Synonyms: Terfenadine, Seldane, Triludan, Teldane

structure

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

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

References for Quintine:

1. Kosior, D. A., Kochanowski, J., Scislo, P., Piatkowski, R., Postula, M., Rabczenko, D., and Opolski, G. Efficacy and tolerability of oral propafenone versus quinidine in the treatment of recent onset atrial fibrillation: A randomized, prospective study. Cardiol J, 16: 521-527, 2009.

2. Daubert, J. P. Is newer better? Propafenone versus quinidine for conversion of atrial fibrillation. Cardiol J, 16: 491-492, 2009.

3. Izuwa, Y., Kusaba, J., Horiuchi, M., Aiba, T., Kawasaki, H., and Kurosaki, Y. Comparative study of increased plasma quinidine concentration in rats with glycerol- and cisplatin-induced acute renal failure. Drug Metab Pharmacokinet, 24: 451-457, 2009.

4. Haiman, G., Pratt, H., and Miller, A. Effects of dextromethorphan/quinidine on auditory event-related potentials in multiple sclerosis patients with pseudobulbar affect. J Clin Psychopharmacol, 29: 444-452, 2009.

5. Baruteau, A. E., Mabo, P., and Probst, V. Quinidine therapy in children affected by Brugada syndrome: are we far from a safe alternative? Cardiol Young, 19: 652-654, 2009.

6. Barrows, B., Cheung, K., Bialobrzeski, T., Foster, J., Schulze, J., and Miller, A. Extracellular potassium dependency of block of HERG by quinidine and cisapride is primarily determined by the permeant ion and not by inactivation. Channels (Austin), 3: 239-248, 2009.

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

References for Quercetin:

1. Yu, Z. J., He, L. Y., Chen, Y., Wu, M. Y., Zhao, X. H., and Wang, Z. Y. [Effects of quercetin on the expression of VEGF-C and VEGFR-3 in human cancer MGC-803 cells]. Xi Bao Yu Fen Zi Mian Yi Xue Za Zhi, 25: 678-680, 2009.

2. Seufi, A. M., Ibrahim, S. S., Elmaghraby, T. K., and Hafez, E. E. Preventive effect of the flavonoid, quercetin, on hepatic cancer in rats via oxidant/antioxidant activity: molecular and histological evidences. J Exp Clin Cancer Res, 28: 80, 2009.

3. Shan, B. E., Wang, M. X., and Li, R. Q. Quercetin inhibit human SW480 colon cancer growth in association with inhibition of cyclin D1 and survivin expression through Wnt/beta-catenin signaling pathway. Cancer Invest, 27: 604-612, 2009.

4. Jagtap, S., Meganathan, K., Wagh, V., Winkler, J., Hescheler, J., and Sachinidis, A. Chemoprotective mechanism of the natural compounds, epigallocatechin-3-O-gallate, quercetin and curcumin against cancer and cardiovascular diseases. Curr Med Chem, 16: 1451-1462, 2009.

5. Xavier, C. P., Lima, C. F., Preto, A., Seruca, R., Fernandes-Ferreira, M., and Pereira-Wilson, C. Luteolin, quercetin and ursolic acid are potent inhibitors of proliferation and inducers of apoptosis in both KRAS and BRAF mutated human colorectal cancer cells. Cancer Lett, 281: 162-170, 2009.

6. Lee, Y. K., Park, S. Y., Kim, Y. M., Lee, W. S., and Park, O. J. AMP kinase/cyclooxygenase-2 pathway regulates proliferation and apoptosis of cancer cells treated with quercetin. Exp Mol Med, 41: 201-207, 2009.

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

References for Omeprazole:

1. Freeman, K. L. and Trezevant, M. S. Interaction between liquid protein solution and omeprazole suspension. Am J Health Syst Pharm, 66: 1901-1902, 2009.

2. Fang, H. M., Xu, J. M., Mei, Q., Diao, L., Chen, M. L., Jin, J., and Xu, X. H. Involvement of cytochrome P450 3A4 and P-glycoprotein in first-pass intestinal extraction of omeprazole in rabbits. Acta Pharmacol Sin, 30: 1566-1572, 2009.

3. Haffey, M. B., Buckwalter, M., Zhang, P., Homolka, R., Martin, P., Lasseter, K. C., and Ermer, J. C. Effects of omeprazole on the pharmacokinetic profiles of lisdexamfetamine dimesylate and extended-release mixed amphetamine salts in adults. Postgrad Med, 121: 11-19, 2009.

4. Panti, A., Bennett, R. C., Corletto, F., Brearley, J., Jeffery, N., and Mellanby, R. J. The effect of omeprazole on oesophageal pH in dogs during anaesthesia. J Small Anim Pract, 50: 540-544, 2009.

5. Cuisset, T., Frere, C., Quilici, J., Poyet, R., Gaborit, B., Bali, L., Brissy, O., Morange, P. E., Alessi, M. C., and Bonnet, J. L. Comparison of omeprazole and pantoprazole influence on a high 150-mg clopidogrel maintenance dose the PACA (Proton Pump Inhibitors And Clopidogrel Association) prospective randomized study. J Am Coll Cardiol, 54: 1149-1153, 2009.

6. Van Der Straeten, F., Al-Afandi, A., De Paepe, K., Bovy, J., and Plaizier-Vercammen, J. [Pharmacy compounding of an omeprazole suspension]. J Pharm Belg: 54-63, 2009.

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

References for Diltiazem:

1. Sultana, Y., Mall, S., Maurya, D. P., Kumar, D., and Das, M. Preparation and in vitro characterization of diltiazem hydrochloride loaded alginate microspheres. Pharm Dev Technol, 14: 321-331, 2009.

2. Demir, M., Ozaydin, M., Varol, E., Dogan, A., and Altinbas, A. Effects of metoprolol and diltiazem on plasma homocysteine levels in patients with isolated coronary artery ectasia. Anadolu Kardiyol Derg, 9: 69-70, 2009.

3. Ezeugo, U. and Glasser, S. P. Clinical benefits versus shortcomings of diltiazem once-daily in the chronotherapy of cardiovascular diseases. Expert Opin Pharmacother, 10: 485-491, 2009.

4. Rigat, B. and Mahuran, D. Diltiazem, a L-type Ca(2+) channel blocker, also acts as a pharmacological chaperone in Gaucher patient cells. Mol Genet Metab, 96: 225-232, 2009.

5. Matsumura, C. Y., Pertille, A., Albuquerque, T. C., Santo Neto, H., and Marques, M. J. Diltiazem and verapamil protect dystrophin-deficient muscle fibers of MDX mice from degeneration: a potential role in calcium buffering and sarcolemmal stability. Muscle Nerve, 39: 167-176, 2009.

6. Bertera, F. M., Mayer, M. A., Opezzo, J. A., Taira, C. A., and Hocht, C. Increased sensitivity to diltiazem hypotensive effect in an experimental model of high-renin hypertension. J Pharm Pharmacol, 61: 79-87, 2009.

7. Bojanic, V., Bojanic, Z., Najman, S., Savic, T., Jakovljevic, V., Najman, S., and Jancic, S. Diltiazem prevention of toxic effects of monosodium glutamate on ovaries in rats. Gen Physiol Biophys, 28 Spec No: 149-154, 2009.

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

References for Clotrimazole :

1. Parmar, P. and Mehta, A. Development and Validation of HPTLC Method for the Estimation of Clotrimazole in Bulk drug and Tablet Formulation. Indian J Pharm Sci, 71: 451-454, 2009.

2. Harish, N. M., Prabhu, P., Charyulu, R. N., Gulzar, M. A., and Subrahmanyam, E. V. Formulation and Evaluation of in situ Gels Containing Clotrimazole for Oral Candidiasis. Indian J Pharm Sci, 71: 421-427, 2009.

3. Sholapurkar, A. A., Pai, K. M., and Rao, S. Comparison of efficacy of fluconazole mouthrinse and clotrimazole mouthpaint in the treatment of oral candidiasis. Aust Dent J, 54: 341-346, 2009.

4. Iannelli, A., de Sousa, G., Zucchini, N., Peyre, L., Gugenheim, J., and Rahmani, R. Clotrimazole protects the liver against normothermic ischemia-reperfusion injury in rats. Transplant Proc, 41: 4099-4104, 2009.

5. Furrow, E. and Groman, R. P. Intranasal infusion of clotrimazole for the treatment of nasal aspergillosis in two cats. J Am Vet Med Assoc, 235: 1188-1193, 2009.

6. Rasouli, M. R., Rahimi-Movaghar, V., and Vaccaro, A. R. Re: Usul H, Arslan E, Cansever T, et al. Effects of clotrimazole on experimental spinal cord ischemia/reperfusion injury in rats. Spine 2008;33:2863-7. Spine (Phila Pa 1976), 34: 1884, 2009.

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

References for 8-Phenyltheophylline:

1. Murray, S., Odupitan, A. O., Murray, B. P., Boobis, A. R., and Edwards, R. J. Inhibition of human CYP1A2 activity in vitro by methylxanthines: potent competitive inhibition by 8-phenyltheophylline. Xenobiotica, 31: 135-151, 2001.

2. Lee, S. C., Mallet, R. T., Shizukuda, Y., Williams, A. G., Jr., and Downey, H. F. Canine coronary vasodepressor responses to hypoxia are attenuated but not abolished by 8-phenyltheophylline. Am J Physiol, 262: H955-960, 1992.

3. Sawynok, J., Espey, M. J., and Reid, A. 8-Phenyltheophylline reverses the antinociceptive action of morphine in the periaqueductal gray. Neuropharmacology, 30: 871-877, 1991.

4. Wei, H. M., Kang, Y. H., and Merrill, G. F. Canine coronary vasodepressor responses to hypoxia are abolished by 8-phenyltheophylline. Am J Physiol, 257: H1043-1048, 1989.

5. Wormald, A., Bowmer, C. J., Yates, M. S., and Collis, M. G. Pharmacokinetics of 8-phenyltheophylline in the rat. J Pharm Pharmacol, 41: 418-420, 1989.

6. Nicholson, C. D. and Wilke, R. 8-phenyltheophylline as an inhibitor of cyclic AMP hydrolysis by cyclic nucleotide phosphodiesterase. J Auton Pharmacol, 9: 159-165, 1989.

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

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