Analysis of Some Drugs Affecting the Respiratory System
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1 Analysis of Some Drugs Affecting the Respiratory System A Thesis Presented By Nehal Fayek Farid Faragallah B. Pharm. Sci. (1996) M.Sc. in Analytical Chemistry (2003) For The Degree of Doctor of Philosophy in Pharmaceutical Sciences (Analytical Chemistry) Under the supervision of Prof. Dr. Mohamed Abdelkawy Mohamed Professor of Analytical Chemistry Faculty of Pharmacy Cairo University Prof. Dr. Nariman Abd El Ghany El Ragehy Professor of Analytical Chemistry Faculty of Pharmacy Cairo University Prof. Dr. Fadia Hussein Metwally Professor of Analytical Chemistry Faculty of Pharmacy Cairo University Dr. Maha Abd El Moneim Hegazy Professor of Analytical Chemistry Faculty of Pharmacy Cairo University (2012)
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3 ACKNOWLEDGEMENT I would like to acknowledge with sincere thanks and appreciation Prof. Dr. Mohamed Abdelkawy Mohamed, Professor of Analytical Chemistry, Faculty of Pharmacy, Cairo University, to whom, I am indebted for suggesting the point of research, continuous guidance, encouragement and stimulant discussions without which this work would have never been finished. I wish to convey my deep appreciation and thanks to Prof. Dr. Nariman Abd El Ghany El Ragehy, Professor of Analytical Chemistry, Faculty of Pharmacy, Cairo University for her valuable advice, keen supervision and constructive comments. I am grateful to Prof. Dr. Fadia Hussein Metwally, Professor of Analytical Chemistry, Faculty of Pharmacy, Cairo University, for her assistance and guidance. Special thanks to Dr. Maha Abd EL Monein Hegazy, Lecturer of Analytical Chemistry, Faculty of Pharmacy, Cairo University for her continuous support, guidance, solving problems and teaching me new techniques especially in the practical part without which this work would have never been finished. I would like to express my appreciation to my parents, my husband and my two daughters, who provided the warm atmosphere for completing the thesis. I would like to extend my thanks to the staff members and my colleagues in Faculty of Pharmacy, Cairo University and Beni Suef University for their cooperation and encouragement. Nehal Fayek
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5 Analysis of Some Drugs Affecting the Respiratory System Abstract Simultaneous determination of a mixture of Ambroxol HCl (AMB) and Guaifenesin (G) in presence of the oxidative degradate of AMB and guaicol, the main impurity of G by RP-HPLC, TLC-spectrodensitometry and multivariate calibration methods was done. Model update of multivariate calibration was used to determine AMB and G in syrup dosage form due to interfering additives. Simultaneous determination of a quaternary mixture of Oxomemazine, Sodium benzoate, Guaifenesin and Paracetamol by RP-HPLC, TLC-spectrodensitometry and multivariate calibration methods was also done. Spectrophotometric determination of Oxomemazine HCl, Guaifenesin and Carbocisteine in pure form and in tablets was also done. Simultaneous determination of a ternary mixture of Terbutaline sulfate, Guaifenesin and Bromhexine HCl by RP-HPLC, TLC-spectrodensitometry and multivariate calibration methods was done and the three methods were applied for the determination of the drugs in syrup dosage form. Key Words: Ambroxol HCl Guaifenesin Guaicol HPLC TLCspectrodensitometry PLS PCR Oxomemazine Paracetamol Sodium benzoate Carbocisteine Terbutaline sulfate Bromhexine HCl.
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7 Contents: List of Figures List of Tables... List of Abbreviations. Preface. Summary.. Page xii xvi xxii xxv xxvi Part I General Introduction I.1. Pharmacology of drugs affecting respiratory system 2 I.1.1. Bronchodilators. 3 I.1.2. Corticosteroids 4 I.1.3. Cromolyn and nedocromil... 5 I.1.4. Leukotriene receptor antagonists 5 I.1.5. Antihistamines 5 I.1.6. Cough preparations. 7 I.1.7. Nasal Decongestants Antibacterial agents for respiratory tract infections.. 8 I.2. Studied Drugs 9 Part II Simultaneous determination of Ambroxol Hydrochloride and Guaifenesin in presence of the oxidative degradation product of Ambroxol HCl and Guaicol the main impurity of Guaifenesin by RP-HPLC, TLC-spectrodensitometric and multivariate calibration methods. Section A Literature review of Ambroxol HCl and Guaifenesin II.A. Literature review for the determination of Ambroxol HCl (AMB) and i
8 Guaifenesin (G) 20 II. A.1. Literature review of Ambroxol HCl 20 II.A.1.1. Titrimetric methods. 20 II.A.1.2. Spectroscopic methods 20 II.A.1.3. Chromatographic methods.. 22 II.A.1.4. Electro-analytical methods.. 27 II.A.2. Literature review of Guaifenesin. 28 II.A.2.1. Pharmacopeial methods II.A.2.2. Spectrophotometric methods 28 II.A.2.3. Chemometric methods. 29 II.A.2.4. Chromatographic methods.. 31 II.A.2.5. Electro-analytical methods.. 39 II.A.2.6. X ray diffraction method 40 II.A.3. Simultaneous determination of Ambroxol HCl and Guaifenesin.. 40 II.A.3.1. High performance liquid chromatography 40 II.A.3.2. Capillary electrophoresis.. 41 Section B Simultaneous determination of Ambroxol HCl and Guaifenesin in presence of the oxidative degradation product of Ambroxol HCl and Guaicol, the main impurity of Guaifenesin by HPLC method. II.B.1. Introduction. 43 II.B.2. Experimental II.B.2.1. Instruments II.B.2.2. Samples II.B.2.3. Reagents and solvents 46 II.B.2.4. Standard solutions ii
9 II.B.2.5. Procedure II.B Chromatographic conditions. 47 II.B Method validation. 47 II.B Assay of pharmaceutical dosage forms using the proposed HPLC method. 49 II.B.3. Results and discussion Section C Simultaneous determination of Ambroxol HCl and Guaifenesin in presence of the oxidative degradation product of Ambroxol HCl and Guaicol, the main impurity of Guaifenesin by TLC- Spectrodensitometric method. II.C.1. Introduction. 67 II.C.2. Experimental 67 II.C.2.1. Instruments.. 67 II.C.2.2. Samples II.C.2.3. Reagents and solvents.. 68 II.C.2.4. Stock standard solutions II.C.2.5. Procedure II.C Chromatographic conditions 69 II.C Method validation II.C Assay of pharmaceutical dosage forms 71 II.C.3. Results and discussion Section D Simultaneous determination of quaternary mixture of Ambroxol HCl, its oxidative degradation product, Guaifenesin and its main impurity (Guaicol) by Multivariate Calibration Methods. II.D.1. Introduction 85 II.D.2. Experimental.. 86 iii
10 II.D.2.1. Instruments. 86 II.D.2.2. Samples II.D.2.3. Reagents and solvents. 87 II.D.2.4. Solutions. 87 II.D.2.5. Procedure. 89 II.D Spectral characteristics 89 II.D Calibration and validation sets II.D Assay of pharmaceutical dosage forms 90 II.D.3. Results and discussion. 90 Part III Simultaneous determination of a quaternary mixture of Oxomemazine, Sodium benzoate, Guaifenesin and Paracetamol by RP-HPLC, TLC-spectrodensitometric and multivariate calibration methods. Section A Literature review of Oxomemazine, Sodium benzoate and Paracetamol III.A. Literature review for the determination of Oxomemazine, Sodium benzoate and Paracetamol III.A.1. Literature review of Oxomemazine III.A.1.1 Colorimetric methods III. A.1.2. Chromatographic Methods III.A.2. Literature review of Sodium benzoate. 107 III.A.2.1. Pharmacopeial methods 107 III.A.2.2. Titrimetric procedures III.A.2.3. Spectrophotometric methods 108 III. A.2.4. Chemometric methods III.A.2.5. Chromatographic methods 109 iv
11 III.A.2.6. Electro-analytical methods III.A.3. Literature review for Paracetamol III.A.3.1. Pharmacopeial methods 112 III.A.3.2. Gravimetric method IIII.A.3.3. Titrimetric method 113 III.A.3.4. Spectroscopic methods 114 III.A.3.5. Chemometric methods. 117 III.A.3.6. Flow injection analysis. 118 III.A.3.7. Chromatographic methods III.A.3.8. Electro - analytical methods. 126 III.A.4. Simultaneous determination of a quaternary mixture of Guaifenesin, Paracetamol, Sodium benzoate and Oxomemazine. 127 Section B Simultaneous determination of a quaternary mixture of Oxomemazine, Sodium benzoate, Guaifenesin and Paracetamol by RP-HPLC method. III.B.1. Introduction III.B.2. Experimental. 130 III.B.2.1. Instruments III.B.2.2. Samples. 130 III.B.2.3. Reagents and solvents III.B.2.4. Standard solutions 132 III.B.2.5. Procedure III.B Chromatographic conditions. 132 III.B Method validation III.B Assay of pharmaceutical dosage forms using the proposed HPLC method v
12 III.B.3. Results and discussion Section C Simultaneous determination of a quaternary mixture of Oxomemazine, Paracetamol, Guaifenesin and Sodium benzoate by TLC-spectrodensitometric III.C. 1. Introduction III.C. 2. Experimental. 148 III.C.2.1. Instruments III.C.2.2. Samples. 148 III.C.2.3. Reagents and solvents III.C.2.4. Standard solutions. 149 III.C.2.5. Procedure. 149 III.C Chromatographic conditions 149 III.C Method validation III.C Application of the proposed TLC-spectrodensitometric method for analysis of pharmaceutical dosage forms 152 III.C.3. Results and discussion. 152 Section D Simultaneous determination of a quaternary mixture of Oxomemazine, Sodium benzoate, Guaifenesin and Paracetamol by multivariate calibration methods. III.D.1. Introduction III.D.2. Experimental 167 III.D.2.1. Instruments III.D.2.2. Samples. 167 III.D.2.3. Reagents and solvents III.C.2.4. Standard Solutions 168 III.D.2.5. Procedure vi
13 III.D Spectral characteristics. 169 III.D Calibration and validation 169 III.D Assay of dosage form III.D.3. Results and discussion Part IV Spectrophotometric determination of Oxomemazine HCl, Guaiphenesin and Carbocisteine in pure form and in Ultrasolv tablets. Section A Literature review of Carbocisteine IV.A.1. Literature review for the determination of Carbocisteine IV.A.1.1. Pharmacopeial methods 184 IV.A.1.2. Colorimetric methods IV.A.1.3. Chromatographic methods IV.A.1.4. Electrochemical methods Section B Spectrophotometric Determination of Guaiphenesin and Oxomemazine HCl in presence of Carbocisteine IV.B.1. Introduction. 190 IV.B.2. Experimental 190 IV.B.2.1. Instruments IV.B.2.2. Samples. 190 IV.B.2.3. Reagents and solvents IV.B.2.4. Standard solutions 191 IV.B.2.5. Procedure vii
14 IV.B Spectral characteristics IV.B Method validation 192 IV.B Assay of Ultrasolv tablets IV.B.3. Results and discussion. 194 Section C Colorimetric determination of Carbocisteine using p-benzoquinone. IV.C.1. Introduction IV.C.2. Experimental 207 IV.C.2.1. Instruments IV.C.2.2. Samples. 207 IV.C.2.3. Reagents and solvents IV.C.2.4. Standard solutions 208 IV.C.2.5. Procedure IV.C Spectral characteristics. 208 IV.C Linearity and range IV.C Assay of Ultrasolv tablets 209 IV.C.3. Results and discussion. 209 Part V Simultaneous determination of a ternary mixture of Terbutaline sulfate, Guaifenesin and Bromhexine HCl by RP-HPLC, TLC-spectrodensitometric and multivariate calibration methods. Section A Literature review of Terbutaline sulfate and Bromhexine HCl V.A.1. Literature review for the determination of Guaifenesin (G), Terbutaline 219 viii
15 sulfate (TS) and Bromhexine hydrochloride (BH) V.A.1. Literature review of Terbutaline sulfate. 219 V.A.1.1. Pharmacopeial methods. 219 V.A.1.2. Spectroscopic methods V.A.1.3. Chromatographic methods. 221 V.A.1.4. Electro-analytical methods. 226 V.A.2. Literature review of Bromhexine hydrochloride 227 V.A.2.1. Pharmacopeial methods. 227 V.A.2.2. Titrimetric methods 227 V.A.2.3. Spectroscopic methods V.A.2.4. Chemometric methods 229 V.A.2.5. Chromatographic methods V.A.2.6. Electro-analytical methods V.A.3. Simultaneous determination of a ternary mixture of Terbutaline sulfate, Bromhexine HCl and Guaifenesin. Section B 233 Simultaneous determination of a ternary mixture of Terbutaline sulfate, Guaifenesin and Bromhexine HCl by HPLC method V.B.1. Introduction. 236 V.B.2. Experimental V.B.2.1. Instruments V. B.2.2. Samples V. B.2.3. Reagents and solvents. 237 V. B.2.4. Standard solutions 238 V. B.2.5. Procedure ix
16 V.B Chromatographic conditions. 238 V.B Method validation V.B Assay of pharmaceutical dosage form 240 V.B.3. Results and discussion 240 Section C Simultaneous determination of a ternary mixture of Terbutaline sulfate, Bromhexine HCl and Guaifenesin by TLC-spectrodensitometric method V. C.1. Introduction. 253 V.C.2. Experimental V.C.2.1. Instruments. 253 V.C.2.2. Samples V.C.2.3. Reagents and solvents 254 V.C.2.4. Standard solutions V.C.2.5. Procedure 254 V.C Chromatographic conditions V.C Method validation V.C Assay of Pharmaceutical dosage form. 257 V.C.3. Results and discussion 257 Section D Simultaneous determination of a quaternary mixture of Terbutaline sulfate, Bromhexine HCl, Guaifenesin and Sodium benzoate by multivariate calibration methods V.D.1. Introduction. 271 V.D.2. Experimental V.D.2.1. Instruments 271 x
17 V.D.2.2. Samples V.D.2.3. Reagents and solvents V.D.2.4. Standard solutions V.D.2.5. Procedure 272 V.D Spectral characteristic. 272 V.D Calibration and validation V.D Assay of dosage form. 273 V.D.3. Results and Discussion References. 285 xi
18 List of Figures: Figure No. Page 1 Suggested mechanism for the oxidation reaction of Ambroxol HCl by hydrogen peroxide 52 2 IR for Ambroxol HCl and Ambroxol HCl oxidative degradation product Mass spectroscopy for Ambroxol HCl and Ambroxol HCl oxidative degradation product HPLC Chromatogram of Ambroxol HCl and Guaifenesin Linearity of Ambroxol HCl and Guaifenesin by the proposed HPLC method Thin layer chromatogram of laboratory prepared mixture containing Ambroxol HCl, Guaifenesin, Ambroxol HCl oxidative degradation product and Guaicol TLC chromatogram of Ambroxol HCl 75 8 TLC chromatogram of Guaifenesin 75 9 Calibration curve of Ambroxol HCl and Guaifenesin by the proposed TLCspectrodensitometric method UV-Spectra of 40 µg ml -1 Ambroxol HCl, 20 µg ml -1 Ambroxol degradation product, 40 µg ml -1 Guaifenesin, and 20 µg ml -1 Guaicol RMSEC plot of the cross validation of the training set as a function of the number of principal components used to construct PLS and PCR models for Ambroxol HCl RMSEC plot of the cross validation of the training set as a function of the number of principal components used to construct PLS and PCR calibrations for Guaifenesin. 94 xii
19 13 RMSEC plot of the cross validation of the training set as a function of the number of principal components used to construct PLS and PCR calibrations for Ambroxol HCl oxidative degradation product RMSEC plot of the cross validation of the training set as a function of the number of principal components used to construct PLS and PCR calibrations for Guaicol HPLC chromatograms of (A) laboratory prepared mixture of Paracetamol, Guaifenesin, Sodium benzoate (t R = 6.05) and Oxomemazine and (B) Toplexil syrup Linearity of Oxomemazine, Sodium benzoate, Guaifenesin and (D) Paracetamol by the proposed HPLC method TLC Chromatogram of laboratory prepared mixture containing Oxomemazine, Paracetamol, Guaifenesin and Sodium benzoate TLC chromatogram of Oxomemazine TLC chromatogram of Paracetamol TLC chromatogram of Guaifenesin TLC chromatogram of Sodium benzoate Calibration curves of relative peak area at 270 nm to the corresponding concentration of Oxomemazine, Paracetamol, Guaifenesin and Sodium benzoate Zero order absorption spectra of Oxomemazine, Sodium benzoate, Guaifenesin and Paracetamol RMSEC plot of the cross validation of the training set as a function of the number of principal components used to construct PLS and PCR calibrations for Oxomemazine RMSEC plot of the cross validation of the training set as a function of the number of principal components used to construct PLS and PCR calibrations for Sodium benzoate xiii
20 26 RMSEC plot of the cross validation of the training set as a function of the number of principal components used to construct PLS and PCR calibrations for Guaifenesin RMSEC plot of the cross validation of the training set as a function of the number of principal components used to construct PLS and PCR calibrations for Paracetamol Zero order absorption spectra of solutions of Oxomemazine HCl, Guaifenesin and Carbocisteine in 0.1N HCl First Derivative absorption spectra of Oxomemazine HCl, Guaifenesin and Carbocisteine in 0.1N HCl Zero order absorption spectra of Oxomemazine HCl in the range of 5 60 µg ml Linearity of Oxomemazine HCl in the range of 5 60 µg ml -1 by zero order absorption spectrophotometric method at and 294.4nm First derivative absorption spectra of Guaifenesin as solvent in the range of µg ml Linearity of Guaifenesin in the range of µg ml -1 by first derivative absorption spectrophotometric method at nm and 266.6nm Absorption spectra of Carbocisteine with PBQ, Oxomemazine HCl with PBQ, Guaifnesin with PBQ against a blank of PBQ in phosphate buffer and spectrum of 0.1 M PBQ in phosphate buffer ph 7 against a blank of distilled water Mechanism of reaction between Carbocisteine and p-benzoquinone Absorption spectra of Carbocisteine in the range of µg ml -1 with 0.1 M PBQ in phosphate buffer ph Linearity of Carbocisteine in the range of µg ml -1 with 0.1 M PBQ in phosphate buffer ph 7 at 490 nm HPLC Chromatogram on XTerra C18 column of a. Laboratory prepared mixture of Terbutaline sulfate, Guaifenesin and Bromhexine HCl and b. All Vent syrup 241 xiv
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