Identification and quantification of vinpocetine and picamilon in dietary supplements sold in the United States

Drug Testing and Analysis

Volumn 8, Issue 3-4, 2016, Pages 334-343

  Avula, Bharathi ^a   Chittiboyina, Amar G ^a   Sagi, Satyanarayanaraju ^a   Wang, Yan Hong ^a   Wang, Mei ^a   Khan, Ikhlas A ^a   Cohen, Pieter A ^b,c  

^a UNIVERSITY OF MISSISSIPPI   (United States)

^b CAMBRIDGE HEALTH ALLIANCE   (United States)

^c HARVARD MEDICAL SCHOOL   (United States)

Author keywords

Dietary supplements; Lesser periwinkle; Picamilon; UHPLC PDA; Vinpocetine

Indexed keywords

FOOD ADDITIVES; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NUTRITION; PHOTODIODES; VITAMINS;

CEREBROVASCULAR DISORDERS; LESSER PERIWINKLE; PHOTODIODE ARRAYS; PHOTODIODE-ARRAY DETECTION; PICAMILON; REVERSED PHASE; UHPLC-PDA; ULTRA-HIGH PERFORMANCE LIQUID CHROMATOGRAPHIES; US FOOD AND DRUG ADMINISTRATION; VINPOCETINE;

DIETARY SUPPLEMENTS;

ACETONITRILE; PICAMILON; VINPOCETINE; WATER; 4 AMINOBUTYRIC ACID; NICOTINOYL-GABA; VINCA ALKALOID;

ANALYTIC METHOD; ARTICLE; CONCENTRATION (PARAMETERS); CONTROLLED STUDY; DIET SUPPLEMENTATION; DRUG DETERMINATION; DRUG IDENTIFICATION; DRUG STRUCTURE; LIMIT OF DETECTION; LIMIT OF QUANTITATION; MEASUREMENT ACCURACY; MEASUREMENT PRECISION; PHASE SEPARATION; PHOTODIODE ARRAY METHOD; PRIORITY JOURNAL; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; STRUCTURE ANALYSIS; ULTRA PERFORMANCE LIQUID CHROMATOGRAPHY; UNITED STATES; VALIDATION PROCESS; ANALOGS AND DERIVATIVES; ANALYSIS; DIETARY SUPPLEMENT; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; ISOLATION AND PURIFICATION; PACKAGING; PROCEDURES; STANDARD; VALIDATION STUDY;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DIETARY SUPPLEMENTS; GAMMA-AMINOBUTYRIC ACID; HUMANS; LIMIT OF DETECTION; PRODUCT LABELING; REFERENCE STANDARDS; UNITED STATES; VINCA ALKALOIDS;

EID: 84945895080     PISSN: 19427603     EISSN: 19427611     Source Type: Journal    
DOI: 10.1002/dta.1853     Document Type: Article

References (36)

1. D. Bereczki, I. Fekete . Vinpocetine for acute ischaemic stroke. Cochrane Database of Systematic Reviews 2008, Issue 1. Art. No.: CD000480.
2. D. Bereczki, I. Fekete . A systematic review of vinpocetine therapy in acute ischaemic stroke. Eur. J. Clin. Pharmacol. 1999, 55, 349.
3. S. Szatmári, P. Whitehouse . Vinpocetine for cognitive impairment and dementia. Cochrane Database of Systematic Reviews 2003, Issue 1. Art. No.: CD003119.
4. National Toxicology Program. Chemical information review document for vinpocetine. CAS No. 42971-09-5, September 2013; Available at: http://ntp.niehs.nih.gov/ntp/htdocs/chem_background/exsumpdf/vinpocetine091613_508.pdf [12 August 2015]
5. Natural Medicines Comprehensive Database. 2014. Available at: http://www.naturaldatabase.com [12 August 2015]
6. P. Bonoczk, B. Gulyas, V. Adam-Vizi, A. Nemes, E. Karpati, B. Kiss, M. Kapas, C. Szantay, I. Koncz, T. Zelles, A. Vas . Role of sodium channel inhibition in neuroprotection: Effect of vinpocetine. Brain Res. Bull. 2000, 53, 245.
7. C. Lorincz, K. Szasz, L. Kisfaludy . The synthesis of ethyl apovincaminate. Arzneimittelforschung. 1976, 26, 1907.
8. B. S. Nayak, L. M. P. Pereira . Catharanthus roseus flower extract has wound-healing activity in Sprague Dawley rats. BMC Complement. Altern. Med. 2006, 6, 41.
9. S. Bhadra, S. Chandra Das, S. Roy, S. Arefeen, A. S. S. Rouf . Development and validation of RP-HPLC method for quantitative estimation of vinpocetine in pure and pharmaceutical dosage forms. Chromatogr. Res. Int. 2011Article ID 801656. DOI:10.4061/2011/801656.
10. Y. Kuge, H. Nakazawa, T. Kometani, T. Sugaya, K. Mochida, S. Tomioka . A facile one-pot synthesis of vinpocetine. Synth. Commun. 1994, 24, 759.
11. 1) A New Synthetic Route to (+)-Vincaminic and (+)-Apovincaminic Esters. Arch. Pharm. 1983, 316, 629.
12. L. Szabo, J. Sapi, G. Kalaus, G. Argay, A. Kalman, E. Baitz-gacs, J. Tamas, C. Szantay . Synthesis of vinca alkaloids and related compounds-XVI: New route to the stereoselective synthesis of (+)-vincamine, (-)-vincamone and (+)-apovincaminic acid esters. Tetrahedron. 1983, 39, 3737.
13. A. Nemes, L. Czibula, G. Visky, M. Farkas, L. Kreidl . Alternative routes to vincamine. Heterocycles. 1991, 32, 2329.
14. É. A. Bendikov, L. M. Shmuilovich, V. M. Kopelevich . Effect of γ-aminobutyric acid, nicotinoyl-γ-aminobutyric acid, and its ethyl ester on central vasomotor reflex formation. Bull. Exp. Biol. Med. 1972, 73, 67.
15. V. M. Kopelevich, V. I. Gunar . Some approaches to the directed search for new drugs based on nicotinic acid. Pharm. Chem. J. 1999, 33, 177.
16. R. A. Shephard . Behavioral effects of GABA agonists in relation to anxiety and benzodiazepine action. Life Sci. 1987, 40, 2429.
17. P. Krogsgaard-Larsen, P. Lenicque, P. Jacobsen . In CRC Handbook of Stereoisomers: Drugs in Psychopharmacology; D. F. Smith, Ed.; CRC Press: Boca Raton, FL, 1984. 369.
18. M. Desarmennieni, P. Feltz, P. M. Headley, F. Santangelo . SL 75 102 AS A γ-Aminobutyric acid agonist: Experiments on Dorsal Root Ganglion Neurones in Vitro. Br. J. Pharmacol. 1981, 72, 355.
19. M. P. Remler, W. H. Marcussen . A GABA-EEG test of the blood-brain barrier near epileptic foci. Appl. Neurophysiol. 1983, 46, 276.
20. B. F. Dorofeev, L. E. Kholodov . Pikamilon pharmacokinetics in animals. Farmakologiia i toksikologiia (in Russian). 1991, 54, 66.
21. A. Gille, E. T. Bodor, K. Ahmed, S. Offermanns . Nicotinic acid: pharmacological effects and mechanisms of action. Annu. Rev. Pharmacol. Toxicol. 2008, 48, 79.
22. R. S. Mirzoian, T. S. Gan'shina . The new cerebrovascular preparation pikamilon. Farmakologiia i toksikologiia (in Russian). 1989, 52, 23.
23. K. Matsuyama, C. Yamashita, A. Noda, S. Goto, H. Noda, Y. Ichimaru, Y. Gomita . Evaluation of isonicotinoyl-gamma-aminobutyric acid (GABA) and nicotinoyl-GABA as pro-drugs of GABA. Chem. Pharm. Bull. 1984, 32, 4089.
24. I.G. Gitlin, A.I. Dorozhko, N.T. Ioffe, V.A. Serebryanyi, S.I. Fokin, A.A. Shereshevskii . Process for preparation of N-nicotinoyl-γ-aminobutyric acid by ring opening of 2-pyrrolidone and subsequent reaction with ethyl nicotinate. RU2400476C2, 2010.
25. Z.-Z. Qin, F.-B. Zhang, T.-N. Jiang, M.-J. Li, R.-X. Wang, Y.-I. Li . Synthesis and evaluation of nicotinoylamino acid compounds as radiosensitizer. Chem. Res. Chin. Univ. 2008, 24, 496.
26. A. El-Gindy, S. Emara, M. K. Mesbah, G. M. Hadad . Spectrophotometric and liquid chromatographic determination of fenofibrate and vinpocetine and their hydrolysis products. II Farmaco. 2005, 60, 425.
27. A. Abd Elbary, N. Foda, O. El-Gazayerly, M. El Khatib . Reversed Phase Liquid Chromatographic Determination of Vinpocetine In Human Plasma and Its Pharmacokinetic Application. Anal. Lett. 2002, 35, 1041.
28. H.-M. Xia, L.-N. Su, J.-W. Guo, G.-M. Liu, Z.-Q. Pang, X.-G. Jiang, J. Chen . Determination of vinpocetine and its primary metabolite, apovincaminic acid, in rat plasma by liquid chromatography-tandem mass spectrometry. J. Chromatogr. B. 2010, 878, 1959.
29. M. Vatsova, S. Tzvetanov, A. Drenska, J. Goranscheva, N. Tyutyulkova . Improved gas chromatographic-mass spectrometric method for the quantitative determination of vinpocetine in human plasma. J. Chromatogr. B Biomed. Sci. Appl. 1997, 702, 221.
30. W. Cuia, X. Chen, Y. Zhan, Z. Zhang, Y. Zhang, D. Zhong . Determination of picamilon concentration in human plasma by liquid chromatography-tandem mass spectrometry. J. Chromatogr. B. 2010, 878, 1181.
31. ICH. Validation of Analytical Procedures: Text and Methodology. ICH Harmonized Tripartite Guidelines Available at: http://www.ich.org/fileadmin/Public_Web_Site/ICH_Products/Guidelines/Quality/Q2_R1/Step4/Q2_R1__Guideline.pdf [12 August 2015]
32. H. Yin, Y.-H. Sun . Vincamine-producing endophytic fungus isolated from Vinca minor. Phytomed. 2011, 18, 802.
33. P. A. Cohen . Assessing supplement safety-the FDA's controversial proposal. New Engl. J. Med. 2012, 366, 389.
34. Food and Drug Administration. Draft Guidance for Industry: dietary supplements: new dietary ingredient notifications and related issues. Available at: http://www.fda.gov/regulatoryinformation/guidances/ucm257563.htm [3 September 2015].
35. J. Tanner . New dietary ingredient: vinpocetine. Available at: http://www.fda.gov/ohrms/dockets/dockets/95s0316/rpt0012_01.pdf [29 August 1997].
36. P. A. Cohen . Vinpocetine: an unapproved drug sold as a dietary supplement. Mayo Clin. Proc. 2015, DOI: 10.1016/j.mayocp.2015.07.008.