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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 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 Formula	C₂₂H₂₅ClO₇
Molecular Weight	436.9 g/mol
XLogP3	1.7
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	6
Exact Mass	436.1288808 g/mol
Monoisotopic Mass	436.1288808 g/mol
Topological Polar Surface Area	109 Å²
Heavy Atom Count	30
Formal Charge	0
Complexity	586
Isotope Atom Count	0
Defined Atom Stereocenter Count	5
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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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Biophore India Pharmaceuticals Pvt...

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