Terfenadine

Catalog #:

IN0046

IN0046-50mg

USD39.0

Synonyms: Terfenadine, Seldane, Triludan, Teldane

IUPAC Name:

α-[4-(1,1-Dimethylethyl)phenyl]-4-(h ydroxydiphenylmethyl)-1-piperidinebutanol

Functional Activity:

Terfenadine is an antihistamine formerly used for the treatment of allergic conditions.

Terfenadine is a prodrug, generally completely metabolised to the active form fexofenadine in the liver by the enzyme cytochrome P450 CYP3A4 isoform. Due to its near complete metabolism by the liver immediately after leaving the gut, terfenadine normally is not measurable in the plasma. Terfenadine itself, however, is cardiotoxic at higher doses while its major, active metabolite is not. Toxicity is possible after years of continued use with no previous problems as a result of an interaction with other medications such as erythromycin, or foods like grapefruit. The addition of, or dosage change in, these CYP3A4 inhibitors makes it harder for the body to metabolize and remove terfenadine. In larger plasma concentrations, terfenadine may lead to toxic effects on the heart's rhythm (e.g. ventricular tachycardia and torsades de pointes).

Technical Data:

M.Wt: 471.67

Formula: C₃₂H₄₁ NO₂

Solubility: Soluble to 100 mM in DMSO and to 25 mM in ethanol

Purity: >98%

Storage: Store at 4 degree C

CAS No.: 50679-08-8

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References for Terfenadine:

1. Chen, C., Li, G., Liao, W., Wu, J., Liu, L., Ma, D., Zhou, J., Elbekai, R. H., Edin, M. L., Zeldin, D. C., and Wang, D. W. Selective inhibitors of CYP2J2 related to terfenadine exhibit strong activity against human cancers in vitro and in vivo. J Pharmacol Exp Ther, 329: 908-918, 2009.

2. Jangi, S. M., Ruiz-Larrea, M. B., Nicolau-Galmes, F., Andollo, N., Arroyo-Berdugo, Y., Ortega-Martinez, I., Diaz-Perez, J. L., and Boyano, M. D. Terfenadine-induced apoptosis in human melanoma cells is mediated through Ca2+ homeostasis modulation and tyrosine kinase activity, independently of H1 histamine receptors. Carcinogenesis, 29: 500-509, 2008.

3. Liu, J. D., Wang, Y. J., Chen, C. H., Yu, C. F., Chen, L. C., Lin, J. K., Liang, Y. C., Lin, S. Y., and Ho, Y. S. Molecular mechanisms of G0/G1 cell-cycle arrest and apoptosis induced by terfenadine in human cancer cells. Mol Carcinog, 37: 39-50, 2003.

4. Wang, Y. J., Yu, C. F., Chen, L. C., Chen, C. H., Lin, J. K., Liang, Y. C., Lin, C. H., Lin, S. Y., Chen, C. F., and Ho, Y. S. Ketoconazole potentiates terfenadine-induced apoptosis in human Hep G2 cells through inhibition of cytochrome p450 3A4 activity. J Cell Biochem, 87: 147-159, 2002.

5. Munakata, Y., Umezawa, Y., Iwata, S., Dong, R. P., Yoshida, S., Ishii, T., and Morimoto, C. Specific inhibition of TH2-type cytokine production from human peripheral T cells by terfenadine in vitro. Clin Exp Allergy, 29: 1281-1286, 1999.

6. Kamisako, T., Adachi, Y., Nakagawa, H., and Yamamoto, T. Torsades de pointes associated with terfenadine in a case of liver cirrhosis and hepatocellular carcinoma. Intern Med, 34: 92-95, 1995.

7. Campbell, A. M., Chanez, P., Marty-Ane, C., Albat, B., Bloom, M., Michel, F. B., Godard, P., and Bousquet, J. Modulation of eicosanoid and histamine release from human dispersed lung cells by terfenadine. Allergy, 48: 125-129, 1993.

8. Hait, W. N., Gesmonde, J. F., Murren, J. R., Yang, J. M., Chen, H. X., and Reiss, M. Terfenadine (Seldane): a new drug for restoring sensitivity to multidrug resistant cancer cells. Biochem Pharmacol, 45: 401-406, 1993.

Certificate of Analysis/MSDS is available upon request with lot number