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Purity: ≥98%
Nateglinide (formerly A-4166; trade names: Fastic, Starlix), a meglitinide analog, is a potent and orally bioavailable antihyperglycemic medication used for treating type 2 diabetes [non-insulin-dependent diabetes mellitus (NIDDM)]. It lowers blood glucose levels by acting as an insulin secretagog agent which stimulates insulin secretion from the pancreas. It is a short-acting insulin secretagogue that inhibits ATP-sensitive K+ channels in pancreatic β-cells, which depolarizes the β cells and opens voltage-gated calcium channels, leading to calcium influx and fusion of insulin-containing vesicles with the cell membrane, and insulin secretion occurs.
| ln Vitro |
In a concentration-dependent manner, nateglinide blocks typical recordings of dinitrophenol-induced KATP currents. For 5 mM (G5) and 16 mM (G16) glucose, nateglinide has IC50 values of 7.4 μM and 2.4 μM, respectively[2].
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| ln Vivo |
Oral administration of nateglinide (50 mg/kg) to mice results in increased postprandial glucose concentrations and stimulation of human C-peptide production in the humanized mice[3].
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| Cell Assay |
Cell Types: Rat pancreatic β-cells.
Tested Concentrations: 0-100 μM. Incubation Duration: ~20 min. Experimental Results: Produced a complete inhibition of KATP current at concentration of 3 μM. |
| Animal Protocol |
Animal/Disease Models: Mice[3].
Doses: 50mg/kg. Route of Administration: Orally at 60min before oral administration of 4 g/kg glucose. Experimental Results: Stimulates human C-peptide secretion. |
| ADME/Pharmacokinetics |
Metabolism / Metabolites
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. |
| References | |
| Additional Infomation |
Nateglinide is an N-acyl-D-phenylalanine resulting from the formal condensation of the amino group of D-phenylalanine with the carboxy group of trans-4-isopropylcyclohexanecarboxylic acid. An orally-administered, rapidly-absorbed, short-acting insulinotropic agent, it is used for the treatment of type 2 diabetes mellitus. It has a role as an EC 3.4.14.5 (dipeptidyl-peptidase IV) inhibitor and a hypoglycemic agent.
Nateglinide is a Glinide. The mechanism of action of nateglinide is as a Potassium Channel Antagonist. 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. See also: Nateglinide (annotation moved to). |
| Molecular Formula |
C19H27NO3
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|---|---|---|
| Molecular Weight |
317.42
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| Exact Mass |
317.199
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| CAS # |
105816-04-4
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| Related CAS # |
Nateglinide-d5;1227666-13-8
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| PubChem CID |
5311309
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| Appearance |
White to off-white solid powder
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| Density |
1.1±0.1 g/cm3
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| Boiling Point |
527.6±39.0 °C at 760 mmHg
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| Melting Point |
137-141ºC
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| Flash Point |
272.9±27.1 °C
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| Vapour Pressure |
0.0±1.5 mmHg at 25°C
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| Index of Refraction |
1.536
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| LogP |
4.21
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
6
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| Heavy Atom Count |
23
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| Complexity |
393
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| Defined Atom Stereocenter Count |
1
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| SMILES |
CC(C)C1CCC(CC1)C(=O)N[C@H](CC2=CC=CC=C2)C(=O)O
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| InChi Key |
OELFLUMRDSZNSF-BRWVUGGUSA-N
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| InChi Code |
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
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| Chemical Name |
(R)-2-((1r,4R)-4-isopropylcyclohexanecarboxamido)-3-phenylpropanoic acid
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| Synonyms |
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
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| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (7.88 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (7.88 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (7.88 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.1504 mL | 15.7520 mL | 31.5040 mL | |
| 5 mM | 0.6301 mL | 3.1504 mL | 6.3008 mL | |
| 10 mM | 0.3150 mL | 1.5752 mL | 3.1504 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
| NCT Number | Recruitment | interventions | Conditions | Sponsor/Collaborators | Start Date | Phases |
| NCT00858013 | Completed Has Results | Drug: Nateglinide Drug: Glimepiride |
Type 2 Diabetes Mellitus | Ajou University School of Medicine | April 24, 2009 | Phase 4 |
| NCT01160029 | Completed | Drug: Nateglinide | Healthy | Dr. Reddy's Laboratories Limited | October 2004 | Phase 1 |
| NCT01159158 | Recruiting | Drug: Larotrectinib Sulfate Procedure: Bone Scan |
Recurrent Glioma Refractory Glioma |
Dr. Reddy's Laboratories Limited | February 2007 | Phase 1 |
| NCT00928889 | Completed Has Results | Drug: Nateglinide 120 mg Drug: Acarbose 50 mg |
Diabetes Mellitus, Type 2 | Novartis Pharmaceuticals | July 2009 | Phase 4 |
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