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| CAS No.: | 105816-04-4 |
|---|---|
| Name: | Nateglinide |
| Article Data: | 14 |
| Molecular Structure: | |
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| Formula: | C19H27NO3 |
| Molecular Weight: | 317.428 |
| Synonyms: | Nateglinide [INN];Fastic;trans-N-((4-(1-Methylethyl)cyclohexyl)carbonyl)-D-phenylalanine;A 4166;Starlix;Nateglinide(105816-04-4 );Nateglinide,105816-04-4;Starsis (TN);(2R)-3-phenyl-2-[[(1S,3S)-3-propan-2-ylcyclohexanecarbonyl]amino]propanoic acid;D-Phenylalanine,N-[[trans-4-(1-methylethyl)- cyclohexyl]carbonyl]-;Starsis;(-)-N-(trans-4-Isopropylcyclohexanecarbonyl)-D-phenylalanine;Nateglynide;Nateglinide intermediate;Nateglinide-H;AY 4166;D-Phenylalanine, N-((4-(1-methylethyl)cyclohexyl)carbonyl)-, trans-; |
| Density: | 1.104 g/cm3 |
| Melting Point: | 137-141 °C |
| Boiling Point: | 527.6 °C at 760 mmHg |
| Flash Point: | 272.9 °C |
| Appearance: | white crystalline powder |
| Hazard Symbols: |
 Xn
|
| Risk Codes: | 22 |
| Safety: | 24/25-36 |
| PSA: | 66.40000 |
| LogP: | 3.65180 |
- 144851-82-1METHYL2-AMINO-3-FLUOROBENZOATE
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- 1219080-61-1IMIDAZOLE-2-BORONIC ACID
- 105746-47-2
N-<(trans-4-Isopropylcyclohexyl)carbonyl>-D-phenylalanine methyl ester
- 105816-04-4
nateglinide
| Conditions | Yield |
|---|---|
| Stage #1: N-<(trans-4-Isopropylcyclohexyl)carbonyl>-D-phenylalanine methyl ester With water; sodium hydroxide In methanol at 25 - 30℃; for 5h; Stage #2: With hydrogenchloride In water pH=2.0 - 2.5; | 80.8% |
| With sodium hydroxide In methanol Yield given; | |
| Stage #1: N-<(trans-4-Isopropylcyclohexyl)carbonyl>-D-phenylalanine methyl ester With sodium hydroxide In acetone at 20 - 25℃; for 2h; Stage #2: With hydrogenchloride In water at 10℃; for 1h; pH=2 - 3; Product distribution / selectivity; |
- 7077-05-6
trans-4-isopropylcyclohexane-1-carboxylic acid
- 673-06-3
D-(R)-phenylalanine
- 541-41-3
chloroformic acid ethyl ester
A
- 21488-23-3
N-(ethoxycarbonyl)-(D)-phenylalanine
B
- 105816-04-4
nateglinide
| Conditions | Yield |
|---|---|
| Stage #1: trans-4-isopropylcyclohexane-1-carboxylic acid; chloroformic acid ethyl ester With triethylamine In acetone at -10 - -5℃; for 1.25h; Stage #2: D-(R)-phenylalanine With 4-methyl-morpholine; triethylamine In water; acetone at -10 - -5℃; | A n/a B 80% C n/a |
| Conditions | Yield |
|---|---|
| In dichloromethane at 25 - 30℃; for 18.5h; | 75% |
- 673-06-3
D-(R)-phenylalanine
- 100597-38-4
4-iso-propylcyclohexanecarbonyl chloride
- 105816-04-4
nateglinide
| Conditions | Yield |
|---|---|
| With sodium hydroxide; sulfuric acid | 65% |
| With sodium hydroxide; sulfuric acid In n-heptane; ethyl acetate | 65% |
| With potassium hydroxide In water; acetone |
- 84855-54-9
trans-4-iso-propylcyclohexylcarbonyl chloride
- 105816-04-4
nateglinide
| Conditions | Yield |
|---|---|
| In acetonitrile at -5 - 0℃; for 3.58333 - 3.66667h; Heating / reflux; |
- 7077-05-6
trans-4-isopropylcyclohexane-1-carboxylic acid
- 105816-04-4
nateglinide
| Conditions | Yield |
|---|---|
| Multi-step reaction with 2 steps 1: 1) N-hydroxysuccinimide, dicyclohexylcarbodiimide / 1) CHCl3, 3 h, 2) CHCl3, 25 deg C, 1 d 2: 2N NaOH / methanol View Scheme |
- 21685-51-8
D-phenylalanine methyl ester
- 105816-04-4
nateglinide
| Conditions | Yield |
|---|---|
| Multi-step reaction with 2 steps 1: 1) N-hydroxysuccinimide, dicyclohexylcarbodiimide / 1) CHCl3, 3 h, 2) CHCl3, 25 deg C, 1 d 2: 2N NaOH / methanol View Scheme | |
| Multi-step reaction with 2 steps 1.1: benzotriazol-1-ol / dichloromethane / 0.25 h / 25 °C / Inert atmosphere 1.2: 3.25 h / 0 - 15 °C 2.1: sodium hydroxide / acetone / 2 h / 20 - 25 °C 2.2: 1 h / 10 °C / pH 2 - 3 View Scheme |
- 175284-00-1
p-menthan-7-oic acid methyl ester
- 105816-04-4
nateglinide
| Conditions | Yield |
|---|---|
| Multi-step reaction with 3 steps 1: 1) NaH, 2) 2N aq. NaOH / 1) 150 deg C, 2 h, 2) MeOH, 20 deg C, 10 min 2: 1) N-hydroxysuccinimide, dicyclohexylcarbodiimide / 1) CHCl3, 3 h, 2) CHCl3, 25 deg C, 1 d 3: 2N NaOH / methanol View Scheme |
- 594837-86-2
C19H26NO3(1-)*K(1+)
- 105816-04-4
nateglinide
| Conditions | Yield |
|---|---|
| With hydrogenchloride In water at 15 - 20℃; pH=2.0 - 3.0; Product distribution / selectivity; |
- 594837-85-1
C19H26NO3(1-)*Na(1+)
- 105816-04-4
nateglinide
| Conditions | Yield |
|---|---|
| With hydrogenchloride; water at 25℃; for 0.5h; pH=2 - 3; Product distribution / selectivity; |
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Specification
The CAS registry number of Nateglinide is 105816-04-4. The systematic name is N-{[trans-4-(propan-2-yl)cyclohexyl]carbonyl}-D-phenylalanine. In addition, the molecular formula is C19H27NO3 and the molecular weight is 317.42. What's more, it belongs to the meglitinide class of blood glucose-lowering drugs. It is a drug for the treatment of type 2 diabetes. And it can be used as an amino-acid derivative that stimulates insulin secretion. Besides, it also can be used as an antidiabetic.
Physical properties about this chemical are: (1)ACD/LogP: 2.35; (2)ACD/LogD (pH 5.5): 2; (3)ACD/LogD (pH 7.4): 1; (4)ACD/BCF (pH 5.5): 5; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 27; (7)ACD/KOC (pH 7.4): 1; (8)#H bond acceptors: 4; (9)#H bond donors: 2; (10)#Freely Rotating Bonds: 6; (11)Polar Surface Area: 66.4 Å2; (12)Index of Refraction: 1.536; (13)Molar Refractivity: 89.612 cm3; (14)Molar Volume: 287.347 cm3; (15)Polarizability: 35.525 ×10-24cm3; (16)Surface Tension: 44.58 dyne/cm; (17)Density: 1.105 g/cm3; (18)Flash Point: 272.869 °C; (19)Enthalpy of Vaporization: 84.443 kJ/mol; (20)Boiling Point: 527.578 °C at 760 mmHg.
When you are using this chemical, please be cautious about it as the following:
This chemical is harmful if swallowed. During using it, wear suitable protective clothing and you should avoid contact with skin and eyes.
You can still convert the following datas into molecular structure:
(1)SMILES: O=C(N[C@H](Cc1ccccc1)C(O)=O)[C@H]2CC[C@@H](CC2)C(C)C
(2)InChI: InChI=1/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
(3)InChIKey: OELFLUMRDSZNSF-BRWVUGGUBB
The toxicity data is as follows:
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| dog | LD | oral | > 2gm/kg (2000mg/kg) | GASTROINTESTINAL: NAUSEA OR VOMITING | Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 25(Suppl, |
| rat | LD | oral | > 2gm/kg (2000mg/kg) | SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" | Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 25(Suppl, |