CN110187038A - The detection method of adjacent Hydrazinobenzenesulfonamide hydrochloride in a kind of celecoxib - Google Patents
The detection method of adjacent Hydrazinobenzenesulfonamide hydrochloride in a kind of celecoxib Download PDFInfo
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- CN110187038A CN110187038A CN201910610484.4A CN201910610484A CN110187038A CN 110187038 A CN110187038 A CN 110187038A CN 201910610484 A CN201910610484 A CN 201910610484A CN 110187038 A CN110187038 A CN 110187038A
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- G01N30/02—Column chromatography
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- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
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Abstract
The present invention relates to drug measurement techniques field, in particular to the detection method of adjacent Hydrazinobenzenesulfonamide hydrochloride in a kind of celecoxib.This method comprises: celecoxib sample is dissolved using organic solvent, sample solution is obtained；Sample solution is detected using reversed-phased high performace liquid chromatographic, chromatographic condition is as follows: C18 chromatographic column；Mobile phase A is the potassium dihydrogen phosphate aqueous solution of 0.005~0.015mol/L；Mobile phase B is acetonitrile；Gradient elution.Technical solution provided by the invention shows the detection advantage to celecoxib latent gene toxic impurities neighbour's Hydrazinobenzenesulfonamide hydrochloride, the detection method that a kind of specificity is strong, accuracy is high can be provided for the detection of celecoxib latent gene toxic impurities neighbour's Hydrazinobenzenesulfonamide hydrochloride content, to realize the control to drug quality.
Description
Technical field
The present invention relates to drug measurement techniques field, in particular to adjacent Hydrazinobenzenesulfonamide hydrochloride in a kind of celecoxib
Detection method.
Background technique
Celecoxib is Transitional cell carcinomas (COX-2) specific inhibitor, is that treatment osteoarthritis and rheumatoid are closed
Scorching anti-inflammation analgesia medicine is saved, a length of 1~10 year drug when treatment is belonged to.Its No. CAS are as follows: 169590-42-5, molecular formula are
C17H14F3N3O2S, molecular weight are as follows: 381.37, chemical structure are as follows:
Celecoxib (Celecoxib) is 1,5- diaryl substituted pyrazole class compound, entitled 4- [5- (the 4- methyl of chemistry
Phenyl) -3- (trifluoromethyl) -1H- pyrazol-1-yl] benzsulfamide, pKa value 11.1.Celecoxib trade name " Celebrex "
(Celebrex), it is to be developed by Pharmacia company, passes through first choosing of FDA examination & approval listing on December 31st, 1998
Selecting property cyclooxygenase-2 (COX-2) inhibitor, 1999 formal applied to clinic.Pfizer passes through purchase within 2003
The capsule preparations Celebrex of Pharmacia acquisition celecoxib.
Genotoxicity impurity is the substance for referring to cause DNA mutation, chromosome breakage or DNA recombination, this substance
It is also possible to lead to the generation of human tumor.Genotoxicity impurity be mainly derived from the starting material in bulk pharmaceutical chemicals synthesis process, in
Mesosome, reagent and byproduct of reaction.In addition, drug may also can degrade in synthesis, storage or production process generates gene
Toxic impurities.
Adjacent Hydrazinobenzenesulfonamide hydrochloride be brought into celecoxib starting material 4- sulfoamido hydrazinobenzene hydrochloride salt it is latent
In genotoxicity impurity.The structural formula of adjacent Hydrazinobenzenesulfonamide hydrochloride is as follows:
Molecular formula: C6H9N3O2S.HCl, molecular weight: 223.68.
For the quality for guaranteeing celecoxib bulk pharmaceutical chemicals, starting material 4- sulfoamido hydrazinobenzene hydrochloride salt latent gene toxicity is miscellaneous
Matter neighbour's Hydrazinobenzenesulfonamide hydrochloride answers strict control, therefore need to establish the analysis method that a kind of specificity is strong, accuracy is high and be used for
Measure the content of celecoxib latent gene toxic impurities neighbour's Hydrazinobenzenesulfonamide hydrochloride.
Summary of the invention
In view of this, the present invention provides a kind of detection methods of Hydrazinobenzenesulfonamide hydrochloride adjacent in celecoxib.It should
It is a kind of accurate that method provides for the measurement of latent gene toxic impurities neighbour's Hydrazinobenzenesulfonamide hydrochloride content of celecoxib
, efficient detection method.
In order to achieve the above-mentioned object of the invention, the present invention the following technical schemes are provided:
The present invention provides a kind of detection methods of Hydrazinobenzenesulfonamide hydrochloride adjacent in celecoxib, including walk as follows
It is rapid:
Celecoxib sample is dissolved using organic solvent, obtains sample solution；
Sample solution is detected using reversed-phased high performace liquid chromatographic, chromatographic condition is as follows:
Chromatographic column: C18 chromatographic column；
Mobile phase A is the potassium dihydrogen phosphate aqueous solution of 0.005~0.015mol/L；
Mobile phase B is acetonitrile；
Gradient elution program are as follows:
| Elution time | A phase (%) | B phase (%) |
| 0min | 80 | 20 |
| 5min | 80 | 20 |
| 18min | 10 | 90 |
| 21min | 10 | 90 |
| 22min | 80 | 20 |
| 30min | 80 | 20 |
。
In the present invention, the content of adjacent Hydrazinobenzenesulfonamide hydrochloride is calculated by external standard method.
Preferably, mobile phase A is the potassium dihydrogen phosphate aqueous solution of 0.01mol/L.
Preferably, the packing material size of chromatographic column is 3.0~5.0 μm, column length is 150~250mm, column diameter
For 2.0~5.0nm.
Preferably, the packing material size of chromatographic column is 3.5 μm, column length 250mm, column diameter 4.6nm.
Preferably, the Detection wavelength of reversed-phased high performace liquid chromatographic is 240~250nm.
Preferably, the Detection wavelength of reversed-phased high performace liquid chromatographic is 245nm.
Preferably, 33~37 DEG C of the column temperature of reversed-phased high performace liquid chromatographic.
Preferably, 35 DEG C of the column temperature of reversed-phased high performace liquid chromatographic.
Preferably, the flow velocity of reversed-phased high performace liquid chromatographic is 0.8~1.2mL/min, sample volume is 8~12 μ L.
Preferably, the flow velocity of reversed-phased high performace liquid chromatographic is 1.0mL/min, and sample volume is 10 μ L.
Preferably, organic solvent is methanol aqueous solution.
Preferably, the volume ratio of methanol and water is (65~75): (25~35) in methanol aqueous solution.
Preferably, the volume ratio of methanol and water is 70:30 in methanol aqueous solution.
Preferably, the concentration of celecoxib sample is 5~10mg/mL in sample solution.
The present invention provides a kind of detection methods of Hydrazinobenzenesulfonamide hydrochloride adjacent in celecoxib, this method comprises:
Celecoxib sample is dissolved using organic solvent, obtains sample solution；Using reversed-phased high performace liquid chromatographic to sample solution
It is detected, chromatographic condition is as follows: C18 chromatographic column；Mobile phase A is the potassium dihydrogen phosphate aqueous solution of 0.005~0.015mol/L；
Mobile phase B is acetonitrile；Gradient elution.Beneficial effects of the present invention are as follows:
Technical solution provided by the invention is shown to celecoxib latent gene toxic impurities neighbour's Hydrazinobenzenesulfonamide salt
The detection advantage of hydrochlorate can mention for the detection of celecoxib latent gene toxic impurities neighbour's Hydrazinobenzenesulfonamide hydrochloride content
The detection method that a kind of specificity is strong, accuracy is high is supplied, to realize the control to drug quality.
Detailed description of the invention
Fig. 1 is the reference substance solution testing result schematic diagram of embodiment 1, wherein RT=4.6min is adjacent diazanyl benzene sulfonyl
The peak of amine hydrochlorate；
Fig. 2 is the test solution testing result schematic diagram of embodiment 1；
Fig. 3 is the mixed solution testing result schematic diagram of embodiment 2, wherein RT=4.6min is adjacent Hydrazinobenzenesulfonamide
The peak of hydrochloride；
Fig. 4 is the mixed solution testing result schematic diagram of comparative example 1, wherein RT=4.7min is adjacent Hydrazinobenzenesulfonamide
The peak of hydrochloride；
Fig. 5 is the mixed solution testing result schematic diagram of comparative example 2, wherein RT=4.8min is adjacent Hydrazinobenzenesulfonamide
The peak of hydrochloride；
Fig. 6 is the mixed solution testing result schematic diagram of comparative example 3, wherein RT=4.7min is adjacent Hydrazinobenzenesulfonamide
The peak of hydrochloride.
Specific embodiment
The invention discloses a kind of detection method of Hydrazinobenzenesulfonamide hydrochloride adjacent in celecoxib, those skilled in the art
Member can use for reference present disclosure, be suitably modified realization of process parameters.In particular, it should be pointed out that all similar substitutions and modifications
Apparent to those skilled in the art, they are considered as being included in the present invention.Method and application of the invention
Be described by preferred embodiment, related personnel obviously can not depart from the content of present invention, in spirit and scope it is right
Method described herein and application are modified or appropriate changes and combinations, carry out implementation and application the technology of the present invention.
Raw materials used medicine, reagent in the detection method of adjacent Hydrazinobenzenesulfonamide hydrochloride in celecoxib provided by the invention
Or instrument or auxiliary material are available on the market.
Below with reference to embodiment, the present invention is further explained:
Embodiment 1
High performance liquid chromatograph:
Mobile phase: A phase: 0.01mol/L potassium dihydrogen phosphate aqueous solution；
B phase: acetonitrile；
Gradient:
1 gradient elution program of table
| Elution time | A phase (%) | B phase (%) |
| 0min | 80 | 20 |
| 5min | 80 | 20 |
| 18min | 10 | 90 |
| 21min | 10 | 90 |
| 22min | 80 | 20 |
| 30min | 80 | 20 |
Chromatographic column: ZORBAX SB-C18 4.6*250mm, 3.5 μm；
Detection wavelength: 245nm；
Flow velocity: 1.0mL/min；
Column temperature: 35 DEG C；
Sample volume: 10 μ L；
Dilution: methanol: water=70:30；
Reference substance solution: adjacent Hydrazinobenzenesulfonamide hydrochloride 20mg is weighed, accurately weighed in 100mL volumetric flask, use is dilute
Liquid is released to dissolve and be diluted to scale.Precision pipettes 2.0mL in 50mL volumetric flask, with diluted to scale, shakes up.It is smart again
The close 1.0mL that pipettes, with diluted to scale, shakes up in 100mL volumetric flask.
Test solution: taking 64mg celecoxib, accurately weighed in 10mL volumetric flask, with diluted to scale.
Testing result: for result referring to attached drawing 1, attached drawing 2, RT=4.6min is the peak of adjacent Hydrazinobenzenesulfonamide hydrochloride.
Embodiment 2
High performance liquid chromatograph:
Mobile phase: A phase: 0.01mol/L potassium dihydrogen phosphate aqueous solution；
B phase: acetonitrile；
Gradient:
2 gradient elution program of table
| Elution time | A phase (%) | B phase (%) |
| 0min | 80 | 20 |
| 5min | 80 | 20 |
| 18min | 10 | 90 |
| 21min | 10 | 90 |
| 22min | 80 | 20 |
| 30min | 80 | 20 |
Chromatographic column: ZORBAX SB-C18 4.6*250mm, 3.5 μm；
Detection wavelength: 245nm；
Flow velocity: 1.0mL/min；
Column temperature: 35 DEG C；
Sample volume: 10 μ L；
Dilution: methanol: water=70:30；
Reference substance solution: adjacent Hydrazinobenzenesulfonamide hydrochloride 20mg is weighed, accurately weighed in 100mL volumetric flask, use is dilute
Liquid is released to dissolve and be diluted to scale.Precision pipettes reference substance stock solution 2.0mL and is placed in 50mL volumetric flask, uses diluted
Constant volume shakes up.Precision pipettes this solution 1.0mL and is placed in 100mL volumetric flask, is shaken up with diluted constant volume.
Test sample positions solution: 64mg celecoxib is weighed, it is accurately weighed in 10mL volumetric flask, and it is shaken up with dilution constant volume.
Mixed solution: weighing 64mg celecoxib, accurately weighed in 10mL volumetric flask, is shaken with reference substance solution dilution constant volume
It is even.
Testing result: for result referring to attached drawing 3, RT=4.6min is the peak of adjacent Hydrazinobenzenesulfonamide hydrochloride.
Comparative example 1
Compared with Example 1, Detection wavelength is different, high performance liquid chromatograph:
Mobile phase: A phase: 0.01mol/L potassium dihydrogen phosphate aqueous solution；
B phase: acetonitrile；
Gradient:
3 gradient elution program of table
| Elution time | A phase (%) | B phase (%) |
| 0min | 80 | 20 |
| 5min | 80 | 20 |
| 18min | 10 | 90 |
| 21min | 10 | 90 |
| 22min | 80 | 20 |
| 30min | 80 | 20 |
Chromatographic column: ZORBAX SB-C18 4.6*250mm, 3.5 μm；
Detection wavelength: 260nm；
Flow velocity: 1.0mL/min；
Column temperature: 35 DEG C；
Sample volume: 10 μ L；
Dilution: methanol: water=70:30；
Reference substance solution: adjacent Hydrazinobenzenesulfonamide hydrochloride 20mg is weighed, accurately weighed in 100mL volumetric flask, use is dilute
Liquid is released to dissolve and be diluted to scale.Precision pipettes reference substance stock solution 2.0mL and is placed in 50mL volumetric flask, uses diluted
Constant volume shakes up.Precision pipettes this solution 1.0mL and is placed in 100mL volumetric flask, is shaken up with diluted constant volume.
Mixed solution: weighing 64mg celecoxib, accurately weighed in 10mL volumetric flask, is shaken with reference substance solution dilution constant volume
It is even.
Testing result: for result referring to attached drawing 4, RT=4.7min is the peak of adjacent Hydrazinobenzenesulfonamide hydrochloride, can from figure
To find out at 260nm wavelength, the UV absorption of adjacent Hydrazinobenzenesulfonamide hydrochloride is very weak.
Comparative example 2
Compared with Example 1, mobile phase A concentration is different, high performance liquid chromatograph:
Mobile phase: A phase: 0.005mol/L potassium dihydrogen phosphate aqueous solution；
B phase: acetonitrile；
Gradient:
4 gradient elution program of table
| Elution time | A phase (%) | B phase (%) |
| 0min | 80 | 20 |
| 5min | 80 | 20 |
| 18min | 10 | 90 |
| 21min | 10 | 90 |
| 22min | 80 | 20 |
| 30min | 80 | 20 |
Chromatographic column: ZORBAX SB-C18 4.6*250mm, 3.5 μm；
Detection wavelength: 245nm；
Flow velocity: 1.0mL/min；
Column temperature: 35 DEG C；
Sample volume: 10 μ L；
Dilution: methanol: water=70:30；
Reference substance solution: adjacent Hydrazinobenzenesulfonamide hydrochloride 20mg is weighed, accurately weighed in 100mL volumetric flask, use is dilute
Liquid is released to dissolve and be diluted to scale.Precision pipettes reference substance stock solution 2.0mL and is placed in 50mL volumetric flask, uses diluted
Constant volume shakes up.Precision pipettes this solution 1.0mL and is placed in 100mL volumetric flask, is shaken up with diluted constant volume.
Mixed solution: weighing 64mg celecoxib, accurately weighed in 10mL volumetric flask, is shaken with reference substance solution dilution constant volume
It is even.
Testing result: for result referring to attached drawing 5, RT=4.8min is the peak of adjacent Hydrazinobenzenesulfonamide hydrochloride, can from figure
When finding out that flowing phase concentration is 0.005mol/L, the UV absorption of adjacent Hydrazinobenzenesulfonamide hydrochloride is weakened, and chromatography
The baseline noise of figure is very big.
Comparative example 3
Compared with Example 1, elution program is different, high performance liquid chromatograph:
Mobile phase: A phase: 0.01mol/L potassium dihydrogen phosphate aqueous solution；
B phase: acetonitrile；
Gradient:
5 gradient elution program of table
| Elution time | A phase (%) | B phase (%) |
| 0min | 80 | 20 |
| 10min | 80 | 20 |
| 18min | 10 | 90 |
| 21min | 10 | 90 |
| 22min | 80 | 20 |
| 30min | 80 | 20 |
Chromatographic column: ZORBAX SB-C18 4.6*250mm, 3.5 μm；
Detection wavelength: 245nm；
Flow velocity: 1.0mL/min；
Column temperature: 35 DEG C；
Sample volume: 10 μ L；
Dilution: methanol: water=70:30；
Reference substance solution: adjacent Hydrazinobenzenesulfonamide hydrochloride 20mg is weighed, accurately weighed in 100mL volumetric flask, use is dilute
Liquid is released to dissolve and be diluted to scale.Precision pipettes reference substance stock solution 2.0mL and is placed in 50mL volumetric flask, uses diluted
Constant volume shakes up.Precision pipettes this solution 1.0mL and is placed in 100mL volumetric flask, is shaken up with diluted constant volume.
Mixed solution: weighing 64mg celecoxib, accurately weighed in 10mL volumetric flask, is shaken with reference substance solution dilution constant volume
It is even.
Testing result: for result referring to attached drawing 6, RT=4.7min is the peak of adjacent Hydrazinobenzenesulfonamide hydrochloride, can from figure
To find out, the too long main peak appearance that will lead to of the second gradient timetable is moved back, under the influence of a needle baseline balance.
The above is only a preferred embodiment of the present invention, it is noted that for the ordinary skill people of the art
For member, various improvements and modifications may be made without departing from the principle of the present invention, these improvements and modifications are also answered
It is considered as protection scope of the present invention.
Claims (10)
1. the detection method of adjacent Hydrazinobenzenesulfonamide hydrochloride in a kind of celecoxib, which comprises the steps of:
Celecoxib sample is dissolved using organic solvent, obtains sample solution；
Sample solution is detected using reversed-phased high performace liquid chromatographic, chromatographic condition is as follows:
Chromatographic column: C18 chromatographic column；
Mobile phase A is the potassium dihydrogen phosphate aqueous solution of 0.005~0.015mol/L；
Mobile phase B is acetonitrile；
Gradient elution program are as follows:
。
2. detection method according to claim 1, which is characterized in that the mobile phase A is the biphosphate of 0.01mol/L
Aqueous solutions of potassium.
3. detection method according to claim 1, which is characterized in that the packing material size of the chromatographic column is 3.0~5.0 μ
M, column length are 150~250mm, and column diameter is 2.0~5.0nm.
4. detection method according to claim 1, which is characterized in that the packing material size of the chromatographic column is 3.5 μm, chromatography
Column length is 250mm, column diameter 4.6nm.
5. detection method according to claim 1, which is characterized in that the Detection wavelength of the reversed-phased high performace liquid chromatographic
For 240~250nm.
6. detection method according to claim 1, which is characterized in that the column temperature 33 of the reversed-phased high performace liquid chromatographic~
37℃。
7. detection method according to claim 1, which is characterized in that the flow velocity of the reversed-phased high performace liquid chromatographic is
0.8~1.2mL/min, sample volume are 8~12 μ L.
8. detection method according to claim 1, which is characterized in that the organic solvent is methanol aqueous solution.
9. detection method according to claim 8, which is characterized in that the volume ratio of methanol and water in the methanol aqueous solution
For (65~75): (25~35).
10. detection method according to claim 8 or claim 9, which is characterized in that celecoxib sample in the sample solution
Concentration is 5~10mg/mL.
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Cited By (1)
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Address after: Suzhou City, Jiangsu province 215000 Guan Hu Zhen Hu Qing Road No. 122 Applicant after: Suzhou Zhengji Pharmaceutical Co.,Ltd. Address before: Suzhou City, Jiangsu province 215000 Guan Hu Zhen Hu Qing Road No. 122 Applicant before: SUZHOU TIANMA PHARMACEUTICAL Co.,Ltd. |
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Application publication date: 20190830 |
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