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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
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)
| Molecular Weight | 317.4 g/mol |
|---|---|
| Molecular Formula | C19H27NO3 |
| 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 Ų |
| 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 |
| 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 |
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.
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.
Hypoglycemic Agents
Substances which lower blood glucose levels. (See all compounds classified as Hypoglycemic Agents.)
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
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
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
1.5 hours
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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