CN105954419B - The method of HPLC method separation determination levo-cetirizine hydrochlorides and its enantiomter - Google Patents

The method of HPLC method separation determination levo-cetirizine hydrochlorides and its enantiomter Download PDF

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CN105954419B
CN105954419B CN201610382247.3A CN201610382247A CN105954419B CN 105954419 B CN105954419 B CN 105954419B CN 201610382247 A CN201610382247 A CN 201610382247A CN 105954419 B CN105954419 B CN 105954419B
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levo
enantiomter
mobile phase
cetirizine hydrochloride
solution
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CN105954419A (en
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林晓兵
张波
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Chongqing Huapont Pharm Co Ltd
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    • 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
    • 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
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    • G01N2030/027—Liquid chromatography

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Abstract

The invention belongs to analytical chemistry field, and in particular to a kind of method of HPLC methods separation determination levo-cetirizine hydrochloride and its enantiomter.The chromatographic column used in methods described be using surface chemistry bonding beta cyclodextrin silica gel as filler, eluted using mobile phase A and Mobile phase B, detected into detector；Described mobile phase A is inorganic salts buffer system, and described Mobile phase B is organic solvent.This method is reversed-phased high performace liquid chromatographic, the separation and detection of levo-cetirizine hydrochloride and its enantiomter can be realized simultaneously, and there are excellent separating property and durability, simple and feasible, favorable reproducibility is efficiently quick, it significantly shorten analysis time, tailing factor and theoretical pedal number can reach extraordinary effect, can effectively determine the content of enantiomter in levo-cetirizine hydrochloride, and specificity is strong.

Description

The method of HPLC method separation determination levo-cetirizine hydrochlorides and its enantiomter
Technical field
The invention belongs to analytical chemistry field, and in particular to a kind of HPLC methods separation determination levo-cetirizine hydrochloride and its right Reflect the method for isomers.
Background technology
Levo-cetirizine hydrochloride (Levocetirizine Hydrochloride) listed in 2 months 2001, was the third generation Antihistamine, it is the single optical isomer (cetirizine TP- isomers) of second generation antihistamine cetirizine, it is public by UCB Department's research and development, are selective histamine H l receptor antagonists, the effect without obvious cholinolytic and medmain, central inhibitory action compared with It is small, it is mainly used in treating the anaphylactia of respiratory system, skin and eyes etc., such as allergic rhinoconjunctivitis, anaphylaxis skin Skin disease, allergic asthma etc., have that onset of action is fast, effect is strong and persistently and the advantages of few side effects.
The applicable crowd of levo-cetirizine hydrochloride is extensive, available for children and the gestational period and women breast-feeding their children, safe and reliable, Clinical effectiveness is notable.Levo-cetirizine hydrochloride chemical name R-2- [2- [4- [(4- chlorphenyls) phenyl methyl] -1- piperazinyls] ethoxies Base] acetic acid, dihydrochloride, molecular formula C21H25ClN2O3·2HCl.Levo-cetirizine hydrochloride structural formula is：
The chemical name and structural formula of isomers are as follows：
Found during clinical research test the cetirizine enantiomter carried out the effect of, left-handed west is for profit Piperazine curative effect is better than its raceme cetirizine, and dextrocetirizine is then without any drug action.Because the two is pharmacologically Larger difference be present, therefore the enantiomter impurity content to levo-cetirizine hydrochloride is needed in pharmaceutical synthesis and production process Strictly controlled.And analysis, the separation of the enantiomter containing asymmetric carbon atom are always chiral drug synthesis and preparation mistake The difficult point and emphasis of quality control in journey, realize that the separation of levo-cetirizine hydrochloride and its corresponding isomers replaces profit in the left west of hydrochloric acid There is very important social effect and economic benefit in terms of the synthesis of piperazine medicine and the quality control of production process.
For preparing caused isomers during levo-cetirizine hydrochloride, whether it is both needed in bulk drug or preparation Strictly controlled.Medicine levo-cetirizine hydrochloride has been recorded in USP at present, and has had isomery body detecting method, but USP Middle levo-cetirizine hydrochloride isomery body detecting method, very late, main peak appearance time is 35 minutes to appearance time, and a sample needle is at least 60 minutes are needed, and symmetrical factor is very big, and theoretical pedal number is not high.Publication date is 20041231 protein and cellulose Derivative chiral stationary phase separates levo-cetirizine hydrochloride enantiomer, and Zhang Zhefeng, what is limited in Acta Pharmaceutica Sinica is protein and fibre Tie up plain derivative chiral stationary phase, and this method is using the silica gel of beta-schardinger dextrin is bonded using surface chemistry as filler, specifically Using ULTRON ES-CD, the chromatographic column has excellent separating property and durability.Application No. 201010595648.X hair Bright patent discloses a kind of detection method of Analyze ＆ separate levocetirizine and its optical isomer, and this method uses CHIRAL- AGP chiral columns, it is normal phase chromatography.Chromatographic column filler is α first in that patent1- sour glycoprotein, service life are not grown, very It is easily bad.Secondly the patented method is reported as normal phase chromatography, normal phase chromatography taste weight, and toxicity is big.There is presently no one kind The silica gel of beta-schardinger dextrin is used as filler, and can durable in use, environmentally friendly, small toxicity, and can also the left west of quick separating hydrochloric acid replace The open method of sharp piperazine and its enantiomter is reported.
Therefore exploitation is using the silica gel of beta-schardinger dextrin as filler, durable in use, environmentally friendly, small toxicity and an energy quick separating hydrochloric acid left side The analysis method of cetirizine and its enantiomter, quality control and degraded for Pharmaceutical Analysis personnel health and products thereof Study of way is all very significant work.
The content of the invention
In view of this, it is an object of the invention to provide a kind of HPLC methods separation determination levo-cetirizine hydrochloride and its mapping The method of isomers, this method are reversed-phased high performace liquid chromatographic, can realize levo-cetirizine hydrochloride and its enantiomerism simultaneously The separation and detection of body, and have excellent separating property and durability, analysis time is significantly shorten, tailing factor and theory are stepped on Plate number can reach extraordinary effect.
To achieve the above object, the technical scheme is that：
A kind of method of HPLC (high performance liquid chromatography) method separation determination levo-cetirizine hydrochloride and its enantiomter, institute State the chromatographic column used in method be using surface chemistry bonding beta-schardinger dextrin silica gel as filler, using mobile phase A and Mobile phase B Eluted, detected into detector；Described mobile phase A is inorganic salts buffer system, and described Mobile phase B is organic Solvent.
The levo-cetirizine hydrochloride structural formula is：
The chemical name and structural formula of the levo-cetirizine hydrochloride enantiomter are as follows：
When splitting enantiomter with cyclodextrin chiral Bonded Phase, there is particular/special requirement to the structure of sample, first, sample Molecule partly must can enter cyclodextrin inner chamber, second, in the polar group and cyclodextrin cavity on sample molecule chiral centre Association occurs for hydroxyl.The separated compound of the present invention contains phenyl ring, can occur to contain complexing with cyclodextrin inner chamber, Hydrogen can be formed with the hydroxyl of cyclodextrin accent to build, so levo-cetirizine hydrochloride and its enantiomer are on cyclodextrin bonded stationary phase Can preferably it be separated.
As a preferred embodiment, that described chromatographic column selection is ULTRON ES-CD, ULTRON ES-CD：ES-CD is chiral Stationary phase is beta-schardinger dextrin, and ES-CD has excellent separating property and durability.ES-CD and post all may be used to anti-phase positive mobile phase With the chiral separation applied to hydrophobic cyclic agent, agricultural chemicals and organic compound.
Further, the concentration of inorganic salts is 0.04mol/L-0.06mol/L in the inorganic salts buffer system.
As a preferred embodiment, the concentration of inorganic salts is 0.05mol/L in the inorganic salts buffer system.
Further, the inorganic salts buffer system is the buffer system of Potassium Hexafluorophosphate.
Influence chiral separation factor it is a lot, it is determined that stationary phase under the conditions of, to determine sample for, mobile phase Composition is the key factor for influenceing separation.Hexafluorophosphoric acid potassium concn is high, mix easily precipitation solid with acetonitrile, and concentration is low to be reached Less than ion-pairing agent effect, therefore concentration range is selected as 0.04mol/L-0.06mol/L.
Further, the inorganic salts buffer system pH value is 2-4.
The pH and ionic strength of mobile phase have a great impact to the selectivity and efficiency of cyclodextrin bonded phase, in mobile phase Middle addition salt, cushioning liquid is formed, it is big to reservation and the influence of the influence comparison selectivity of efficiency, due to buffer and analyte Cyclodextrin cavity is captured in competition, so with the intensity increase of buffer, the reservation of solute reduces, efficiency increase.Mobile phase pH's Change has a great impact to non-dissociable solute.
As a preferred embodiment, the inorganic salts buffer system pH value is 3.0.
Further, the volume ratio 60 of the mobile phase A and Mobile phase B：40；The organic solvent includes acetonitrile.
In the chiral separation rp mode of cyclodextrin bonded phase, the organic solvent that can be typically used in mobile phase has： Methanol, ethanol, propyl alcohol, acetonitrile, dimethylformamide, dioxane etc., but most commonly used is methanol and acetonitrile.Generally in water The ability of cyclodextrin inclusion organic molecule is most strong, with the addition of organic modifiers, due to organic modifiers and solute molecule Vie each other and occupy cyclodextrin inner chamber, reduce Binding ability, methanol is displacer most weak in alcohols, the replacement ability of acetonitrile It is stronger than methanol and ethanol.Different organic solvents is selected, the selectivity of Chiral Separation can be improved.
Further, the flow rate of mobile phase is 0.3-0.7ml/min, and the chromatographic column post case temperature is 20-30 DEG C.
Solute is influenced by temperature very big, binding constant increase, but matter transmission at low temperature to the binding constant of cyclodextrin It can be deteriorated, can increase the selectivity of cyclodextrin bonded phase so reducing column temperature, while may also can reduce separating degree, but increase The separation of solute of the strutting temperature to retaining by force can make moderate progress, so by verification experimental verification, the selection of chromatographic column post case temperature scope For 20-30 DEG C.
Further, the specification of the chromatographic column is 150 × 6.0mm, 5 μm.
To the ULTRON ES-CD analytical columns of this specification, optimal flow rate of mobile phase scope should be 0.3-0.7ml/min, (0.7-2.0ml/min) peak diffusion caused by matter transmission effects can cause to reduce post effect and separating degree under high flow rate.
Further, the Detection wavelength of the detector is 220-240nm.
Further, the method for the HPLC methods separation determination levo-cetirizine hydrochloride and its enantiomter, is specifically included Following steps：
1) levo-cetirizine hydrochloride and its reference substance of enantiomter are taken respectively, and testing sample is made with diluent dissolving And its reference substance solution of enantiomter, testing sample levo-cetirizine hydrochloride and its reference substance of enantiomter are taken respectively Solution sample introduction, efficient liquid phase chromatographic analysis is carried out, determine the retention time of levo-cetirizine hydrochloride and its enantiomter；
2) take levo-cetirizine hydrochloride test sample to add diluent that need testing solution is made, then take diluent molten as blank Liquid, need testing solution and blank solution sample introduction being taken respectively, carrying out efficient liquid phase chromatographic analysis, record chromatogram, it is left to complete hydrochloric acid The separation determination of cetirizine and its enantiomter.
Further, the step 1) diluent is the aqueous dissolution sample of acetonitrile or acetonitrile, in the aqueous solution of institute's acetonitrile The volume ratio of acetonitrile and water is 40:60.
Method of the present invention, as a preferred embodiment, can specifically realize in accordance with the following methods：
(1) take levo-cetirizine hydrochloride appropriate, with 40% acetonitrile solution (acetonitrile V：Water V=40:60) sample dissolution, match somebody with somebody The hydrochloric levocetirizine 0.1-0.5mg of every 1ml sample solution is made；
(2) select model Shimadzu LC-20AT chromatograph, chromatographic column model ULTRON ES-CD (150 × 6.0mm), the preparation of mobile phase A：Potassium Hexafluorophosphate 9.25g (0.05mol/L Potassium Hexafluorophosphates) is weighed in 1000ml volumetric flasks In, it is dissolved in water and is diluted to scale, with phosphorus acid for adjusting pH value to 3.0 ± 0.1；Mobile phase B is acetonitrile；Mobile phase A and flowing Phase B ratio is 60：40, take the μ l of sample solution 10 of step (1) to inject in liquid chromatograph, setting flow rate of mobile phase is 0.5ml/min, Detection wavelength 231nm, chromatographic column post case temperature are 25 DEG C, complete levo-cetirizine hydrochloride and its enantiomerism The separation of body and measure.
The present invention also aims to provide a kind of stationary phase and mobile phase to separate and/or determining levo-cetirizine hydrochloride And its application in the chromatography of enantiomter, the stationary phase are bonded the silica gel of beta-schardinger dextrin, the stream for surface chemistry Dynamic is mutually the buffer system and organic solvent of Potassium Hexafluorophosphate, and the concentration of the hexafluorophosphoric acid potassium solution is 0.04mol/L- 0.06mol/L；The pH value of the hexafluorophosphoric acid potassium solution is 2-4；The organic solvent is acetonitrile.
The beneficial effects of the present invention are：
1) method of a kind of HPLC methods separation determination levo-cetirizine hydrochloride of the invention and its enantiomter, using anti- Phase high performance liquid chromatography is separated and detected to levo-cetirizine hydrochloride and its enantiomter, can be in 25 minutes by salt Sour levocetirizine and its enantiomter are kept completely separate and detected, and significantly shorten disengaging time, and have excellent point From performance and durability.
2) present invention is using the silica gel of beta-schardinger dextrin as filler, and the filler is durable in use, environmentally friendly, small toxicity and can quick separating The analysis method of levo-cetirizine hydrochloride and its enantiomter, the quality control for Pharmaceutical Analysis personnel health and products thereof All it is very significant work with degradation pathway research.
3) present invention solves the problems, such as levo-cetirizine hydrochloride and its separation determination of enantiomter, this method separating degree Good, specificity is strong, high sensitivity；And it is simple to operate, there is the advantages of easy, quick, ensure that levo-cetirizine hydrochloride And its preparation is quality controllable, and the safe and effective of product is finally determined, the quality control for levo-cetirizine hydrochloride has weight Want meaning.
Brief description of the drawings
Fig. 1 is the high-efficient liquid phase chromatogram of blank solvent.
Fig. 2 is levo-cetirizine hydrochloride and its mixed solution high-efficient liquid phase chromatogram of enantiomter.
Embodiment
Hereinafter with reference to accompanying drawing, the preferred embodiments of the present invention are described in detail.Unreceipted tool in preferred embodiment The experimental method of concrete conditions in the establishment of a specific crime, generally according to normal condition, illustrated embodiment is to preferably be said to present disclosure It is bright, but be not that present disclosure is only limitted to illustrated embodiment.So those skilled in the art are according to foregoing invention Content carries out nonessential modifications and adaptations to embodiment, still falls within protection scope of the present invention.
In following examples, the instrument and chromatographic condition of use are as follows：
High performance liquid chromatograph：Shimadzu LC-20AT
Chromatographic column：ULTRON ES-CD(150×6.0mm)
Mobile phase：
Mobile phase A：Inorganic salts buffer system buffer salt：Weigh Potassium Hexafluorophosphate 9.25g (0.05mol/L Potassium Hexafluorophosphates) In 1000ml volumetric flasks, it is dissolved in water and is diluted to scale, with phosphorus acid for adjusting pH value to 3.0 ± 0.1；
Mobile phase B：Acetonitrile
The ratio of mobile phase A and Mobile phase B is 60：40
Detector Detection wavelength：231nm
Flow rate of mobile phase：0.5ml/min
Chromatographic column post case column temperature：25℃
Sample size：10μl
Diluent (solvent of dissolving reference substance and testing sample)：40% acetonitrile (acetonitrile V：Water V=40：60).
The separation determination levo-cetirizine hydrochloride of embodiment 1 and its enantiomter
The preparation of enantiomerism liquid solution：Enantiomter reference substance about 25mg is taken respectively, is put in 100ml measuring bottles, is added dilute Release agent to dissolve and be diluted to scale, shake up, produce enantiomter stock solution.Precision pipettes above-mentioned solution 0.5ml, puts In 100ml measuring bottles, add diluent to be diluted to scale, shake up, produce the reference substance liquid that enantiomerism bulk concentration is 1.25 μ g/ml.
The preparation of mixed solution：Levo-cetirizine hydrochloride about 25mg is weighed, is put in 100ml measuring bottles, it is different that precision pipettes mapping Structure body stock solution 0.5ml, puts in above-mentioned same measuring bottle, adds diluent to dissolve and is diluted to scale, shakes up, produce.
Diluent and mixed solution is taken to record chromatogram, measurement result is shown in Table 1 by above-mentioned chromatographic condition sample introduction respectively.Knot Fruit sees Fig. 1, Fig. 2.
Table 1 tests measurement result
Conclusion：Disturbed specimen does not determine for plain dilution agent；Main peak is more than 1.5 with the peak-to-peak separating degree of enantiomter；It is above-mentioned Experiment proves that levo-cetirizine hydrochloride separates well with enantiomter peak, and specificity is strong.
Comparative example 1
In the comparative example, except the mobile phase A of use is different, remaining condition is same as Example 1.
Mobile phase A：Water.
Mixed solution is taken to record chromatogram, measurement result is shown in Table 2 by above-mentioned chromatographic condition sample introduction.
Table 2 tests measurement result
Conclusion：In the different separation test of only mobile phase A identical from above-described embodiment other conditions, the left west of hydrochloric acid is replaced Sharp piperazine is less than 1.5 with stage enantiomer separation degree, and main peak tailing factor is more than 2.0, it is impossible to meets levo-cetirizine hydrochloride It is effectively separated with enantiomter.
Comparative example 2
In the comparative example, except the mobile phase A of use is different, remaining condition is same as Example 1.
Mobile phase A：Inorganic salts buffer system buffer salt：Weigh potassium dihydrogen phosphate 6.8g (0.05mol/L potassium dihydrogen phosphates) In 1000ml volumetric flasks, it is dissolved in water and is diluted to scale, with phosphorus acid for adjusting pH value to 3.0 ± 0.1.
Mixed solution is taken to record chromatogram, measurement result is shown in Table 3 by above-mentioned chromatographic condition sample introduction.
Table 3 tests measurement result
Conclusion：In the different separation test of only mobile phase A identical from above-described embodiment other conditions, the left west of hydrochloric acid is replaced Sharp piperazine is less than 1.5 with stage enantiomer separation degree, and main peak tailing factor is more than 2.0, it is impossible to reaches levo-cetirizine hydrochloride The requirement efficiently separated with enantiomter.
The chromatographic system of embodiment 2 is to the test limit of levo-cetirizine hydrochloride and enantiomter, quantitative limit basic research
Quantitative limit solution：Precision weighs levo-cetirizine hydrochloride and shines product with enantiomter, is made into certain density solution, And quantitative limit solution is diluted to obtain step by step, as shown in table 2.
Test limit solution：Precision pipettes quantitative limit solution 7.0ml, puts in 20ml measuring bottles, adds diluent to be diluted to scale, shakes It is even, test limit solution is produced, as shown in table 3.
Assay method：
Take above-mentioned quantitative limit solution continuous sample introduction 3 times, test limit solution continuous sample introduction 2 times, calculate main peak peak height and noise Ratio (signal to noise ratio).Chromatogram is recorded, result of the test is shown in Table 4 and table 5.
The quantitative limit measurement result of table 4
The test limit measurement result of table 5
Conclusion：It was found from upper table test data, under this chromatographic system, the detection of levo-cetirizine hydrochloride and enantiomter Limit, quantitative limit correspond with S/N=3 (10)：1 requirement.
Finally illustrate, the above embodiments are merely illustrative of the technical solutions of the present invention and it is unrestricted, although with reference to compared with The present invention is described in detail good embodiment, it will be understood by those within the art that, can be to the skill of the present invention Art scheme is modified or equivalent substitution, and without departing from the objective and scope of technical solution of the present invention, it all should cover at this Among the right of invention.

Claims (7)

  1. The method of 1.HPLC method separation determination levo-cetirizine hydrochlorides and its enantiomter, it is characterised in that
    The chromatographic column used in methods described be the silica gel using surface chemistry bonding beta-schardinger dextrin as filler, using mobile phase A and Mobile phase B is eluted, and is detected into detector；Described mobile phase A is inorganic salts buffer system, described mobile phase B is organic solvent；
    The inorganic salts buffer system is the buffer system of Potassium Hexafluorophosphate；
    The concentration of Potassium Hexafluorophosphate is 0.04mol/L-0.06mol/L in the inorganic salts buffer system；
    The inorganic salts buffer system pH value is 2-4.
  2. 2. according to the method for claim 1, it is characterised in that the volume ratio 60 of the mobile phase A and Mobile phase B：40；Institute Stating organic solvent includes acetonitrile.
  3. 3. according to the method for claim 1, it is characterised in that the flow rate of mobile phase is 0.3-0.7ml/min, the color It is 20-30 DEG C to compose post post case temperature.
  4. 4. according to the method for claim 1, it is characterised in that the specification of the chromatographic column is 150 × 6.0mm, 5 μm.
  5. 5. according to the method for claim 1, it is characterised in that the Detection wavelength of the detector is 220-240nm.
  6. 6. according to the method described in claim any one of 1-5, it is characterised in that specifically include following steps：
    1) levo-cetirizine hydrochloride and its reference substance of enantiomter are taken respectively, with diluent dissolving be made testing sample and its The reference substance solution of enantiomter, the reference substance solution of testing sample levo-cetirizine hydrochloride and its enantiomter is taken respectively Sample introduction, efficient liquid phase chromatographic analysis is carried out, determine the retention time of levo-cetirizine hydrochloride and its enantiomter；
    2) take levo-cetirizine hydrochloride test sample to add diluent that need testing solution is made, then take diluent as blank solution, Need testing solution and blank solution sample introduction are taken respectively, carries out efficient liquid phase chromatographic analysis, records chromatogram, are completed the left west of hydrochloric acid and are replaced The separation determination of sharp piperazine and its enantiomter.
  7. 7. according to the method for claim 6, it is characterised in that the step 1) diluent is the aqueous solution of acetonitrile or acetonitrile Sample dissolution, the volume ratio of acetonitrile and water is 40 in the aqueous solution of the acetonitrile:60.
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