4. VISIBLE SPECTROPHOTOMETRIC DETERMINATION OF. Fulvestrant is primarily used in the treatment of hormone receptor

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1 VISIBLE SPECTROPHOTOMETRIC DETERMINATION OF FULVESTRANT 4.1 INTRODUCTION Fulvestrant is primarily used in the treatment of hormone receptor positive metastatic breast cancer in post-menopausal women with disease progression following anti-estrogen therapy. The drug is official in Martindale, The Extra Pharmacopoeia 103. Drug profile of Fulvestrant is shown in the following table 4.1

2 122 TABLE 4.1: DRUG PROFILE OF FULVESTRANT 1 Official Name Fulvestrant 2 Chemical Name 13-Methyl-7-[9-(4,4,5,5,5-pentafluropentyl sulfinyl)nonyl]-7,8,9,11,12,13,14,15,16,17- decahydro-6h-cyxlopenta{a} phenanthrene- 3,17- diol 3 Chemical Structure Fig Analytically useful functional group Hydroxyl group 5 Molecular Formula 6 Molecular Weight C32H47F5O3 S Color White powder 8 Solubility Methanol 9 Therapeutic Use Fulvestrant is primarily used in the treatment of hormone receptor positive metastatic breast cancer in post-menopausal women with disease progression following anti-estrogen therapy.

3 Mechanism of Action It is an estrogen receptor antagonist with no agonist effects, which works both by downregulating and by degrading the estrogen receptor.it produces its anti-cancer effect by binding to estrogen receptors in a cell so that estrogen cannot. Estrogen is a female hormone that produces growth stimulatory effects on a significant portion of breast cancer cells. By binding to estrogen receptors, fulvestrant inhibits the growth stimulatory effects that estrogen would normally produce. In addition, fulvestrant causes the estrogen receptors to degrade, leaving fewer receptors for estrogen to bind 103. Aim of the work Few HPLC methods for quantitative determination of fulvestrant were reported in the literature. These methods were applied in the determination of fulvestrant and it s metabolites in biological fluids and are mainly useful for therapeutic monitoring of the drug (Table 4.1). No visible spectrophotometric method for quantitative determination of fulvestrant in bulk drug samples and formulations was reported. The aim of the present work is to develop and validate rapid, economical and sensitive visible spectrophotometric method for quantitative determination of fulvestrant in bulk drug samples and

4 124 formulations. In the present investigation, two new visible spectrophotometric methods were developed for fulvestrant with two chromogenic reagents namely 1:10 Phenanthroline and 2, 2 Bipyridyl. TABLE 4.2: LIST OF REPORTED METHODS FOR FULVESTRANT Sample Internal Colu Mobile Detector Reference standard mn Phase Rat Camptothecin Hyper 0.1M Florescence 105 plasma sil potassium samples C18 dihydroge n phosphate containing 0.01 M TBAHS (ph 6.4)- acetonitril e (75:25, v/v)

5 EXPERIMENTAL Instruments ELICO-SL-164 Ultraviolet-Visible spectrophotometer (double beam) was used for all spectral measurements. Digisun model DI-707 ph meter was used for all the ph measurements. CHEMICALS AND REAGENTS: All the chemicals used were of analytical grade. i) 1:10 Phenanthroline (0.02 M) : was prepared by dissolving 400 mg of 1:10 Phenanthroline in small quantity of water and the solution was heated for half an hour, cooled and the final volume was made up to 100 ml with distilled water. ii) 2, 2 -bipyridyl (0.1 M): was prepared by dissolving 780 mg of 2, 2 - bipyridyl in 50 ml of distilled water. iii) Ferric Chloride (0.3 % w/v): was prepared by dissolving 300 mg of ferric chloride hexahydrate in 100 ml of distilled water. iv) O-Phosphoric acid: 0.2 M. PROCEDURE: Preparation of standard drug solution: A standard drug solution of fulvestrant was prepared by dissolving 100 mg of drug in 100 ml of methanol in a standard volumetric flask to obtain a stock solution of 1 mg/ml. This solution was further

6 126 diluted with methanol to get working standard solutions of 100 µg/ml (Method FVT1) and 40 µg/ml (Method FVT2). Preparation of sample solution: Volume of injection equivalent to 20 mg of drug was diluted to 20 ml with methanol and analyzed by taking an aliquot and treated as per the procedure for standard. For Bulk Drug Samples Method FVT1: Aliquots of standard drug solution ( ml) were transferred into series of 10 ml graduated test tubes, 2 ml of ferric chloride and 2 ml of 1:10 phenanthroline were added to each test tube. The test tubes were then heated on water bath for 15 min and then cooled to room temperature and 1 ml of o-phosphoric acid (0.2 M) was added to each test tube and the total volume was brought to 10 ml with methanol. The absorbance of the blood red colored species was measured at 510 nm against reagent blank. The amount of fulvestrant present in the sample solution was computed from its calibration curve. Method FVT2: Aliquots of standard drug solution ( ml) were transferred into series of 10 ml graduated test tubes, 2 ml of ferric chloride and 2 ml of 2, 2 -bipyridyl were added to each test tube. The test tubes were then heated on water bath for 15 min and then cooled to room temperature and 1 ml of o-phosphoric acid (0.2 M) was added

7 127 to each test tube and the total volume was brought to 10 ml with methanol. The absorbance of the blood red colored species was measured at 520 nm against reagent blank. The amount of fulvestrant present in the sample solution was computed from its calibration curve. Analysis of Formulations: Method FVT1: About 1 ml of sample solution was transferred into 10 ml graduated test tube, 2 ml of ferric chloride and 2 ml of 1:10 phenanthroline were added to the test tube. The test tube was then heated on water bath for 15 min and then cooled to room temperature and 1 ml of o-phosphoric acid (0.2 M) was added to the test tube and the total volume was brought to 10 ml with methanol. The absorbance of the blood red colored species was measured at 510 nm against reagent blank. Method FVT2: About 1 ml of sample solution was transferred into 10 ml graduated test tube, 2 ml of ferric chloride and 2 ml of 2, 2 - bipyridyl were added to each test tube. The test tube was then heated on water bath for 15 min and then cooled to room temperature and 1 ml of o-phosphoric acid (0.2 M) was added to the test tube and the total volume was brought to 10 ml with methanol. The absorbance of the blood red colored species was measured at 520 nm against reagent blank.

8 RESULTS AND DISCUSSION Analytical Data and Method Validation Optimization of parameters for Methods FVT1 and FVT2 The optimum conditions were established by changing one parameter while fixing the other parameters and noting the effect on absorbance of chromogen. In both the methods, fulvestrant forms iron complexes with 1:10- phenanthroline and 2, 2 -bipyridyl to yield blood red colored chromogen. The effect of temperature of the reaction, quantity, concentration and order of addition of various reagents were studied, optimized after several experiments with respect to maximum sensitivity, colour stability, adherence to Beer s law and other optimum conditions are incorporated in the procedure (Table 4.3).

9 129 TABLE 4.3: OPTIMUM CONDITIONS ESTABLISHED FOR METHODS FVT1 AND FVT2 Parameter Volume of 0.3% of ferric chloride solution required for complex formation Volume of 1:10 phenanthroline/2,2 - bipyridyl Time and temperature required for complex formation Stability after complete color development Optimum Range Conditions In The Methods Remarks 1-2 ml 2 ml Addition of less than 2 ml results in low absorbance 1-2 ml 2 ml particularly with high concentrations of Beer s law limits. Addition of more than 2 ml results in high blank value. 15 min at Change of time temp(70 0 C) and temperature beyond optimum limits produced erratic results. 40 min >40 min Complex formed is stable for sufficient period of time.

10 Absorbance Absorbance 130 Absorption Maximum Absorption spectra of fulvestrant for methods FVT1 and FVT2 were shown in figures 4.2 and 4.3. Absorption Spectrum Of Fulvestrant with 1,10 Phenanthroline Chromogen vs 1,10 Phenanthroline, 1,10 Phenanthroline-0.02 M in distilled Water,FVT- 30 µg/ml Reagent Blank vs Distilled water Wavelength (nm) Fig 4.2 Absorption spectrum of Fulvestrant with 1,10 Phenanthroline Absorption Spectrum Of Fulvestrant With 2,2 Bipyridyl Wavelength (nm) Chromogen vs 2, 2 - Bipyridyl, 2, 2 -Bipyridyl M in distilled Water,FVT- 8 µg/ml Reagent Blank vs Distilled Water Fig 4.3 Absorption spectrum of Fulvestrant with 2, 2-Bipyridyl

11 131 Linearity By using the method of least squares regression analysis was performed to evaluate the slope (m), intercept (b) and correlation coefficient (r) was computed from various concentrations and the results are presented in Tables 4.4 and 4.5. The graph showed negligible intercept as described by the regression equation y = mx + b where y is the absorbance and x is the concentration in µg/ml. Calibration curves for methods FVT1 and FVT2 were shown in figures 4.4 and 4.5 The optical characteristics such as absorption maxima, Beer s law limits, molar absorptivity and Sandell s sensitivity are presented in Table 4.6.

12 Absorbance 132 Table 4.4 Linearity data of fulvestrant for FVT1 Conc µg/ml Absorbance Calibration Curve of FVT with 1,10 Phenanthroline y = x R 2 = Concentration µg/ml Fig 4.4: Calibration Curve of Fulvestrant with 1,10 Phenanthroline

13 Absorbance 133 Table 4.5 Linearity data of fulvestrant for FVT2 Conc µg/ml Absorbance Calibration Curve of FVT with 2,2-Bipyridyl y = x R 2 = Concentration µg/ml Fig 4.5 Calibration Curve of Fulvestrant with 2,2-Bipyridyl

14 134 Table 4.6: Optical characteristics and precision of the methods S. NO Parameter Method FVT1 Method FVT2 01 λ max (nm) Beer s law range (μg/ml) 03 Molar extinction coefficient(l.mole -1 cm -1 ) 04 Sandell s sensitivity (μg/cm 2 /0.001) x x Regression equation (y = mx + b) * Slope (m) Intercept (b) Correlation coefficient (r) 07 Precision (%Relative Standard Deviation) Standard Error Of Mean * y = mx + b, where y is the absorbance unit and x is the concentration in µg/ml.

15 135 Accuracy and Recovery Commercially available injections of fulvestrant (Table 4.7) were analyzed by the proposed methods. As an additional check on the accuracy of the method, recovery experiments were also conducted by spiking known amounts of pure drug in preanalysed injection and the recovery was calculated in each of the case using the regression line equation developed under the Linearity experiment. Assay results of the proposed methods were compared with that of reference method and statistically evaluated using one-way ANOVA with post-test followed by Dunnett multiple comparison test. The means of the proposed methods are not significantly different from that of reference method (p>0.05). The assay and accuracy results were presented in Table 4.8. The interference studies indicated the common additives and excipients present in formulations did not interfere with the proposed methods.

16 136 Table 4.7: Commercially Available Formulations of Fulvestrant Generic Name Proprietary Name Dosage Form Content Fulvestrant Faslodex,USA Injection 20 Mg Table 4.8: Evaluation of Fulvestrant in pharmaceutical dosage forms (n=6) Sample a Labelled Amount (mg) Amount obtained (mg) b Proposed method d Method FVT1 Method FVT2 Reference method HPLC e Percentage Recovery b,c Method FVT1 Method FVT2 T ± ± ± ± ±1.84 T ± ± ± ± ±0.84 a - T1 and T2 are the injections from different batches (Faslodex, USA). b Mean ± SD of 6 determinations. c 10 mg of pure drug was added and recovered. d For both the samples T1 and T2 One-way ANOVA with post-test followed by Dunnett multiple comparison test was performed. The results showed that P > 0.05 and the means of the proposed methods are not significantly different from that of reference method. e HPLC method developed by the author

17 Chemistry of the colored species formed Fulvestrant has a hydroxyl group in the molecular structure making it possible to form iron complexes of the drug with two reagents 1:10 Phenanthroline and 2, 2 Bipyridyl in ferric chloride solution to form blood red colored chromogen. 107, 108. Methods FVT1 and FVT2 are based on the formation of blood red coloured complexes when Fulvestrant treated with 2,2 -bipyridyl and 1,10-phenanthroline, respectively in the presence of ferric chloride (Proposed schemes 4.1 and 4.2). + Fe (III) Drug + Fe2+ 2,2'-Bipyridine 1,10-phenanthroline N N N N N Fe2+ N N Fe2+ N N N N N

18 Conclusion The proposed visible spectrophotometric methods enable quantitative determination of fulvestrant in bulk drug samples and injections. Efficient visible spectrophotometric detection at the respective absorption maxima enabled determination with no interference from the excipients or solvents of injectable solution. The calibration curves were linear over a concentration range from 5-40 µg/ml for method FVT1 and 2-12 µg/ml for method FVT2.The relative standard deviation s (R.S.D.) were less than 1% and average recovery was above %. Assay results of the proposed methods were compared with that of reference method and statistically evaluated using one-way ANOVA with post-test followed by Dunnett multiple comparison test. The means of the proposed methods are not significantly different from that of reference method (p>0.05). The proposed method is fast, sensitive, precise, accurate, and efficient and can be used in for analysis in quality control laboratories.

19 VISIBLE SPECTROPHOTOMETRIC DETERMINATION OF IMATINIB MESYLATE 5.1 INTRODUCTION Imatinib is an antineoplastic agent used to treat chronic myelogenous leukemia. Drug profile of Imatinib is shown in the following table 5.1 The drug is official in Merck Index 109. TABLE 5.1: DRUG PROFILE OF IMATINIB MESYLATE 1 Official Name Imatinib Mesylate 2 Chemical Name 4-[(4-methyl-1-piperazinyl)methyl]-N-[4- methyl-3-[[4-(3-pyridinyl)-2- pyrimidinyl]amino]-phenyl]benzamide methanesulfonate 3 Chemical Structure 4 Analytically useful functional group 5 Molecular Fig 5.1 Secondary amino group C29H31N7O Formula 6 Molecular Weight Color White powder 8 Solubility Water 9 Therapeutic Use Antineoplastic agent that is used for the treatment of chronic myelogenous leukemia. 10 Mechanism of Action Imatinib is a protein tyrosine kinase inhibitor that inhibits Bcr-Abl tyrosine kinase. It inhibits proliferation induces apoptosis in Bcr-Abl positive cell lines as well as fresh leukemic cells from Philadelphia chromosome positive chronic myeloid leukemia.

20 140 Aim of the Work Few HPLC methods for quantitative determination of imatinib were reported in the literature and are mainly useful for therapeutic monitoring of the drug and it s metabolites in biological fluids (Table 5.2). No visible spectrophotometric method for quantitative determination of imatinib in bulk drug samples and formulations was reported. The aim of the present work is to develop and validate rapid, economical and sensitive visible spectrophotometric method for quantitative determination of imatinib in bulk drug samples and formulations. In the present investigation,two new visible spectrophotometric methods were developed for imatinib with two chromogenic reagents namely BCG and MBTH with FeCl3.

21 141 TABLE 5.2: LIST OF REPORTED METHODS FOR IMATINIB MESYLATE Sample Internal standard Column Mobile Phase Detector Referen ce Human whole blood and Murine Specime ns Cultured tumour cells Bulk drug and formulati ons 4- Hydroxybenz ophenone clozapine narrow bore (2.1 x 150 mm) stainless steel Symmetry C(18) column Phenomen ex Gemini C18 reversed phase column (150 mm x 2.0 mm, 5 µm mobile phase consisted of 28% (v/v) acetonitrile in 50 mm ammonium acetate buffer ph 6.8 containing M 1- octane sulfonic acid and was delivered at 0.2 ml/min Mixture of 65% CH(3)OH (methanol) and 35% NH(4)Ac (Ammoniu m acetate) buffer (20mM, ph 10) The method has demonstrated excellent linearity over the range of microg/ml with regression equation: absorbance (AU) = x concentration (microg/ml) and r2 = The developed method Detected by UV at 265 nm 110 UV 111 UV spectropho tometric method at 285 nm 115

22 142 demonstrated consistent high recoveries (99-102%) and low relative standard deviation (< 5%) at 285 nm. Moreover, the method was found to be highly sensitive with low limit of detection (0.57 microg/ml) and limit of quantitation (1.71 microg/ml). The apparent molar absorptivity and Sandell's sensitivity was found to be 2.75 x 10(3) L/M cm and 2.15 microg/cm2 respectively. 5.2 EXPERIMENTAL Instruments: Pharmaspec-1700 Ultraviolet-Visible spectrophotometer (double beam) was used for all spectral measurements. Digisun model DI-707 ph meter was used for all the ph measurements. Chemicals and reagents: All the chemicals used were of analytical grade. BCG (0.1% w/v): was prepared by dissolving 100 mg of BCG in 0.72 ml of 0.1N NaOH and 20 ml of methanol. After solution was affected, sufficient distilled water was added to produce 100 ml. Phthalate buffer: of ph 2.2 was prepared as per I.P.

23 143 MBTH (0.2 % w/v): was prepared by dissolving 100 mg of MBTH in 50 ml of distilled water. FeCl3 (0.3 % w/v): was prepared by dissolving 300 mg of ferric chloride hexahydrate in 100 ml of distilled water. Chloroform: AR grade chloroform was used directly. Procedure: Preparation of standard drug solution: Method IMT1: About 100 mg of imatinib was accurately weighed and dissolved in 100 ml of distilled water in a standard volumetric flask to obtain a stock solution of 1 mg/ml. Mehod IMT2: A volume of 10 ml of 1 mg/ml solution was further diluted to 100 ml with distilled water to get 100 µg/ml working standard. Preparation of sample solution: A quantity of the powder from capsules equivalent to 50 mg of drug was dissolved in 50 ml of distilled water and analyzed by taking an aliquot and treated as per the procedure for standard. For Bulk Drug Samples Method IMT1: Aliquots of standard drug solution ( ml) were transferred into series of 10 ml graduated test tubes, 2 ml of ferric chloride and 1 ml of MBTH were added to each test tube, mixed well and volume was made upto 10 ml with water. The absorbance of

24 144 resulting solution was measured at 569 nm against reagent blank prepared simultaneously and a linear graph was obtained.the amount of imatinib present in the sample solution was computed from its calibration curve. Method IMT2: Aliquots of standard drug solution ( ml) were added to 5 ml of phthalate buffer of ph 2.2 contained in a separating funnel followed by 0.5 ml of 0.1% w/v BCG solution.the solution was extracted with chloroform and collected chloroform layer was dried over anhydrous sodium sulfate. Volume was made up to 10 ml. A linear graph was obtained at 417 nm after the waiting period of 15 min, against reagent blank prepared simultaneously. The amount of imatinib present in the sample solution was computed from its calibration curve. Analysis of Formulations Method IMT1: A quantity of the powder from capsules equivalent to 50 mg of drug was dissolved in 50 ml of distilled water. Sample solution was transferred into 10 ml graduated test tube, 2 ml of ferric chloride and 1 ml of MBTH were added to the test tube, mixed well and volume was made up to 10 ml with water. The absorbance of resulting solution was measured at 569 nm against reagent blank prepared simultaneously.

25 145 Method IMT2: A quantity of the powder from capsules equivalent to 50 mg of drug was dissolved in 50 ml of distilled water. Sample solution was added to 5 ml of phthalate buffer of ph 2.2 contained in a separating funnel followed by 0.5 ml of 0.1% w/v BCG solution.the solution was extracted with chloroform and collected chloroform layer was dried over anhydrous sodium sulfate. Volume was made up to 10 ml. The absorbance of resulting solution was measured at 417 nm after the waiting period of 15 min, against reagent blank prepared simultaneously.

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