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Prestwick3_000558

Prestwick3_000558

Synopsis, Chemistry

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Also known as: 21187-98-4, Glimicron, 1-(3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-2-yl)-3-(4-methylphenyl)sulfonylurea, 1-(3-azabicyclo(3.3.0)oct-3-yl)-3-(p-tolylsulfonyl)urea, Chebi:31654, 1-(hexahydrocyclopenta(c)pyrrol-2(1h)-yl)-3-(p-tolylsulfonyl)urea

Molecular Formula

C₁₅H₂₁N₃O₃S

Molecular Weight

323.4 g/mol

InChI Key

BOVGTQGAOIONJV-UHFFFAOYSA-N

An oral sulfonylurea hypoglycemic agent which stimulates insulin secretion.

1 2D Structure

Prestwick3_000558

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

1-(3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-2-yl)-3-(4-methylphenyl)sulfonylurea

2.1.2 InChI

InChI=1S/C15H21N3O3S/c1-11-5-7-14(8-6-11)22(20,21)17-15(19)16-18-9-12-3-2-4-13(12)10-18/h5-8,12-13H,2-4,9-10H2,1H3,(H2,16,17,19)

2.1.3 InChI Key

BOVGTQGAOIONJV-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC1=CC=C(C=C1)S(=O)(=O)NC(=O)NN2CC3CCCC3C2

2.2 Synonyms

2.2.1 MeSH Synonyms

1. Diabrezide

2. Diaglyk

3. Diaikron

4. Diamicron

5. Gen Gliclazide

6. Gen-gliclazide

7. Gliklazid

8. Glyade

9. Glyclazide

10. Novo Gliclazide

11. Novo-gliclazide

12. S 1702

13. S 852

14. S-1702

15. S-852

16. S1702

17. S852

2.2.2 Depositor-Supplied Synonyms

1. 21187-98-4

2. Glimicron

3. 1-(3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-2-yl)-3-(4-methylphenyl)sulfonylurea

4. 1-(3-azabicyclo(3.3.0)oct-3-yl)-3-(p-tolylsulfonyl)urea

5. Chebi:31654

6. 1-(hexahydrocyclopenta(c)pyrrol-2(1h)-yl)-3-(p-tolylsulfonyl)urea

7. Gliclazidum [inn-latin]

8. Gliclazida [inn-spanish]

9. Gliclazida

10. N-(hexahydrocyclopenta[c]pyrrol-2(1h)-ylcarbamoyl)-4-methylbenzenesulfonamide

11. 1-[(4-methylbenzene)sulfonyl]-3-{octahydrocyclopenta[c]pyrrol-2-yl}urea

12. Nsc-758673

13. Se-1702

14. S1702;se1702

15. Dsstox_cid_3095

16. N-((hexahydrocyclopenta[c]pyrrol-2(1h)-yl)carbamoyl)-4-methylbenzenesulfonamide

17. Dsstox_rid_76872

18. Dsstox_gsid_23095

19. S-852

20. S-1702

21. N-(4-methylbenzenesulfonyl)-n'-(3-azabicyclo(3.3.0)oct-3-yl)urea

22. Glimicron (tn)

23. Smr000542971

24. Sr-01000816184

25. 1-(3-azabicyclo[3.3.0]oct-3-yl)-3-p-tolylsulphonylurea

26. Mfcd00409893

27. J3.151h

28. Gliclazide,(s)

29. Benzenesulfonamide, N-[[(hexahydrocyclopenta[c]pyrrol-2(1h)-yl)amino]carbonyl]-4-methyl-

30. Ncgc00016751-01

31. Prestwick_869

32. Cas-21187-98-4

33. Gliclazide (diamicron)

34. Spectrum_001478

35. Specplus_000870

36. Prestwick0_000558

37. Prestwick1_000558

38. Prestwick2_000558

39. Prestwick3_000558

40. Spectrum3_001862

41. Spectrum4_000598

42. Spectrum5_000753

43. Gliclazide (jp17/inn)

44. Schembl16387

45. Bspbio_000635

46. Bspbio_003304

47. Kbiogr_001096

48. Kbioss_001958

49. Mls001215197

50. Mls001304077

51. Mls001304118

52. Divk1c_006966

53. Gliclazide, Powder, >=98%

54. Spectrum1504145

55. Spectrum1505013

56. Spbio_002556

57. Bpbio1_000699

58. Chembl427216

59. Dtxsid9023095

60. Urea, 1-(hexahydrocyclopenta[c]pyrrol-2(1h)-yl)-3-(p-tolylsulfonyl)-

61. Kbio1_001910

62. Kbio2_001958

63. Kbio2_004526

64. Kbio2_007094

65. Kbio3_002806

66. 1-[3-azabicyclo[3.3.0]oct-3-yl]-3-p-toluenesulfonylurea

67. Hms1569p17

68. Hms1922d15

69. Hms2090k16

70. Hms2096p17

71. Hms2855p09

72. Hms3656c22

73. Hms3713p17

74. Hms3744o13

75. Pharmakon1600-01504145

76. Bcp21240

77. Hy-b0753

78. Tox21_110590

79. Bbl012275

80. Bdbm50103512

81. Nsc758673

82. Nsc813216

83. S2601

84. Se1702

85. Stk803142

86. Akos003237903

87. Akos016340698

88. Tox21_110590_1

89. Ab05958

90. Ccg-213918

91. Db01120

92. Ks-1067

93. Nsc-813216

94. N-[(hexahydrocyclopenta[c]pyrrol-2(1h)-ylamino)carbonyl]-4-methylbenzenesulfonamide

95. Ncgc00095107-01

96. Ncgc00095107-02

97. Ncgc00095107-03

98. Ncgc00095107-04

99. Ncgc00095107-05

100. Ncgc00095107-06

101. Ncgc00095107-09

102. Ncgc00095107-10

103. Ac-12045

104. Sbi-0052662.p002

105. Ab00053165

106. Ft-0626712

107. G0381

108. Sw196994-3

109. D01599

110. D83168

111. Ab00053165-09

112. Ab00053165_10

113. Ab00053165_11

114. 187g984

115. A815188

116. Q290001

117. J-013905

118. J-522753

119. Sr-01000816184-2

120. Sr-01000816184-3

121. Sr-01000816184-4

122. Brd-a61154809-001-04-3

123. Gliclazide, British Pharmacopoeia (bp) Reference Standard

124. Gliclazide, European Pharmacopoeia (ep) Reference Standard

125. 1-(4-methylbenzenesulfonyl)-3-{octahydrocyclopenta[c]pyrrol-2-yl}urea

126. 1-(3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-2-yl)-3-(4-methylphenyl)sulfonyl-urea

127. Benzenesulfonamide,n-[[(hexahydrocyclopenta[c]pyrrol-2(1h)-yl)amino]carbonyl]-4-methyl-

128. Benzenesulfonamide, N-[[(hexahydrocyclopenta[c]pyrrol-2(1h)-yl)amino]carbonyl]-4-methyl

2.3 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₁₅H₂₁N₃O₃S
Molecular Weight	323.4 g/mol
XLogP3	1.5
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	3
Exact Mass	323.13036271 g/mol
Monoisotopic Mass	323.13036271 g/mol
Topological Polar Surface Area	86.9 Å²
Heavy Atom Count	22
Formal Charge	0
Complexity	497
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	2
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 NIDDM in conjunction with diet and exercise.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Based on the pharmacological properties, gliclazide is a second generation sulphonylurea which acts as a hypoglycemic agent. It stimulates β cells of the islet of Langerhans in the pancreas to release insulin. It also enhances peripheral insulin sensitivity. Overall, it potentiates insulin release and improves insulin dynamics.

5.2 MeSH Pharmacological Classification

Hypoglycemic Agents

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

5.3 ATC Code

A10BB09

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

A10BB09 - Gliclazide

5.4 Absorption, Distribution and Excretion

Absorption

Rapidly and well absorbed but may have wide inter- and intra-individual variability. Peak plasma concentrations occur within 4-6 hours of oral administration.

Route of Elimination

Metabolites and conjugates are eliminated primarily by the kidneys (60-70%) and also in the feces (10-20%).

5.5 Metabolism/Metabolites

Extensively metabolized in the liver. Less than 1% of the orally administered dose appears unchanged in the urine. Metabolites include oxidized and hydroxylated derivates, as well as glucuronic acid conjugates.

Gliclazide has known human metabolites that include 6-hydroxy-gliclazide, 7-hydroxy-gliclazide, and Methylhydroxygliclazide.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

5.6 Biological Half-Life

10.4 hours. Duration of action is 10-24 hours.

5.7 Mechanism of Action

Gliclazide binds to the β cell sulfonyl urea receptor (SUR1). This binding subsequently blocks the ATP sensitive potassium channels. The binding results in closure of the channels and leads to a resulting decrease in potassium efflux leads to depolarization of the β cells. This opens voltage-dependent calcium channels in the β cell resulting in calmodulin activation, which in turn leads to exocytosis of insulin containing secretorty granules.