Isolation and structural characterization of two tadalafil analogs found in dietary supplements

Journal of Pharmaceutical and Biomedical Analysis

Volumn 59, Issue 1, 2012, Pages 50-57

  Toomey, Valerie M ^a   Litzau, Jonathan J ^a   Flurer, Cheryl L ^a  

^a CENTER FOR DRUG EVALUATION AND RESEARCH   (United States)

Author keywords

Dietary supplement; LC MS; NMR; PDE 5 inhibitors; Tadalafil analog

Indexed keywords

2 HYDROXYPROPYLNORTADALAFIL; BUTYLNORTADALAFIL; TADALAFIL; UNCLASSIFIED DRUG;

ARTICLE; DIET SUPPLEMENTATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL;

BENZODIOXOLES; CARBOLINES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DIETARY SUPPLEMENTS; DRUG CONTAMINATION; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; MOLECULAR STRUCTURE; PHOSPHODIESTERASE 5 INHIBITORS;

EID: 82255175543     PISSN: 07317085     EISSN: 1873264X     Source Type: Journal    
DOI: 10.1016/j.jpba.2011.09.038     Document Type: Article

References (14)

1. Tseng M.-C., Lin J.-H. Determination of sildenafil citrate adulterated in a dietary supplement capsule by LC/MS/MS. J. Food Drug Anal. 2002, 10:112-119.
2. Gratz S.R., Flurer C.L., Wolnik K.A. Analysis of undeclared synthetic phosphodiesterase-5 inhibitors in dietary supplements and herbal matrices by LC-ESI-MS and LC-UV. J. Pharm. Biomed. Anal. 2004, 36:525-533.
3. Zhu X., Xiao S., Chen B., Zhang F., Yao S., Wan Z., Yang D., Han H. Simultaneous determination of sildenafil, vardenafil and tadalafil as forbidden components in natural dietary supplements for male sexual potency by high-performance liquid chromatography-electrospray ionization mass spectrometry. J. Chromatogr. A 2005, 1066:89-95.
4. Zou P., Oh S.S.-Y., Hou P., Low M.-Y., Koh H.-L. Simultaneous determination of synthetic phosphodiesterase-5 inhibitors found in a dietary supplement and pre-mixed bulk powders for dietary supplements using high-performance liquid chromatography with diode array detection and liquid chromatography-electrospray ionization tandem mass spectrometry. J. Chromatogr. A 2006, 1104:113-122.
5. Singh S., Prasad B., Savaliya A.A., Shah R.P., Gohil V.M., Kaur A. Strategies for characterizing sildenafil, vardenafil, tadalafil and their analogues in herbal dietary supplements, and detecting counterfeit products containing these drugs. Trends Anal. Chem. 2009, 28:13-28.
6. Zou P., Hou P., Low M.-Y., Koh H.-L. Structural elucidation of a tadalafil analogue found as an adulterant of a herbal product. Food Addit. Contam. 2006, 23:446-451.
7. Gratz S.R., Gamble B.M., Flurer R.A. Accurate mass measurement using Fourier transform ion cyclotron resonance mass spectrometry for structure elucidation of designer drug analogs of tadalafil, vardenafil and sildenafil in herbal and pharmaceutical matrices, Rapid Commun. Mass Spectrom. 2006, 20:2317-2327.
8. Zou P., Hou P., Oh S.S.-Y., Low M.-Y., Koh H.-L. Electrospray tandem mass spectrometric investigations of tadalafil and its analogue. Rapid Commun. Mass Spectrom. 2006, 20:3488-3490.
9. Hasegawa T., Takahashi K., Saijo M., Ishii T., Nagata T., Kurihara M., Haishima Y., Goda Y., Kawahara N. Isolation and structural elucidation of cyclopentynafil and N-octylnortadalafil found in a dietary supplement. Chem. Pharm. Bull. 2009, 57:185-189.
10. Hasegawa T., Saijo M., Ishii T., Nagata T., Haishima Y., Kawahara N., Goda Y. Structural elucidation of a tadalafil analogue found in a dietary supplement. J. Food Hyg. Soc. Jpn. 2008, 49:311-315.
11. Daugan A., Grondin P., Ruault C., Le Monnier de Gouville A.-C., Coste H., Linget J.M., Kirilovsky J., Hyafil F., Labaudinière R. The discovery of tadalafil: a novel and highly selective PDE5 inhibitor. 2: 2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione analogues. J. Med. Chem. 2003, 46:4533-4542.
12. Beghyn T., Hounsou C., Deprez B.P. PDE5 inhibitors: an original access to novel potent arylated analogues of tadalafil. Bioorg. Med. Chem. Lett. 2007, 17:789-792.
13. Shi X.-X., Liu S.-L., Xu W., Xu Y.-L. Highly stereoselective Pictet-Spengler reaction of d-tryptophan methyl ester with piperonal: convenient syntheses of Cialis (tadalafil), 12a-epi-Cialis, and their deuterated analogues. Tetrahedron: Asymmetry 2008, 19:435-442.
14. Häberli A., Girard P., Low M.-Y., Ge X. Isolation and structure elucidation of an interaction product of aminotadalafil found in an illegal health food product. J. Pharm. Biomed. Anal. 2010, 53:24-28.