CN110672782A - Method for determining and analyzing glycols in levophosphorus dextroamine salt - Google Patents
Method for determining and analyzing glycols in levophosphorus dextroamine salt Download PDFInfo
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Abstract
The invention belongs to the technical field of chemical analysis and detection, and particularly relates to a method for determining and analyzing a diol in levophosphorus dextroamine salt. The method for determining and analyzing the diol in the levophosphorus dextroamine salt can prepare and conveniently determine the content of the diol in the levophosphorus dextroamine salt. The iodometry method based on the method is simple and reliable, so that the method for determining and analyzing the iodometry is simple, reliable and easy to implement.
Description
Technical Field
The invention belongs to the technical field of chemical analysis and detection, and particularly relates to a method for determining and analyzing a diol in levophosphorus dextroamine salt.
Background
Fosfomycin sodium is a novel broad-spectrum antibiotic, the sterilization mechanism of the fosfomycin sodium is to inhibit the early synthesis of bacterial cell walls, the probability of anaphylactic shock is very small, the fosfomycin sodium is mainly used for treating the infection of urinary tract, skin, soft tissue, intestinal tract and the like, the fosfomycin sodium has strong sterilization effect on most gram-positive bacteria and gram-negative bacteria, the clinical application is wide, and the market demand is large. Wherein, (1R,2S) - (-) -cis-1, 2-epoxypropylphosphonic acid (R) - (+) -alpha-phenylethylamine salt, called levofosfomycin dextroamine salt for short, is an important intermediate for synthesizing fosfomycin, and is usually prepared by an epoxidation process. The impurity content of the product directly influences the quality of downstream products. In order to ensure the quality and safety of the medicine, a detection method needs to be established to control and monitor the content of the diol in the intermediate. The fosfomycin sodium diol is an epoxy bond ring-opening product of fosfomycin sodium, is a main impurity of fosfomycin sodium for injection, and is controlled by Chinese pharmacopoeia, European pharmacopoeia and British pharmacopoeia. However, the prior art discloses few methods for measuring and analyzing the glycols in levofosfomycin dextroamine salt, and the methods are used as references.
Disclosure of Invention
In order to solve the defects of the prior art, the invention provides a method for determining and analyzing the diol in the levophosphorus dextroamine salt.
The technical scheme provided by the invention is as follows:
a method for determining and analyzing a diol in levofosfomycin dextroamine salt comprises the following steps:
1) taking a standard sample of the levo-phosphorus dextro-amine salt, dissolving the standard sample of the levo-phosphorus dextro-amine salt in an acidic buffer solution, and adding an excessive potassium periodate solution for reaction;
2) adding excessive potassium iodide solution for reaction when the reaction in the step 1) is complete and the yellow color is not changed any more;
3) after the reaction in the step 2) is complete and the yellow color is not changed any more, titrating the generated iodine with sodium thiosulfate, and recording the using amount of the sodium thiosulfate;
4) performing blank control, taking the same amount of the acidic buffer solution in the step 1), and adding the same amount of the potassium periodate solution in the step 1);
5) adding the potassium iodide solution with the same amount as that in the step 2) for reaction;
6) after the reaction in the step 5) is complete and the yellow color is not changed any more, titrating the generated iodine with the sodium thiosulfate, and recording the using amount of the sodium thiosulfate;
7) the weight percentage of the glycols in the levophosphorus dextroamine salt was calculated according to the following formula:
wherein C is the concentration of the sodium thiosulfate titration solution, and the unit is mol/L;
V0the volume of the sodium thiosulfate titration solution consumed in step 6) in the blank control is mL;
V1the volume of the sodium thiosulfate titration solution consumed in the step 3) is mL;
m is the molar mass of the levo-phosphamide salt, 176.12 g/mol;
w is the mass of the standard sample of the levo-phosphorus dextro-amine salt, and the unit is g;
z is the number of moles of periodic acid required to be consumed for one mole of sample and has a value of 1.
In the above technical scheme:
potassium periodate can oxidize compounds with 2 or more adjacent alcoholic hydroxyl groups, but is unreactive with compounds with a single alcoholic hydroxyl group or compounds with nonadjacent alcoholic hydroxyl groups. The reaction formula of the o-alcoholic hydroxyl compound oxidized by periodate can be represented as follows:
the commonly used measurement method is iodometry. From the above results, it can be seen that each molecule of periodate reacts to produce a molecule of iodic acid, both of which are capable of oxidizing potassium iodide in an acidic medium, but the amount of iodine evolved by the reaction is different:
2HIO4+14KI+14H+＝14K++8H2O+8I2
2HIO3+10KI+10H+＝10K++6H2O+6I2
one molecule of periodic acid is consumed and one molecule of iodic acid is produced per molecule of ortho-dihydroxy compound oxidized, while one molecule of iodine is produced. The following relationship can be derived:
1 molecule of o-dihydroxy compound ═ 1 molecule of HIO41-molecule less produced I2
The difference between the blank titration and the sample titration performed in parallel can be used to calculate the amount of ortho-dihydroxy contained in the sample.
The technical scheme is based on an iodometry method, is simple and reliable, and is easier to realize than the method for directly measuring the generated carbonyl compound or iodate under the condition of excess periodate.
Specifically, in the step 3), the judgment mode of the reaction end point is as follows: and titrating with the sodium thiosulfate until the solution is light yellow, adding 1-2 ml of starch indicator, shaking up, and continuously dropwise adding the sodium thiosulfate until the solution is colorless, thus obtaining the reaction end point.
Based on the technical scheme, the reaction endpoint can be accurately judged.
Specifically, in step 6), the reaction end point is determined by the following method: and titrating with the sodium thiosulfate until the solution is light yellow, adding 1-2 ml of starch indicator, shaking up, and continuously dropwise adding the sodium thiosulfate until the solution is colorless, thus obtaining the reaction end point.
Based on the technical scheme, the reaction endpoint can be accurately judged.
Specifically, in the step 1), after adding excessive potassium periodate solution, shaking and uniformly mixing, standing in a dark place for 1-2 hours, and waiting for complete reaction.
Based on the technical scheme, the complete reaction can be ensured.
Specifically, in the step 4), after the potassium periodate solution is added, the mixture is shaken and uniformly mixed, and is placed in a dark place for standing for 1-2 hours until the reaction is complete.
Based on the technical scheme, the complete reaction can be ensured.
Specifically, the acidic buffer solution is a potassium hydrogen phthalate buffer solution, and the pH value of the acidic buffer solution is 6.3-6.5.
Based on the technical scheme, the reaction of oxidizing the o-alcoholic hydroxyl compound by periodate can be completely carried out.
Specifically, the preparation method of the potassium hydrogen phthalate buffer solution comprises the following steps: dissolving every 100g of potassium hydrogen phthalate in 600ml of water, heating to 75 ℃, cooling after the potassium hydrogen phthalate is dissolved, and adjusting the pH value to 6.3-6.5 by using a saturated sodium hydroxide solution to obtain the potassium hydrogen phthalate.
Based on the technical scheme, the potassium hydrogen phthalate buffer solution can be conveniently and conveniently prepared.
In general, the method for determining and analyzing the diol in the levophosphorus dextroamine salt provided by the invention can prepare and conveniently determine the content of the diol in the levophosphorus dextroamine salt. The iodometry method based on the method is simple and reliable, so that the method for determining and analyzing the iodometry is simple, reliable and easy to implement.
Detailed Description
The principles and features of this invention are described below in conjunction with examples which are set forth to illustrate, but are not to be construed to limit the scope of the invention.
Example 1
The method for measuring and analyzing the content of the diol in the levofosfomycin dextroamine salt comprises the following steps:
step 1: preparing solution
(1) Preparation of potassium hydrogen phthalate buffer: 100g of potassium hydrogen phthalate and 1000ml of water are accurately weighed, 600ml of water is added into a beaker, the temperature is heated to 75 ℃ to dissolve the potassium hydrogen phthalate, and after the mixture is cooled, the pH value is adjusted to 6.50 by using a saturated sodium hydroxide solution. Dissolving in a 1000ml volumetric flask, shaking uniformly, and measuring the pH value to be 6.50;
(2) preparation of 10% potassium iodide solution: accurately weighing 10g of potassium iodide, dissolving the potassium iodide in distilled water, and fixing the volume in a 100ml volumetric flask;
(3) preparing 0.01mol/L sodium thiosulfate titration solution: accurately weighing 0.620g of sodium thiosulfate pentahydrate, dissolving the sodium thiosulfate pentahydrate with distilled water, and fixing the volume in a volumetric flask of 250 ml;
(4) preparing 0.005mol/L potassium periodate solution: accurately weighing 0.115g of potassium periodate, dissolving the potassium periodate in distilled water, and fixing the volume in a 100ml volumetric flask;
(5) 1% starch indicator: taking 0.5g of soluble starch, adding a proper amount of water, stirring uniformly to form a thin paste, pouring into 50mL of boiling water, continuously boiling for 2min, cooling, and taking supernatant;
step 2: determination of the experiment
Quantitatively weighing 0.2g of diluted levo-phosphamidon salt in a 250mL iodine flask, adding 100mL of pure water, adding 50mL of potassium hydrogen phthalate buffer (pH 6.50) and 10mL of potassium periodate solution (concentration is 0.005mol/L), shaking and uniformly mixing, and standing in a dark place for half an hour; after the solution fully reacts, adding 10ml of potassium iodide solution (10%), shaking and mixing uniformly; titrating the sample solution by sodium thiosulfate titration solution (0.01mol/L), recording the volume of the consumed titration solution and the color change to judge the reaction end point, adding 1ml of starch indicator (1%) when the titration solution is dripped to be light yellow, shaking up, continuously dripping the titration solution until the solution is colorless to obtain the reaction end point, and recording the data as the sample bottle 1.
The above procedure was repeated and data was recorded for use as the sample vial 2.
Repeating the above operations without adding a sample, and performing a blank control experiment; the content of the diol in the levofosfomycin dextroamine salt was calculated from the difference in the titration volumes.
And step 3: data result analysis
| Reference numerals | Titration volume | Difference from blank | Content of diol |
| Blank bottle | 9.7mL (pale yellow) → 10.2mL (colorless) | ||
| Sample bottle 1 | 9.3mL (pale yellow) → 9.5mL (colorless) | 0.7 | 0.31％ |
| Sample bottle 2 | 9.35mL (pale yellow) → 9.55mL (colorless) | 0.65 | 0.0.29％ |
| Sample bottle 3 | 9.1mL (pale yellow) → 9.5mL (colorless) | 0.7 | 0.31％ |
In the formula: c is the concentration of sodium thiosulfate titration solution, mol/L; v0Consuming the volume of sodium thiosulfate titration solution for a blank experiment, mL; v1Consuming the volume of the sodium thiosulfate titration solution, mL, for the sample solution; m is the molar mass of the levo-phosphamide salt, 176.12 g/mol; w is the mass of a standard sample of the levo-phosphorus dextro-amine salt, g; z is the number of moles of periodic acid that need to be consumed for one mole of sample.
Calculation of RSD:
the calculated RSD shows that the detection method has high accuracy.
Example 2
The method for measuring and analyzing the content of the diol in the levofosfomycin dextroamine salt comprises the following steps:
step 1: preparing solution
(1) Preparation of potassium hydrogen phthalate buffer: 100g of potassium hydrogen phthalate and 1000ml of water are accurately weighed, 600ml of water is added into a beaker, the temperature is heated to 75 ℃ to dissolve the potassium hydrogen phthalate, and after the mixture is cooled, the pH value is adjusted to 6.50 by using a saturated sodium hydroxide solution. Dissolving in a 1000ml volumetric flask, shaking uniformly, and measuring the pH value to be 6.50;
(2) preparation of 10% potassium iodide solution: accurately weighing 10g of potassium iodide, dissolving the potassium iodide in distilled water, and fixing the volume in a 100ml volumetric flask;
(3) preparing 0.01mol/L sodium thiosulfate titration solution: accurately weighing 0.620g of sodium thiosulfate pentahydrate, dissolving the sodium thiosulfate pentahydrate with distilled water, and fixing the volume in a volumetric flask of 250 ml;
(4) preparing 0.005mol/L potassium periodate solution: accurately weighing 0.115g of potassium periodate, dissolving the potassium periodate in distilled water, and fixing the volume in a 100ml volumetric flask;
(5) 1% starch indicator: taking 0.5g of soluble starch, adding a proper amount of water, stirring uniformly to form a thin paste, pouring into 50mL of boiling water, continuously boiling for 2min, cooling, and taking supernatant;
step 2: determination of the experiment
Quantitatively weighing 0.1g of diluted levo-phosphamidon salt in a 250mL iodine flask, adding 100mL of pure water, adding 50mL of potassium hydrogen phthalate buffer (pH 6.50) and 10mL of potassium periodate solution (concentration is 0.005mol/L), shaking and uniformly mixing, and standing in a dark place for half an hour; after the solution fully reacts, adding 10ml of potassium iodide solution (10%), shaking and mixing uniformly; titrating the sample solution by sodium thiosulfate titration solution (0.01mol/L), recording the volume of the consumed titration solution and the color change to judge the reaction end point, adding 1ml of starch indicator (1%) when the titration solution is dripped to be light yellow, shaking up, continuously dripping the titration solution until the solution is colorless to obtain the reaction end point, and recording the data as the sample bottle 1.
Repeating the above steps, recording data, and using as sample bottle 2
The above procedure was repeated, and data was recorded for the sample vial 3.
Repeating the above operations without adding a sample, and performing a blank control experiment; the content of the diol in the levofosfomycin dextroamine salt was calculated from the difference in the titration volumes.
And step 3: data result analysis
| Reference numerals | Titration volume | Difference value | Content of diol |
| Blank bottle | 9.7mL (pale yellow) → 10.2mL (colorless) | ||
| Sample bottle 1 | 9.4mL (pale yellow) → 9.62mL (colorless) | 0.58 | 0.51％ |
| Sample bottle 2 | 9.1mL (pale yellow) → 9.55mL (colorless) | 0.65 | 0.57％ |
| Sample bottle 3 | 9.25mL (pale yellow) → 9.6mL (colorless) | 0.6 | 0.53％ |
In the formula: c is sodium thiosulfateDetermining the concentration of the solution, mol/L; v0Consuming the volume of sodium thiosulfate titration solution for a blank experiment, mL; v1Consuming the volume of the sodium thiosulfate titration solution, mL, for the sample solution; m is the molar mass of the levo-phosphamide salt, 176.12 g/mol; w is the mass of a standard sample of the levo-phosphorus dextro-amine salt, g; z is the number of moles of periodic acid that need to be consumed for one mole of sample.
Calculation of RSD:
the calculated RSD shows that the detection method has high accuracy.
Example 3
The method for measuring and analyzing the content of the diol in the levofosfomycin dextroamine salt comprises the following steps:
step 1: preparing solution
(1) Preparation of potassium hydrogen phthalate buffer: 100g of potassium hydrogen phthalate and 1000ml of water are accurately weighed, 600ml of water is added into a beaker, the temperature is heated to 75 ℃ to dissolve the potassium hydrogen phthalate, and after the mixture is cooled, the pH value is adjusted to 6.50 by using a saturated sodium hydroxide solution. Dissolving in a 1000ml volumetric flask, shaking uniformly, and measuring the pH value to be 6.50;
(2) preparation of 10% potassium iodide solution: accurately weighing 1g of potassium iodide, dissolving the potassium iodide in distilled water, and fixing the volume in a 100ml volumetric flask;
(3) preparing 0.02mol/L sodium thiosulfate titration solution: accurately weighing 1.24g of sodium thiosulfate pentahydrate, dissolving the sodium thiosulfate pentahydrate with distilled water, and fixing the volume in a volumetric flask of 250 ml;
(4) preparing 0.005mol/L potassium periodate solution: accurately weighing 0.115g of potassium periodate, dissolving the potassium periodate in distilled water, and fixing the volume in a 100ml volumetric flask;
(5) 0.5% starch indicator: taking 0.5g of soluble starch, adding a proper amount of water, stirring uniformly to form a thin paste, pouring into 100mL of boiling water, continuously boiling for 2min, cooling, and taking supernatant;
step 2: determination of the experiment
Quantitatively weighing 0.2g of diluted levo-phosphamidon salt in a 250mL iodine flask, adding 100mL of pure water, adding 50mL of potassium hydrogen phthalate buffer (pH 6.50) and 20mL of potassium periodate solution (concentration is 0.005mol/L), shaking and uniformly mixing, and standing in a dark place for half an hour; after the solution fully reacts, 20ml of potassium iodide solution (10%) is added, and the mixture is shaken and uniformly mixed; titrating the sample solution by sodium thiosulfate titration solution (0.02mol/L), recording the volume of the consumed titration solution and the color change to judge the reaction end point, adding 1ml of starch indicator (1%) when the titration solution is dripped to be light yellow, shaking up, continuously dripping the titration solution until the solution is colorless to obtain the reaction end point, and recording the data as the sample bottle 1.
Repeating the above steps, recording data, and using as sample bottle 2
The above procedure was repeated, and data was recorded for the sample vial 3.
Repeating the above operations without adding a sample, and performing a blank control experiment; the content of the diol in the levofosfomycin dextroamine salt was calculated from the difference in the titration volumes.
And step 3: data result analysis
| Reference numerals | Titration volume | Difference value | Content of diol |
| Blank bottle | 9.2mL (pale yellow) → 9.6mL (colorless) | ||
| Sample bottle 1 | 9.0mL (pale yellow) → 9.3mL (colorless) | 0.3 | 0.26％ |
| Sample bottle 2 | 9.1mL (pale yellow) → 9.3mL (colorless) | 0.3 | 0.26％ |
| Sample bottle 3 | 9.1mL (pale yellow) → 9.45mL (colorless) | 0.25 | 0.22％ |
In the formula: c is the concentration of sodium thiosulfate titration solution, mol/L; v0Consuming the volume of sodium thiosulfate titration solution for a blank experiment, mL; v1Consuming the volume of the sodium thiosulfate titration solution, mL, for the sample solution; m is the molar mass of the levo-phosphamide salt, 176.12 g/mol; w is the mass of a standard sample of the levo-phosphorus dextro-amine salt, g; z is the number of moles of periodic acid that need to be consumed for one mole of sample.
Calculation of RSD:
the calculated RSD shows that the detection method has high accuracy.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents, improvements and the like that fall within the spirit and principle of the present invention are intended to be included therein.
Claims (5)
1. A method for measuring and analyzing a diol in levofosfomycin dextroamine salt is characterized by comprising the following steps:
1) taking a standard sample of the levo-phosphorus dextro-amine salt, dissolving the standard sample of the levo-phosphorus dextro-amine salt in an acidic buffer solution, and adding an excessive potassium periodate solution for reaction;
2) adding excessive potassium iodide solution for reaction when the reaction in the step 1) is complete and the color is not changed any more;
3) after the reaction in the step 2) is complete and the color is not changed any more, titrating the generated iodine with sodium thiosulfate, and recording the using amount of the sodium thiosulfate;
4) performing blank control, taking the same amount of the acidic buffer solution in the step 1), and adding the same amount of the potassium periodate solution in the step 1);
5) adding the potassium iodide solution with the same amount as that in the step 2) for reaction;
6) after the reaction in the step 5) is complete and the color is not changed any more, titrating the generated iodine with the sodium thiosulfate, and recording the using amount of the sodium thiosulfate;
7) the weight percentage of the glycols in the levophosphorus dextroamine salt was calculated according to the following formula:
wherein C is the concentration of the sodium thiosulfate titration solution, and the unit is mol/L;
V0the thiosulfuric acid consumed for step 6) of the blankThe volume of the sodium titration solution is mL;
V1the volume of the sodium thiosulfate titration solution consumed in the step 3) is mL;
m is the molar mass of the levo-phosphamide salt, 176.12 g/mol;
w is the mass of the standard sample of the levo-phosphorus dextro-amine salt, and the unit is g;
z is the number of moles of periodic acid required to be consumed for one mole of sample and has a value of 1.
2. The method for assaying glycols in levofosfomycin dextroamine salt according to claim 1, characterized in that:
in the step 3), the judgment mode of the reaction end point is as follows: titrating the solution with the sodium thiosulfate until the solution is light yellow, adding 1-2 ml of starch indicator, shaking up, and continuously dropwise adding the sodium thiosulfate until the solution is colorless, thus obtaining a reaction end point;
in the step 6), the judgment mode of the reaction end point is as follows: and titrating with the sodium thiosulfate until the solution is light yellow, adding 1-2 ml of starch indicator, shaking up, and continuously dropwise adding the sodium thiosulfate until the solution is colorless, thus obtaining the reaction end point.
3. The method for assaying glycols in levofosfomycin dextroamine salt according to claim 1, characterized in that:
in the step 1), adding excessive potassium periodate solution, shaking and uniformly mixing, standing in a dark place for 1-2 hours, and waiting for complete reaction;
and 4) adding a corresponding amount of potassium periodate solution in the step 4), shaking and uniformly mixing, standing in a dark place for 1-2 hours, and waiting for complete reaction.
4. The method for assaying glycols in levophosphorus dextroamine salt according to any one of claims 1 to 3, characterized in that: the acidic buffer solution is a potassium hydrogen phthalate buffer solution, and the pH value of the acidic buffer solution is 6.3-6.5.
5. The method for assaying diol compounds in levofosetyl amine salt according to claim 4, wherein the potassium hydrogen phthalate buffer is prepared by: dissolving every 100g of potassium hydrogen phthalate in 600ml of water, heating to 75 ℃, cooling after the potassium hydrogen phthalate is dissolved, and adjusting the pH value to 6.3-6.5 by using a saturated sodium hydroxide solution to obtain the potassium hydrogen phthalate.
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| CN108997424A (en) * | 2017-06-06 | 2018-12-14 | 湖南华纳大药厂手性药物有限公司 | A kind of simple and direct method for preparing fosfomycin trometamol |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US20080274560A1 (en) * | 2007-03-12 | 2008-11-06 | Versitech Limited | Reagents for detection of hypochlorous acid |
| CN102183593A (en) * | 2011-03-23 | 2011-09-14 | 山西省药品检验所 | Method for detecting mannitol content of cordyceps hawkesii |
| CN108997424A (en) * | 2017-06-06 | 2018-12-14 | 湖南华纳大药厂手性药物有限公司 | A kind of simple and direct method for preparing fosfomycin trometamol |
| CN107607635A (en) * | 2017-08-15 | 2018-01-19 | 东北制药集团股份有限公司 | A kind of method that propine alcohol content in fosfomycin phenylethylamine calt is detected using headspace gas chromatography |
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Application publication date: 20200110 |