Investigating the degradation of the sympathomimetic drug phenylephrine by electrospray ionisation-mass spectrometry

Journal of Pharmaceutical and Biomedical Analysis

Volumn 52, Issue 2, 2010, Pages 203-209

  Trommer, Hagen ^a   Raith, Klaus ^a   Neubert, Reinhard H H ^a  

^a MARTIN LUTHER UNIVERSITY HALLE WITTENBERG   (Germany)

Author keywords

Degradation; Electrospray ionisation mass spectrometry; Fragmentation; Phenylephrine; Stability

Indexed keywords

ADRENERGIC RECEPTOR STIMULATING AGENT; METHAMPHETAMINE; PHENYLEPHRINE; PHENYLEPHRINE BITARTRATE; PHENYLPROPANOLAMINE; PSEUDOEPHEDRINE; TARTARIC ACID; UNCLASSIFIED DRUG;

ARTICLE; DRUG DEGRADATION; DRUG OXIDATION; DRUG STRUCTURE; ELECTROSPRAY MASS SPECTROMETRY; FRAGMENTATION REACTION; PRIORITY JOURNAL; SOLAR RADIATION; TANDEM MASS SPECTROMETRY; ULTRAVIOLET IRRADIATION;

DRUG STABILITY; MASS SPECTROMETRY; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PHENYLEPHRINE; PHOTOCHEMICAL PROCESSES; SOLUTIONS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SPECTROPHOTOMETRY, ULTRAVIOLET; SYMPATHOMIMETICS; TANDEM MASS SPECTROMETRY; WATER;

EID: 77349127043     PISSN: 07317085     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jpba.2010.01.024     Document Type: Article

References (45)

1. Akita H., Akamatsu H., Matsunaga K. Allergic contact dermatitis due to phenylephrine hydrochloride, with an unusual patch test reaction. Contact Dermatitis 2003, 49:232-235.
2. Miller-Meeks M.J., Farrell T.A., Munden P.M., Folk J.C., Rao C., Schoenwald R.D. Phenylephrine prodrug. Report of clinical trials. Ophthalmology 1991, 98:222-226.
3. Goskonda V.R., Ghandehari H., Reddy I.K. Novel site-specific chemical delivery system as a potential mydriatic agent: formation of phenylephrine in the iris-ciliary body from phenylephrone chemical delivery systems. J. Pharm. Sci. 2001, 90:12-22.
4. Hoffman B.B. Catecholamines, sympathomimetic drugs, and adrenergic receptor antagonists. Goodman and Gilman's: The Pharmacological Basis of Therapeutics 2001, 215-268. McGraw-Hill, Med. Pub. Div., New York. 10th ed. J.G. Hardman, L.E. Limbrid, A.G. Gilman (Eds.).
5. D. Steinhilber, M. Schubert-Zsilavecz, H.J. Roth, Medizinische Chemie. Targets und Arzneistoffe, DAV, Stuttgart, 2005.
6. Kanfer I., Dowse R., Vuma V. Pharmacokinetics of oral decongestants. Pharmacotherapy 1993, 13:116S-128S.
7. Hengstmann J.H., Goronzym J. Pharmacokinetics of 3H-phenylephrine in man. Eur. J. Clin. Pharmacol. 1982, 21:335-341.
8. Drug Enforcement Administration, General Information Regarding the Combat Methamphetamine Epidemic Act of 2005 (Title VII of Public Law 109-177), 2006 http://www.deadiversion.usdoj.gov/meth/cma2005_general_info.pdf.
9. Eccles R. Substitution of phenylephrine for pseudoephedrine as a nasal decongeststant. An illogical way to control methamphetamine abuse. Br. J. Clin. Pharmacol. 2007, 63:10-14.
10. K. Hillenmeyer, All stuffed up. Reformulated cold medicines might not be able to do the job, Herald Tribune, 30.01.2007.
11. Hendeles L., Hatton R.C. Oral phenylephrine: an ineffective replacement for pseudoephedrine? Letters to the editor. J. Allergy Clin. Immunol. 2006, 118:279-280.
12. Eccles R. Efficacy of phenylephrine. Letter to the editor. Br. J. Clin. Pharmacol. 2007, 64:557.
13. Desjardins P.J., Berlin R.G. Efficacy of phenylephrine. Letter to the editors. Br. J. Clin. Pharmacol. 2007, 64:555-556.
14. Traynor K. FDA advisers want more data about phenylephrine. Am. J. Health Syst. Pharm. 2008, 65:193-194.
15. FDA, Nasal Decongestant Drug Products: Phenylephrine Bitartrate. Final Rule: Adds effervescent tablet as GRASE dosage form, 2006 (71FR43358) http://www.fda.gov/OHRMS/DOCKETS/98fr/E6-12265.pdf.
16. Troup A.E., Mitchner H. Degradation of phenylephrine hydrochloride in tablet formulations containing aspirin. J. Pharm. Sci. 1964, 53:375-379.
17. Gaglia C.A. Phenylephrine hydrochloride. Analytical Profiles of Drug Substances 1974, vol. 3:483-512. Academic Press, New York.
18. El-Shibini H.A.M., Daabis N.A., Motawi M.M. The stability of phenylephrine. I. The rate of degradation of the amino group. Arzneimittelforschung 1969, 19:676-678.
19. El-Shibini H.A.M., Daabis N.A., Motawi M.M. The stability of phenylephrine. II. The discolouration reaction and the influence of some ions on the rate of degradation of the drug. Arzneimittelforschung 1969, 19:828-831.
20. El-Shibini H.A.M., Daabis N.A., Motawi M.M. The stability of phenylephrine. III. The racemisation reaction. Arzneimittelforschung 1969, 19:1613-1614.
21. Vuma V., Kanfer I. High-performance liquid chromatographic determination of phenylephrine in human serum with coulometric detection. J. Chromatogr. B: Biomed. Appl. 1996, 678:245-252.
22. Papac D.I., Shahrokh Z. Mass spectrometry innovations in drug discovery and development. Pharm. Res. 2001, 18:131-145.
23. Galmier M.J., Bouchon B., Madelmont J.C., Mercier F., Pilotaz F., Lartigue C. Identification of degradation products of diclofenac by electrospray ion trap mass spectrometry. J. Pharm. Biomed. Anal. 2005, 38:790-796.
24. (n). J. Pharm. Biomed. Anal. 2009, 49:55-63.
25. International Conference on Harmonisation, Q1A(R2), Stability Testing of New Drug Substances and Products, November 2003.
26. International Conference on Harmonisation, Q1B, Photostability Testing of New Active Substances and Medicinal Products, May 1997.
27. Baertschi S.W. Analytical methodologies for discovering and profiling degradation-related impurities. Trends Anal. Chem. 2006, 25:758-767.
28. Brustugun J., Kristensen S., Tønnesen H.H. Photostability of epinephrine - the influence of bisulfite and degradation products. Pharmazie 2004, 59:457-463.
29. Millard B.J., Priaulx D.J., Shotton E. The stability of aqueous solutions of phenylephrine at elevated temperatures: identification of the decomposition products. J. Pharm. Pharmacol. 1973, 25(Suppl.):24P-31P.
30. West G.B., Whittet T.D. A note on the stability of solutions of phenylephrine. J. Pharm. Pharmacol. 1960, 12(Suppl.):113-115.
31. Shotton E., Priaulx D.J. An assay for phenylephrine applicable to stability studies. J. Pharm. Pharmacol. 1974, 26:197-200.
32. Schieffer G.W., Hughes D.E. Simultaneous stability-indicating determination of phenylephrine hydrochloride, phenylpropanolamine hydrochloride, and guaifenesin in dosage forms by reversed-phase paired-ion high-performance liquid chromatography. J. Pharm. Sci. 1983, 72:55-59.
33. Marín A., Barbas C. LC/MS for the degradation profiling of cough-cold products under forced conditions. J. Pharm. Biomed. Anal. 2004, 35:1035-1045.
34. Kiser T.H., Oldland A.R., Fish D.N. Stability of phenylephrine hydrochloride injection in polypropylene syringes. Am. J. Health Syst. Pharm. 2007, 64:1092-1095.
35. Luduena F.P., Snyder A.L., Lands A.M. Effect of ultra-violet irradiation of phenylephrine solutions. J. Pharm. Pharmacol. 1963, 15:538-543.
36. Chafetz L., Chow L.H. Photochemical hydroxylation of phenylephrine to epinephrine (adrenaline). J. Pharm. Biomed. Anal. 1988, 6:511-514.
37. Marín A., Espada A., Vidal P., Barbas C. Major degradation product identified in several pharmaceutical formulations against the common cold. Anal. Chem. 2005, 77:471-477.
38. Wong J., Wiseman L., Al-Mamoon S., Cooper T., Zhang L.K., Chan T.M. Major degradation product identified in several pharmaceutical formulations against the common cold. Anal. Chem. 2006, 78:7891-7895.
39. Weiler J.M., Gellhaus M., Donnelly A., Weiler K. Randomized, double-blind, parallel groups, placebo-controlled study of efficacy and safety of Rynatan in the treatment of allergic rhinitis using an acute model. Ann. Allergy 1990, 64:63-67.
40. Mindel J.S., Shaikewitz S.T., Podos S.M. Is phenylephrine pivalate a prodrug?. Arch. Ophthalmol. 1980, 98:2220-2223.
41. Qiu Y., Guillory J.K., Schoenwald R.D. Formulation, in vitro dissolution, and ocular bioavailability of high- and low-melting phenylephrine oxazolidines. Pharm. Res. 1993, 10:1627-1631.
42. Goskonda V.R., Khan M.A., Bodor N.S., Reddy I.K. Chemical delivery systems: evaluation of physicochemical properties and enzymatic stability of phenylephrone derivatives. Pharm. Develop. Technol. 1999, 4:189-198.
43. Muralidharan S., Maher G.M., Boyle W.A., Nerbonne J.M. " Caged" phenylephrine: development and application to probe the mechanism of alpha-receptor-mediated vasoconstriction. Proc. Natl. Acad. Sci. U.S.A. 1993, 90:5199-5203.
44. Thevis M., Schänzer W. Mass spectrometry in sports drug testing: structure characterization and analytical assays. Mass Spectrom. Rev. 2007, 26:79-107.
45. Rodriguez-Cruz S.E. Rapid analysis of controlled substances using desorption electrospray ionization mass spectrometry. Rapid Commun. Mass Spectrom. 2006, 20:53-60.