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Prestwick2_000991

Prestwick2_000991

Synopsis, Chemistry

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Also known as: 33342-05-1, Glurenorm, Gliquidonum, Ardf 26, Beglynor, Gliquidone (inn)

Molecular Formula

C₂₇H₃₃N₃O₆S

Molecular Weight

527.6 g/mol

InChI Key

LLJFMFZYVVLQKT-UHFFFAOYSA-N

FDA UNII

C7C2QDD75P

Gliquidone is a potent, second-generation sulfonylurea with antihyperglycemic activity. Like other second-generation compounds, gliquidone exerts greater binding affinity to SUR1 and increased potency compared to first-generation compounds. In addition, this agent exerts peroxisome proliferator-activated receptor (PPAR) gamma agonistic activity.

1 2D Structure

Prestwick2_000991

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

1-cyclohexyl-3-[4-[2-(7-methoxy-4,4-dimethyl-1,3-dioxoisoquinolin-2-yl)ethyl]phenyl]sulfonylurea

2.1.2 InChI

InChI=1S/C27H33N3O6S/c1-27(2)23-14-11-20(36-3)17-22(23)24(31)30(25(27)32)16-15-18-9-12-21(13-10-18)37(34,35)29-26(33)28-19-7-5-4-6-8-19/h9-14,17,19H,4-8,15-16H2,1-3H3,(H2,28,29,33)

2.1.3 InChI Key

LLJFMFZYVVLQKT-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC1(C2=C(C=C(C=C2)OC)C(=O)N(C1=O)CCC3=CC=C(C=C3)S(=O)(=O)NC(=O)NC4CCCCC4)C

2.2 Other Identifiers

2.2.1 UNII

C7C2QDD75P

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Ar-df 26

2. Beglynor

3. Beglynora

4. Glikvidon

5. Gliquidone, Calcium Salt

6. Gliquidone, Monosodium Salt

7. Glurenor

8. Glurenorm

9. Glycvidon

2.3.2 Depositor-Supplied Synonyms

1. 33342-05-1

2. Glurenorm

3. Gliquidonum

4. Ardf 26

5. Beglynor

6. Gliquidone (inn)

7. Ardf-26

8. 1-cyclohexyl-3-[4-[2-(7-methoxy-4,4-dimethyl-1,3-dioxoisoquinolin-2-yl)ethyl]phenyl]sulfonylurea

9. C7c2qdd75p

10. N-(cyclohexylcarbamoyl)-4-(2-(7-methoxy-4,4-dimethyl-1,3-dioxo-3,4-dihydroisoquinolin-2(1h)-yl)ethyl)benzenesulfonamide

11. Ncgc00016819-01

12. Gliquidona

13. Gliquidone [inn]

14. Cas-33342-05-1

15. Dsstox_cid_3096

16. Dsstox_rid_76873

17. Dsstox_gsid_23096

18. Gliquidonum [inn-latin]

19. 3-cyclohexyl-1-[4-[2-(7-methoxy-4,4-dimethyl-1,3-dioxo-isoquinolin-2-yl)ethyl]phenyl]sulfonyl-urea

20. Gliquidona [inn-spanish]

21. Ardf 26 Se

22. Ar-df 26

23. Glurenorm (tn)

24. 1-cyclohexyl-3-({4-[2-(7-methoxy-4,4-dimethyl-1,3-dioxo-1,2,3,4-tetrahydroisoquinolin-2-yl)ethyl]benzene}sulfonyl)urea

25. Smr000685793

26. Gliquidone [inn:ban]

27. Einecs 251-463-2

28. Mfcd00631870

29. Unii-c7c2qdd75p

30. Brn 1559726

31. Gliquidon

32. Gliquidone,(s)

33. Gliquidone, 98%

34. Gliquidone [mi]

35. Prestwick0_000991

36. Prestwick1_000991

37. Prestwick2_000991

38. Prestwick3_000991

39. Gliquidone [mart.]

40. Gliquidone [who-dd]

41. Oprea1_069443

42. Schembl37769

43. Bspbio_001081

44. 1-cyclohexyl-3-((p-(2-(3,4-dihydro-7-methoxy-4,4-dimethyl-1,3-dioxo-2(1h)-isoquinolyl)ethyl)phenyl)sulfonyl)urea

45. 1-cyclohexyl-3-(p-beta-(4,4-dimethyl-2-methoxy-1,3-(2h,4h)-isoquinolinedione-2-yl)phenethyl)sulfonylurea

46. Benzenesulfonamide, N-((cyclohexylamino)carbonyl)-4-(2-(3,4-dihydro-7-methoxy-4,4-dimethyl-1,3-dioxo-2(1h)-isoquinolinyl)ethyl)-

47. Mls000881123

48. Mls000881174

49. Mls002154087

50. Spbio_002972

51. Bpbio1_001191

52. Chembl383634

53. Dtxsid4023096

54. Chebi:93416

55. Hms1571g03

56. Hms2098g03

57. Hms2964j06

58. Hms3652o05

59. Hms3715g03

60. Act06290

61. Bcp11927

62. Hy-b1114

63. Zinc1482077

64. Tox21_110629

65. Bdbm50248247

66. Akos001037880

67. Tox21_110629_1

68. Ccg-220991

69. Cs-4646

70. Db01251

71. Ks-5239

72. Ncgc00016819-02

73. Ncgc00016819-03

74. Ncgc00016819-05

75. Ncgc00016819-06

76. Ncgc00179315-01

77. Ac-23356

78. N-[(cyclohexylamino)carbonyl]-4-{2-[4,4-dimethyl-7-(methyloxy)-1,3-dioxo-3,4-dihydroisoquinolin-2(1h)-yl]ethyl}benzenesulfonamide

79. N-(cyclohexylcarbamoyl)-4-(2-(7-methoxy-

80. Ab00513989

81. Ft-0630570

82. G0332

83. S3151

84. Sw197285-3

85. D02430

86. T72318

87. 4,4-dimethyl-1,3-dioxo-3,4-dihydroisoquinolin

88. Ab00513989_07

89. 342g051

90. A821736

91. Sr-01000833866

92. J-019153

93. Q5569924

94. Sr-01000833866-2

95. Brd-k80396088-001-03-9

96. 1-cyclohexyl-3-(((p-(2-(3,4-dihydro-7-methoxy-4,4-dimethyl-1,3-dioxo-2(1h)-isoquinolyl)ethyl)phenyl)sulfonyl)urea

97. 1-cyclohexyl-3-[4-[2-(7-methoxy-4,4-dimethyl-1,3-dioxo-2-isoquinolinyl)ethyl]phenyl]sulfonylurea

98. 1-cyclohexyl-3-[4-[2-(7-methoxy-4,4-dimethyl-1,3-dioxo-2-isoquinolyl)ethyl]phenyl]sulfonyl-urea;gliquidone

99. 3-cyclohexyl-1-({4-[2-(7-methoxy-4,4-dimethyl-1,3-dioxo-1,2,3,4-tetrahydroisoquinolin-2-yl)ethyl]benzene}sulfonyl)urea

100. N-cyclohexylcarbamoyl-4-[2-(7-methoxy-4,4-dimethyl-1,3-dioxo-1,2,3,4- Tetrahydroisoquinolin-2-yl)ethyl]benzenesulfonamide

2.4 Create Date

2005-07-11

3 Chemical and Physical Properties

Molecular Formula	C₂₇H₃₃N₃O₆S
Molecular Weight	527.6 g/mol
XLogP3	4.6
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	7
Exact Mass	527.20900695 g/mol
Monoisotopic Mass	527.20900695 g/mol
Topological Polar Surface Area	130 Å²
Heavy Atom Count	37
Formal Charge	0
Complexity	948
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
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

Used in the treatment of diabetes mellitus type 2.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Gliquidone is an anti-diabetic drug in the sulfonylurea class. In patients with diabetes mellitus, there is a deficiency or absence of a hormone manufactured by the pancreas called insulin. Insulin is the main hormone responsible for the control of sugar in the blood. Gliquidone is an antidiabetic medication which is used in those patients with adult maturity onset or non-insulin dependent diabetes (NIDDM). It works by lowering blood sugar levels by stimulating the production and release of insulin from the pancreas. It also promotes the movement of sugar from the blood into the cells in the body which need it.

5.2 MeSH Pharmacological Classification

Hypoglycemic Agents

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

5.3 ATC Code

A10BB08

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

A10BB - Sulfonylureas

A10BB08 - Gliquidone

5.4 Biological Half-Life

The mean terminal half-life was approximately 8 hours (range 5.7-9.4 hours)

5.5 Mechanism of Action

The mechanism of action of gliquidone in lowering blood glucose appears to be dependent on stimulating the release of insulin from functioning pancreatic beta cells, and increasing sensitivity of peripheral tissues to insulin. Gliquidone likely binds to ATP-sensitive potassium channel receptors on the pancreatic cell surface, reducing potassium conductance and causing depolarization of the membrane. Membrane depolarization stimulates calcium ion influx through voltage-sensitive calcium channels. This increase in intracellular calcium ion concentration induces the secretion of insulin.