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Chemistry

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Also known as: 105816-04-4, Starlix, Senaglinide, Starsis, Fastic, Ay-4166

Molecular Formula

C₁₉H₂₇NO₃

Molecular Weight

317.4 g/mol

InChI Key

OELFLUMRDSZNSF-OFLPRAFFSA-N

FDA UNII

XTM4DQP5S5

A phenylalanine and cyclohexane derivative that acts as a hypoglycemic agent by stimulating the release of insulin from the pancreas. It is used in the treatment of TYPE 2 DIABETES.

Nateglinide is a Glinide. The mechanism of action of nateglinide is as a Potassium Channel Antagonist.

1 2D Structure

Nateglinide

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2R)-3-phenyl-2-[(4-propan-2-ylcyclohexanecarbonyl)amino]propanoic acid

2.1.2 InChI

InChI=1S/C19H27NO3/c1-13(2)15-8-10-16(11-9-15)18(21)20-17(19(22)23)12-14-6-4-3-5-7-14/h3-7,13,15-17H,8-12H2,1-2H3,(H,20,21)(H,22,23)/t15?,16?,17-/m1/s1

2.1.3 InChI Key

OELFLUMRDSZNSF-OFLPRAFFSA-N

2.1.4 Canonical SMILES

CC(C)C1CCC(CC1)C(=O)NC(CC2=CC=CC=C2)C(=O)O

2.1.5 Isomeric SMILES

CC(C)C1CCC(CC1)C(=O)N[C@H](CC2=CC=CC=C2)C(=O)O

2.2 Other Identifiers

2.2.1 UNII

XTM4DQP5S5

2.3 Synonyms

2.3.1 MeSH Synonyms

1. A 4166

2. A-4166

3. A4166

4. Ay 4166

5. Ay-4166

6. Ay4166

7. Djn 608

8. Fastic

9. N-((4-isopropylcyclohexyl)carbonyl)phenylalanine

10. Nate-glinide

11. Nateglinide, (cis,d-phe)-isomer

12. Nateglinide, (d-phe)-isomer

13. Senaglinide

14. Starlix

15. Starsis

2.3.2 Depositor-Supplied Synonyms

1. 105816-04-4

2. Starlix

3. Senaglinide

4. Starsis

5. Fastic

6. Ay-4166

7. Nateglinide [inn]

8. Trazec

9. A-4166

10. Sdz-djn-608

11. D-nateglinide

12. 105816-06-6

13. Djn 608

14. Djn-608

15. Ay4166

16. Mfcd00875706

17. Sdz Djn 608

18. Sdz-djn 608

19. Ay 4166

20. (2r)-3-phenyl-2-[(4-propan-2-ylcyclohexanecarbonyl)amino]propanoic Acid

21. N-[(trans-4-isopropylcyclohexyl)carbonyl]-d-phenylalanine

22. A 4166

23. Xtm4dqp5s5

24. Chembl783

25. 41x3pwk4o2

26. Chebi:31897

27. N-[[trans-4-(1-methylethyl)cyclohexyl]carbonyl]-d-phenylalanine

28. Nsc-758695

29. 105746-37-0

30. (-)-n-(trans-4-isopropylcyclohexanecarbonyl)-d-phenylalanine

31. N-{[trans-4-(propan-2-yl)cyclohexyl]carbonyl}-d-phenylalanine

32. D-phenylalanine, N-((trans-4-(1-methylethyl)cyclohexyl)carbonyl)-

33. D-phenylalanine, N-[[trans-4-(1-methylethyl)cyclohexyl]carbonyl]-

34. (r)-2-((1r,4r)-4-isopropylcyclohexanecarboxamido)-3-phenylpropanoic Acid

35. Dsstox_cid_20687

36. Dsstox_rid_79543

37. N-[[cis-4-(1-methylethyl)cyclohexyl]carbonyl]-d-phenylalanine(nateglinide Impurity)

38. Dsstox_gsid_40687

39. N-((cis-4-isopropylcyclohexyl)carbonyl)-d-phenylalanine

40. N-(trans-4-isopropylcyclohexylcarbonyl)-d-phenyl Alanine

41. D-phenylalanine, N-((cis-4-(1-methylethyl)cyclohexyl)carbonyl)-

42. N-((cis-4-(1-methylethyl)cyclohexyl)carbonyl)-d-phenylalanine

43. Trans-n-((4-(1-methylethyl)cyclohexyl)carbonyl)-d-phenylalanine

44. D-phenylalanine, N-((4-(1-methylethyl)cyclohexyl)carbonyl)-, Cis-

45. D-phenylalanine, N-[[4-(1-methylethyl)cyclohexyl]carbonyl]-, Cis-

46. (r)-2-rel-((1r,4r)-4-isopropylcyclohexanecarboxamido)-3-phenylpropanoic Acid

47. Smr000466372

48. Cas-105816-04-4

49. Nateglinida

50. Nateglinidum

51. Unii-41x3pwk4o2

52. Trans-n-{[4-(1-methylethyl)cyclohexyl]carbonyl}-d-phenylalanine

53. Ncgc00095121-01

54. Nateglinide [usan:usp:inn:ban]

55. Starsis (tn)

56. Nateglinide, Starlix

57. Ym-026

58. Nateglinide (starlix)

59. Nateglinide Impurity C

60. Nateglinide Cis Impurity

61. Nateglinide [mi]

62. Unii-xtm4dqp5s5

63. Nateglinide [jan]

64. Nateglinide [usan]

65. Nateglinide [vandf]

66. Nateglinide [mart.]

67. Schembl22088

68. Nateglinide [usp-rs]

69. Nateglinide [who-dd]

70. Nateglinide Impurity C [ep]

71. Mls000759500

72. Mls001424043

73. Mls003915639

74. Mls006011429

75. Bidd:gt0257

76. Nateglinide Cis-isomer [usp]

77. Schembl303827

78. Nateglinide [ema Epar]

79. Gtpl6833

80. Schembl7880361

81. Schembl9232138

82. Zinc9689

83. Nateglinide (jp17/usp/inn)

84. Chembl2114389

85. Dtxsid9040687

86. Schembl13753829

87. Chebi:94617

88. Nateglinide [orange Book]

89. Hms2051g20

90. Hms2089a10

91. Hms2235o08

92. Hms3675g17

93. Hms3715f12

94. N-(trans-4-isopropylcylolohexylcarboxyl)-d-phenylpropylicacid

95. Nateglinide [ep Monograph]

96. Nateglinide [usp Monograph]

97. Bcp28400

98. Carboxamido)-3-phenylpropanoic Acid

99. Hy-b0422

100. Tox21_111432

101. Bbl033469

102. Bdbm50344967

103. S2489

104. Stk647123

105. Nateglinide Related Compound C [usp]

106. Akos005577723

107. Akos015841612

108. Akos015960899

109. Nateglinide, >=98% (hplc), Solid

110. Tox21_111432_1

111. Zinc100015346

112. Zinc101489663

113. Ac-1690

114. Ccg-100898

115. Db00731

116. Ks-5143

117. Nc00148

118. Nsc 758695

119. Ncgc00178741-03

120. Ncgc00271534-02

121. Ncgc00271534-03

122. (r)-2-((1r,4r)-4-isopropylcyclohexane

123. Nateglinide 100 Microg/ml In Acetonitrile

124. N0912

125. Nateglinide Cis-isomer [usp Impurity]

126. Nateglinide Impurity C [ep Impurity]

127. Sw197528-2

128. D01111

129. Ab00639979-06

130. Ab00639979-08

131. Ab00639979-09

132. Ab00639979-11

133. Ab00639979_12

134. 816n044

135. A801324

136. A1-02996

137. Q-201449

138. Q2254797

139. Nateglinide Related Compound C [usp Impurity]

140. Q27166439

141. N-(trans-4-isopropylcyclohexylcarbonyl)-d-phenylalanine

142. (trans-4-isopropylcyclohexane-1-carbonyl)-d-phenylalanine

143. N-[[4-(1-methylethyl)cyclohexyl]carbonyl]-d-phenylalanine

144. Nateglinide, European Pharmacopoeia (ep) Reference Standard

145. ((1r,4r)-4-isopropylcyclohexane-1-carbonyl)-d-phenylalanine

146. 2-[(4-isopropyl-cyclohexanecarbonyl)-amino]-3-phenyl-propionic Acid

147. N-(4alpha-isopropylcyclohexane-1alpha-yl)carbonyl-d-phenylalanine

148. Nateglinide, United States Pharmacopeia (usp) Reference Standard

149. (2r)-2-[(4-isopropylcyclohexanecarbonyl)amino]-3-phenyl-propanoic Acid

150. D-phenylalanine, N-((4-(1-methylethyl)cyclohexyl)carbonyl)-, Trans-

151. (2r)-2-[(4-isopropylcyclohexanecarbonyl)amino]-3-phenyl-propanoic Acid;nateglinide

152. (2r)-2-[[oxo-(4-propan-2-ylcyclohexyl)methyl]amino]-3-phenylpropanoic Acid

153. (r)-2-rel-((1r,4r)-4-isopropylcyclohexanecarboxamido)-3-phenylpropanoicacid

154. N-[[cis-4-(1-methylethyl)cyclohexyl]carbonyl]-d-phenylalanine (nateglinide Impurity)

2.4 Create Date

2005-12-16

3 Chemical and Physical Properties

Molecular Formula	C₁₉H₂₇NO₃
Molecular Weight	317.4 g/mol
XLogP3	3.2
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	6
Exact Mass	317.19909372 g/mol
Monoisotopic Mass	317.19909372 g/mol
Topological Polar Surface Area	66.4 Å²
Heavy Atom Count	23
Formal Charge	0
Complexity	393
Isotope Atom Count	0
Defined Atom Stereocenter Count	1
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 4
Drug Name	Nateglinide
PubMed Health	Nateglinide (By mouth)
Drug Label	Nateglinide tablets are oral antidiabetic agent used in the management of Type 2 diabetes mellitus [also known as non-insulin dependent diabetes mellitus (NIDDM) or adult-onset diabetes]. Nateglinide, (-)-N-[(trans-4-isopropylcyclohexane)carbonyl]-D-...
Active Ingredient	Nateglinide
Dosage Form	Tablet
Route	Oral
Strength	120mg; 60mg
Market Status	Prescription
Company	Par Pharm; Watson Labs; Dr Reddys Labs

2 of 4
Drug Name	Starlix
PubMed Health	Nateglinide (By mouth)
Drug Label	Starlix (nateglinide) is an oral antidiabetic agent used in the management of Type 2 diabetes mellitus [also known as non-insulin dependent diabetes mellitus (NIDDM) or adult-onset diabetes]. Starlix, (-)-N-[(trans-4-isopropylcyclohexane)carbonyl]-...
Active Ingredient	Nateglinide
Dosage Form	Tablet
Route	Oral
Strength	120mg; 60mg
Market Status	Prescription
Company	Novartis

3 of 4
Drug Name	Nateglinide
PubMed Health	Nateglinide (By mouth)
Drug Label	Nateglinide tablets are oral antidiabetic agent used in the management of Type 2 diabetes mellitus [also known as non-insulin dependent diabetes mellitus (NIDDM) or adult-onset diabetes]. Nateglinide, (-)-N-[(trans-4-isopropylcyclohexane)carbonyl]-D-...
Active Ingredient	Nateglinide
Dosage Form	Tablet
Route	Oral
Strength	120mg; 60mg
Market Status	Prescription
Company	Par Pharm; Watson Labs; Dr Reddys Labs

4 of 4
Drug Name	Starlix
PubMed Health	Nateglinide (By mouth)
Drug Label	Starlix (nateglinide) is an oral antidiabetic agent used in the management of Type 2 diabetes mellitus [also known as non-insulin dependent diabetes mellitus (NIDDM) or adult-onset diabetes]. Starlix, (-)-N-[(trans-4-isopropylcyclohexane)carbonyl]-...
Active Ingredient	Nateglinide
Dosage Form	Tablet
Route	Oral
Strength	120mg; 60mg
Market Status	Prescription
Company	Novartis

4.2 Drug Indication

For the treatment of non-insulin dependent-diabetes mellitus in conjunction with diet and exercise.

FDA Label

Nateglinide is indicated for combination therapy with metformin in type-2 diabetic patients inadequately controlled despite a maximally tolerated dose of metformin alone.

Nateglinide is indicated for combination therapy with metformin in type 2 diabetic patients inadequately controlled despite a maximally tolerated dose of metformin alone.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Insulin secretion by pancreatic 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. Nateglinide 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

NATEGLINIDE

5.3.2 FDA UNII

41X3PWK4O2

5.3.3 Pharmacological Classes

Potassium Channel Antagonists [MoA]; Glinide [EPC]

5.4 ATC Code

A10BX03

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

A10BX03 - Nateglinide

5.5 Absorption, Distribution and Excretion

Absorption

Rapidly absorbed following oral administration prior to a meal, absolute bioavailability is estimated to be approximately 73%. Peak plasma concentrations generally occur within 1 hour of oral administration. Onset of action is <20 minutes and the duration of action is approximately 4 hours.

Route of Elimination

Urine (83%) and feces (10%)

Volume of Distribution

10 liters in healthy subjects

5.6 Metabolism/Metabolites

Hepatic, via cytochrome P450 isoenzymes CYP2C9 (70%) and CYP3A4 (30%). Metabolism is via hydroxylation followed by glucuronidation. The major metabolites have less antidiabetic activity than nateglinide, but the isoprene minor metabolite has antidiabetic activity comparable to that of nateglinide.

Nateglinide has known human metabolites that include (2S,3S,4S,5R)-3,4,5-trihydroxy-6-[(2R)-3-phenyl-2-[(4-propan-2-ylcyclohexanecarbonyl)amino]propanoyl]oxyoxane-2-carboxylic acid.

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

5.7 Biological Half-Life

1.5 hours

5.8 Mechanism of Action

Nateglinide activity is dependent on the presence functioning cells and glucose. In contrast to sulfonylurea insulin secretatogogues, nateglinide 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, nateglinide 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 nateglinide 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). Nateglinide appears to be selective for pancreatic cells and does not appear to affect skeletal or cardiac muscle or thyroid tissue.

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Number of Transactions

Total Quantity (KGS)

Total Value (USD)

Quantity (KGS) & Unit rate (USD/KGS) over time

API Imports and Exports

Importing Country	Total Quantity (KGS)	Average Price (USD/KGS)	Number of Transactions

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DOSAGE - TABLET;ORAL - 120MG **Federal Regist...DOSAGE - TABLET;ORAL - 120MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 21204

DOSAGE - TABLET;ORAL - 60MG **Federal Registe...DOSAGE - TABLET;ORAL - 60MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 21204

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ACTIVE PHARMA INGREDIENTS

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TABLET;ORAL - 120MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

TABLET;ORAL - 60MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

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54 Coating Systems & Additives

50 Direct Compression

44 Disintegrants & Superdisintegrants

33 Controlled & Modified Release

31 Granulation

TABLET;ORAL - 120MG Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons

TABLET;ORAL - 60MG Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons