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    Synopsis

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    Chemistry

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    Also known as: 864070-44-0, Jardiance, Bi 10773, Bi-10773, Bi10773, Empagliflozin (bi 10773)
    Molecular Formula
    C23H27ClO7
    Molecular Weight
    450.9  g/mol
    InChI Key
    OBWASQILIWPZMG-QZMOQZSNSA-N
    FDA UNII
    HDC1R2M35U
    Empagliflozin
    Empagliflozin is an orally available competitive inhibitor of sodium-glucose co-transporter 2 (SGLT2; SLC5A2) with antihyperglycemic activity. Upon oral administration, empagliflozin selectively and potently inhibits SGLT2 in the kidneys, thereby suppressing the reabsorption of glucose in the proximal tubule. Inhibition of SGLT2 increases urinary glucose excretion by the kidneys, resulting in a reduction of plasma glucose levels in an insulin-independent manner. Inhibition of SGLT2 in the kidneys also suppresses the renal reabsorption of 1,5-anhydroglucitol (1,5AG). This lowers serum 1,5AG and neutrophil 1,5-anhydroglucitol-6-phosphate (1,5AG6P) levels, which may improve neutropenia and neutrophil dysfunction in patients with glycogen storage disease type Ib (GSD Ib). SGLT2, a transport protein exclusively expressed in the proximal renal tubules, mediates approximately 90% of renal glucose reabsorption from tubular fluid.
    Empagliflozin is a Sodium-Glucose Cotransporter 2 Inhibitor. The mechanism of action of empagliflozin is as a Sodium-Glucose Transporter 2 Inhibitor.
    1 2D Structure

    Empagliflozin

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (2S,3R,4R,5S,6R)-2-[4-chloro-3-[[4-[(3S)-oxolan-3-yl]oxyphenyl]methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol
    2.1.2 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
    2.1.3 InChI Key
    OBWASQILIWPZMG-QZMOQZSNSA-N
    2.1.4 Canonical SMILES
    C1COCC1OC2=CC=C(C=C2)CC3=C(C=CC(=C3)C4C(C(C(C(O4)CO)O)O)O)Cl
    2.1.5 Isomeric SMILES
    C1COC[C@H]1OC2=CC=C(C=C2)CC3=C(C=CC(=C3)[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)Cl
    2.2 Other Identifiers
    2.2.1 UNII
    HDC1R2M35U
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 1-chloro-4-(glucopyranos-1-yl)-2-(4-(tetrahydrofuran-3-yloxy)benzyl)benzene

    2. Bi 10773

    3. Bi-10773

    4. Bi10773

    5. Jardiance

    2.3.2 Depositor-Supplied Synonyms

    1. 864070-44-0

    2. Jardiance

    3. Bi 10773

    4. Bi-10773

    5. Bi10773

    6. Empagliflozin (bi 10773)

    7. (2s,3r,4r,5s,6r)-2-(4-chloro-3-(4-(((s)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2h-pyran-3,4,5-triol

    8. Hdc1r2m35u

    9. 1-chloro-4-(glucopyranos-1-yl)-2-(4-(tetrahydrofuran-3-yloxy)benzyl)benzene

    10. Chebi:82720

    11. (1s)-1,5-anhydro-1-(4-chloro-3-{4-[(3s)-tetrahydrofuran-3-yloxy]benzyl}phenyl)-d-glucitol

    12. (2s,3r,4r,5s,6r)-2-[4-chloro-3-({4-[(3s)-oxolan-3-yloxy]phenyl}methyl)phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol

    13. (2s,3r,4r,5s,6r)-2-[4-chloro-3-[[4-[(3s)-oxolan-3-yl]oxyphenyl]methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol

    14. (1s)-1,5-anhydro-1-c-{4-chloro-3-((4-{((3s)-oxolan-3-yl)oxy}phenyl)methyl)phenyl}-d-glucitol

    15. (2s,3r,4r,5s,6r)-2-[4-chloranyl-3-[[4-[(3s)-oxolan-3-yl]oxyphenyl]methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol

    16. D-glucitol, 1,5-anhydro-1-c-(4-chloro-3-((4-(((3s)-tetrahydro-3-furanyl)oxy)phenyl)methyl)phenyl)-, (1s)-

    17. Empagliflozin [inn]

    18. Unii-hdc1r2m35u

    19. Empagliflozin [usan:inn]

    20. Mfcd22566222

    21. Jardiance (tn)

    22. (s)-empagliflozin D4

    23. Empagliflozin [mi]

    24. Bi-10773;empagliflozin

    25. Empagliflozin [jan]

    26. Empagliflozin [usan]

    27. Empagliflozin (bi10773)

    28. Empagliflozin [vandf]

    29. Schembl899986

    30. Empagliflozin [who-dd]

    31. Gtpl4754

    32. Chembl2107830

    33. Empagliflozin (jan/usan/inn)

    34. Amy1858

    35. Ex-a414

    36. Bdbm150162

    37. Dtxsid601026093

    38. Empagliflozin [orange Book]

    39. Bbl104150

    40. S8022

    41. Stl557964

    42. Us8980829, Empagliflozin

    43. Zinc36520252

    44. Akos024464680

    45. Glyxambi Component Empagliflozin

    46. Ccg-269242

    47. Cs-0940

    48. Db09038

    49. Ds-9824

    50. Pb23119

    51. (1s)-1,5-anhydro-1-c-[4-chloro-3-[[4-[[(3s)-tetrahydro-3-furanyl]oxy]phenyl]methyl]phenyl]-d-glucitol

    52. Ac-27643

    53. Empagliflozin Component Of Glyxambi

    54. Empagliflozin Component Of Synjardy

    55. Hy-15409

    56. Trijardy Xr Component Empagliflozin

    57. Empagliflozin Component Of Trijardy Xr

    58. Sw219120-1

    59. C22194

    60. D10459

    61. A852380

    62. Au-004/43508285

    63. Q5373824

    64. Empagliflozin (bi-10773;bi 10773;bi10773)

    65. 1,5-anhydro-1-{4-chloro-3-[4-(tetrahydro-3-furanyloxy)benzyl]phenyl}hexitol

    66. (1s)-1,5-anhydro-1-c-(4-chloro-3-((4-(((3s)-oxan-3-yl)oxy)phenyl)methyl)phenyl)-d-glucitol

    67. (2s,3r,4r,5s,6r)-2-(4-chloro-3-(4-((s)-tetrahydrofuran-3-yloxy)benzyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2h-pyran-3,4,5-triol

    68. (2s,3r,4r,5s,6r)-2-(4-chloro-3-(4-((s)-tetrahydrofuran-3-yloxy)benzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2h-pyran-3,4,5-triol

    69. (2s,3r,4r,5s,6r)-2-[4-chloro-3-[[4-[(3s)-tetrahydrofuran-3-yl]oxyphenyl]methyl]phenyl]-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol

    70. 7r3

    2.4 Create Date
    2006-11-20
    3 Chemical and Physical Properties
    Molecular Weight 450.9 g/mol
    Molecular Formula C23H27ClO7
    XLogP32
    Hydrogen Bond Donor Count4
    Hydrogen Bond Acceptor Count7
    Rotatable Bond Count6
    Exact Mass450.1445309 g/mol
    Monoisotopic Mass450.1445309 g/mol
    Topological Polar Surface Area109 Ų
    Heavy Atom Count31
    Formal Charge0
    Complexity558
    Isotope Atom Count0
    Defined Atom Stereocenter Count6
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug 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. Empagliflozin is also available as a combination product with either metformin and linagliptin 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. Empagliflozin is also approved to reduce the risk of cardiovascular mortality and hospitalization in adults with heart failure with reduced ejection fraction regardless of whether or not the patient has concomitant diabetes. Empagliflozin is not approved for use in patients with type 1 diabetes.

    Type 2 diabetes mellitus

    Jardiance is indicated for the treatment of adults with insufficiently controlled type 2 diabetes mellitus as an adjunct to diet and exercise - as monotherapy when metformin is considered inappropriate due to intolerance - in addition to other medicinal products for the treatment of diabetes For study results with respect to combinations, effects on glycaemic control and cardiovascular events, and the populations studied, see sections 4. 4, 4. 5 and 5. 1.

    Heart failure

    Jardiance is indicated in adults for the treatment of symptomatic chronic heart failure.

    Treatment of type I diabetes mellitus

    Treatment of chronic kidney disease

    Prevention of cardiovascular events in patients with chronic heart failure

    Treatment of type II diabetes mellitus

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Empagliflozin lowers blood glucose levels by preventing glucose reabsorption in the kidneys, thereby increasing the amount of glucose excreted in the urine. 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. 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 - including urosepsis, pyelonephritis, mycotic infections, and even Fournier's gangrene - in both male and female patients - monitor closely for signs and symptoms of developing infection.

    5.2 MeSH Pharmacological Classification

    Sodium-Glucose Transporter 2 Inhibitors

    Compounds that inhibit SODIUM-GLUCOSE TRANSPORTER 2. They lower blood sugar by preventing the reabsorption of glucose by the kidney and are used in the treatment of TYPE 2 DIABETES MELLITUS. (See all compounds classified as Sodium-Glucose Transporter 2 Inhibitors.)

    5.3 FDA Pharmacological Classification
    5.3.1 Active Moiety
    EMPAGLIFLOZIN
    5.3.2 FDA UNII
    HDC1R2M35U
    5.3.3 Pharmacological Classes
    Sodium-Glucose Transporter 2 Inhibitors [MoA]; Sodium-Glucose Cotransporter 2 Inhibitor [EPC]
    5.4 ATC Code

    A10BK03

    A - Alimentary tract and metabolism

    A10 - Drugs used in diabetes

    A10B - Blood glucose lowering drugs, excl. insulins

    A10BK - Sodium-glucose co-transporter 2 (sglt2) inhibitors

    A10BK03 - Empagliflozin

    5.5 Absorption, Distribution and Excretion

    Absorption

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

    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.

    Volume of Distribution

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

    Clearance

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

    5.6 Metabolism/Metabolites

    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. No metabolite represented more than 10% of total drug-related material.

    5.7 Biological Half-Life

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

    5.8 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. 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. 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.

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MAHARASHTRA","supplier":"ZHEJIANG HUAHAI PHARMACEUTICAL","supplierCountry":"CHINA","foreign_port":"SHANGHAI","customer":"GLENMARK PHARMACEUTICALS","customerCountry":"INDIA","quantity":"1.00","actualQuantity":"1","unit":"KGS","unitRateFc":"1300","totalValueFC":"1316.3","currency":"USD","unitRateINR":"109720","date":"02-May-2024","totalValueINR":"109720","totalValueInUsd":"1316.3","indian_port":"Bombay Air","hs_no":"29420090","bill_no":"3305211","productDescription":"API","marketType":"REGULATED MARKET","country":"CHINA","selfForZScoreResived":"Pharma Grade","supplierPort":"SHANGHAI","supplierAddress":"XUNQIAO, LINHAI, ZHEJIANG 317024, CHINA , , ChinaSDNF China","customerAddress":"B\/2 MAHALAXMI CHAMBERS"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q2","strtotime":1719340200,"product":"EMPAGLIFLOZIN","address":"A-802, CRESCENZO, C\/38-39,,G-BLOCK","city":"MUMBAI,MAHARASHTRA","supplier":"ZHEJIANG HUAHAI PHARMACEUTICAL","supplierCountry":"CHINA","foreign_port":"SHANGHAI","customer":"ZENTIVA","customerCountry":"INDIA","quantity":"5.00","actualQuantity":"5","unit":"KGS","unitRateFc":"2000","totalValueFC":"10098.3","currency":"USD","unitRateINR":"168600","date":"26-Jun-2024","totalValueINR":"843000","totalValueInUsd":"10098.3","indian_port":"Bombay Air","hs_no":"29339990","bill_no":"4197906","productDescription":"API","marketType":"REGULATED MARKET","country":"CHINA","selfForZScoreResived":"Pharma Grade","supplierPort":"SHANGHAI","supplierAddress":"XUNQIAO , LINHAI ZHEJIANG 317024 CHINA Zhenjiang, , ChinaSDNF China","customerAddress":"A-802, CRESCENZO, C\/38-39,,G-BLOCK"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q3","strtotime":1722623400,"product":"EMPAGLIFLOZIN","address":"HETERO CORPORATE, NO. 7-2-A2,","city":"HYDERABAD","supplier":"HONOUR LABS LIMITED","supplierCountry":"INDIA","foreign_port":"HIPL SEZ","customer":"HETERO DRUGS","customerCountry":"INDIA","quantity":"3.00","actualQuantity":"3","unit":"KGS","unitRateFc":"5319.1","totalValueFC":"16094.7","currency":"USD","unitRateINR":"450000","date":"03-Aug-2024","totalValueINR":"1350000","totalValueInUsd":"16094.7","indian_port":"Vizag-HIPL SEZ","hs_no":"29321990","bill_no":"4853416","productDescription":"Re-Import","marketType":"REGULATED MARKET","country":"INDIA","selfForZScoreResived":"Pharma Grade","supplierPort":"HIPL SEZ","supplierAddress":"PLOT NO 4 HETERO INFRASTRUCTURE SEZ N.NARASAPURAM VILLAGE, NAKKAPALLY M SDNF India","customerAddress":"HETERO CORPORATE, NO. 7-2-A2,"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q3","strtotime":1727634600,"product":"EMPAGLIFLOZIN","address":"21-22, KALPATARU SQUARE, KONDIVITA","city":"ANDHERI (E), MUMBAI,MAHARASHTRA","supplier":"ZHEJIANG HUAHAI PHARMACEUTICAL","supplierCountry":"CHINA","foreign_port":"SHANGHAI","customer":"TEVA PHARMACEUTICAL INDUSTRIES","customerCountry":"INDIA","quantity":"2.00","actualQuantity":"2","unit":"KGS","unitRateFc":"1500","totalValueFC":"4240","currency":"USD","unitRateINR":"177660","date":"30-Sep-2024","totalValueINR":"355320","totalValueInUsd":"4240","indian_port":"Bombay Air","hs_no":"29420090","bill_no":"5887807","productDescription":"API","marketType":"REGULATED MARKET","country":"CHINA","selfForZScoreResived":"Pharma Grade","supplierPort":"SHANGHAI","supplierAddress":"XUNQIAO LINHAI ZHEJIANG 317024 CHIN A ZHEJIANG , , China SDNF China","customerAddress":"21-22, KALPATARU SQUARE, KONDIVITA"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q4","strtotime":1727807400,"product":"EMPAGLIFLOZIN","address":"A-802, CRESCENZO, C\/38-39,,G-BLOCK","city":"MUMBAI,MAHARASHTRA","supplier":"ZHEJIANG HUAHAI PHARMACEUTICAL","supplierCountry":"CHINA","foreign_port":"SHANGHAI","customer":"ZENTIVA","customerCountry":"INDIA","quantity":"5.00","actualQuantity":"5","unit":"KGS","unitRateFc":"2000","totalValueFC":"10068.2","currency":"USD","unitRateINR":"169200","date":"02-Oct-2024","totalValueINR":"846000","totalValueInUsd":"10068.2","indian_port":"Bombay Air","hs_no":"29339990","bill_no":"5915237","productDescription":"API","marketType":"REGULATED MARKET","country":"CHINA","selfForZScoreResived":"Pharma Grade","supplierPort":"SHANGHAI","supplierAddress":"XUNQIAO , LINHAI ZHEJIANG 317024 CH INA Zhenjiang, , China SDNF China","customerAddress":"A-802, CRESCENZO, C\/38-39,,G-BLOCK"}]
    05-Jan-2021
    23-Oct-2024
    KGS
    overview
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    Average Price (USD/KGS)

    Number of Transactions

    Total Quantity (KGS)

    Total Value (USD)

    Quantity (KGS) & Unit rate (USD/KGS) over time

    API Imports and Exports

    Importing Country Total Quantity
    (KGS)    		 Average Price
    (USD/KGS)    		 Number of Transactions

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