CN110954629A - Control method for measuring content of furfuryl amine in furosemide - Google Patents
Control method for measuring content of furfuryl amine in furosemide Download PDFInfo
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- CN110954629A CN110954629A CN201911345481.9A CN201911345481A CN110954629A CN 110954629 A CN110954629 A CN 110954629A CN 201911345481 A CN201911345481 A CN 201911345481A CN 110954629 A CN110954629 A CN 110954629A
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- furosemide
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- DDRPCXLAQZKBJP-UHFFFAOYSA-N furfurylamine Chemical compound NCC1=CC=CO1 DDRPCXLAQZKBJP-UHFFFAOYSA-N 0.000 title claims abstract description 46
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 title claims abstract description 37
- 229960003883 furosemide Drugs 0.000 title claims abstract description 37
- 238000000034 method Methods 0.000 title claims abstract description 22
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims abstract description 15
- 238000004458 analytical method Methods 0.000 claims abstract description 4
- 239000008363 phosphate buffer Substances 0.000 claims abstract description 4
- 239000011259 mixed solution Substances 0.000 claims abstract 2
- 150000003839 salts Chemical class 0.000 claims abstract 2
- 239000000243 solution Substances 0.000 claims description 33
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 27
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 26
- 239000003085 diluting agent Substances 0.000 claims description 16
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 12
- 239000007788 liquid Substances 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 238000012360 testing method Methods 0.000 claims description 7
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 6
- 238000004128 high performance liquid chromatography Methods 0.000 claims description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 4
- 239000008055 phosphate buffer solution Substances 0.000 claims description 4
- 239000006228 supernatant Substances 0.000 claims description 4
- 239000012085 test solution Substances 0.000 claims description 4
- 239000003153 chemical reaction reagent Substances 0.000 claims description 3
- 230000003472 neutralizing effect Effects 0.000 claims description 3
- 238000003556 assay Methods 0.000 claims description 2
- 239000000945 filler Substances 0.000 claims description 2
- 150000002500 ions Chemical class 0.000 claims description 2
- 238000005259 measurement Methods 0.000 claims description 2
- YTJSFYQNRXLOIC-UHFFFAOYSA-N octadecylsilane Chemical group CCCCCCCCCCCCCCCCCC[SiH3] YTJSFYQNRXLOIC-UHFFFAOYSA-N 0.000 claims description 2
- 239000000377 silicon dioxide Substances 0.000 claims description 2
- 238000004440 column chromatography Methods 0.000 claims 1
- 230000035945 sensitivity Effects 0.000 abstract description 5
- 239000013558 reference substance Substances 0.000 description 17
- 239000012071 phase Substances 0.000 description 13
- 239000000523 sample Substances 0.000 description 13
- 239000012535 impurity Substances 0.000 description 9
- 238000001514 detection method Methods 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000007865 diluting Methods 0.000 description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 239000012488 sample solution Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 238000011002 quantification Methods 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- REFMEZARFCPESH-UHFFFAOYSA-M sodium;heptane-1-sulfonate Chemical compound [Na+].CCCCCCCS([O-])(=O)=O REFMEZARFCPESH-UHFFFAOYSA-M 0.000 description 3
- 238000005303 weighing Methods 0.000 description 3
- 239000005711 Benzoic acid Substances 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000010812 external standard method Methods 0.000 description 2
- 238000004811 liquid chromatography Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 206010019280 Heart failures Diseases 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- PBCJIPOGFJYBJE-UHFFFAOYSA-N acetonitrile;hydrate Chemical compound O.CC#N PBCJIPOGFJYBJE-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229940046250 furosemide injection Drugs 0.000 description 1
- 229940090044 injection Drugs 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000012417 linear regression Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000003908 quality control method Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- QEVHRUUCFGRFIF-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C(C5=CC=C(OC)C=C5N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 QEVHRUUCFGRFIF-MDEJGZGSSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- HRQDCDQDOPSGBR-UHFFFAOYSA-M sodium;octane-1-sulfonate Chemical compound [Na+].CCCCCCCCS([O-])(=O)=O HRQDCDQDOPSGBR-UHFFFAOYSA-M 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000000825 ultraviolet detection Methods 0.000 description 1
- 238000012795 verification Methods 0.000 description 1
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/04—Preparation or injection of sample to be analysed
- G01N30/06—Preparation
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/62—Detectors specially adapted therefor
- G01N30/74—Optical detectors
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Immunology (AREA)
- Pathology (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
Abstract
The invention discloses an analysis method for measuring the content of furfuryl amine in furosemide18And the chromatographic column takes a mixed solution of phosphate buffer salt and acetonitrile as a mobile phase. The method for rapidly determining the furfuryl amine in the furosemide is strong in specificity, high in sensitivity, high in accuracy and simple and convenient to operate, and can effectively control the quality of the furosemide.
Description
Technical Field
The invention belongs to the technical field of analytical chemistry, and particularly relates to an analysis method for determining the content of furfuryl amine in furosemide by using a high performance liquid chromatography.
Background
Furosemide, chemical name Furosemide. The traditional Chinese medicine composition is widely used for treating edema related to heart failure in clinic, and can be used for treating hypertension alone or in combination with other antihypertensive medicines. The structural formula is as follows:
the furosemide is synthesized by taking furfurylamine and 2, 4-dichloro-5-sulfamide benzoic acid as initial raw materials and carrying out steps of substitution reaction, refining and the like to obtain the furosemide, the reaction end point is monitored by the content of the 2, 4-dichloro-5-sulfamide benzoic acid in the production process, and the residual amount of the furfurylamine is easily ignored. The structural formula of furfuryl amine is as follows:
it is challenging to quickly and accurately determine the residual furfuryl amine content in furosemide. Furfuryl amine is liquid at room temperature, and the first choice is determined by gas chromatography: the furfuryl amine is micromolecular amine, the response on an FID detector is low, the furosemide is not easy to volatilize and is easy to decompose at high temperature, and the furfuryl amine with the content of less than 1 percent in the furosemide cannot be directly and accurately measured; the furfuryl amine has high boiling point and the furosemide has low solubility, and the detection requirement cannot be met by the gas-phase headspace method.
Because the amine impurities in the gas chromatography have large residue, poor repeatability and low sensitivity in the detection process, the furfurylamine residue in the furosemide is difficult to be quantitatively determined by adopting the general gas chromatography.
The furfuryl amine has strong polarity, does not have sensitive ultraviolet absorption groups, and has weaker ultraviolet absorption. To overcome the sensitivity defect of furfuryl amine, the limit concentration can be increased by increasing the concentration of the test sample.
The solubility of the furosemide in the sodium hydroxide solution is high, but the furosemide directly enters into an acidic mobile phase, so that the risk of precipitation of the furosemide is increased, and even an instrument can be blocked. Therefore, the furosemide is precipitated and filtered out in a neutralization mode, and the furfuryl amine is completely dissolved.
The quantification of trace furfuryl amine usually requires the use of mass spectrometry. The liquid chromatography is adopted for control in the research, the operation is simple, the sensitivity can reach 30ppm, and the minimum limit requirement is met.
Disclosure of Invention
The invention aims to provide a method for separating and measuring trace furfuryl amine in furosemide by using a liquid chromatography, which adopts a pretreatment mode of dissolving acid and neutralizing by sodium hydroxide and filtering, and adopts an ultraviolet detector for measurement. The method can effectively achieve quantitative determination of a small amount of furfuryl amine through verification, thereby realizing effective control of the quality of furosemide. The method solves the problem of effective quality control of furfurylamine residues in furosemide in the prior art, and is simple, rapid and accurate. The method is characterized in that:
the diluent is 0.05-0.2 mol/L hydrochloric acid solution, 95% acetonitrile water solution, sodium hydroxide solution and methanol, preferably the diluent is 0.05-0.3mol/L hydrochloric acid solution, and more preferably 0.1mol/L hydrochloric acid solution.
The concentration of the furosemide in the test sample is 1mg/ml-50mg/ml, preferably 2-10 mg/ml.
The pretreatment mode is as follows: dissolving all furosemide in 0.2-0.5M sodium hydroxide solution, neutralizing with hydrochloric acid, and quantitatively diluting to a scale with a diluent.
The method adopts a chromatographic column with octadecylsilane chemically bonded silica as a filler.
The water phase in the mobile phase is phosphate buffer solution which contains 0.1-1% of ion pair reagent, and the pH value is adjusted to 2.3-4.0 by phosphoric acid. The method is preferably carried out at a pH of 2.5-3.0.
The method is characterized in that the flow rate of a mobile phase is set to be 0.5-2.0 ml/min, and the column temperature is controlled to be 35-50 ℃.
In the method, an ultraviolet detector is adopted, and the detection wavelength is preferably 190-220 nm.
The specific method for measuring the residual amount of the furfuryl amine in the furosemide is as follows:
instrument and reagent
Shijin 2030plus high performance liquid chromatograph, xiang instrument L420 type centrifuge, acetonitrile (chromatographically pure), hydrochloric acid (analytically pure), sodium hydroxide (analytically pure), sodium heptanesulfonate (analytically pure), and phosphoric acid (chromatographically pure).
Diluent agent: hydrochloric acid solution.
Phosphate buffer solution: dissolving sodium heptanesulfonate in 1000ml of water, and adjusting the pH value of phosphoric acid to 2.5-3.0;
control solution: taking a proper amount of furfuryl amine reference substance, quantitatively diluting with hydrochloric acid solution, and shaking up to obtain reference substance solution.
Secondly, measuring the sample:
(1) sample pretreatment: and (3) operating in a dark place, taking a furosemide sample, precisely weighing, adding 0.5ml of sodium hydroxide for dissolving, adding a diluent for quantitatively diluting to a scale, shaking, centrifuging, and taking a supernatant as a test solution.
(2) Chromatographic conditions are as follows:
mobile phase: and (3) taking phosphate buffer solution as a water phase and acetonitrile as an organic phase, and eluting.
The ultraviolet detection wavelength is 210nm by adopting high performance liquid chromatography for determination.
(3) Specificity test
Under the chromatographic conditions, the blank solvent, the furfuryl amine reference substance, the furosemide and other known impurity solutions are sequentially and respectively taken, the separation degree of the furfuryl amine and the adjacent chromatographic peak is more than 1.5, and the blank solvent, the furosemide and other impurities do not interfere with the furfuryl amine determination, so that the requirements are met.
(4) Limit of quantification
Under the chromatographic conditions, the limit of quantitation is determined according to the response concentration when the signal-to-noise ratio of a chromatographic peak is 10:1, the limit of detection is determined according to the response concentration when the signal-to-noise ratio is 3:1, the limit of detection of the furfuryl amine is determined to be 0.05 mu g/ml, and the limit of quantitation is 0.2 mu g/ml.
(5) Linearity
Preparing furfuryl amine reference substance solutions with different concentrations, recording peak areas, and performing linear regression by taking the concentration as a horizontal coordinate and the peak area as a vertical coordinate to obtain a regression equation: y =61152x + 1586, R = 0.9999.
(6) Precision test of instrument
Preparing one part of reference substance solution with quantitative limit concentration, continuously injecting sample 6 needles according to the above conditions, recording peak area, calculating standard average deviation of relative peak area to be 2.6%,
accuracy test 11 parts of sample were weighed, 2 parts of which were prepared as test solution. The other 9 parts are divided into 3 groups, and each group is respectively added with a reference substance solution with 3 concentrations of furfuryl amine, each concentration is prepared into 3 parts in parallel, and a standard sample is prepared and is measured according to the chromatographic conditions. The average recovery of furfuryl amine was calculated to be 93.8% with an RSD of 2.8%.
(7) Stability of the solution furfuryl amine-containing reference substance solution is taken and placed for 13 hours, sample injection is respectively carried out to determine peak area, and RSD is calculated to be 1.1%. The furfuryl amine control solution stability assay was stable over 13 h.
The method has the characteristics of strong specificity, high sensitivity, wide linear range, accurate quantification, good solution stability and the like. Provides powerful scientific basis for feasible determination of residual furfuryl amine in furosemide raw materials and preparations.
The invention has the following positive effects: the method adopts high performance liquid chromatography for determination, and particularly adopts a special pretreatment method and diluent obtained through creative work, so that the quantitative determination of the residual trace furfuryl amine in the furosemide is realized, and the effectiveness and the safety of the furosemide are finally ensured.
Drawings
FIG. 1: the liquid chromatogram of the furfuryl amine control solution obtained in example 1 of the invention.
FIG. 2 is a drawing: according to the liquid chromatogram of the furosemide test sample solution obtained in the embodiment 1 of the invention.
Detailed Description
The following examples are intended to illustrate the invention, but not to limit the scope of the invention.
Example 1
An instrument high performance liquid chromatograph: shimadzu, LC-2030C, UV detector.
A chromatographic column: ultimate AQ-C18（4.6mm ×250mm，5μm）。
Mobile phase: the aqueous phase was phosphate buffer (0.5 g sodium heptanesulfonate dissolved in 1000ml water, phosphoric acid adjusted to pH 2.6); the organic phase was acetonitrile.
Elution gradient:
| time (min) | Mobile phase A (%) | Mobile phase B (%) |
| 0 | 95 | 5 |
| 20 | 95 | 5 |
| 23 | 30 | 70 |
| 29 | 30 | 70 |
| 30 | 95 | 5 |
| 45 | 95 | 5 |
The flow rate was 1.0ml/min
The column temperature was 35 deg.C
Detection wavelength: 210nm
Sample introduction amount: 50 μ l
Diluent agent: 0.1mol/L hydrochloric acid solution
Sample treatment: weighing 20mg of the product, accurately weighing, placing in a 10ml measuring flask, adding 0.5ml of 0.2M sodium hydroxide solution for dissolving, quantitatively diluting with diluent (0.1 mol/L hydrochloric acid solution) to scale, shaking, centrifuging, and collecting supernatant as sample solution; taking a proper amount of an impurity furfurylamine reference substance, dissolving the impurity furfurylamine reference substance by using a diluent, and quantitatively diluting the impurity furfurylamine reference substance to prepare a solution of about 2 mug per lml, wherein the solution is used as a reference substance solution.
Precisely measuring reference substance and sample solution, respectively injecting into liquid chromatograph, recording chromatogram as shown in fig. 1 and fig. 2, respectively, and measuring furfuryl amine content to be 0.01% by external standard method.
As can be seen in fig. 2: the method disclosed by the invention can be used for effectively determining the content of residual furfuryl amine in the furosemide, and can be used for quality detection of furosemide raw materials and intermediates.
Example 2.
The apparatus is as in example 1.
A chromatographic column: thermo Hypersil BDS C184.6 mm. times.250 mm, 5 μm is suitable).
Diluent as in example 1
Mobile phase: the water phase is phosphate buffer (0.3 g sodium octane sulfonate dissolved in 1000ml water, phosphoric acid to adjust pH to 2.8); the organic phase was methanol. Water phase: organic phase =90: 10.
The flow rate was 1.5ml/min
The column temperature was 40 deg.C
Detection wavelength: 210nm
Sample introduction amount: 10 μ l
Diluent agent: 0.05mol/L hydrochloric acid solution
Sample treatment: 2ml of furosemide injection is put into a 10ml measuring flask, the diluent is quantitatively diluted to a scale, shaken up and centrifuged, and the supernatant is taken as a test solution; taking a proper amount of an impurity furfurylamine reference substance, dissolving the impurity furfurylamine reference substance by using a diluent, and quantitatively diluting the impurity furfurylamine reference substance to prepare a solution of about 20 mug per lml, wherein the solution is used as a reference substance solution.
Precisely measuring reference substance and sample solution, respectively injecting into liquid chromatograph, and recording chromatogram, wherein the furfuryl amine content is 0.02% by external standard method.
Claims (5)
1. A method for determining and analyzing the content of furfuryl amine in furosemide features that the furosemide is pretreated and then high-performance liquid chromatography is used18And (3) performing column chromatography determination by using a mixed solution of phosphate buffer salt and acetonitrile as a mobile phase.
2. The assay of claim 1, wherein the furosemide sample is treated by: dissolving with sodium hydroxide solution, neutralizing with hydrochloric acid, quantifying, shaking, centrifuging, and collecting supernatant as test solution.
3. The analytical method according to claim 1, wherein the furfuryl amine content is measured by high performance liquid chromatography and an ultraviolet detector.
4. The analytical method according to claim 1, wherein octadecylsilane bonded silica (C) is used18) Is a filler chromatographic column.
5. The method according to claim 1, characterized in that the method comprises the following main contents:
(1) the preferable diluent of the diluent is 0.05-0.3mol/L hydrochloric acid solution;
(2) the concentration of the furosemide in the test sample is 1mg/ml-50mg/ml, preferably 2-10 mg/ml;
(3) the pretreatment mode needs to completely dissolve by using 0.2-0.5M sodium hydroxide solution, needs to neutralize by using hydrochloric acid, and quantitatively dilutes to a scale by using a diluent;
(4) the mobile phase water phase is phosphate buffer solution containing 0.1-1% of ion pair reagent, and the pH value is adjusted to 2.5-4.0 by phosphoric acid; the method is preferably pH2.5-3.0;
(5) the method adopts a high performance liquid chromatograph and an ultraviolet detector for measurement.
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| CN112142833A (en) * | 2020-09-24 | 2020-12-29 | 华南农业大学 | A kind of furosemide artificial antigen, antibody and its application in detecting furosemide |
| CN113219084A (en) * | 2021-03-26 | 2021-08-06 | 天圣制药集团股份有限公司 | HPLC detection method for 2-furanmethanamine and condensation reaction impurities thereof in furosemide and preparation thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN112142833A (en) * | 2020-09-24 | 2020-12-29 | 华南农业大学 | A kind of furosemide artificial antigen, antibody and its application in detecting furosemide |
| CN112142833B (en) * | 2020-09-24 | 2021-10-29 | 华南农业大学 | A kind of furosemide artificial antigen, antibody and its application in detecting furosemide |
| CN113219084A (en) * | 2021-03-26 | 2021-08-06 | 天圣制药集团股份有限公司 | HPLC detection method for 2-furanmethanamine and condensation reaction impurities thereof in furosemide and preparation thereof |
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