CN111323519A - Method for detecting triethylamine in propane fumarate tenofovir disoproxil through gas chromatography - Google Patents
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Abstract
The invention discloses a method for detecting triethylamine in tenofovir disoproxil fumarate by gas chromatography, which comprises the steps of respectively detecting a sample solution of the tenofovir disoproxil fumarate and a reference solution by the gas chromatography, recording chromatograms of the sample solution and the reference solution, obtaining peak areas of triethylamine in the sample solution of the tenofovir disoproxil fumarate and the reference solution, and quantitatively analyzing the triethylamine in the sample solution by an external standard method.
Description
Technical Field
The invention relates to the technical field of drug analysis, in particular to a method for detecting triethylamine in propane fumarate tenofovir through gas chromatography.
Background
Propofovir fumarate, chemically known as L-alanine- [ N- [ (S) - [ [ (1R) -2- (6-amino-9H-purin-9-yl) -1-methylethoxy ] methyl ] phenoxyphosphoryloxy ] ] -1-methylethyl ester, (2E) -2-butenedioate (2: 1), having the chemical structure:
the valproic acid Propofovir fumarate is a second-generation oral prodrug of tenofovir, and prodrug groups on two hydroxyl groups in phosphoric acid are converted on the basis of the structure of tenofovir, namely, the dipivoxil is converted into an amide and a phenolic ester, so that the valproic acid fumarate is an esterified amidated prodrug. The reconstruction overcomes the defects that tenofovir disoproxil is unstable in blood plasma and is easy to be hydrolyzed by esterase, further improves the delivery rate of tenofovir to liver cells, Peripheral Blood Mononuclear Cells (PBMC) and lymphoid organs, achieves obvious attenuation and synergism effects, and has the effective dose about 25 times lower than TDF.
Triethylamine is a solvent adopted in the synthesis process of the propane fumarate tenofovir, and the fumaric acid in the structure of the propane fumarate tenofovir can interfere with the detection of triethylamine in a sample, so that the research establishes a method for detecting triethylamine in the propane fumarate tenofovir by gas chromatography (headspace sampling), can effectively avoid the interference of the fumaric acid on the detection of the triethylamine, and has the advantages of high sensitivity, strong specificity and high accuracy.
Disclosure of Invention
The invention aims to solve the problems and provides a method for determining triethylamine in the propane fumarate tenofovir, which is simple to operate, accurate in result and high in sensitivity.
The technical scheme of the invention is that the method for detecting triethylamine in the propane fumarate tenofovir comprises the steps of respectively detecting a test solution and a reference solution of the propane fumarate tenofovir by using a gas chromatography, recording chromatograms of the test solution and the reference solution, obtaining peak areas of triethylamine in the test solution and the reference solution of the propane fumarate tenofovir, and carrying out quantitative analysis on the triethylamine in the propane fumarate tenofovir by using an external standard method.
As a further description of the method for determining triethylamine in the fumaric acid, namely, propanphenol tenofovir disoproxil, the present invention uses N, N-dimethylformamide as a solvent for dissolving a sample, and 0.3ml of sodium hydroxide solution (300mg/ml) is added to neutralize fumaric acid in the sample structure in advance.
As a further description of the method for determination of triethylamine in the fumaric acid, propofol, tenofovir, the formulation of a blank solution: 1ml of N, N-dimethylformamide was precisely measured and placed in a 20ml headspace bottle, and 0.3ml of sodium hydroxide solution (300mg/ml) was added thereto and sealed.
As a further description of the method for determining triethylamine in the malonic acid fumarate, tenofovir disoproxil was prepared: taking a proper amount of triethylamine, precisely weighing, adding N, N-dimethylformamide to dissolve and dilute to prepare a solution containing about 500 mu g of triethylamine in each 1ml, precisely weighing 1ml, placing in a 20ml headspace bottle, adding 0.3ml of sodium hydroxide solution (300mg/ml), and sealing.
As a further description of the method for determining triethylamine in the malonic acid fumarate, a test solution was prepared: precisely weighing 0.1g of sample, placing in a 20ml headspace bottle, adding 1ml of N, N-dimethylformamide for dissolving, adding 0.3ml of sodium hydroxide solution (300mg/ml), and sealing.
As a further description of the method for determining triethylamine in the Propofovir fumarate, an Agilent 7890B gas chromatograph is adopted, an Agi lent7697A headspace sample injector is adopted, a chromatographic column is Agi lent CP-Volamines (30 × 0.32mm), the initial column temperature is 45 ℃, the initial column temperature is maintained for 5 minutes, the temperature is raised to 220 ℃ at the rate of 20 ℃ per minute, the injection port temperature is 220 ℃, a detector is a hydrogen flame ionization detector, the detector temperature is 220 ℃, carrier gas is nitrogen, the split ratio is 50: 1, the hydrogen flow is 30ml/min, the oxygen flow is 300ml/min, the nitrogen flow is 25ml/min, the flow rate is 2.0ml/min, the equilibrium temperature of a headspace bottle is 85 ℃, the quantitative ring temperature is 120 ℃, the transmission line temperature is 130 ℃, and the equilibrium time is 30 minutes.
As a further description of the method for determining triethylamine in the propane fumarate tenofovir, the column flow rate may be set to 1.8ml/min to 2.2 ml/min.
As a further description of the method for determining triethylamine in the propane fumarate tenofovir, the injection inlet temperature may be set to 210-230 ℃.
As a further description of the method for determining triethylamine in the propane fumarate tenofovir, the initial column temperature may be set at 40 ℃ to 50 ℃.
Compared with the common residual solvent detection technology, the method has the advantages that a proper amount of sodium hydroxide solution is added to react with fumaric acid in a test sample, so that the interference of the fumaric acid can be eliminated, and the method is more favorable for accurately determining the triethylamine content in the test sample. Through verification, the method is high in sensitivity, strong in specificity and high in accuracy.
Drawings
FIG. 1 is a chromatogram of a control solution from example 1;
FIG. 2 is a chromatogram of a sample solution added with a standard in example 1;
FIG. 3 is a chromatogram of a control solution from example 2;
FIG. 4 is a chromatogram of a sample solution added with a standard in example 2;
FIG. 5 is a chromatogram of a control solution from example 3;
FIG. 6 is a chromatogram of the test sample solution added in example 3;
FIG. 7 is a chromatogram of a control solution from example 4;
FIG. 8 is a chromatogram of the test sample solution added in example 4;
FIG. 9 is a chromatogram of a control solution from example 5;
FIG. 10 is a chromatogram of the test sample solution added with the standard of example 5;
FIG. 11 is a chromatogram of a blank solution from example 5;
FIG. 12 is a chromatogram of the test solution of example 5.
Detailed Description
The examples are provided for better illustration of the present invention, but the present invention is not limited to the examples.
The instrument and chromatographic conditions used in the following examples were Agi lent 7890B gas chromatograph with Agi lent7697A headspace sampler, Agi lent CP-Volamines (30 × 0.32.32 mm) as chromatographic column, initial column temperature of 45 deg.C, 5 minutes hold, and then 20 deg.C per minute rate of temperature up to 220 deg.C, inlet temperature of 220 deg.C, detector temperature of 220 deg.C, carrier gas of nitrogen, split ratio of 50: 1, hydrogen flow of 30ml/min, oxygen flow of 300ml/min, nitrogen flow of 25ml/min, flow rate of 2.0ml/min, headspace bottle equilibrium temperature of 85 deg.C, quantitative loop temperature of 120 deg.C, transmission line temperature of 130 deg.C, and equilibration time of 30 minutes.
EXAMPLE 1 treatment of test articles without sodium hydroxide solution
Solution preparation:
table 1 example 1 solution formulation
And (4) respectively taking the solutions to perform headspace sample injection, and recording a chromatogram. The test results are as follows:
table 2 example 1 test results
| Name of solution | Peak area of triethylamine |
| Control solution | 1066.2 |
| Test solution | Not detected out |
| Adding standard sample solution | 153.8 |
The result shows that the peak area of triethylamine in the solution of the standard sample is obviously lower than that of the reference sample at the same concentration, and the recovery rate is 14.4%, which indicates that the method is not suitable for detecting triethylamine in the propane fumarate tenofovir.
Example 2 sodium hydroxide solution addition: 150mg/ml, 0.2ml
Solution preparation:
table 3 example 2 solution formulation
And (4) respectively taking the solutions to perform headspace sample injection, and recording a chromatogram. The test results are as follows:
table 4 example 2 test results
| Name of solution | Peak area of triethylamine |
| Control solution | 1834.6 |
| Test solution | Not detected out |
| Adding standard sample solution | 1424.1 |
The result shows that the area of the triethylamine peak in the standard sample solution is obviously increased, the sodium hydroxide adding amount is already excessive under the condition, but the recovery rate is only 77.6%.
Example 3 sodium hydroxide solution addition: 300mg/ml, 0.2ml
Solution preparation:
table 5 example 3 solution formulation
And (4) respectively taking the solutions to perform headspace sample injection, and recording a chromatogram. The test results are as follows:
table 6 example 3 test results
| Name of solution | Peak area of triethylamine |
| Control solution | 1979.6 |
| Test solution | Not detected out |
| Adding standard sample solution | 1838.1 |
The result shows that the recovery rate of triethylamine in the standard sample is 92.9%, and the requirement on the recovery rate in the verification guidance principle of the four-part general rule 9101 drug quality standard analysis method in the Chinese pharmacopoeia 2015 edition is met.
Example 4 sodium hydroxide solution addition: 300mg/ml, 0.4ml
Solution preparation:
table 7 example 4 solution formulation
And (4) respectively taking the solutions to perform headspace sample injection, and recording a chromatogram. The test results are as follows:
table 8 example 4 test results
| Name of solution | Peak area of triethylamine |
| Control solution | 1911.3 |
| Test solution | Not detected out |
| Adding standard sample solution | 2016.4 |
The result shows that the recovery rate of triethylamine in the added standard test sample is 105.5 percent, the requirement on the recovery rate in the verification and guidance principle of the four-part rule 9101 drug quality standard analysis method in the Chinese pharmacopoeia 2015 edition is met, but more sodium hydroxide is precipitated in the test sample solution.
Example 5 sodium hydroxide solution addition: 300mg/ml, 0.3ml
Solution preparation:
table 9 example 5 solution formulation
And (4) respectively taking the solutions to perform headspace sample injection, and recording a chromatogram. The test results are as follows:
table 10 example 5 test results
| Name of solution | Peak area of triethylamine |
| Control solution | 1922.6 |
| Test solution | Not detected out |
| Adding standard sample solution | 1851.9 |
The result shows that the recovery rate of triethylamine in the standard sample is 96.3%, the requirement on the recovery rate in the verification guidance principle of the quality standard analysis method of 9101 drugs in the four-part general rule of the national pharmacopoeia 2015 edition is met, and sodium hydroxide is not precipitated, so that the methodological verification is carried out by the method.
Methodology validation results:
TABLE 11 Linear verification results
TABLE 12 accuracy verification results
The verification result shows that the detection method has strong specificity, high sensitivity and high accuracy.
The technical solutions described above only represent the preferred technical solutions of the present invention, and some possible modifications to some parts of the technical solutions by those skilled in the art all represent the principles of the present invention, and fall within the protection scope of the present invention.
Claims (9)
1. The method for detecting triethylamine in the fumaric acid Propofol tenofovir through gas chromatography is characterized by comprising the following steps: respectively detecting the propane fumarate tenofovir disoproxil fumarate test solution and the reference solution by adopting a gas chromatography, recording chromatograms of the test solution and the reference solution, obtaining peak areas of triethylamine in the propane fumarate tenofovir disoproxil test solution and the reference solution, and quantitatively analyzing the triethylamine in the test solution by using an external standard method; the reference solution is a pure triethylamine solution.
2. The method for detecting triethylamine in the preparation of propiofuravir fumarate by gas chromatography as claimed in claim 1, wherein N, N-dimethylformamide is used as a solvent for dissolving the sample, and 0.3ml of sodium hydroxide solution (300mg/ml) is added to neutralize the fumaric acid in the structure of propiofuravir fumarate in advance.
3. The method for detecting triethylamine in the propanefenovir fumarate according to claim 1, characterized in that an Agilent 7890B gas chromatograph is used with an Agilent7697A headspace sample injector.
4. The method for detecting triethylamine in the propanefenovir fumarate according to claim 1, wherein the chromatographic column is Agilent CP-Volamines (30 × 0.32.32 mm), and the flow rate of the column can be set to 1.8 ml/min-2.2 ml/min.
5. The gas chromatography detection method for triethylamine in tenofovir disoproxil fumarate according to claim 1, wherein the initial column temperature can be set to 40-50 ℃, maintained for 5 minutes, and then increased to 220 ℃ at a rate of 20 ℃ per minute.
6. The gas chromatography detection method for triethylamine in the propanefenovir fumarate as claimed in claim 1, wherein the injection port temperature can be set to 210-230 ℃.
7. The gas chromatography detection method for triethylamine in the propanefenovir fumarate as claimed in claim 1, wherein the detector is a hydrogen flame ionization detector, and the temperature of the detector is 220 ℃.
8. The gas chromatography detection method for triethylamine in the fumaric acid Propofovir through the method according to claim 1, wherein the carrier gas is nitrogen, and the split ratio is 50: 1, hydrogen flow 30ml/min, oxygen flow 300ml/min, nitrogen flow 25 ml/min.
9. The gas chromatography detection method for triethylamine in propylphenol fumarate tenofovir according to claim 1, wherein the equilibrium temperature of the headspace bottle is 85 ℃, the quantitative loop temperature is 120 ℃, the transfer line temperature is 130 ℃, and the equilibrium time is 30 minutes.
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Cited By (5)
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| CN111735884A (en) * | 2020-08-04 | 2020-10-02 | 精晶药业股份有限公司 | High performance gas chromatography detection method for triethylamine content in feed liquid |
| CN112379019A (en) * | 2020-11-06 | 2021-02-19 | 郑州原理生物科技有限公司 | Method for detecting residual solvent diethylamine in lidocaine hydrochloride |
| CN112782311A (en) * | 2020-12-30 | 2021-05-11 | 南京百泽医药科技有限公司 | HPLC (high performance liquid chromatography) determination method of L-isopropyl alanine in tenofovir disoproxil fumarate |
| CN112903866A (en) * | 2021-02-02 | 2021-06-04 | 郑州泰丰制药有限公司 | Method for determining triethylamine content in propane fumarate tenofovir |
| WO2022151842A1 (en) * | 2021-01-14 | 2022-07-21 | 浙江海正药业股份有限公司 | Gas-phase chromatography detection method for dicyclohexylamine in favipiravir |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111735884A (en) * | 2020-08-04 | 2020-10-02 | 精晶药业股份有限公司 | High performance gas chromatography detection method for triethylamine content in feed liquid |
| CN112379019A (en) * | 2020-11-06 | 2021-02-19 | 郑州原理生物科技有限公司 | Method for detecting residual solvent diethylamine in lidocaine hydrochloride |
| CN112782311A (en) * | 2020-12-30 | 2021-05-11 | 南京百泽医药科技有限公司 | HPLC (high performance liquid chromatography) determination method of L-isopropyl alanine in tenofovir disoproxil fumarate |
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