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    J Pharm Biomed Anal. 2010 Feb 5;51(3):723-7. Epub 2009 Aug 14.

    The identification of (-)-trans-tadalafil, tadalafil, and sildenafil in counterfeit Cialis and the optical purity of tadalafil stereoisomers.

    Source

    National Institute for Public Health and the Environment, Postbox 1, 3721MA Bilthoven, The Netherlands. venhuisb@rivm.nl

    Abstract

    Four blisters with suspect Cialis (tadalafil) 20mg tablets were screened for authenticity using near infrared spectroscopy (NIRS) and for the presence of phosphodiesterase 5 (PDE-5) inhibitors using LC-DAD-MS. All samples were identified as counterfeit Cialis and contained sildenafil or a combination of tadalafil and sildenafil. Although the tablets contained efficacious amounts of PDE-5 inhibitors, neither the active ingredient nor the dosage corresponded to the description on the blister. This is the first reported case of a diastereomeric mixture of tadalafil and trans-tadalafil (3:1) being identified in a counterfeit medicine. The LC-DAD-CD revealed that both diastereomers had a high optical purity. The optical rotation of the diastereomeric mixture was measured indicating the presence of (-)-trans-tadalafil, which is the only other stereoisomer with some PDE-5 inhibitory activity. As no safety profiles are known for the stereoisomers of tadalafil, there is a potential health risk. In addition, the optical purity of tadalafil needs to be taken into account when calculating the dosage in illegal medicines.

    PMID:
    19782492
    [PubMed - indexed for MEDLINE]

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