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IJCRR - 14(1), January, 2022

Pages: 124-131

Date of Publication: 03-Jan-2022


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Identification of the Organic Volatile Impurities in Telmisartan Active Pharmaceutical Ingredient and Its Pharmaceutical dosage forms by using Head Space Gas Chromatography Technique

Author: J. Krishna Kishore, K. Prasada Rao

Category: Healthcare

Abstract:Introduction: Residual Solvents or Organic Volatile Impurities are potential risk for quality and stability of drug products as well as human body if intake exceeds the permitted daily exposure. They do not provide any therapeutic benefit and must be removed to the maximum possible level Objective: The work presented in this paper explains the simple and rapid Head Space Gas Chromatography (HS-GC) technique for the Quantitative estimation of Three Organic Volatile Impurities (OVIs) in Telmisartan Active Pharmaceutical Ingredient (API) and its Pharmaceutical dosage forms. Methods: Organic solvents such as methanol, acetone, and n-butanol are frequently used in the manufacturing of Telmisartan. The process for quantification of OVIs in Telmisartan API has been done with Head Space Gas Chromatographic method with detector of Flame Ionization and utilizing the Shimadzu GC- 2010 with a capillary column of FID (DB-624, 30 m × 0.53 mm, 3 \?), with a carrier gas nitrogen at 4.0 mL/min flow rate. The experimental parameters like injection temperature, oven temperature, make-up flow, zero air, injection temperature; split ratio, headspace conditions, and the diluent selection have been considered and were optimized. Results: Retention times are 2.23 min for methanol, 3.04 min for acetone, and 7.20 min for n-butanol respectively. The proposed technique has been statistically validated based on standard International Conference on Harmonization guidelines (ICH). The % Relative Standard Deviation (% RSD) for the system precision of six injections was should be not more than 10.0 %. The percentage recovery was found between 85-115 %. The correlation coefficient (R2) is not less than 0.99. Limit of Detection (LOD) was found as 19 ppm (methanol), 26 ppm (acetone), and 21 ppm (n-butanol). The Limit of Quantification (LOQ) was found as 58 ppm (methanol), 77 ppm (acetone), and 64 ppm for n-butanol. The intermediate precision and method precision were found to be within the limit of acceptance. Conclusion: From the obtained validation results the proposed technique has been fruitfully applied for quantification of organic volatile impurities in Telmisartan Active Pharmaceutical Ingredient as well as its pharmaceutical dosage forms.

Keywords: Method development, Organic volatile impurities, Telmisartan API, Validation, Chromatography, Quantification

Full Text:

INTRODUCTION 

Organic solvents are commonly used in the synthesis of various drugs, excipients and in the formulation of the drug. The presence of these solvents in the final product should not be present as they are highly harmful and they impact the drug substance stability and even impart taste and odour and which would be harmful. In the literature there are various procedures and technologies being reported to eliminate these organic solvents.1 Some drugs contain even small amounts of these organic solvents after carrying out several operations to remove them and such minute concentrations of these solvents are regarded as residual chemical solvents. The major challenge faced by the pharma industries is to find various analytical activities to detect these residual solvents in the medicinally important compounds and drug products. The use of various active ingredients of medicinal importance and their formulations into pharmaceutical drug compounds under good conditions of industrial practice needs necessary quality control of these ingredients used in the synthesis. Hence, before the synthesis of medicinal compounds by any useful process these solvents need to be regulated and the compound purity has to be maintained.2 The reports of the regulatory guidance shows the required amounts of various organic solvents.3-5 Chemically the Telmisartan is 2-(4-{[4-methyl-6-(1- benzodiazol-1-yl] methyl} phenyl) benzoic acid. This is an Angiotensin Receptor Blocker and exhibits great affinity towards receptors of angiotensin II type 1, and its duration of action is long, and have higher long life than any other ARB.6-8 The following scheme shows its synthetic route (Scheme-I).

In the preparation of the Telmisartan, the organic solvents like methanol, acetone, and n-butanol are used. These solvents are grouped with class-3 according to ICH Q3C (R6) guidance.9 These organic solvents of this class have toxic effects on humans as a result we need to regulate the presence of these solvents in Telmisartan.     

The main objective of this work is to develop and validate a fast, simple, and reliable Quantitative identification of these OVIs (methanol, acetone, and n-butanol) in Telmisartan API and its Pharmaceutical dosage forms.10 The various prominent aspects and novelty of the method described include short elution time, easy sample treatment at ambient temperature with sonication of little amount of powder, good precision, and more recovery rate (>100±15%). The applicability of the method designed and validated as per guidelines of ICH for determination of above said organic solvents in the bulk as well as in the tablet dosage form.

Methanol, acetone, and n-butanol are the generally used chemical solvents during the synthesis of many pharmaceutical drug compounds. These chemicals must be controlled in the finished product to minimum level and based on their toxic effects their limits are fixed according to ICH guidelines for residual solvents.

The level of these organic volatile impurities has to be determined and controlled. There is no literature available to simultaneously determination of methanol, acetone, and n-butanol in this Telmisartan. These structures are followed in (Figure 2).

MATERIALS AND METHODS

Chemicals and reagents

Telmisartan API was taken from local well-known laboratory. GC grade Methanol, Acetone,     n-Butanol and Di methyl sulfoxide (DMSO) were obtained from Merck -Mumbai. The structures of the compounds are shown in figure 1.

Instrumentation

Chromatography was carried out on Shimadzu chromatography equipped with GC-2010 system with FID (Shimadzu). The samples have been injected by Teledyne tekmar HT3TM Headspace and acquisition and integration of data was done using GC-solution software.

Chromatographic condition

Column: DB-624 (30 m, 0.53 mm ID, 3 μm); Carrier gas: Nitrogen with a rate of flow of 3.6 mL/min; temperature of the Injector: 180 ºC; split ratio: 1:20; Oven program: initial 60 ºC hold for 5 min, increase @ 8 ºC/min up to 140 ºC, hold for 0.0 min, increase @ 30 ºC/min up to 200 ºC, hold for 13 min; temperature of the Detector (FID): 240 ºC; Flow of the air gas: 400 mL/min; flow of the hydrogen, 40 mL/min; overall run time: 30 min.

Condition of the Headspace sampler

Temperature of the Vial: 90 ºC; The needle temperature: 100 ºC; Temperature Transfer line: 115 ºC; Conditioning time of vial: 30 min; Pressurize time of Vial: 3.0 min; Volume of the Injection: 1.0 mL; Inject time: 1.0 min; Cycle time of GC: 45 min.

Preparations

Specifications for Organic volatile impurities

Methanol is 3000 ppm, Acetone is 5000 ppm and n-Butanol is 5000 ppm.

Standard Solution preparation

Weighed and transferred about each 750.35 mg of methanol, 1250.95 mg of acetone and 1250.85 mg of n-butanol along with 70 mL of diluents into 100 mL volumetric flask and it is diluted with the diluents. Further into 50 mL of volumetric flask 5 mL of the above solution is taken and diluted to a volume with the diluent.

Meanwhile with 2 mL of standard solution the standard Headspace vials have been prepared and sealed it aluminum closure. (The standard solution has been prepared as per the sample concentrations of Telmisartan).

Preparation of Telmisartan API sample solution (250 mg/mL)

About 500 mg of Telmisartan pure sample weighed accurately into a 10 mL of the vial and 2.0 mL of diluents is added and sealed it with aluminum closure immediately. 

Preparation of Telmisartan Tablet solution

Twenty tablets of Telmisartan were weighed and they were powdered. An amount of powder equivalent to 500 mg Telmisartan was exactly weighed and transferred to a 10 mL of headspace vial, and add 2 mL of the diluent and sealed immediately with aluminum closure. 

Calculation:

Organic volatile impurity content was calculated from,

RESULTS AND DISCUSSION

Development of the Method

 The development of the method was done by following the principles of Quality-by-Design along with column selection and diluents. During the development of HS-GC method, we have selected the appropriate system parameters in order to obtain the best separation, time efficiency and sensitivity the three organic volatile impurities mixtures were injected under various types of conditions. Example, at different GC Columns (DB-5, VF-1, DB-624), HS Vial temperature (70-90 ºC), HS Needle temperature (80-110 ºC), HS Transfer line temperature(90-130 ºC), GC-FID temperatures (200-300 ºC), GC Injector temperatures (100-220 ºC), GC gradients (40-200 ºC, at the rate of 5–40 ºC /min), carrier gas flow rates (2.0-5.0 mL/min), different diluents (NMP, DMSO and DMF) etc. The final HS-GC conditions were used for the validation of the method was obtained on the basis of GC parameters. These solvents were individually injected once separately in order to find the specificity of the method and sensitivity of the signal response.

Method validation

The validation of the method was studied by evaluating repeatability, spe­cificity method, limit of quantification (LOQ),  method precision, limit of detection (LOD), and accuracy, linearity, ruggedness, and stability if the solution Organic volatile impurities according to the guidelines given by ICH.11

Specificity

Table 1 shows the specificity data for three organic volatile impurities Specificity was studied by injecting blank, sample preparation, and Standard solution and showing resolution between all peaks are in both sample solution and Standard Solution and there was no interference from the blank at the retention times of analyte peaks those were obtained from standard solution and resolution of more than 2.0 was obtained between two closely eluting peaks which meet the acceptance criteria. Typical Chromatograms for Specificity is shown in figure 2.

System precision

The system precision has been determined by injecting the six replicate injections of the standard solution respectively and analyzed as per ICH guidelines.  The precision of the system is expressed in terms of % RSD. The RSD was found out to be less than 10 %. A typical overlay chromatogram for System precision is shown in figure 3.

Precision Method

Table 2 shows method precision data for three OVI’S. The method precision is shown in terms of % RSD. The precision method was demonstrated by separately analyzing of sample six preparations as per the method. RSD was found to be less than 10. Typical overlay chromatogram for Method precision is shown in figure 4.

Linearity (Low level) for LOD and LOQ

Linearity of the technique which was proposed is found out over 1-10 % concentration range for three organic volatile impurities. At each level two replicates have been conducted. The correlation coefficient (R2), LOD, SLOPE, LOQ, and STEYX have been measured by this data and the results are have been recorded. Tables 3 contain the linearity data for three organic volatile impurities. Correlation graph for three OVI’S is shown in figure 5.

Linearity with LOQ

 Linearity has been measured by injection of each organic volatile impurity over 50-150 %  range and LOQ level. Two replicates were varied out at every level. By averaging the peak area ratio of these two replicates we obtain calibration curves. The correlation coefficient values (r2) of all organic volatile impurities were observed to be greater than 0.99 and found that in this range the calibration curves are linear.

 LOD and LOQ

Table 4 shows the LOD and LOQ data of OVI’S.  The Limit of Detection and the Limit of Quantification for the method proposed have been measured by using calibration standards and calculations were done using respectively by 3.3 σ /s and 10 σ/s formulae, in which 's' indicates slope of the calibration curve and 'σ' indicates the standard deviation of y-intercept. Typical LOD and LOQ Chromatograms for three OVI'S is shown in figure 6.

The System precision at LOQ

This method's system precision has been shown in terms of % RSD. At the LOQ concentration, the system precision at LOQ concentration was denoted with six replicate injections of the standard solution. The percentage RSD (% RSD) is found out to be less than 10 %. A typical overlay chromatogram for LOQ precision is shown in figure 7.

Accuracy

With the application of the standard addition technique, the method accuracy has been assured. The % recovery has been measured. Mean percentage recovery of each solvent at 50 %, 100 %, 150 % and LOQ levels must not be less than 85.0 and not more than 115.0. The obtained results in this method were lain within the given limits indicate that this process is accurate. Table 5 shows accuracy data for three OVI’S.

Robustness

The study of robustness was carried by making variations that are small in parameters of this method. Changes in flow of the column (±0.4 mL/min) and the temperature of vial condition (±5°C) have been carried out. The results obtained lie within the criteria of acceptance that indicates this process is robust in the specified range. The values of % RSD are less than 10.

Ruggedness

The evaluation of the method's ruggedness was carried out by doing analysis of the sample in six replicates by various analysts on various days. The obtained results lie within the limit of criteria of acceptance which indicates that the process is rugged in the given range. The values of % RSD are less than 10.0. Table 6 shows the ruggedness data for three OVI’S.

Application of the proposed method (Analysis of Telmisartan tablet)

The method proposed has been evaluated by commercially available Telmisartan tablet for quantification of organic volatile impurities present in this. Results obtained for organic volatile impurities have been compared with specified limits of given guidelines and are recorded. It shows the concentrations of organic volatile impurities in Telmisartan tablet in ppm which was less than the limit specified.

Solution stability

The six organic volatile impurities standard and Telmisartan API sample solutions were prepared in Dimethyl sulfoxide as a diluent. So we have to check whether these standard and sample solutions are stable or not. To prepare the standard and sample solutions for Three-time intervals (Initial hours, after 12 h and after 24 h) on the first day and kept at room temperature. These solutions are injected at Initial hours, after 12 hours and after 24 h. Then, we calculated the percentage of solution stability for the area at each time interval. We got a % of solution stability is 100±5%. Based on these data, six organic volatile impurities standard and Telmisartan API solutions were stable up to 24 h. Table 7 shows the solution stability data for three OVI’S.

CONCLUSION

The HS-GC method which is single, rapid and highly selective one has been developed and validation was carried out for the quantification of three organic volatile impurities present in Telmisartan API with the knowledge of the synthetic process, solvents nature, and kind of column stationary phase. The process that has been developed has to evaluate the reliability and the economical result in the determination of Methanol, Acetone and n-Butanol as organic volatile impurities present in Telmisartan. The results obtained in different validation parameters shows that this process is Specific, Limit of Detection, System Suitability, Limit of Quantification, and Accurate (% of recovery studies) as per the guidelines of ICH. The process was found to be applicable for the routine analysis of the Telmisartan API and its pharmaceutical dosage forms in pharmaceutical industry.

ACKNOWLEDGEMENT

Dr. K. Prasada Rao supervised the manuscript preparation and reviewed the manuscript. I  am grateful to the college management and faculty of the department for their support in completing my work.

CONFLICT OF INTEREST

The authors declare that there is no conflict of interests regarding the publication of this article.

Funding: NIL

Author’s Contribution: First author has developed methods and validated the proposed methods. Second author guided in entire work.

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A Study by Kannamani Ramasamy et al. entitled "COVID-19 Situation at Chennai City – Forecasting for the Better Pandemic Management" is awarded best article for  Vol 12 issue 12
A Study by Muhammet Lutfi SELCUK and Fatma entitled "Distinction of Gray and White Matter for Some Histological Staining Methods in New Zealand Rabbit's Brain" is awarded best article for  Vol 12 issue 11
A Study by Anamul Haq et al. entitled "Etiology of Abnormal Uterine Bleeding in Adolescents – Emphasis Upon Polycystic Ovarian Syndrome" is awarded best article for  Vol 12 issue 10
A Study by entitled "Estimation of Reference Interval of Serum Progesterone During Three Trimesters of Normal Pregnancy in a Tertiary Care Hospital of Kolkata" is awarded best article for  Vol 12 issue 09
A Study by Ilona Gracie De Souza & Pavan Kumar G. entitled "Effect of Releasing Myofascial Chain in Patients with Patellofemoral Pain Syndrome - A Randomized Clinical Trial" is awarded best article for  Vol 12 issue 08
A Study by Virendra Atam et. al. entitled "Clinical Profile and Short - Term Mortality Predictors in Acute Stroke with Emphasis on Stress Hyperglycemia and THRIVE Score : An Observational Study" is awarded best article for  Vol 12 issue 07
A Study by K. Krupashree et. al. entitled "Protective Effects of Picrorhizakurroa Against Fumonisin B1 Induced Hepatotoxicity in Mice" is awarded best article for issue Vol 10 issue 20
A study by Mithun K.P. et al "Larvicidal Activity of Crude Solanum Nigrum Leaf and Berries Extract Against Dengue Vector-Aedesaegypti" is awarded Best Article for Vol 10 issue 14 of IJCRR
A study by Asha Menon "Women in Child Care and Early Education: Truly Nontraditional Work" is awarded Best Article for Vol 10 issue 13
A study by Deep J. M. "Prevalence of Molar-Incisor Hypomineralization in 7-13 Years Old Children of Biratnagar, Nepal: A Cross Sectional Study" is awarded Best Article for Vol 10 issue 11 of IJCRR
A review by Chitra et al to analyse relation between Obesity and Type 2 diabetes is awarded 'Best Article' for Vol 10 issue 10 by IJCRR. 
A study by Karanpreet et al "Pregnancy Induced Hypertension: A Study on Its Multisystem Involvement" is given Best Paper Award for Vol 10 issue 09

List of Awardees

A Study by Ese Anibor et al. "Evaluation of Temporomandibular Joint Disorders Among Delta State University Students in Abraka, Nigeria" from Vol 13 issue 16 received Emerging Researcher Award


A Study by Alkhansa Mahmoud et al. entitled "mRNA Expression of Somatostatin Receptors (1-5) in MCF7 and MDA-MB231 Breast Cancer Cells" from Vol 13 issue 06 received Emerging Researcher Award


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International Journal of Current Research and Review (IJCRR) provides platform for researchers to publish and discuss their original research and review work. IJCRR can not be held responsible for views, opinions and written statements of researchers published in this journal

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