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    Also known as: 1210344-57-2, Pf-04971729, Steglatro, Pf04971729, (1s,2s,3s,4r,5s)-5-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-1-(hydroxymethyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triol, Chembl1770248
    Molecular Formula
    C22H25ClO7
    Molecular Weight
    436.9  g/mol
    InChI Key
    MCIACXAZCBVDEE-CUUWFGFTSA-N
    FDA UNII
    6C282481IP
    Ertugliflozin
    Ertugliflozin belongs to the class of potent and selective inhibitors of the sodium-dependent glucose cotransporters (SGLT), more specifically the type 2 which is responsible for about 90% of the glucose reabsorption from glomerulus. This drug was developed under the collaboration of Merck and Pfizer. It was FDA approved as monotherapy and in combination with sitagliptin or metformin hydrochloride on December 22, 2017.
    1 2D Structure

    Ertugliflozin

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (1S,2S,3S,4R,5S)-5-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-1-(hydroxymethyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triol
    2.1.2 InChI
    InChI=1S/C22H25ClO7/c1-2-28-16-6-3-13(4-7-16)9-14-10-15(5-8-17(14)23)22-20(27)18(25)19(26)21(11-24,30-22)12-29-22/h3-8,10,18-20,24-27H,2,9,11-12H2,1H3/t18-,19-,20+,21-,22-/m0/s1
    2.1.3 InChI Key
    MCIACXAZCBVDEE-CUUWFGFTSA-N
    2.1.4 Canonical SMILES
    CCOC1=CC=C(C=C1)CC2=C(C=CC(=C2)C34C(C(C(C(O3)(CO4)CO)O)O)O)Cl
    2.1.5 Isomeric SMILES
    CCOC1=CC=C(C=C1)CC2=C(C=CC(=C2)[C@@]34[C@@H]([C@H]([C@@H]([C@@](O3)(CO4)CO)O)O)O)Cl
    2.2 Other Identifiers
    2.2.1 UNII
    6C282481IP
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 5-(4-chloro-3-(4-ethoxybenzyl)phenyl)-1-hydroxymethyl-6,8-dioxabicyclo(3.2.1)octane-2,3,4-triol

    2. Pf 04971729

    3. Pf-04971729

    4. Pf04971729

    5. Steglatro

    2.3.2 Depositor-Supplied Synonyms

    1. 1210344-57-2

    2. Pf-04971729

    3. Steglatro

    4. Pf04971729

    5. (1s,2s,3s,4r,5s)-5-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-1-(hydroxymethyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triol

    6. Chembl1770248

    7. Pf-04971729-00

    8. 6c282481ip

    9. (1s,2s,3s,4r,5s)-5-(4-chloro-3-(4-ethoxybenzyl)phenyl)-1-(hydroxymethyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triol

    10. Mk-8835

    11. 1,6-anhydro-1-c-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-5-c-(hydroxymethyl)-beta-l-idopyranose

    12. (1s,2s,3s,4r,5s)-5-(4-chloro-3-(4-ethoxybenzyl)phenyl)-1-hydroxymethyl-6,8-dioxabicyclo(3.2.1)octane-2,3,4-triol

    13. Pf 04971729

    14. Ertugliflozin [usan:inn]

    15. Unii-6c282481ip

    16. (1s,2s,3s,4r,5s)-5-[4-chloro-3-(4-ethoxybenzyl)phenyl]-1-hydroxymethyl-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triol

    17. Ertugliflozin [mi]

    18. Ertugliflozin [inn]

    19. Ertugliflozin (usan/inn)

    20. Ertugliflozin [usan]

    21. Pf 04971729-00

    22. Schembl181047

    23. Ertugliflozin [who-dd]

    24. Gtpl8376

    25. Pf-04971729;ertugliflozin

    26. Dtxsid40153120

    27. Ex-a407

    28. Chebi:188719

    29. Ertugliflozin [orange Book]

    30. Amy32613

    31. Bdbm50342885

    32. Mfcd21609259

    33. S5413

    34. Zinc68197809

    35. Akos025404928

    36. Stelujan Component Ertugliflozin

    37. Ccg-269087

    38. Cs-0976

    39. Db11827

    40. Segluromet Component Ertugliflozin

    41. 5-(4-chloro-3-(4-ethoxybenzyl)phenyl)-1-hydroxymethyl-6,8-dioxabicyclo(3.2.1)octane-2,3,4-triol

    42. Ac-29007

    43. As-35204

    44. Beta-l-idopyranose, 1,6-anhydro-1-c-(4-chloro-3-((4-ethoxyphenyl)methyl)phenyl)-5-c-(hydroxymethyl)-

    45. Ertugliflozin Component Of Stelujan

    46. Hy-15461

    47. Ertugliflozin Component Of Segluromet

    48. D10313

    49. J-504029

    50. Q27077223

    51. (1s,2s,3s,4r,5s)-5-(4-chloro-3-((4-ethoxyphenyl)methyl)phenyl)- 1-(hydroxymethyl)-6,8-dioxabicyclo(3.2.1)octane-2,3,4-triol

    52. (1s,2s,3s,4r,5s)-5-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-1-hydroxymethyl-6,8-dioxa-bicyclo[3.2.1]octane-2,3,4-triol

    53. (1s,2s,3s,4r,5s)-5-[4-chloro-3-(4-ethoxybenzyl)phenyl]-1-(hydroxymethyl)-6,8-dioxa-bicyclo[3.2.1]octane-2,3,4-triol

    54. (1s,5s)-1-(hydroxymethyl)-5-[3-(4-ethoxybenzyl)-4-chlorophenyl]-6,8-dioxabicyclo[3.2.1]octane-2beta,3alpha,4beta-triol

    55. .beta.-l-idopyranose, 1,6-anhydro-1-c-(4-chloro-3-((4-ethoxyphenyl)methyl)phenyl)-5-c-(hydroxymethyl)-

    2.4 Create Date
    2010-03-15
    3 Chemical and Physical Properties
    Molecular Weight 436.9 g/mol
    Molecular Formula C22H25ClO7
    XLogP31.7
    Hydrogen Bond Donor Count4
    Hydrogen Bond Acceptor Count7
    Rotatable Bond Count6
    Exact Mass436.1288808 g/mol
    Monoisotopic Mass436.1288808 g/mol
    Topological Polar Surface Area109 Ų
    Heavy Atom Count30
    Formal Charge0
    Complexity586
    Isotope Atom Count0
    Defined Atom Stereocenter Count5
    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

    Ertugliflozin as a monotherapy is indicated to improve the glycemic control in adult patients with type 2 diabetes. Ertugliflozin, in combination with metformin hydrochloride, is indicated to improve glycemic control in patients with diabetes type 2 who are not controlled on a regimen of ertugliflozin or metformin or in patients who are already treated with both ertugliflozin and metformin. The administration of ertugliflozin in combination with sitagliptin is indicated to improve glycemic control in adult patients with type 2 diabetes when treatment with ertugliflozin and sitagliptin is appropriate. It is pointed out that the use of ertugliflozin has to be an adjunct therapy to the use of diet and exercise. The type 2 diabetes mellitus is characterized by insulin resistance in muscle and liver, which results in the elevation of glucose levels in blood, or by presence of insulin deficiency. The insulin resistance is related to genetic factors, obesity, sedentary lifestyle or/and aging. This increase in the blood glucose can cause severe damage to kidney, eyes and vascular system.

    FDA Label

    Steglatro is indicated in adults aged 18 years and older with type 2 diabetes mellitus as an adjunct to diet and exercise to improve glycaemic control:

    - as monotherapy in patients for whom the use of metformin is considered inappropriate due to intolerance or contraindications.

    - in addition to other medicinal products for the treatment of diabetes.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Administration of ertugliflozin increases urinary glucose excretion which leads to a negative balance and osmotic diuresis. Thus, this antidiabetic agent has been reported to significantly reduce the body weight and blood pressure of diabetic patients.

    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 ATC Code

    A10BK04

    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

    A10BK04 - Ertugliflozin

    5.4 Absorption, Distribution and Excretion

    Absorption

    Preclinical studies showed that ertugliflozin is well absorbed and had an oral bioavailability of 70-90%. The reported Tmax occurred at 0.5-1.5 hours after dosage. Following oral administration, the Cmax and AUC appeared to be dose proportional.Administration of 15 mg reported values of Cmax and AUC of 268 ng/ml and 1193 ng h/ml respectively.

    Route of Elimination

    The total recovery of ertugliflozin was 91% and this elimination route is distributed in a ratio of 50% in the urine and 41% in feces. The recovery of the administered dose was achieved approximately 168 hours after initial administration. Urine elimination occurred very rapidly and 80% of the dosage recovered in urine was obtained after 24 hours. The eliminated dose in urine was composed of seven different major metabolites and the unchanged ertugliflozin as a minor metabolite. The elimination rate in feces was depending on the bowel movements of each patient but 98.5% of the eliminated dose in feces was obtained after 168 hours of initial dosage. This eliminated dose was formed mainly by unchanged ertugliflozin and three other minor metabolites.

    Volume of Distribution

    After oral administration of ertugliflozin, the apparent volume of distribution was reported to be 215.3 L. The steady-state volume of distribution after intravenous administration of etrugliflozin is 85.53 L.

    Clearance

    The apparent total plasma clearance rate after oral administration of ertugliflozin is 178.7 ml/min and the systemic total plasma clearance after intravenous administration is reported to be 187.2 ml/min.

    5.5 Metabolism/Metabolites

    In vitro studies showed that the metabolic profile of ertugliflozin in liver microsomes and hepatocytes is formed by reactions of monohydroxylation, O-demethylation and glucuronidation. The metabolism of ertugliflozin is proposed to be formed by 8 different metabolites found in plasma, feces and urine. In plasma, the unchanged form of ertugliflozin was found to be the major component of the administered dose. There were also other six minor metabolites identified in circulating plasma.

    5.6 Biological Half-Life

    The terminal elimination half-life of ertugliflozin is 11-17 hours.

    5.7 Mechanism of Action

    As part of a normal process, the glucose from the blood is filtered for excretion and reabsorbed in the glomerulus so less than one percent of this glucose is excreted in the urine. The reabsorption is mediated by the sodium-dependent glucose cotransporter (SGLT), mainly the type 2 which is responsible for 90% of the reabsorbed glucose. Ertugliflozin is a small inhibitor of the SGLT2 and its activity increases glucose excretion, reducing hyperglycemia without the requirement of excessive insulin secretion.

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    18-Feb-2021
    29-Aug-2024
    KGS
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