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Chemistry

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Also known as: 135062-02-1, Prandin, Novonorm, Gluconorm, Ag-ee 623 zw, Ag-ee 388 zw
Molecular Formula
C27H36N2O4
Molecular Weight
452.6  g/mol
InChI Key
FAEKWTJYAYMJKF-QHCPKHFHSA-N
FDA UNII
668Z8C33LU

Repaglinide
Repaglinide is a nonsulfonylurea insulin secretagogue belonging to the melgitinide class with hypoglycemic activity. Repaglinide is rapidly absorbed and has a rapid onset and short duration of action. This agent is metabolized in the liver by CYP2C8 and CYP3A4 and its metabolites are excreted in the bile. Repaglinide has a half-life of one hour.
Repaglinide is a Glinide. The mechanism of action of repaglinide is as a Potassium Channel Antagonist.
1 2D Structure

Repaglinide

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-ethoxy-4-[2-[[(1S)-3-methyl-1-(2-piperidin-1-ylphenyl)butyl]amino]-2-oxoethyl]benzoic acid
2.1.2 InChI
InChI=1S/C27H36N2O4/c1-4-33-25-17-20(12-13-22(25)27(31)32)18-26(30)28-23(16-19(2)3)21-10-6-7-11-24(21)29-14-8-5-9-15-29/h6-7,10-13,17,19,23H,4-5,8-9,14-16,18H2,1-3H3,(H,28,30)(H,31,32)/t23-/m0/s1
2.1.3 InChI Key
FAEKWTJYAYMJKF-QHCPKHFHSA-N
2.1.4 Canonical SMILES
CCOC1=C(C=CC(=C1)CC(=O)NC(CC(C)C)C2=CC=CC=C2N3CCCCC3)C(=O)O
2.1.5 Isomeric SMILES
CCOC1=C(C=CC(=C1)CC(=O)N[C@@H](CC(C)C)C2=CC=CC=C2N3CCCCC3)C(=O)O
2.2 Other Identifiers
2.2.1 UNII
668Z8C33LU
2.3 Synonyms
2.3.1 MeSH Synonyms

1. (+)-2-ethoxy-alpha-(((s)-alpha-isobutyl-o-piperidinobenzyl)carbamoyl)-p-toluic Acid

2. (+)-repaglinide

3. (-)-repaglinide

4. (s)-2-ethoxy-4-(2-((3-methyl-1-(2-(1-piperidinyl)-phenyl)butyl)amino)-2-oxoethyl)-benzoic Acid

5. 2-ethoxy-4-(2-(((1r)-3-methyl-1-(2-(1-piperidinyl)phenyl)butyl)amino)-2-oxoethyl)benzoic Acid

6. 2-ethoxy-4-(2-((3-methyl-1-(2-(1-piperidinyl)phenyl)butyl)amino)-2-oxoethyl)benzoic Acid

7. 2-ethoxy-n-(alpha-(2-methyl-1-propyl)-2-piperidinobenzyl)-4-carbamoylmethylbenzoic Acid

8. Ag-ee 388

9. Ag-ee 388 Zw

10. Ag-ee 623 Zw

11. Ag-ee 624zw

12. Ag-ee-623-zw

13. Ag-ee-623zw

14. Ag-ee-624zw

15. Agee-623zw

16. Gluconorm

17. Novonorm

18. Prandin

19. Repa-glinide

20. Repaglinide Impurity E

21. Repaglinide Related Compound E

22. Repaglinide, (+-)-isomer

2.3.2 Depositor-Supplied Synonyms

1. 135062-02-1

2. Prandin

3. Novonorm

4. Gluconorm

5. Ag-ee 623 Zw

6. Ag-ee 388 Zw

7. Repaglinidum [inn-latin]

8. Repaglinida [inn-spanish]

9. Agee-623zw

10. (s)-2-ethoxy-4-(2-((3-methyl-1-(2-(piperidin-1-yl)phenyl)butyl)amino)-2-oxoethyl)benzoic Acid

11. C27h36n2o4

12. Ag-ee 623zw

13. Ag-ee-623zw

14. Ag-ee-623-zw

15. 2-ethoxy-4-[2-[[(1s)-3-methyl-1-(2-piperidin-1-ylphenyl)butyl]amino]-2-oxoethyl]benzoic Acid

16. A10bx02

17. Nsc-759893

18. Chembl1272

19. (s)-(+)-2-ethoxy-4-[n-[1-(2-piperidinophenyl)-3-methyl-1-butyl]aminocarbonylmethyl]benzoic Acid

20. (s)-2-ethoxy-4-(2-(3-methyl-1-(2-(piperidin-1-yl)phenyl)butylamino)-2-oxoethyl)benzoic Acid

21. Chebi:8805

22. (-)-repaglinide

23. 668z8c33lu

24. 2-ethoxy-4-({[(1s)-3-methyl-1-[2-(piperidin-1-yl)phenyl]butyl]carbamoyl}methyl)benzoic Acid

25. 2-ethoxy-4-[2-({(1s)-3-methyl-1-[2-(piperidin-1-yl)phenyl]butyl}amino)-2-oxoethyl]benzoic Acid

26. Ncgc00016978-01

27. Repaglinida

28. Repaglinidum

29. Repaglinide [usan]

30. Cas-135062-02-1

31. Actulin

32. Surepost

33. Reglin

34. Mfcd00906179

35. 2-ethoxy-4-(2-{[(1s)-3-methyl-1-(2-piperidin-1-ylphenyl)butyl]amino}-2-oxoethyl)benzoic Acid

36. Smr000466305

37. Prandin (tn)

38. Repaglinide (jan/usp/inn)

39. Unii-668z8c33lu

40. Ag-ee-623 Zw

41. Ag-ee-388

42. Repaglinide,(s)

43. Smp-508

44. Surepost (tn)

45. (s)-2-ethoxy-4-[2-[[3-methyl-1-[2-(piperidin-1-yl)phenyl]butyl]amino]-2-oxoethyl]benzoic Acid

46. Bjx

47. Repaglinide [usan:usp:inn:ban]

48. Repaglinide- Bio-x

49. Nn-623

50. (+)-2-ethoxy-alpha-(((s)-alpha-isobutyl-o-piperidinobenzyl)carbamoyl)-p-toluic Acid

51. 2-ethoxy-4-[2-[[(1s)-3-methyl-1-[2-(1-piperidinyl)phenyl]butyl]amino]-2-oxoethyl]benzoic Acid

52. 111ge012

53. Repaglinide [mi]

54. Prestwick0_001046

55. Prestwick1_001046

56. Prestwick2_001046

57. Prestwick3_001046

58. Repaglinide [inn]

59. Repaglinide [jan]

60. Dsstox_cid_3552

61. Repaglinide [vandf]

62. (s)-2-ethoxy-4-(2-((methyl-1-(2-(1-piperidinyl)phenyl)butyl)amino)-2-oxoethyl)-benzoic Acid

63. Dsstox_rid_77078

64. Repaglinide [mart.]

65. Dsstox_gsid_23552

66. Schembl16137

67. Bspbio_000972

68. Repaglinide [usp-rs]

69. Repaglinide [who-dd]

70. Mls000759407

71. Mls001076684

72. Mls001424111

73. Mls006011560

74. Bidd:gt0338

75. Spbio_002906

76. Repaglinide [ema Epar]

77. Bpbio1_001070

78. Gtpl6841

79. Dtxsid3023552

80. Repaglinide [orange Book]

81. Repaglinide For System Suitability

82. Hms1571a14

83. Hms2051n08

84. Hms2094c07

85. Hms2098a14

86. Hms2231m21

87. Hms3414d09

88. Hms3678d09

89. Hms3715a14

90. Pharmakon1600-01506035

91. Repaglinide [ep Monograph]

92. Repaglinide [usp Monograph]

93. Bcp04250

94. Zinc3798537

95. Tox21_110721

96. Ac-726

97. Bdbm50153520

98. Nsc759893

99. S1426

100. Stk629501

101. Akos005561792

102. Repaglinide, >=98% (hplc), Solid

103. Bs-1010

104. Ccg-101013

105. Cs-0979

106. Db00912

107. Nc00263

108. Nsc 759893

109. Repaglinide 100 Microg/ml In Methanol

110. Ncgc00016978-02

111. Ncgc00016978-04

112. Ncgc00016978-05

113. Benzoic Acid, 2-ethoxy-4-(2-((3-methyl-1-(2-(1-piperidinyl)phenyl)butyl)amino)-2-oxoethyl)-, (s)-

114. Br164332

115. Hy-15209

116. Sbi-0206942.p001

117. Ab00514019

118. Am20090697

119. R0179

120. Sw197344-4

121. 62r021

122. C07670

123. D00594

124. F15001

125. Ab00514019-09

126. Ab00514019_10

127. Ab00514019_11

128. A806877

129. Sr-01000759404

130. Q-201663

131. Q2195995

132. Sr-01000759404-4

133. Brd-k82846253-001-03-0

134. Z1777729210

135. Repaglinide, European Pharmacopoeia (ep) Reference Standard

136. Repaglinide, United States Pharmacopeia (usp) Reference Standard

137. (s)-(+)-2-ethoxy-4-(2-oxo-2-[(alpha-isobutyl-2-piperidinobenzyl)amino]ethyl)-benzoic Acid

138. Repaglinide For System Suitability, European Pharmacopoeia (ep) Reference Standard

139. (+)-2-ethoxy-.alpha.-(((s)-.alpha.-isobutyl-o-piperidinobenzyl)carbamoyl)-p-toluic Acid

140. (2s)-2-[[(2s)-2-[[(2s,3s)-2-[[(2s)-4-amino-2-[[(2s,3s)-2-[[(2s)-2-[[2-[[(2s)-2-[[(2s)-1-[(2s)-2-[[(2s)-2-amino-5-guanidino-pentanoyl]amino]-4-carboxy-butanoyl]pyrrolidine-2-carbonyl]amino]propanoyl]amino]acetyl]amino]-4-methyl-pentanoyl]amino]-3-methyl-pe;(s)-2-ethoxy-4-[2-[[3-methyl-1-[2-(1-piperidyl)phenyl]butyl]amino]-2-oxoethyl]benzoic Acid

141. (s)-2-ethoxy-4-(2-((3-methyl-1-(2-(piperidin-1-yl)phenyl)butyl)amino)-2-oxoethyl)benzoicacid

142. (s)-2-ethoxy-4-(2-(methyl-1-(2-(1-piperidinyl)phenyl)butylamino)-2-oxoethyl)-benzoic Acid

143. (s)-2-ethoxy-4-[2-[[[(1s)-3-methyl-1-[2-(1-piperidinyl)phenyl]butyl]amino]-2-oxoethyl]benzoic Acid

144. (s)-2-ethoxy-4-[n-(1-(2-piperidino-phenyl)-3-methyl-1-butyl)-aminocarbonylmethyl]-benzoic Acid

145. 2-ethoxy-4-[2-[[(1s)-3-methyl-1-[2-(1-piperidinyl)phenyl]butyl]amino]-2-oxoethyl]benz Oic Acid

146. 2-ethoxy-4-{[(s)-3-methyl-1-(2-piperidin-1-yl-phenyl)-butylcarbamoyl]-methyl}-benzoic Acid

147. Benzoic Acid, 2-ethoxy-4-[2-[[(1s)-3-methyl-1-[2-(1-piperidinyl)phenyl]butyl]amino]-2-oxoethyl]-

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 452.6 g/mol
Molecular Formula C27H36N2O4
XLogP35.2
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count5
Rotatable Bond Count10
Exact Mass452.26750763 g/mol
Monoisotopic Mass452.26750763 g/mol
Topological Polar Surface Area78.9 Ų
Heavy Atom Count33
Formal Charge0
Complexity619
Isotope Atom Count0
Defined Atom Stereocenter Count1
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 4  
Drug NamePrandin
PubMed HealthRepaglinide (By mouth)
Drug LabelPRANDIN(repaglinide) is an oral blood glucose-lowering drug of the meglitinide clab used in the management of type 2 diabetes mellitus (also known as non-insulin dependent diabetes mellitus or NIDDM). Repaglinide, S(+)2-ethoxy-4(2((3-methyl-1-(2-(1-...
Active IngredientRepaglinide
Dosage FormTablet
RouteOral
Strength0.5mg; 1mg; 2mg
Market StatusPrescription
CompanyNovo Nordisk

2 of 4  
Drug NameRepaglinide
PubMed HealthRepaglinide (By mouth)
Drug LabelPRANDIN(repaglinide) is an oral blood glucose-lowering drug of the meglitinide clab used in the management of type 2 diabetes mellitus (also known as non-insulin dependent diabetes mellitus or NIDDM). Repaglinide, S(+)2-ethoxy-4(2((3-methyl-1-(2-(1-...
Active IngredientRepaglinide
Dosage FormTablet
Routeoral; Oral
Strength0.5mg; 1mg; 2mg
Market StatusTentative Approval; Prescription
CompanyMylan Pharms; Aurobindo Pharma; Sun Pharm Inds; Actavis Totowa; Sandoz; Paddock

3 of 4  
Drug NamePrandin
PubMed HealthRepaglinide (By mouth)
Drug LabelPRANDIN(repaglinide) is an oral blood glucose-lowering drug of the meglitinide clab used in the management of type 2 diabetes mellitus (also known as non-insulin dependent diabetes mellitus or NIDDM). Repaglinide, S(+)2-ethoxy-4(2((3-methyl-1-(2-(1-...
Active IngredientRepaglinide
Dosage FormTablet
RouteOral
Strength0.5mg; 1mg; 2mg
Market StatusPrescription
CompanyNovo Nordisk

4 of 4  
Drug NameRepaglinide
PubMed HealthRepaglinide (By mouth)
Drug LabelPRANDIN(repaglinide) is an oral blood glucose-lowering drug of the meglitinide clab used in the management of type 2 diabetes mellitus (also known as non-insulin dependent diabetes mellitus or NIDDM). Repaglinide, S(+)2-ethoxy-4(2((3-methyl-1-(2-(1-...
Active IngredientRepaglinide
Dosage FormTablet
Routeoral; Oral
Strength0.5mg; 1mg; 2mg
Market StatusTentative Approval; Prescription
CompanyMylan Pharms; Aurobindo Pharma; Sun Pharm Inds; Actavis Totowa; Sandoz; Paddock

4.2 Drug Indication

As an adjunct to diet and exercise to improve glycemic control in adults with type 2 diabetes mellitus.


FDA Label


Repaglinide is indicated in patients with type-2 diabetes (non-insulin-dependent diabetes mellitus (NIDDM)) whose hyperglycaemia can no longer be controlled satisfactorily by diet, weight reduction and exercise.

Treatment should be initiated as an adjunct to diet and exercise to lower the blood glucose in relation to meals.


Repaglinide is indicated in patients with type-2 diabetes (non-insulin-dependent diabetes mellitus (NIDDM)) whose hyperglycaemia can no longer be controlled satisfactorily by diet, weight reduction and exercise. Repaglinide is also indicated in combination with metformin in type-2 diabetes patients who are not satisfactorily controlled on metformin alone.

Treatment should be initiated as an adjunct to diet and exercise to lower the blood glucose in relation to meals.


Repaglinide is indicated in patients with type-2 diabetes (non-insulin-dependent diabetes mellitus (NIDDM)) whose hyperglycaemia can no longer be controlled satisfactorily by diet, weight reduction and exercise.

Treatment should be initiated as an adjunct to diet and exercise to lower the blood glucose in relation to meals.


Repaglinide is indicated in patients with type-2 diabetes (non-insulin-dependent diabetes mellitus (NIDDM)) whose hyperglycaemia can no longer be controlled satisfactorily by diet, weight reduction and exercise. Repaglinide is also indicated in combination with metformin in type 2 diabetes patients who are not satisfactorily controlled on metformin alone.

Treatment should be initiated as an adjunct to diet and exercise to lower the blood glucose in relation to meals.


Repaglinide is indicated in patients with type-2 diabetes (non-insulin-dependent diabetes mellitus (NIDDM)) whose hyperglycaemia can no longer be controlled satisfactorily by diet, weight reduction and exercise. Repaglinide is also indicated in combination with metformin in type-2-diabetes patients who are not satisfactorily controlled on metformin alone.

Treatment should be initiated as an adjunct to diet and exercise to lower the blood glucose in relation to meals.


Repaglinide is indicated in patients with type-2 diabetes (non-insulin-dependent diabetes mellitus (NIDDM)) whose hyperglycaemia can no longer be controlled satisfactorily by diet, weight reduction and exercise. Repaglinide is also indicated in combination with metformin in type-2 diabetes patients who are not satisfactorily controlled on metformin alone.

Treatment should be initiated as an adjunct to diet and exercise to lower the blood glucose in relation to meals.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Insulin secretion by pancreatic β cells is partly controlled by cellular membrane potential. Membrane potential is regulated through an inverse relationship between the activity of cell membrane ATP-sensitive potassium channels (ABCC8) and extracellular glucose concentrations. Extracellular glucose enters the cell via GLUT2 (SLC2A2) transporters. Once inside the cell, glucose is metabolized to produce ATP. High concentrations of ATP inhibit ATP-sensitive potassium channels causing membrane depolarization. When extracellular glucose concentrations are low, ATP-sensitive potassium channels open causing membrane repolarization. High glucose concentrations cause ATP-sensitive potassium channels to close resulting in membrane depolarization and opening of L-type calcium channels. The influx of calcium ions stimulates calcium-dependent exocytosis of insulin granules. Repaglinide increases insulin release by inhibiting ATP-sensitive potassium channels in a glucose-dependent manner.


5.2 MeSH Pharmacological Classification

Hypoglycemic Agents

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


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
REPAGLINIDE
5.3.2 FDA UNII
668Z8C33LU
5.3.3 Pharmacological Classes
Potassium Channel Antagonists [MoA]; Glinide [EPC]
5.4 ATC Code

A10BX02


A10BX02


A10BX02


A10BX02


A10BX02


A10BX02


A10BX02

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

A10BX - Other blood glucose lowering drugs, excl. insulins

A10BX02 - Repaglinide


5.5 Absorption, Distribution and Excretion

Absorption

Rapidly and completely absorbed following oral administration. Peak plasma concentrations are observed within 1 hour (range 0.5-1.4 hours). The absolute bioavailability is approximately 56%. Maximal biological effect is observed within 3-3.5 hours and plasma insulin levels remain elevated for 4-6 hours. When a single 2 mg dose of repaglinide is given to healthy subjects, the area under the curve (AUC) is 18.0 - 18.7 (ng/mL/h)^3.


Route of Elimination

90% eliminated in feces (<2% as unchanged drug), 8% in urine (0.1% as unchanged drug)


Volume of Distribution

31 L following IV administration in healthy individuals


Clearance

33-38 L/hour following IV administration


5.6 Metabolism/Metabolites

Repaglinide is rapidly metabolized via oxidation and dealkylation by cytochrome P450 3A4 and 2C9 to form the major dicarboxylic acid derivative (M2). Further oxidation produces the aromatic amine derivative (M1). Glucuronidation of the carboxylic acid group of repaglinide yields an acyl glucuronide (M7). Several other unidentified metabolites have been detected. Repaglinide metabolites to not possess appreciable hypoglycemic activity.


Repaglinide has known human metabolites that include 2-Hydroxy-4-[2-[[3-methyl-1-(2-piperidin-1-ylphenyl)butyl]amino]-2-oxoethyl]benzoic acid, 2-ethoxy-4-[2-[[1-[2-(4-hydroxybutylamino)phenyl]-3-methylbutyl]amino]-2-oxoethyl]benzoic acid, 2-ethoxy-4-[2-[[3-hydroxy-3-methyl-1-(2-piperidin-1-ylphenyl)butyl]amino]-2-oxoethyl]benzoic acid, 3'-Hydroxy Repaglinide(Mixture of Diastereomers), and Repaglinide aromatic amine.

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


5.7 Biological Half-Life

1 hour


5.8 Mechanism of Action

Repaglinide activity is dependent on the presence functioning β cells and glucose. In contrast to sulfonylurea insulin secretatogogues, repaglinide has no effect on insulin release in the absence of glucose. Rather, it potentiates the effect of extracellular glucose on ATP-sensitive potassium channel and has little effect on insulin levels between meals and overnight. As such, repaglinide is more effective at reducing postprandial blood glucose levels than fasting blood glucose levels and requires a longer duration of therapy (approximately one month) before decreases in fasting blood glucose are observed. The insulinotropic effects of repaglinide are highest at intermediate glucose levels (3 to 10 mmol/L) and it does not increase insulin release already stimulated by high glucose concentrations (greater than 15 mmol/L). Repaglinide appears to be selective for pancreatic β cells and does not appear to affect skeletal or cardiac muscle or thyroid tissue.


API Reference Price

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22-Jan-2021
18-Jul-2024
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DOSAGE - TABLET;ORAL - 0.5MG **Federal Regist...DOSAGE - TABLET;ORAL - 0.5MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 20741

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DOSAGE - TABLET;ORAL - 1MG **Federal Register...DOSAGE - TABLET;ORAL - 1MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 20741

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DOSAGE - TABLET;ORAL - 2MG **Federal Register...DOSAGE - TABLET;ORAL - 2MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 20741

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DOSAGE - TABLET;ORAL - 500MG;1MG

USFDA APPLICATION NUMBER - 22386

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DOSAGE - TABLET;ORAL - 500MG;2MG

USFDA APPLICATION NUMBER - 22386

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