N-{[(1S,3S)-3-(propan-2-yl)cyclohexyl]carbonyl}-D-phenylalanine
Nateglinide
CAS: 105816-04-4
Molecular Formula: C19H27NO3
N-{[(1S,3S)-3-(propan-2-yl)cyclohexyl]carbonyl}-D-phenylalanine - Names and Identifiers
| Name | Nateglinide |
| Synonyms | ay4166 NATAGLINIDE Nateglinide Nateglinide(H) trans-d-phenylalanin Nateglinide (200 mg) trans-d-phenylalanine nateglinide intermediate N-{[4-(propan-2-yl)cyclohexyl]carbonyl}phenylalanine N-{[4-(propan-2-yl)cyclohexyl]carbonyl}-L-phenylalanine N-(trans-4-Isopropylcylcohexylcarbonyl)-D-phenylalanine N-{[4-(1-methylethyl)cyclohexyl]carbonyl}-D-phenylalanine N-(Trans-4-Isopropylcyclohexyl-1-Carbonyl)-D-Phenylalamine (-)-n-(trans-4-isopropylcyclohexanecarbonyl)-d-phenylalanine N-{[trans-4-(propan-2-yl)cyclohexyl]carbonyl}-D-phenylalanine N-{[(1S,3S)-3-(propan-2-yl)cyclohexyl]carbonyl}-D-phenylalanine 3-Phenyl-2-(4-propan-2-ylcyclohexyl)carbonylamino-propanoic acid |
| CAS | 105816-04-4 |
| EINECS | 641-756-7 |
| 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 |
N-{[(1S,3S)-3-(propan-2-yl)cyclohexyl]carbonyl}-D-phenylalanine - Physico-chemical Properties
| Molecular Formula | C19H27NO3 |
| Molar Mass | 317.42 |
| Density | 1.104±0.06 g/cm3(Predicted) |
| Melting Point | 137-141°C |
| Boling Point | 527.6±39.0 °C(Predicted) |
| Specific Rotation(α) | D20 -9.4° (c = 1 in methanol) |
| Flash Point | 272.869°C |
| Solubility | It is easily soluble in methanol, ethanol, and chloroform, dissolved in acetone and ether, and almost insoluble in water |
| Vapor Presure | 0mmHg at 25°C |
| Appearance | White to white-like solid |
| Color | white to off-white |
| Merck | 14,6428 |
| pKa | 3.61±0.10(Predicted) |
| Storage Condition | room temp |
| Sensitive | Sensitive to light |
| Refractive Index | 1.536 |
| MDL | MFCD00875706 |
| Physical and Chemical Properties | Melting Point 137-141°C |
| Use | For the treatment of diabetes |
N-{[(1S,3S)-3-(propan-2-yl)cyclohexyl]carbonyl}-D-phenylalanine - Risk and Safety
| Hazard Symbols | Xn - Harmful |
| Risk Codes | 22 - Harmful if swallowed |
| Safety Description | S24/25 - Avoid contact with skin and eyes. S36 - Wear suitable protective clothing. |
| WGK Germany | 3 |
| RTECS | SQ7318950 |
| HS Code | 29242990 |
| Toxicity | LD50 orally in rats: >2.0 g/kg (Hasegawa) |
N-{[(1S,3S)-3-(propan-2-yl)cyclohexyl]carbonyl}-D-phenylalanine - Standard
Authoritative Data Verified Data
This product is (-)-N-[(trans-4-isopropylcyclohexyl) carbonyl]-D-phenylalanine. Calculated as dried product, the content of C19H27N03 shall not be less than 99.0%.
Last Update：2024-01-02 23:10:35
N-{[(1S,3S)-3-(propan-2-yl)cyclohexyl]carbonyl}-D-phenylalanine - Trait
Authoritative Data Verified Data
- This product is white or white crystalline powder; Bitter taste.
- This product is soluble in methanol, ethanol, acetone, slightly soluble in acetonitrile, almost insoluble in water, dissolved in 0.lmol/L sodium hydroxide solution, almost insoluble in dilute hydrochloric acid.
melting point
The melting point of this product (General rule 0612) is 136~141°C, and the melting distance is not more than 2°C.
specific rotation
take this product, precision weighing, add 0.1 mol/L sodium hydroxide solution was dissolved and quantitatively diluted to prepare a solution containing about 10 mg per 1 ml, which was measured according to law (General rule 0621). The specific rotation was -36 ° to -40 °.
Last Update：2022-01-01 11:54:23
N-{[(1S,3S)-3-(propan-2-yl)cyclohexyl]carbonyl}-D-phenylalanine - Differential diagnosis
Authoritative Data Verified Data
- take an appropriate amount of this product, add ethanol to dissolve and dilute to make a solution containing about 1 mg per 1 ml, and measure by UV-Vis spectrophotometry (General rule 0401), at 252nm, 258nm and 264nm wavelength has the maximum absorption.
- The infrared absorption spectrum of this product should be consistent with that of the control (Spectrum set 1142).
- The X-ray powder diffraction pattern of this product (measuring range is 3 ° ~ 60 °) should be consistent with the reference product, and the two strong diffraction peaks at 20=19.6 ° and 19.9 ° should be able to separate, while the B type diffraction peak should not appear at 20=4.9 ° (General 0451).
Last Update：2022-01-01 11:54:24
N-{[(1S,3S)-3-(propan-2-yl)cyclohexyl]carbonyl}-D-phenylalanine - Exam
Authoritative Data Verified Data
chloride
take 0.50g of this product, put it in a 50ml Nessler's colorimetric tube, Add 30ml of acetone to dissolve, Add 10ml of dilute nitric acid, shake well, and check according to law (General rule 0801), not more concentrated (0.01%) than the control solution made from of standard sodium chloride solution.
Related substances
take an appropriate amount of this product, precision weighing, add mobile phase to dissolve and dilute to make a solution containing 0.5mg per lml, as a test solution; Take lml for precision, set in a 500ml measuring flask, dilute to the scale with the mobile phase, and shake to serve as a control solution. According to the determination by high performance liquid chromatography (General rule 0512), with eighteen alkyl silane bonded silica gel as filler, phosphate buffer solution (take potassium dihydrogen phosphate 4.08g, add water 800ml to dissolve, add triethylamine 10ml, adjust pH to 4.0 with phosphoric acid, add water to 1000ml)-acetonitrile methanol (32:51:17) as mobile phase, the detection wavelength was 210nm, column temperature was 30°C, the number of theoretical plates is not less than 6000 based on the nateglinide peak. 10 u1 of the test solution and the control solution were respectively injected into the human liquid chromatograph, and the chromatogram was recorded to 2 times of the retention time of the main component peak. If there are impurity peaks in the chromatogram of the test solution, the area of a single impurity peak shall not be greater than the area of the main peak of the control solution (0.2%), the sum of each impurity peak area shall not be greater than 5 times (1.0%) of the main peak area of the control solution.
L-isomer and flask isomer
take an appropriate amount of this product and weigh it accurately. Add mobile phase to dissolve and dilute the solution containing lmg in lml as the test solution, A solution containing lOug per 1 ml was prepared by dilution with mobile phase as a control solution; Appropriate amounts of nateglinide, L-isomer and cis-isomer were also taken, the above three compounds were dissolved by mobile phase to prepare 1mg, 0.01mg, 0.Olmg solution as the system suitability solution; According to the high performance liquid chromatography (General 0512) test, using chiral column (KR100-CHI-TBB, 4.6mm X 250 mm, or equivalent column), N-hexane-isopropanol-glacial acetic acid (95:5:0.2) was used as mobile phase, the detection wavelength was 258mn, the flow rate was 0.6ml per minute, and the number of theoretical plates was not less than 8000 based on the nateglinide peak. Accurately measure 20 u1 of each of the above three solutions, respectively inject human liquid chromatography, record the chromatogram, and the resolution between nateglinide peak and L-isomer peak in the system applicable solution chromatogram shall meet the requirements; the area of each peak in the chromatogram of the test solution shall not be greater than the area of the main peak of the control solution (1.0%) if the peaks in the chromatogram of the test solution are consistent with the peak retention times of the L-isomer and the CIS-isomer.
residual solvent
is measured according to the residual solvent measurement method (General 0861 second method).
chromatographic conditions and system suitability test
The capillary column with 5% phenylmethylpolysiloxane as stationary liquid was used as the chromatographic column, the initial temperature was 35 ° C., and it was maintained for 5 minutes, and then the temperature was raised to 200 ° C. For 5 minutes at 10t per minute; the inlet temperature was 280°C; The detector temperature was 280°C. The reference solution was injected into the gas chromatograph, and the separation degree of each component peak of methanol, acetone, dichloromethane, chloroform, pyridine and internal standard peak should meet the requirements.
preparation of internal standard solution
an appropriate amount of absolute ethanol was accurately weighed and diluted with N ,N-dimethylformamide to prepare a solution containing 0.1 mg of absolute ethanol per 1 ml.
assay
precision weighing methanol, acetone, dichloromethane, chloroform, pyridine appropriate amount, with internal standard solution made in each lml respectively containing 0.6mg, 1.0 mg, 0.12mg, 0.012mg, 0.04mg of the mixed solution was used as a control solution. Another precision weighing the appropriate amount of this product, with the internal standard solution made per 1 ml containing nateglinide 0.2g of the solution, as a test solution. The lul of the test solution and the reference solution were respectively injected into the gas chromatograph, and the chromatogram was recorded. The peak area was calculated according to the internal standard method. Methanol, acetone, dichloromethane, chloroform, pyridine residues shall be in accordance with the provisions.
loss on drying
take this product, dry to constant weight at 105°C, weight loss shall not exceed 0.5% (General rule 0831).
burning residue
take l.Og of this product and determine it according to law (General rule 0841). The remaining residue shall not exceed 0.1%.
Heavy metals
The residue left under the ignition residue item shall not contain more than 20 parts per million of heavy metals as determined by law (general chapter 0821 second method).
Last Update：2022-01-01 11:54:25
N-{[(1S,3S)-3-(propan-2-yl)cyclohexyl]carbonyl}-D-phenylalanine - Content determination
Authoritative Data Verified Data
take about 0.5g of this product, precision weighing, add 50ml of neutral fermentation liquid to dissolve, add 2 drops of phenolphthalein indicator solution, and use sodium hydroxide titration solution (0.lmol/L) to dissolve. Each 1 ml of sodium hydroxide titration solution (0.1 mol/L) corresponds to 31.74mg of C19H27NO3.
Last Update：2022-01-01 11:54:25
N-{[(1S,3S)-3-(propan-2-yl)cyclohexyl]carbonyl}-D-phenylalanine - Category
Authoritative Data Verified Data
hypoglycemic drugs.
Last Update：2022-01-01 11:54:26
N-{[(1S,3S)-3-(propan-2-yl)cyclohexyl]carbonyl}-D-phenylalanine - Storage
Authoritative Data Verified Data
light shielding, sealed storage.
Last Update：2022-01-01 11:54:26
N-{[(1S,3S)-3-(propan-2-yl)cyclohexyl]carbonyl}-D-phenylalanine - Nateglinide Tablets
Authoritative Data Verified Data
This product contains nateglinide (C19H27N03) should be 90.0% to 110.0% of the label.
trait
This product is white or white-like tablets or film-coated tablets, white or white-like after removing the coating.
identification
- take an appropriate amount of fine powder of this product (about 50mg equivalent to nateglinide), put it in a 50ml measuring flask, add an appropriate amount of ethanol, shake to dissolve nateglinide, dilute to the scale with ethanol, shake well, filter, take the filtrate, according to UV-visible spectrophotometry (General 0401), there is maximum absorption at 252nm, 258nm, 264nm wavelength.
- in the chromatogram recorded under the content determination item, the retention time of the main peak of the test solution should be consistent with the retention time of the main peak of the reference solution.
examination
- for related substances, take the test sample solution under the content determination item as the test sample solution; Take 1ml of the test sample solution for precise measurement and put it in a 500ml measuring flask, as a control solution, it was diluted to the mark with 55% acetonitrile solution and shaken. According to the chromatographic conditions under the content of LAN, take the sample solution and the control solution of 10 u1, respectively, and inject the human liquid chromatograph, record the chromatogram to 4 times the retention time of the main peak of the test solution. If there are impurity peaks in the chromatogram of the test solution, the area of a single impurity peak shall not be greater than the area of the main peak of the control solution (0.2% ) , the sum of each impurity peak area shall not be greater than 5 times (1.0%) of the main peak area of the control solution.
- dissolution the dissolution of this product was determined according to the dissolution and release determination method (General rule 0931 second method), and the dissolution medium was 6.8 phosphate buffer (pH), and the rotation speed was 75 revolutions per minute, operate according to law, after 30 minutes, take the appropriate amount of solution, filter, take the filtrate as the test solution; According to the chromatographic conditions under the content determination item, take sample solution 10 u1 accurately, inject it into liquid chromatograph, record chromatogram; Take appropriate amount of nateglinide reference substance accurately, add appropriate amount of acetonitrile (not more than 5% of the total volume) to dissolve, further, a solution corresponding to the concentration of the test solution was prepared by quantitative dilution with the dissolution medium, and the solution was used as a reference solution, and was determined by the same method. The dissolution amount of each tablet was calculated by the peak area according to the external standard method. The limit is 75% of the labeled amount and shall be in accordance with the provisions.
- others shall be in accordance with the relevant provisions under the item of tablets (General rule 0101).
Content determination
- measured by high performance liquid chromatography (General 0512).
- color introduction conditions and system suitability test using eighteen alkyl silane bonded silica gel as filler; Acetonitrile-0.05% trifluoroacetic acid (60:40) as mobile phase; The detection wavelength was 210nm; the column temperature was 30°C. The number of theoretical plates shall not be less than 4000 calculated by nateglinide peak, and the tailing factor of nateglinide peak shall not be more than 1.8.
- determination of 10 tablets of this product, precision weighing, fine grinding, precision weighing an appropriate amount (equivalent to 70mg nateglinide), put it in a 100ml measuring flask, add an appropriate amount of 55% acetonitrile solution, shake for 30 minutes to dissolve nateglinide, dilute to the scale with 55% acetonitrile solution, shake well, filter, take the filtrate as the test solution, take 10ul for precision measurement, and inject human liquid chromatograph, record the chromatogram; Take the reference product of nateglinide (about 35mg, precision weighing), put it in a 50ml measuring flask, add an appropriate amount of 55% acetonitrile solution, shake to dissolve and dilute to the scale, shake well, as a reference solution, same method determination. According to the external standard method to calculate the peak area, that is.
category
Same as nateglinide.
specification
(l)30mg (2)60mg (3)90mg (4)120mg
storage
light-shielded, sealed, and stored in a dry place.
Last Update：2022-01-01 11:54:27
N-{[(1S,3S)-3-(propan-2-yl)cyclohexyl]carbonyl}-D-phenylalanine - Nateglinide capsules
Authoritative Data Verified Data
This product contains nateglinide (C19H27N03) should be 90.0% to 110.0% of the label.
trait
The content of this product is white or white particles or powder.
identification
- take an appropriate amount of the content of this product (about 50mg equivalent to nateglinide), put it in a 50ml measuring flask, add an appropriate amount of ethanol, shake to dissolve nateglinide, dilute to the scale with ethanol, and shake well, after filtration, the filtrate was collected and measured by UV-Vis spectrophotometry (General 0401), which showed the maximum absorption at the wavelengths of 252nm, 258mn and 264mn.
- in the chromatogram recorded under the content determination item, the retention time of the main peak of the test solution should be consistent with the retention time of the main peak of the reference solution.
examination
- for related substances, take the test sample solution under the content determination item as the test sample solution; Take 1ml of the test sample solution for precise measurement and put it in a 500ml measuring flask, as a control solution, it was diluted to the mark with 55% acetonitrile solution and shaken. According to the chromatographic conditions under the content determination item, respectively inject l0ul of the test solution and the control solution into the liquid chromatograph, record the chromatogram to 4 times the retention time of the main peak of the test solution. If there are impurity peaks in the chromatogram of the test solution, the area of a single impurity peak shall not be greater than the area of the main peak of the control solution (0.2%), and the sum of each impurity peak area shall not be greater than 5 times the area of the main peak of the control solution (1.0%).
- dissolution dissolution of this product, according to the dissolution and release determination method (General 0931 second method), phosphate buffer (pH 6.8)900ml as the dissolution medium, the rotation speed is 75 revolutions per minute, and the operation is carried out according to law. After 30 minutes, the appropriate amount of the solution is taken, filtered, and the filtrate is taken as the test solution; According to the chromatographic conditions under the content determination item, accurately measure the sample solution L01, inject into the liquid chromatograph, record the chromatogram; Accurately weigh the appropriate amount of nateglinide reference substance, add the appropriate amount of acetonitrile (not more than 5% of the total volume) to dissolve, further, a solution corresponding to the concentration of the test solution was prepared by quantitative dilution with the dissolution medium, and the solution was used as a reference solution, and was determined by the same method. According to the external standard method, the dissolution amount of each particle was calculated by the peak area. The limit is 75% of the labeled amount and shall be in accordance with the provisions.
- others should comply with the relevant provisions under the capsule (General 0103).
Content determination
- measured by high performance liquid chromatography (General 0512).
- chromatographic conditions and system applicability test using eighteen alkyl silane bonded silica as filler f, acetonitrile-0.05% trifluoroacetic acid (60:40) as mobile phase, the detection wavelength was 2 l0nm; the column temperature was 30°C. The number of theoretical plates shall not be less than 4000 calculated by nateglinide peak, and the tailing factor of nateglinide peak shall not be more than 1.8.
- determine the contents under the item of loading difference, mix evenly, grind finely, accurately weigh an appropriate amount (equivalent to 70mg nateglinide), put it in a 100ml measuring flask, and add an appropriate amount of 55% acetonitrile solution, shake for 30 minutes to dissolve, dilute to the scale with 55% acetonitrile solution, shake, filter, take the continued filtrate as the test solution, take the precision amount of 10 u1, and inject the human liquid chromatograph, record the chromatogram; Take the reference product of nateglinide (about 35mg, precision weighing), put it in a 50ml measuring flask, add an appropriate amount of 55% acetonitrile solution, shake to dissolve and dilute to the scale, shake well, as a reference solution, same method determination. According to the external standard method to calculate the peak area, that is.
category
Same as nateglinide.
specification
30mg
storage
sealed and stored in a dry place.
Last Update：2022-01-01 11:54:28
![N-{[(1S,3S)-3-(propan-2-yl)cyclohexyl]carbonyl}-D-phenylalanine](http://res.chembk.com/assets/str/2d/1/10/105816-04-4.png)
Supplier List
Spot supply
Product Name: Nateglinide Request for quotationCAS: 105816-04-4
Tel: +86-17551318830
Email: r@reformchem.com
Mobile: +86-17551318830
QQ: 3785839865
Product Name: Nateglinide Request for quotation
CAS: 105816-04-4
Tel: 17505222756
Email: pules.cn@gmail.com
Mobile: +86-17551318830
Wechat: 17505222756
CAS: 105816-04-4
Tel: 17505222756
Email: pules.cn@gmail.com
Mobile: +86-17551318830
Wechat: 17505222756
Multiple SpecificationsSpot supply
Product Name: Nateglinide Visit Supplier Webpage Request for quotationCAS: 105816-04-4
Tel: 18301782025
Email: 3008007409@qq.com
Mobile: 18021002903
QQ: 3008007409
Wechat: 18301782025
Spot supply
Product Name: Nateglinide Request for quotationCAS: 105816-04-4
Tel: +86-17551318830
Email: r@reformchem.com
Mobile: +86-17551318830
QQ: 3785839865
Product Name: Nateglinide Request for quotation
CAS: 105816-04-4
Tel: 17505222756
Email: pules.cn@gmail.com
Mobile: +86-17551318830
Wechat: 17505222756
CAS: 105816-04-4
Tel: 17505222756
Email: pules.cn@gmail.com
Mobile: +86-17551318830
Wechat: 17505222756
Multiple SpecificationsSpot supply
Product Name: Nateglinide Visit Supplier Webpage Request for quotationCAS: 105816-04-4
Tel: 18301782025
Email: 3008007409@qq.com
Mobile: 18021002903
QQ: 3008007409
Wechat: 18301782025
View History