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Chemistry

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Also known as: 83480-29-9, Basen, Glustat, Ao-128, Ao 128, A-71100

Molecular Formula

C₁₀H₂₁NO₇

Molecular Weight

267.28 g/mol

InChI Key

FZNCGRZWXLXZSZ-CIQUZCHMSA-N

FDA UNII

S77P977AG8

Voglibose is a valiolamine derivative and inhibitor of alpha-glucosidase with antihyperglycemic activity. Voglibose binds to and inhibits alpha-glucosidase, an enteric enzyme found in the brush border of the small intestines that hydrolyzes oligosaccharides and disaccharides into glucose and other monosaccharides. This prevents the breakdown of larger carbohydrates into glucose and decreases the rise in postprandial blood glucose levels.

1 2D Structure

Voglibose

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(1S,2S,3R,4S,5S)-5-(1,3-dihydroxypropan-2-ylamino)-1-(hydroxymethyl)cyclohexane-1,2,3,4-tetrol

2.1.2 InChI

InChI=1S/C10H21NO7/c12-2-5(3-13)11-6-1-10(18,4-14)9(17)8(16)7(6)15/h5-9,11-18H,1-4H2/t6-,7-,8+,9-,10-/m0/s1

2.1.3 InChI Key

FZNCGRZWXLXZSZ-CIQUZCHMSA-N

2.1.4 Canonical SMILES

C1C(C(C(C(C1(CO)O)O)O)O)NC(CO)CO

2.1.5 Isomeric SMILES

C1[C@@H]([C@@H]([C@H]([C@@H]([C@]1(CO)O)O)O)O)NC(CO)CO

2.2 Other Identifiers

2.2.1 UNII

S77P977AG8

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 3,4-dideoxy-4-((2-hydroxy-1-(hydroxymethyl)ethyl)amino)-2-c-(hydroxymethyl)-d-epi-inositol

2. Basen

3. N-(1,3-dihydroxy-2-propyl)valiolamine

2.3.2 Depositor-Supplied Synonyms

1. 83480-29-9

2. Basen

3. Glustat

4. Ao-128

5. Ao 128

6. A-71100

7. (1s,2s,3r,4s,5s)-5-((1,3-dihydroxypropan-2-yl)amino)-1-(hydroxymethyl)cyclohexane-1,2,3,4-tetraol

8. Chembl476960

9. S77p977ag8

10. 3,4-dideoxy-4-((2-hydroxy-1-(hydroxymethyl)ethyl)amino)-2-c-(hydroxymethyl)-d-epi-inositol

11. Dsstox_cid_1442

12. Dsstox_rid_76161

13. Dsstox_gsid_21442

14. (1s,2s,3r,4s,5s)-5-(1,3-dihydroxypropan-2-ylamino)-1-(hydroxymethyl)cyclohexane-1,2,3,4-tetraol

15. (1s,2s,3r,4s,5s)-5-[(1,3-dihydroxypropan-2-yl)amino]-1-(hydroxymethyl)cyclohexane-1,2,3,4-tetrol

16. Voglibosum

17. Basen Od

18. Voglibose [inn]

19. 3,4-dideoxy-4-[[2-hydroxy-1-(hydroxymethyl)ethyl]amino]-2-c-(hydroxymethyl)-d-epinositol

20. Cas-83480-29-9

21. Basen (tn)

22. Voglibose [usan:inn]

23. Voglibosum [inn-latin]

24. Voglibosa [inn-spanish]

25. N-(1,3-dihydroxy-2-propyl)valiolamine

26. Unii-s77p977ag8

27. Ccris 4540

28. Ncgc00164595-01

29. Voglibose- Bio-x

30. 3,4-dideoxy-4-[[2-hydroxy-1-(hydroxymethyl)ethyl]amino]-2-c-(hydroxymethyl)-d-epi-inositol

31. Vog

32. Voglibose [jan]

33. Voglibose [mi]

34. Voglibose [usan]

35. Voglibose [mart.]

36. Schembl5882

37. Voglibose [who-dd]

38. A 71100

39. (1s,2s,3r,4s,5s)-5-(1,3-dihydroxypropan-2-ylamino)-1-(hydroxymethyl)cyclohexane-1,2,3,4-tetrol

40. Mls003882582

41. Voglibose (jp17/usan/inn)

42. Dtxsid2021442

43. Chebi:32300

44. Bcpp000020

45. Dtxsid501031239

46. Hms3414a17

47. Hms3678a17

48. Voglibose, >=97.0% (tlc)

49. 112653-29-9

50. Hy-b0025

51. Zinc3788703

52. Tox21_112220

53. Bdbm50263044

54. S4101

55. Akos015950839

56. Tox21_112220_1

57. Ccg-267119

58. Db04878

59. Ncgc00164595-02

60. (1s,2s,3r,4s,5s)-5-{[2-hydroxy-1-(hydroxymethyl)ethyl]amino}-1-(hydroxymethyl)cyclohexane-1,2,3,4-tetrol

61. Bv164530

62. Smr002530327

63. A25630

64. D01665

65. Ab01566929_01

66. 480v299

67. Sr-01000883931

68. Q-101310

69. Q7939403

70. Sr-01000883931-1

71. Brd-k66850609-001-01-7

72. Brd-k66850609-001-07-4

73. (1r,2r,3s,4r,5r)-5-(1,3-dihydroxypropan-2-ylamino)-1-(hydroxymethyl)cyclohexane-1,2,3,4-tetraol

74. D-epi-inositol, 3,4-dideoxy-4-((2-hydroxy-1-(hydroxymethyl)ethyl)amino)-2-c-(hydroxymethyl)-

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₁₀H₂₁NO₇
Molecular Weight	267.28 g/mol
XLogP3	-4.1
Hydrogen Bond Donor Count	8
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	5
Exact Mass	267.13180201 g/mol
Monoisotopic Mass	267.13180201 g/mol
Topological Polar Surface Area	154 Å²
Heavy Atom Count	18
Formal Charge	0
Complexity	263
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

For the treatment of diabetes. It is specifically used for lowering post-prandial blood glucose levels thereby reducing the risk of macrovascular complications.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Voglibose, an alpha-glucosidase inhibitor, is a synthetic compound with potent and enduring therapeutic efficacies against disorders of sensory, motor and autonomic nerve systems due to diabetes mellitus. The drug was approved in Japan in 1994 for the treatment of diabetes, and it is under further investigation by Takeda for the treatment of impaired glucose tolerance. Alpha-glucosidase inhibitors are oral anti-diabetic drugs used for diabetes mellitus type 2 that work by preventing the digestion of complex carbohydrates (such as starch). Complex carbohydrates are normally converted into simple sugars (monosaccharides) which can be absorbed through the intestine. Hence, alpha-glucosidase inhibitors reduce the impact of complex carbohydrates on blood sugar.

5.2 MeSH Pharmacological Classification

Hypoglycemic Agents

Substances which lower blood glucose levels. (See all compounds classified as Hypoglycemic Agents.)

Glycoside Hydrolase Inhibitors

Compounds that inhibit or block the activity of GLYCOSIDE HYDROLASES such as ALPHA-AMYLASES and ALPHA-GLUCOSIDASES. (See all compounds classified as Glycoside Hydrolase Inhibitors.)

5.3 ATC Code

A - Alimentary tract and metabolism

A10 - Drugs used in diabetes

A10B - Blood glucose lowering drugs, excl. insulins

A10BF - Alpha glucosidase inhibitors

A10BF03 - Voglibose

5.4 Absorption, Distribution and Excretion

Absorption

Slowly and poorly absorbed. The reported pharmacokinetic parameters of voglibose with metformin are Cmax corresponds to 1.38 mcg/ml while AUC is 8.17 mcg.h/ml and tmax is of 2.5 hours.

5.5 Metabolism/Metabolites

Little metabolism occurs and no metabolites have as yet been identified.

5.6 Biological Half-Life

The half-life of voglibose is very similar to the one found for metformin and it is reported to be of 4.08 hours.

5.7 Mechanism of Action

Alpha-glucosidase inhibitors are saccharides that act as competitive inhibitors of enzymes needed to digest carbohydrates: specifically alpha-glucosidase enzymes in the brush border of the small intestines. The membrane-bound intestinal alpha-glucosidases hydrolyze oligosaccharides, trisaccharides, and disaccharides to glucose and other monosaccharides in the small intestine. Acarbose also blocks pancreatic alpha-amylase in addition to inhibiting membrane-bound alpha-glucosidases. Pancreatic alpha-amylase hydrolyzes complex starches to oligosaccharides in the lumen of the small intestine. Inhibition of these enzyme systems reduces the rate of digestion of complex carbohydrates. Less glucose is absorbed because the carbohydrates are not broken down into glucose molecules. In diabetic patients, the short-term effect of these drugs therapies is to decrease current blood glucose levels: the long term effect is a small reduction in hemoglobin-A1c level. (From Drug Therapy in Nursing, 2nd ed)

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API Reference Price

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