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    Nateglinide

    ACTIVE PHARMA INGREDIENTS

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    2D Structure
    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

    2D Structure

    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 Weight 317.4 g/mol
    Molecular Formula C19H27NO3
    XLogP33.2
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count3
    Rotatable Bond Count6
    Exact Mass317.19909372 g/mol
    Monoisotopic Mass317.19909372 g/mol
    Topological Polar Surface Area66.4 Ų
    Heavy Atom Count23
    Formal Charge0
    Complexity393
    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 NameNateglinide
    PubMed HealthNateglinide (By mouth)
    Drug LabelNateglinide 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 IngredientNateglinide
    Dosage FormTablet
    RouteOral
    Strength120mg; 60mg
    Market StatusPrescription
    CompanyPar Pharm; Watson Labs; Dr Reddys Labs

    2 of 4  
    Drug NameStarlix
    PubMed HealthNateglinide (By mouth)
    Drug LabelStarlix (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 IngredientNateglinide
    Dosage FormTablet
    RouteOral
    Strength120mg; 60mg
    Market StatusPrescription
    CompanyNovartis

    3 of 4  
    Drug NameNateglinide
    PubMed HealthNateglinide (By mouth)
    Drug LabelNateglinide 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 IngredientNateglinide
    Dosage FormTablet
    RouteOral
    Strength120mg; 60mg
    Market StatusPrescription
    CompanyPar Pharm; Watson Labs; Dr Reddys Labs

    4 of 4  
    Drug NameStarlix
    PubMed HealthNateglinide (By mouth)
    Drug LabelStarlix (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 IngredientNateglinide
    Dosage FormTablet
    RouteOral
    Strength120mg; 60mg
    Market StatusPrescription
    CompanyNovartis

    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

    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.