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
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)-
| Molecular Weight | 436.9 g/mol |
|---|---|
| Molecular Formula | C22H25ClO7 |
| 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 Ų |
| 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 |
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.
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.
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.)
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
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.
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.
The terminal elimination half-life of ertugliflozin is 11-17 hours.
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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