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CAS 461432-26-8

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Also known as: 461432-26-8, Bms-512148, Forxiga, Bms 512148, (2s,3r,4r,5s,6r)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2h-pyran-3,4,5-triol, Dagagflozin

Molecular Formula

C₂₁H₂₅ClO₆

Molecular Weight

408.9 g/mol

InChI Key

JVHXJTBJCFBINQ-ADAARDCZSA-N

FDA UNII

1ULL0QJ8UC

Dapagliflozin is a selective sodium-glucose co-transporter subtype 2 (SGLT2) inhibitor with antihyperglycemic activity. Dapagliflozin selectively and potently inhibits SGLT2 compared to SGLT1, which is the cotransporter of glucose in the gut.

Dapagliflozin is a Sodium-Glucose Cotransporter 2 Inhibitor. The mechanism of action of dapagliflozin is as a Sodium-Glucose Transporter 2 Inhibitor.

1 2D Structure

CAS 461432-26-8

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2S,3R,4R,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol

2.1.2 InChI

InChI=1S/C21H25ClO6/c1-2-27-15-6-3-12(4-7-15)9-14-10-13(5-8-16(14)22)21-20(26)19(25)18(24)17(11-23)28-21/h3-8,10,17-21,23-26H,2,9,11H2,1H3/t17-,18-,19+,20-,21+/m1/s1

2.1.3 InChI Key

JVHXJTBJCFBINQ-ADAARDCZSA-N

2.1.4 Canonical SMILES

CCOC1=CC=C(C=C1)CC2=C(C=CC(=C2)C3C(C(C(C(O3)CO)O)O)O)Cl

2.1.5 Isomeric SMILES

CCOC1=CC=C(C=C1)CC2=C(C=CC(=C2)[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)Cl

2.2 Other Identifiers

2.2.1 UNII

1ULL0QJ8UC

2.3 Synonyms

2.3.1 MeSH Synonyms

1. (2s,3r,4r,5s,6r)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6- (hydroxymethyl)tetrahydro-2h-pyran-3,4,5-triol

2. 2-(3-(4-ethoxybenzyl)-4-chlorophenyl)-6-hydroxymethyltetrahydro-2h-pyran-3,4,5-triol

3. Bms 512148

4. Bms-512148

5. Bms512148

6. Farxiga

7. Forxiga

2.3.2 Depositor-Supplied Synonyms

1. 461432-26-8

2. Bms-512148

3. Forxiga

4. Bms 512148

5. (2s,3r,4r,5s,6r)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2h-pyran-3,4,5-triol

6. Dagagflozin

7. (1s)-1,5-anhydro-1-c-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-d-glucitol

8. 1ull0qj8uc

9. Chembl429910

10. Chebi:85078

11. Lyn-045

12. Dapagliflozin [usan:inn]

13. (2s,3r,4r,5s,6r)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6- (hydroxymethyl)tetrahydro-2h-pyran-3,4,5-triol

14. (2s,3r,4r,5s,6r)-2-{4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl}-6-(hydroxymethyl)oxane-3,4,5-triol

15. Bms512148

16. Forxiga (tn)

17. Chembl3125458

18. D-glucitol, 1,5-anhydro-1-c-(4-chloro-3-((4-ethoxyphenyl)methyl)phenyl)-, (1s)-

19. (2s,3r,4r,5s,6r)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol

20. Dapagliflozin [usan]

21. Unii-1ull0qj8uc

22. Bms5121458

23. S1548_selleck

24. C-aryl Glucoside, 6

25. Dapagliflozin [mi]

26. Dapagliflozin [inn]

27. Dapagliflozin (usan/inn)

28. 2-(3-(4-ethoxybenzyl)-4-chlorophenyl)-6-hydroxymethyltetrahydro-2h-pyran-3,4,5-triol

29. Dapagliflozin [vandf]

30. Schembl157820

31. Dapagliflozin [who-dd]

32. Gtpl4594

33. Bdbm20880

34. Dtxsid20905104

35. Ex-a005

36. Bcpp000265

37. Dapagliflozin [orange Book]

38. Amy18541

39. Zinc3819138

40. Bdbm50448923

41. Mfcd13182359

42. S1548

43. Qternmet Component Dapaglifozin

44. Akos005145763

45. Dapagliflozin Component Qternmet

46. Bcp9000583

47. Bl-0052

48. Ccg-229917

49. Cs-0781

50. Db06292

51. Ex-7214

52. Ncgc00250402-09

53. Ac-24699

54. Bd164346

55. Hy-10450

56. Qternmet Xr Component Dapagliflozin

57. Dapagliflozin Component Of Qternmet Xr

58. A25150

59. C22193

60. D08897

61. 432d268

62. Q409898

63. J-500392

64. Brd-k58160573-001-01-3

65. Brd-k58160573-001-05-4

66. 1-[3-(beta-d-glucopyranosyl)-6-chlorobenzyl]-4-ethoxybenzene

67. (1s)-1,5-anhydro-1-[4-chloro-3-(4-ethoxybenzyl)phenyl]-d-glucitol

68. (2s, 3r, 4r, 5s, 6r)-2-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

69. (2s,3r,4r,5s,6r)-2-(3-(4-ethoxybenzyl)-4-chlorophenyl)-6-(hydroxymethyl)-tetrahydro-2h-pyran-3,4,5-triol

70. (2s,3r,4r,5s,6r)-2-(3-(4-ethoxybenzyl)-4-chlorophenyl)-6-(hydroxymethyl)-tetrahydro-2h-pyran-3,4,5-triol;bms-512148

71. (2s,3r,4r,5s,6r)-2-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

2.4 Create Date

2006-10-25

3 Chemical and Physical Properties

Molecular Formula	C₂₁H₂₅ClO₆
Molecular Weight	408.9 g/mol
XLogP3	2.3
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	6
Exact Mass	408.1339662 g/mol
Monoisotopic Mass	408.1339662 g/mol
Topological Polar Surface Area	99.4 Å²
Heavy Atom Count	28
Formal Charge	0
Complexity	472
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 Information

1 of 3
Drug Name	FARXIGA
Active Ingredient	DAPAGLIFLOZIN
Company	ASTRAZENECA AB (Application Number: N202293. Patents: 6414126, 6515117, 6936590, 7456254, 7851502, 7919598, 8221786, 8329648, 8361972, 8431685, 8461105, 8501698, 8685934, 8716251, 8721615, 8906851, 9198925, 9238076)

2 of 3
Drug Name	XIGDUO XR
Active Ingredient	DAPAGLIFLOZIN; METFORMIN HYDROCHLORIDE
Company	ASTRAZENECA AB (Application Number: N205649. Patents: 6414126, 6515117, 6936590, 7919598, 8501698, 8685934, 9198925, 9616028)

3 of 3
Drug Name	QTERN
Active Ingredient	DAPAGLIFLOZIN; SAXAGLIPTIN HYDROCHLORIDE
Company	ASTRAZENECA AB (Application Number: N209091. Patents: 6414126, 6515117, 6936590, 7919598, 8221786, 8361972, 8501698, 8628799, 8716251, 9198925, RE44186)

4.2 Drug Indication

Dapagliflozin is indicated to improve glycemic control in adult patients with type 2 diabetes mellitus along with diet and exercise.

FDA Label

Forxiga is indicated in adults and children aged 10 years and above for the treatment of 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 type 2 diabetes.

For study results with respect to combination of therapies, effects on glycaemic control, cardiovascular and renal events, and the populations studied.

Heart failure

- Forxiga is indicated in adults for the treatment of symptomatic chronic heart failure with reduced ejection fraction.

Chronic kidney disease

- Forxiga is indicated in adults for the treatment of chronic kidney disease.

Type 2 diabetes mellitus

Edistride is indicated in adults and children aged 10 years and above for the treatment of 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 type 2 diabetes.

For study results with respect to combination of therapies, effects on glycaemic control, cardiovascular and renal events, and the populations studied, see sections 4. 4, 4. 5 and 5. 1.

Heart failure

Edistride is indicated in adults for the treatment of symptomatic chronic heart failure with reduced ejection fraction.

Chronic kidney disease

Edistride is indicated in adults for the treatment of chronic kidney disease.

Treatment of chronic kidney disease

Prevention of cardiovascular events in patients with chronic heart failure

Treatment of type I diabetes mellitus

Treatment of type II diabetes mellitus

Treatment of ischaemic heart disease

Treatment of Coronavirus disease 2019 (COVID-19)

5 Pharmacology and Biochemistry

5.1 Pharmacology

Dapagliflozin inhibits the sodium-glucose contransporter 2(SGLT2) which is primarily located in the proximal tubule of the nephron. SGLT2 facilitates 90% of glucose resorption in the kidneys and so its inhibition allows for glucose to be excreted in the urine. This excretion allows for better glycemic control and potentially weight loss in patients with type 2 diabetes mellitus.

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

DAPAGLIFLOZIN

5.3.2 FDA UNII

1ULL0QJ8UC

5.3.3 Pharmacological Classes

Sodium-Glucose Transporter 2 Inhibitors [MoA]; Sodium-Glucose Cotransporter 2 Inhibitor [EPC]

5.4 ATC Code

A10BK01

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

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

A10BK01 - Dapagliflozin

5.5 Absorption, Distribution and Excretion

Absorption

Oral dapagliflozin reaches a maximum concentration within 1 hour of administration when patients have been fasting. When patients have consumed a high fat meal, the time to maximum concentration increases to 2 hours and the maximum concentration decreases by half though a dose adjustment is not necessary. Oral dapagliflozin is 78% bioavailable.

Route of Elimination

75.2% of dapagliflozin is recovered in the urine with 1.6% of the dose unchanged by metabolism. 21% of the dose is excreted in the feces with 15% of the dose unchanged by metabolism.

Volume of Distribution

118L.

Clearance

Oral plasma clearance was 4.9 mL/min/kg, and renal clearance was 5.6 mL/min.

5.6 Metabolism/Metabolites

Dapagliflozin is primarily glucuronidated to become the inactive 3-O-glucuronide metabolite(60.7%). Dapagliflozin also produces another minor glucuronidated metabolite(5.4%), a de-ethylated metabolite(<5%), and a hydroxylated metabolite(<5%). Metabolism of dapagliflozin is mediated by cytochrome p-450(CYP)1A1, CYP1A2, CYP2A6, CYP2C9, CYP2D6, CYP3A4, uridine diphosphate glucuronyltransferase(UGT)1A9, UGT2B4, and UGT2B7. Glucuronidation to the major metabolite is mediated by UGT1A9.

5.7 Biological Half-Life

13.8h.

5.8 Mechanism of Action

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