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Chemical Compound Review

AC1NURIX     1-[(S)-phenyl-(4- phenylphenyl)methyl]imida...

Synonyms: SureCN1551534, NCGC00018254-01, NCGC00018254-06, 1-[PHENYL-(4-PHENYLPHENYL)-METHYL]IMIDAZOLE
 
 
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Disease relevance of bifonazole

 

Psychiatry related information on bifonazole

  • Compared with the majority of topical antifungal drugs, which need to be applied at least twice daily, bifonazole offers the convenience of once daily administration, which may improve patient compliance [2].
 

High impact information on bifonazole

 

Chemical compound and disease context of bifonazole

 

Biological context of bifonazole

 

Anatomical context of bifonazole

 

Associations of bifonazole with other chemical compounds

 

Gene context of bifonazole

  • Reliability and reproducibility of the method was checked by analyzing laboratory mixtures of bifonazole and preservatives (recovery 99.97-102.7%; RDS 0.48-1.46%) [25].
  • The additional fungicidal effects of bifonazole are considered to originate from a sequential action by inhibition of HMG-CoA-reductase and of cytochrome P450 [26].
  • By this, in contrast to clotrimazole, bifonazole possesses a sequential mode of action, namely inhibition of cytochrome P450-dependent C14-demethylation of sterols and direct inhibition of HMG-CoA-reductase [13].
  • The decrease of the cooperativity at the gel to liquid crystalline phase transition, as shown by ESR an DSC measurements, indicates that bifonazole imparts higher fluidity to the lipid matrix [27].
  • We therefore verified the clinical efficacy of 1% bifonazole cream on 15 subjects with SD of the face, 9 of whom were affected with lymphadenopathy syndrome/AIDS-related complex (LAS/ARC) [28].
 

Analytical, diagnostic and therapeutic context of bifonazole

  • Gas chromatographic-mass spectrometric determination of two new antimycotic agents, 1-[(5-chloro-2-benzofuranyl)(2-chlorophenyl)methyl]-1H-imidazole and 1-[(5-bromo-2-benzofuranyl)phenylmethyl]-1H-imidazole, in rabbit plasma following topical administration: a preliminary comparison with bifonazole [12].
  • Treatment with bifonazole shampoo for seborrhea and seborrheic dermatitis: a randomized, double-blind study [29].
  • No side-reactions were observed in any patient, and patch tests carried out in selected patients with known allergy and those with normal skin showed no evidence of any allergic or photosensitivity reaction to bifonazole [30].
  • The aim of this research was to develop and validate a sensitive, rapid, easy, and precise reversed-phase liquid chromatography (LC) method for stability studies of bifonazole (I) formulated with tinctures of calendula flower (II) [31].
  • Western blot analyses demonstrated that bifonazole also induced P4502B1/2B2, P4503A and P4501A1, but not P4502E1 [32].

References

  1. Topical treatment with butenafine significantly lowers relapse rate in an interdigital tinea pedis model in guinea pigs. Arika, T., Yokoo, M., Yamaguchi, H. Antimicrob. Agents Chemother. (1992) [Pubmed]
  2. Bifonazole. A review of its antimicrobial activity and therapeutic use in superficial mycoses. Lackner, T.E., Clissold, S.P. Drugs (1989) [Pubmed]
  3. Clotrimazole and bifonazole detach hexokinase from mitochondria of melanoma cells. Penso, J., Beitner, R. Eur. J. Pharmacol. (1998) [Pubmed]
  4. Structure of microsomal cytochrome P450 2B4 complexed with the antifungal drug bifonazole: insight into P450 conformational plasticity and membrane interaction. Zhao, Y., White, M.A., Muralidhara, B.K., Sun, L., Halpert, J.R., Stout, C.D. J. Biol. Chem. (2006) [Pubmed]
  5. Antifungal agents. 11. N-substituted derivatives of 1-[(aryl)(4-aryl-1H-pyrrol-3-yl)methyl]-1H-imidazole: synthesis, anti-Candida activity, and QSAR studies. Di Santo, R., Tafi, A., Costi, R., Botta, M., Artico, M., Corelli, F., Forte, M., Caporuscio, F., Angiolella, L., Palamara, A.T. J. Med. Chem. (2005) [Pubmed]
  6. Effect of cytochrome P-450 inhibitors econazole, bifonazole and clotrimazole on prostanoid formation. Köfeler, H.C., Fauler, G., Windischhofer, W., Leis, H.J. Br. J. Pharmacol. (2000) [Pubmed]
  7. Treatment of tinea palmaris with Mycospor. Meisel, C. Dermatologica (1984) [Pubmed]
  8. A comparative study of once daily bifonazole cream versus twice daily miconazole cream in the treatment of tinea pedis. Roberts, D.T., Adriaans, B., Gentles, J.C. Mykosen. (1985) [Pubmed]
  9. Terbinafine 1% cream vs. bifonazole 1% cream in the treatment of tinea cruris. Budimulja, U. International journal of dermatology. (1998) [Pubmed]
  10. A comparative clinical study between 2 weeks of luliconazole 1% cream treatment and 4 weeks of bifonazole 1% cream treatment for tinea pedis. Watanabe, S., Takahashi, H., Nishikawa, T., Takiuchi, I., Higashi, N., Nishimoto, K., Kagawa, S., Yamaguchi, H., Ogawa, H. Mycoses (2006) [Pubmed]
  11. Efficacy of flutrimazole 1% powder in the treatment of tinea pedis. Pereda, J., Noguera, X., Boncompte, E., Algueró, M., Izquierdo, I. Mycoses (2003) [Pubmed]
  12. Gas chromatographic-mass spectrometric determination of two new antimycotic agents, 1-[(5-chloro-2-benzofuranyl)(2-chlorophenyl)methyl]-1H-imidazole and 1-[(5-bromo-2-benzofuranyl)phenylmethyl]-1H-imidazole, in rabbit plasma following topical administration: a preliminary comparison with bifonazole. Triolo, A., Mannucci, C., Perico, A. J. Chromatogr. (1991) [Pubmed]
  13. Bifonazole, a biochemist's view. Berg, D., Plempel, M. Dermatologica (1984) [Pubmed]
  14. The toxicology of bifonazole. Schlüter, G. Arzneimittel-Forschung. (1983) [Pubmed]
  15. Mechanism of bifonazole-induced [Ca2+]i increases in MDCK renal tubular cells. Cho, K.J., Su, W., Chen, W.C., Law, Y.P., Fang, H.C., Liu, C.P., Cheng, J.S., Lee, K.C., Lo, Y.K., Chang, H.T., Huang, J.K., Jan, C.R. The Chinese journal of physiology. (2001) [Pubmed]
  16. Diverse mechanisms of calcium mobilization by peroxisome proliferators in rat hepatocytes. Shackleton, G.L., Gibson, G.G., Sharma, R.K., Howes, D., Orrenius, S., Kass, G.E. Toxicol. Appl. Pharmacol. (1995) [Pubmed]
  17. Induction of hepatic peroxisomes by a new, non-carboxylate-containing drug, bifonazole. Horie, S., Fukumori, N., Suga, T. Toxicol. Lett. (1991) [Pubmed]
  18. Effects of the newer antifungal agents (bifonazole, ICI 195, 739 and amorolfin) on in vitro phagocytic, lymphocytic and natural-killer cell responses. Vuddhakul, V., McCormack, J.G., Seow, W.K., Thong, Y.H. Int. J. Immunopharmacol. (1989) [Pubmed]
  19. Lack of antiandrogenic effects of topical bifonazole on sebaceous glands and hairs in the hamster flank organ. Aricò, M., Noto, G., Pravatà, G., Bongiorno, M.R. Skin Pharmacol. (1993) [Pubmed]
  20. In-vitro antifungal activity of sertaconazole, bifonazole, ketoconazole, and miconazole against yeasts of the Candida genus. Carrilo-Muñoz, A.J., Tur, C., Torres, J. J. Antimicrob. Chemother. (1996) [Pubmed]
  21. Selective calmodulin antagonists fail to inhibit phorbol ester-induced superoxide anion release from human neutrophils: effects of antifungal azole derivatives. Hegemann, L., Webster, G.F., Wolff, K. Br. J. Dermatol. (1996) [Pubmed]
  22. Investigation of the role of cytochrome P450 2B4 active site residues in substrate metabolism based on crystal structures of the ligand-bound enzyme. Hernandez, C.E., Kumar, S., Liu, H., Halpert, J.R. Arch. Biochem. Biophys. (2006) [Pubmed]
  23. A novel method using micropig stratum corneum in vitro for the evaluation of anti-Trichophyton mentagrophytes activity. Nakashima, T., Nozawa, A., Majima, T. Microbiol. Immunol. (2002) [Pubmed]
  24. Bifonazole (Mycospor cream) in the treatment of moccasin-type tinea pedis. Comparison between combination therapy of bifonazole cream + 10% urea ointment (Urepearl) and occlusive dressing therapy with the same agents. Tanuma, H., Doi, M., Sato, N., Nishiyama, S., Abe, M., Kume, H., Katsuoka, K. Mycoses (2000) [Pubmed]
  25. Determination of bifonazole in creams containing methyl- and propyl p-hydroxybenzoate by derivative spectrophotometric method. Popović, G., Cakar, M., Agbaba, D. Journal of pharmaceutical and biomedical analysis. (2003) [Pubmed]
  26. Bifonazole and clotrimazole. Their mode of action and the possible reason for the fungicidal behaviour of bifonazole. Berg, D., Regel, E., Harenberg, H.E., Plempel, M. Arzneimittel-Forschung. (1984) [Pubmed]
  27. Membrane fluidization by animycotic bifonazole. Albertini, G., Bossi, G., Dubini, B., Phadke, R.S., Ponzi Bossi, M.G., Pugnaloni, A., Srivastava, S. Physiological chemistry and physics and medical NMR. (1995) [Pubmed]
  28. Seborrheic dermatitis in otherwise healthy patients and in patients with lymphadenopathy syndrome/AIDS-related complex: treatment with 1% bifonazole cream. Massone, L., Borghi, S., Pestarino, A., Piccini, R., Solari, G., Casini Lemmi, M., Isola, V. Chemioterapia : international journal of the Mediterranean Society of Chemotherapy. (1988) [Pubmed]
  29. Treatment with bifonazole shampoo for seborrhea and seborrheic dermatitis: a randomized, double-blind study. Segal, R., David, M., Ingber, A., Lurie, R., Sandbank, M. Acta Derm. Venereol. (1992) [Pubmed]
  30. Bifonazole in the treatment of fungal skin infections in the tropics: a clinical and mycological study. Soyinka, F. Current medical research and opinion. (1987) [Pubmed]
  31. Simultaneous determination of bifonazole and tinctures of calendula flower in pharmaceutical creams by reversed-phase liquid chromatography. Ferreyra, C.F., Ortiz, C.S. Journal of AOAC International. (2005) [Pubmed]
  32. Bifonazole, but not the structurally-related clotrimazole, induces both peroxisome proliferation and members of the cytochrome P4504A sub-family in rat liver. Sabzevari, O., Hatcher, M., Kentish, P., O'Sullivan, M., Gibson, G.G. Toxicology (1996) [Pubmed]
 
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