	2020-12-16	Not applicable

Categories

ATC Codes

A10BD19 — Linagliptin and empagliflozin

• A10BD — Combinations of oral blood glucose lowering drugs
• A10B — BLOOD GLUCOSE LOWERING DRUGS, EXCL. INSULINS
• A10 — DRUGS USED IN DIABETES
• A — ALIMENTARY TRACT AND METABOLISM

A10BD20 — Metformin and empagliflozin

• A10BD — Combinations of oral blood glucose lowering drugs
• A10B — BLOOD GLUCOSE LOWERING DRUGS, EXCL. INSULINS
• A10 — DRUGS USED IN DIABETES
• A — ALIMENTARY TRACT AND METABOLISM

A10BK03 — Empagliflozin

• A10BK — Sodium-glucose co-transporter 2 (SGLT2) inhibitors
• A10B — BLOOD GLUCOSE LOWERING DRUGS, EXCL. INSULINS
• A10 — DRUGS USED IN DIABETES
• A — ALIMENTARY TRACT AND METABOLISM

Drug Categories

• Alimentary Tract and Metabolism
• BCRP/ABCG2 Substrates
• Benzene Derivatives
• Blood Glucose Lowering Agents
• Diuretics
• Drugs that are Mainly Renally Excreted
• Drugs Used in Diabetes
• Glycosides
• Hypotensive Agents
• OAT3/SLC22A8 Substrates
• OATP1B1/SLCO1B1 Substrates
• OATP1B3 substrates
• Oral Hypoglycemics
• P-glycoprotein substrates
• Sodium-glucose co-transporter 2 (SGLT2) inhibitors
• Sodium-glucose Cotransporter 2 (SGLT2) Inhibitors
• Sodium-Glucose Transporter 2 Inhibitors
• UGT1A3 substrates
• UGT1A9 Substrates
• UGT2B7 substrates

Chemical TaxonomyProvided by Classyfire

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 / C-glycosyl compounds / Phenoxy compounds / Phenol ethers / Alkyl aryl ethers / Chlorobenzenes / Aryl chlorides / Oxanes / Monosaccharides / Tetrahydrofurans / Secondary alcohols / Polyols / Oxacyclic compounds / Dialkyl ethers / Organochlorides / Primary alcohols / Hydrocarbon derivatives

show 7 more

Substituents

Alcohol / Alkyl aryl ether / Aromatic heteromonocyclic compound / Aryl chloride / Aryl halide / Benzenoid / C-glycosyl compound / Chlorobenzene / Dialkyl ether / Diphenylmethane / Ether / Halobenzene / Hydrocarbon derivative / Monocyclic benzene moiety / Monosaccharide / Organochloride / Organohalogen compound / Organoheterocyclic compound / Oxacycle / Oxane / Phenol ether / Phenolic glycoside / Phenoxy compound / Polyol / Primary alcohol / Secondary alcohol / Tetrahydrofuran

show 17 more

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

aromatic ether, monochlorobenzenes, C-glycosyl compound, tetrahydrofuryl ether (CHEBI:82720)

Affected organisms

• Humans and other mammals

Chemical Identifiers

UNII

HDC1R2M35U

CAS number

864070-44-0

InChI Key

OBWASQILIWPZMG-QZMOQZSNSA-N

InChI

InChI=1S/C23H27ClO7/c24-18-6-3-14(23-22(28)21(27)20(26)19(11-25)31-23)10-15(18)9-13-1-4-16(5-2-13)30-17-7-8-29-12-17/h1-6,10,17,19-23,25-28H,7-9,11-12H2/t17-,19+,20+,21-,22+,23-/m0/s1

IUPAC Name

(2S,3R,4R,5S,6R)-2-[4-chloro-3-({4-[(3S)-oxolan-3-yloxy]phenyl}methyl)phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol

SMILES

OC[C@H]1O[C@H]([C@H](O)[C@@H](O)[C@@H]1O)C1=CC=C(Cl)C(CC2=CC=C(O[C@H]3CCOC3)C=C2)=C1

References

Synthesis Reference

Wang XJ, Zhang L, Byrne D, Nummy L, Weber D, Krishnamurthy D, Yee N, Senanayake CH: Efficient synthesis of Empagliflozin, an inhibitor of SGLT-2, utilizing an AlCl3-promoted silane reduction of a beta-glycopyranoside. Org Lett. 2014 Aug 15;16(16):4090-3.

General References

1. Scheen AJ: Pharmacokinetics, Pharmacodynamics and Clinical Use of SGLT2 Inhibitors in Patients with Type 2 Diabetes Mellitus and Chronic Kidney Disease. Clin Pharmacokinet. 2015 Jul;54(7):691-708. doi: 10.1007/s40262-015-0264-4. [Article]
2. Gangadharan Komala M, Mather A: Empagliflozin for the treatment of Type 2 diabetes. Expert Rev Clin Pharmacol. 2014 May;7(3):271-9. doi: 10.1586/17512433.2014.908703. Epub 2014 Apr 9. [Article]
3. Lamos EM, Younk LM, Davis SN: Empagliflozin, a sodium glucose co-transporter 2 inhibitor, in the treatment of type 1 diabetes. Expert Opin Investig Drugs. 2014 Jun;23(6):875-82. doi: 10.1517/13543784.2014.909407. Epub 2014 Apr 19. [Article]
4. Liakos A, Karagiannis T, Athanasiadou E, Sarigianni M, Mainou M, Papatheodorou K, Bekiari E, Tsapas A: Efficacy and safety of empagliflozin for type 2 diabetes: a systematic review and meta-analysis. Diabetes Obes Metab. 2014 Oct;16(10):984-93. doi: 10.1111/dom.12307. Epub 2014 May 28. [Article]
5. Haring HU, Merker L, Seewaldt-Becker E, Weimer M, Meinicke T, Broedl UC, Woerle HJ: Empagliflozin as add-on to metformin in patients with type 2 diabetes: a 24-week, randomized, double-blind, placebo-controlled trial. Diabetes Care. 2014 Jun;37(6):1650-9. doi: 10.2337/dc13-2105. Epub 2014 Apr 10. [Article]
6. Neumiller JJ: Empagliflozin: a new sodium-glucose co-transporter 2 (SGLT2) inhibitor for the treatment of type 2 diabetes. Drugs Context. 2014 Jun 11;3:212262. doi: 10.7573/dic.212262. eCollection 2014. [Article]
7. Bogdanffy MS, Stachlewitz RF, van Tongeren S, Knight B, Sharp DE, Ku W, Hart SE, Blanchard K: Nonclinical safety of the sodium-glucose cotransporter 2 inhibitor empagliflozin. Int J Toxicol. 2014 Nov-Dec;33(6):436-49. doi: 10.1177/1091581814551648. Epub 2014 Sep 26. [Article]
8. Authors unspecified: Empagliflozin (Jardiance) for diabetes. Med Lett Drugs Ther. 2014 Oct 13;56(1453):99-100. [Article]
9. Jahagirdar V, Barnett AH: Empagliflozin for the treatment of type 2 diabetes. Expert Opin Pharmacother. 2014 Nov;15(16):2429-41. doi: 10.1517/14656566.2014.966078. [Article]
10. Kalra S: Sodium Glucose Co-Transporter-2 (SGLT2) Inhibitors: A Review of Their Basic and Clinical Pharmacology. Diabetes Ther. 2014 Dec;5(2):355-66. doi: 10.1007/s13300-014-0089-4. Epub 2014 Nov 26. [Article]
11. Verma S, McMurray JJV: SGLT2 inhibitors and mechanisms of cardiovascular benefit: a state-of-the-art review. Diabetologia. 2018 Oct;61(10):2108-2117. doi: 10.1007/s00125-018-4670-7. Epub 2018 Aug 22. [Article]
12. Choi CI: Sodium-Glucose Cotransporter 2 (SGLT2) Inhibitors from Natural Products: Discovery of Next-Generation Antihyperglycemic Agents. Molecules. 2016 Aug 27;21(9). pii: molecules21091136. doi: 10.3390/molecules21091136. [Article]
13. FDA Approved Drug Products: Trijardy XR (empagliflozin/linagliptin/metformin) extended-release tablets [Link]
14. FDA Summary Review: Empagliflozin [Link]
15. FDA Approved Drug Products: Glyxambi (empagliflozin/linagliptin) oral tablets [Link]
16. FDA Approved Drug Products: Synjardy (empagliflozin/metformin) oral tablets [Link]
17. FDA Approved Drug Products: Synjardy XR (empagliflozin/metformin) extended-release tablets [Link]
18. FDA Approved Drug Products: Jardiance (empagliflozin) oral tablets [Link]
19. Health Canada Product Monograph: Jardiance (empagliflozin) oral tablets [Link]
20. CaymanChem: Empagliflozin MSDS [Link]
21. EMA Summary of Product Characteristics: Jardiance (Empagliflozin) Oral Tablets [Link]
22. BusinessWire News: Jardiance® (empagliflozin) becomes the first and only approved treatment in Europe for adults with symptomatic chronic heart failure regardless of ejection fraction [Link]

External Links

KEGG Drug

D10459

PubChem Compound

11949646

PubChem Substance

310264986

ChemSpider

10123957

BindingDB

150162

RxNav

1545653

ChEBI

82720

ChEMBL

CHEMBL2107830

ZINC

ZINC000036520252

PharmGKB

PA166163327

PDBe Ligand

7R3

RxList

RxList Drug Page

Drugs.com

Drugs.com Drug Page

Wikipedia

Empagliflozin

PDB Entries

7vsi

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
4	Active Not Recruiting	Treatment	Dumping Syndrome / Reactive Hypoglycemia	1
4	Active Not Recruiting	Treatment	Fatty Liver, Non-alcoholic Fatty Liver Disease, NAFLD	1
4	Active Not Recruiting	Treatment	Safety Issues / Self Efficacy / Type 2 Diabetes Mellitus	1
4	Active Not Recruiting	Treatment	Type 2 Diabetes Mellitus	3
4	Completed	Basic Science	Type 2 Diabetes Mellitus	1
4	Completed	Prevention	Cardiovascular Risk / Type 2 Diabetes Mellitus	1
4	Completed	Prevention	Visceral Obesity	1
4	Completed	Treatment	(NAFLD) / Type 2 Diabetes Mellitus	1
4	Completed	Treatment	Cardiovascular Disease (CVD)	1
4	Completed	Treatment	Coronary Artery Disease (CAD) / Diabetes Mellitus / Percutaneous Coronary Intervention (PCI)	1

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage Forms

Form	Route	Strength
Tablet, film coated	Oral
Tablet, coated	Oral
Tablet, film coated	Oral	10.00 mg
Tablet, film coated	Oral	25.00 mg
Tablet	Oral	10 mg
Tablet	Oral	25 mg
Tablet, film coated	Oral
Tablet, film coated	Oral	10 mg/1
Tablet, film coated	Oral	25 mg/1
Tablet, coated	Oral	10 mg
Tablet, film coated	Oral	10 mg
Tablet, coated	Oral	25 mg
Tablet, film coated	Oral	12.5 mg
Tablet, film coated	Oral	5 mg
Tablet, delayed release	Oral
Tablet, film coated	Oral	25.00 mg
Tablet, film coated	Oral	10.0 mg
Tablet, film coated	Oral	25 mg
Tablet	Oral
Tablet, extended release	Oral

Prices

Not Available

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)	Region
USWO201416191	No	2014-04-03	2034-04-03
US7407955	No	2008-08-05	2023-08-12
US6488962	No	2002-12-03	2020-06-20
US6303661	No	2001-10-16	2017-04-24
US6890898	No	2005-05-10	2019-02-02
US7078381	No	2006-07-18	2019-02-02
US7459428	No	2008-12-02	2019-02-02
US8119648	No	2012-02-21	2023-08-12
US8178541	No	2012-05-15	2023-08-12
US8846695	No	2014-09-30	2030-06-04
US9173859	No	2015-11-03	2027-05-04
US8673927	No	2014-03-18	2027-05-04
US8883805	No	2014-11-11	2025-11-26
US9155705	No	2015-10-13	2030-05-21
US8551957	No	2013-10-08	2029-10-19
US7713938	No	2010-05-11	2027-04-15
US7579449	No	2009-08-25	2025-11-05
US9415016	No	2016-08-16	2029-04-02
US9949998	No	2018-04-24	2034-06-11
US9949997	No	2018-04-24	2034-05-17
US10022379	No	2018-07-17	2029-04-02
US10258637	No	2019-04-16	2034-04-03
US10406172	No	2019-09-10	2030-06-15
US10596120	No	2020-03-24	2032-03-07
US10610489	No	2020-04-07	2030-09-30
US11090323	No	2021-08-17	2034-04-03
US11033552	No	2021-06-15	2027-05-04

Properties

State

Solid

Experimental Properties

Property	Value	Source
water solubility	0.28 mg/mL	Canadian monograph

Predicted Properties

Property	Value	Source
Water Solubility	0.111 mg/mL	ALOGPS
logP	1.79	ALOGPS
logP	1.66	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	12.57	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	108.61 Å2	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	113.79 m3·mol-1	ChemAxon
Polarizability	46.12 Å3	ChemAxon
Number of Rings	4	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	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available

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Details1. Sodium/glucose cotransporter 2

Kind

Protein

Organism

Humans

Pharmacological action

Yes

Actions

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. Vivian EM: Sodium-glucose co-transporter 2 (SGLT2) inhibitors: a growing class of antidiabetic agents. Drugs Context. 2014 Dec 19;3:212264. doi: 10.7573/dic.212264. eCollection 2014. [Article]
2. DailyMed Label: Jardiance (empagliflozin) tablet, film coated [Link]

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Drug created at April 01, 2015 02:20 / Updated at August 09, 2022 10:05