Conazoles

This review provides a historical overview of the analog based drug discovery of miconazole and its congeners, and is focused on marketed azole antifungals bearing the generic suffix “conazole”. The antifungal activity of miconazole, one of the first broad-spectrum antimycotic agents has been mainly restricted to topical applications. The attractive in vitro antifungal spectrum was a starting point to design more potent and especially orally active antifungal agents such as ketoconazole, itraconazole, posaconazole, fluconazole and voriconazole. The chemistry, in vitro and in vivo antifungal activity, pharmacology, and clinical applications of these marketed conazoles has been described.

[1]  R. N. Brogden,et al.  Econazole: A Review of its Antifungal Activity and Therapeutic Efficacy , 2012, Drugs.

[2]  R. N. Brogden,et al.  Miconazole: A Preliminary Review of its Therapeutic Efficacy in Systemic Fungal Infections , 2012, Drugs.

[3]  L. Goldani,et al.  Novel triazole antifungal drugs: focus on isavuconazole, ravuconazole and albaconazole. , 2010, Current opinion in investigational drugs.

[4]  M. Pfaller,et al.  Epidemiology of Invasive Mycoses in North America , 2010, Critical reviews in microbiology.

[5]  S. Krishnan-Natesan.  Terbinafine: a pharmacological and clinical review , 2009, Expert opinion on pharmacotherapy.

[6]  C. Girmenia.  New generation azole antifungals in clinical investigation , 2009, Expert opinion on investigational drugs.

[7]  J. Kosterink,et al.  Clinical relevance of the pharmacokinetic interactions of azole antifungal drugs with other coadministered agents. , 2009, Clinical infectious diseases : an official publication of the Infectious Diseases Society of America.

[8]  Ana Espinel-Ingroff,et al.  Antifungal drug resistance mechanisms , 2009, Expert review of anti-infective therapy.

[9]  A. Goffeau,et al.  Efflux-Mediated Antifungal Drug Resistance , 2009, Clinical Microbiology Reviews.

[10]  J. Guinea,et al.  Isavuconazole: a new and promising antifungal triazole for the treatment of invasive fungal infections. , 2008, Future microbiology.

[11]  N. Scheinfeld,et al.  Pramiconazole, a triazole compound for the treatment of fungal infections. , 2008, IDrugs : the investigational drugs journal.

[12]  H. Lipp.  Antifungal agents – clinical pharmacokinetics and drug interactions , 2008, Mycoses.

[13]  C. Lass‐Flörl,et al.  Changing epidemiology of systemic fungal infections. , 2008, Clinical microbiology and infection : the official publication of the European Society of Clinical Microbiology and Infectious Diseases.

[14]  H. Hof.  Is there a serious risk of resistance development to azoles among fungi due to the widespread use and long-term application of azole antifungals in medicine? , 2008, Drug resistance updates : reviews and commentaries in antimicrobial and anticancer chemotherapy.

[15]  S. Deresinski,et al.  Reviews of anti-infective agents: posaconazole: a broad-spectrum triazole antifungal agent. , 2007, Clinical infectious diseases : an official publication of the Infectious Diseases Society of America.

[16]  P. Gubbins.  Mould-active azoles: pharmacokinetics, drug interactions in neutropenic patients , 2007, Current opinion in infectious diseases.

[17]  Daryl S Schiller,et al.  Posaconazole: an extended-spectrum triazole antifungal agent. , 2007, Clinical therapeutics.

[18]  D. Stevens,et al.  Posaconazole therapy for chronic refractory coccidioidomycosis. , 2007, Chest.

[19]  O. Lortholary,et al.  Simultaneous quantification of voriconazole and posaconazole in human plasma by high-performance liquid chromatography with ultra-violet detection. , 2007, Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.

[20]  B. Elewski,et al.  Advances in topical and systemic antifungals. , 2007, Dermatologic clinics.

[21]  J. Perfect,et al.  Treatment of invasive aspergillosis with posaconazole in patients who are refractory to or intolerant of conventional therapy: an externally controlled trial. , 2007, Clinical infectious diseases : an official publication of the Infectious Diseases Society of America.

[22]  H. Hof,et al.  A new, broad‐spectrum azole antifungal: posaconazole – mechanisms of action and resistance, spectrum of activity , 2006, Mycoses.

[23]  F. Odds.  Drug evaluation: BAL-8557--a novel broad-spectrum triazole antifungal. , 2006, Current opinion in investigational drugs.

[24]  N. Brown,et al.  Invasive fungal infections: a review of epidemiology and management options. , 2006, Journal of medical microbiology.

[25]  J. Perfect,et al.  Safety of long-term oral posaconazole use in the treatment of refractory invasive fungal infections. , 2006, Clinical infectious diseases : an official publication of the Infectious Diseases Society of America.

[26]  E. Mylonakis,et al.  Newer triazole antifungal agents: pharmacology, spectrum, clinical efficacy and limitations , 2006, Expert opinion on investigational drugs.

[27]  M. Akova,et al.  Treatment of invasive infections due to rare or emerging yeasts and moulds , 2006, Expert opinion on pharmacotherapy.

[28]  G. Krishna,et al.  Effect of a Nutritional Supplement on Posaconazole Pharmacokinetics following Oral Administration to Healthy Volunteers , 2006, Antimicrobial Agents and Chemotherapy.

[29]  J. Perfect,et al.  Emerging echinocandins for treatment of invasive fungal infections , 2006, Expert opinion on emerging drugs.

[30]  W. L. Nelson,et al.  STEREOCHEMICAL ASPECTS OF ITRACONAZOLE METABOLISM IN VITRO AND IN VIVO , 2006, Drug Metabolism and Disposition.

[31]  D. Denning,et al.  In vitro activity of a new triazole BAL4815, the active component of BAL8557 (the water-soluble prodrug), against Aspergillus spp. , 2006, The Journal of antimicrobial chemotherapy.

[32]  C. K. Skokos,et al.  An evaluation of butoconazole nitrate 2% site release vaginal cream (Gynazole-1) compared to fluconazole 150 mg tablets (Diflucan) in the time to relief of symptoms in patients with vulvovaginal candidiasis. , 2005, Infectious diseases in obstetrics and gynecology.

[33]  G. Quindós,et al.  Sertaconazole: updated review of a topical antifungal agent , 2005, Expert review of anti-infective therapy.

[34]  M. Ruhnke,et al.  Voriconazole: review of a broad spectrum triazole antifungal agent , 2005, Expert opinion on pharmacotherapy.

[35]  J. Heeres,et al.  Synthesis and in vitro and in vivo structure-activity relationships of novel antifungal triazoles for dermatology. , 2005, Journal of medicinal chemistry.

[36]  F. D. D'Auria,et al.  Antifungal activity of ketoconazole and other azoles againstMalassezia furfur in vitro andin vivo , 1997, Infection.

[37]  J. Heeres,et al.  Ketoconazole — a new broad spectrum orally active antimycotic , 1979, Experientia.

[38]  I. Paulsen,et al.  The ergosterol biosynthesis pathway, transporter genes, and azole resistance in Aspergillus fumigatus. , 2005, Medical mycology.

[39]  L. Meerpoel,et al.  The Novel Azole R126638 Is a Selective Inhibitor of Ergosterol Synthesis in Candida albicans, Trichophyton spp., and Microsporum canis , 2004, Antimicrobial Agents and Chemotherapy.

[40]  J. Heeres,et al.  In Vitro and In Vivo Activities of the Novel Azole Antifungal Agent R126638 , 2004, Antimicrobial Agents and Chemotherapy.

[41]  A. Ventosa,et al.  In vitro activity of cloconazole, sulconazole, butoconazole, isoconazole, fenticonazole, and five other antifungal agents against clinical isolates of Candida albicans and Candida spp. , 1992, Mycopathologia.

[42]  W. Beggs.  Rapid fungicidal action of tioconazole and miconazole , 1987, Mycopathologia.

[43]  V. Schuermans,et al.  Systemic antifungal potential, safety, biotransport and transformation of micronazole nitrate , 1972, European Journal of Clinical Pharmacology.

[44]  M. Pfaller,et al.  In vitro activity of a new triazole antifungal agent, Sch 56592, against clinical isolates of filamentous fungi , 2004, Mycopathologia.

[45]  P. Lewi,et al.  Pharmacokinetic profile of intravenous miconazole in man , 2004, European Journal of Clinical Pharmacology.

[46]  B. Dupont.  Nouveaux antifongiques : voriconazole et caspofungine , 2003 .

[47]  D. Bonner,et al.  In vitro activity of ravuconazole against Zygomycetes, Scedosporium and Fusarium isolates. , 2003, Clinical microbiology and infection : the official publication of the European Society of Clinical Microbiology and Infectious Diseases.

[48]  M. Nucci.  Emerging moulds: Fusarium, Scedosporium and Zygomycetes in transplant recipients , 2003, Current opinion in infectious diseases.

[49]  A. Johnston,et al.  The pharmacokinetics of voriconazole. , 2003, British journal of clinical pharmacology.

[50]  D. Denning.  Echinocandin antifungal drugs , 2003, The Lancet.

[51]  David W Bates,et al.  Clinical impact of drug-drug interactions with systemic azole antifungals. , 2003, Drugs of today.

[52]  A. Grooters,et al.  Update on antifungal therapy. , 2003, The Veterinary clinics of North America. Small animal practice.

[53]  Dominique Sanglard,et al.  Resistance of human fungal pathogens to antifungal drugs. , 2002, Current opinion in microbiology.

[54]  E. Wang,et al.  Interaction of Common Azole Antifungals with P Glycoprotein , 2002, Antimicrobial Agents and Chemotherapy.

[55]  A. Offidani,et al.  In Vitro Activity of Posaconazole against Clinical Isolates of Dermatophytes , 2001, Journal of Clinical Microbiology.

[56]  E. Manavathu,et al.  Isolation and in vitro susceptibility to amphotericin B, itraconazole and posaconazole of voriconazole-resistant laboratory isolates of Aspergillus fumigatus. , 2001, Clinical microbiology and infection : the official publication of the European Society of Clinical Microbiology and Infectious Diseases.

[57]  F. Odds.  Sordarin antifungal agents , 2001 .

[58]  A. Pettman,et al.  Process Development of Voriconazole: A Novel Broad-Spectrum Triazole Antifungal Agent , 2001 .

[59]  D. Loebenberg,et al.  Comparison of a New Triazole, Posaconazole, with Itraconazole and Amphotericin B for Treatment of Histoplasmosis following Pulmonary Challenge in Immunocompromised Mice , 2000, Antimicrobial Agents and Chemotherapy.

[60]  J. Graybill.  Changing strategies for treatment of systemic mycoses. , 2000, The Brazilian journal of infectious diseases : an official publication of the Brazilian Society of Infectious Diseases.

[61]  T J Walsh,et al.  New drugs and novel targets for treatment of invasive fungal infections in patients with cancer. , 2000, The oncologist.

[62]  M. Klepser,et al.  Novel triazole antifungal agents , 2000, Expert opinion on investigational drugs.

[63]  D. Loebenberg,et al.  Pharmacokinetics of SCH 56592, a New Azole Broad-Spectrum Antifungal Agent, in Mice, Rats, Rabbits, Dogs, and Cynomolgus Monkeys , 2000, Antimicrobial Agents and Chemotherapy.

[64]  P. Nyirjesy,et al.  Terconazole cream for non-Candida albicans fungal vaginitis: results of a retrospective analysis. , 2000, Infectious diseases in obstetrics and gynecology.

[65]  L. Koymans,et al.  Contribution of mutations in the cytochrome P450 14alpha-demethylase (Erg11p, Cyp51p) to azole resistance in Candida albicans. , 1999, Microbiology.

[66]  V. Kulkarni,et al.  Three‐Dimensional Quantitative Structure—Activity Relationship (QSAR) and Receptor Mapping of Cytochrome P‐45014αDM Inhibiting Azole Antifungal Agents. , 1999 .

[67]  J. M. Torres-Rodríguez,et al.  In Vitro Susceptibilities of Clinical Yeast Isolates to the New Antifungal Eberconazole Compared with Their Susceptibilities to Clotrimazole and Ketoconazole , 1999, Antimicrobial Agents and Chemotherapy.

[68]  E. Anaissie,et al.  Treatment of Murine Fusariosis with SCH 56592 , 1999, Antimicrobial Agents and Chemotherapy.

[69]  D. Loebenberg,et al.  Comparison of a New Triazole Antifungal Agent, Schering 56592, with Itraconazole and Amphotericin B for Treatment of Histoplasmosis in Immunocompetent Mice , 1999, Antimicrobial Agents and Chemotherapy.

[70]  M H Tarbit,et al.  Molecular modelling of lanosterol 14 alpha-demethylase (CYP51) from Saccharomyces cerevisiae via homology with CYP102, a unique bacterial cytochrome P450 isoform: quantitative structure-activity relationships (QSARs) within two related series of antifungal azole derivatives. , 1999, Journal of enzyme inhibition.

[71]  D. Loebenberg,et al.  SCH56592 treatment of murine invasive aspergillosis. , 1998, The Journal of antimicrobial chemotherapy.

[72]  C. Y. Yu,et al.  Voriconazole against fluconazole-susceptible and resistant candida isolates: in-vitro efficacy compared with that of itraconazole and ketoconazole. , 1998, The Journal of antimicrobial chemotherapy.

[73]  J Ramis,et al.  New azole antifungals. 2. Synthesis and antifungal activity of heterocyclecarboxamide derivatives of 3-amino-2-aryl-1-azolyl-2-butanol. , 1998, Journal of medicinal chemistry.

[74]  V. Kulkarni,et al.  Docking analysis of a series of cytochrome P-450(14) alpha DM inhibiting azole antifungals. , 1998, Drug design and discovery.

[75]  J Ramis,et al.  New azole antifungals. 3. Synthesis and antifungal activity of 3-substituted-4(3H)-quinazolinones. , 1998, Journal of medicinal chemistry.

[76]  F. Odds.  Should resistance to azole antifungals in vitro be interpreted as predicting clinical non-response? , 1998, Drug resistance updates : reviews and commentaries in antimicrobial and anticancer chemotherapy.

[77]  M. H. Nguyen,et al.  In Vitro Comparative Efficacy of Voriconazole and Itraconazole against Fluconazole-Susceptible and -Resistant Cryptococcus neoformans Isolates , 1998, Antimicrobial Agents and Chemotherapy.

[78]  D. Bonner,et al.  In Vitro Activity of a New Oral Triazole, BMS-207147 (ER-30346) , 1998, Antimicrobial Agents and Chemotherapy.

[79]  Y. Koltin,et al.  The search for new triazole antifungal agents. , 1997, Current opinion in chemical biology.

[80]  W. Haiyan,et al.  Advances in the chemistry of novel broad-spectrum orally active azole antifungals: recent studies leading to the discovery of SCH 56592. , 1997 .

[81]  D. Stevens,et al.  Activity of the triazole SCH 56592 against disseminated murine coccidioidomycosis , 1997, Antimicrobial agents and chemotherapy.

[82]  D. Denning,et al.  Efficacy of SCH-56592 in a temporarily neutropenic murine model of invasive aspergillosis with an itraconazole-susceptible and an itraconazole-resistant isolate of Aspergillus fumigatus , 1997, Antimicrobial agents and chemotherapy.

[83]  A. Bell,et al.  Novel Antifungal 2-Aryl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol Derivatives with High Activity Against Aspergillus fumigatus. , 1996 .

[84]  W. Haiyan,et al.  Concise Asymmetric Routes to 2,2,4-Trisubstituted Tetrahydrofurans via Chiral Titanium Imide Enolates: Key Intermediates Towards Synthesis of Highly Active Azole Antifungals Sch 51048 and Sch 56592. , 1996 .

[85]  A. Sierra,et al.  Candida glabrata: in vitro susceptibility of 84 isolates to eight antifungal agents. , 1996, Chemotherapy.

[86]  A. Sugar,et al.  In vitro and in vivo activities of SCH 56592 against Blastomyces dermatitidis , 1996, Antimicrobial agents and chemotherapy.

[87]  K. Richardson.  The discovery of fluconazole , 1996 .

[88]  H. Yamaguchi,et al.  Short-term topical therapy of experimental tinea pedis in guinea pigs with lanoconazole, a new imidazole antimycotic agent , 1995, Antimicrobial agents and chemotherapy.

[89]  D. Roseeuw,et al.  Pulse therapy with one-week itraconazole monthly for three or four months in the treatment of onychomycosis. , 1995, Cutis.

[90]  H. Degreef,et al.  Current therapy of dermatophytosis. , 1994, Journal of the American Academy of Dermatology.

[91]  H. Yamaguchi,et al.  Therapeutic efficacy of lanoconazole, a new imidazole antimycotic agent, for experimental cutaneous candidiasis in guinea pigs , 1994, Antimicrobial Agents and Chemotherapy.

[92]  C. Kauffman.  Newer developments in therapy for endemic mycoses. , 1994, Clinical infectious diseases : an official publication of the Infectious Diseases Society of America.

[93]  A. M. Baciewicz,et al.  Ketoconazole and fluconazole drug interactions. , 1993, Archives of internal medicine.

[94]  D. Rotstein,et al.  The synthesis and antifungal activity of the enantiomers of butoconazole nitrate , 1993 .

[95]  H. Gugnani,et al.  Isoconazole nitrate versus clotrimazole in foot and nail infections due to Hendersonula toruloidea, Scytalidium hyalinum and dermatophytes , 1992, Mycoses.

[96]  J. Ortiz,et al.  In vitro activity of sertaconazole. , 1992, Arzneimittel-Forschung.

[97]  J. Ortiz,et al.  In vivo activity of sertaconazole in experimental dermatophytosis in guinea pigs. , 1992, Arzneimittel-Forschung.

[98]  P. Roset,et al.  Therapeutic efficacy and safety of the new antimycotic sertaconazole in the treatment of Pityriasis versicolor. , 1992, Arzneimittel-Forschung.

[99]  N. Ryder,et al.  Allylamine antifungal drugs. , 1992, Current topics in medical mycology.

[100]  P. Marichal,et al.  Mode of action of anti-Candida drugs: focus on terconazole and other ergosterol biosynthesis inhibitors. , 1991, American journal of obstetrics and gynecology.

[101]  B. Jegasothy,et al.  Oxiconazole nitrate: pharmacology, efficacy, and safety of a new imidazole antifungal agent. , 1991, Clinical therapeutics.

[102]  H. Waskin,et al.  Treatment of systemic sporotrichosis with ketoconazole. , 1991, Reviews of infectious diseases.

[103]  M. Pfaller,et al.  Effects of terconazole and other azole antifungal agents on the sterol and carbohydrate composition of Candida albicans. , 1990, Diagnostic microbiology and infectious disease.

[104]  H. Vanden Bossche,et al.  Terconazole. Pharmacology of a new antimycotic agent. , 1989, The Journal of reproductive medicine.

[105]  H. A. Hirsch.  Clinical evaluation of terconazole. European experience. , 1989, The Journal of reproductive medicine.

[106]  H. Merk,et al.  Azole antifungals. , 1989, Clinics in dermatology.

[107]  D. Classen,et al.  Treatment of coccidioidal meningitis with fluconazole. , 1988, The Journal of infectious diseases.

[108]  F. Odds,et al.  Effects of azole antifungals in vitro on host/parasite interactions relevant to Candida infections. , 1988, The Journal of antimicrobial chemotherapy.

[109]  J. Graybill,et al.  Pharmacokinetics of itraconazole following oral administration to normal volunteers , 1988, Antimicrobial Agents and Chemotherapy.

[110]  H. Matsumoto,et al.  Synthesis and antifungal activity of new 1-vinylimidazoles. , 1987, Journal of medicinal chemistry.

[111]  C. E. Hughes,et al.  Action of fluconazole (UK-49,858) in relation to other systemic antifungal azoles. , 1987, The Journal of antimicrobial chemotherapy.

[112]  N. Georgopapadakou,et al.  Effect of antifungal agents on lipid biosynthesis and membrane integrity in Candida albicans , 1987, Antimicrobial Agents and Chemotherapy.

[113]  M. Borgers,et al.  Degenerative changes in fungi after itraconazole treatment. , 1987, Reviews of infectious diseases.

[114]  F. Odds,et al.  Antifungal effects of fluconazole (UK 49858), a new triazole antifungal, in vitro. , 1986, The Journal of antimicrobial chemotherapy.

[115]  J. Heykants,et al.  Pharmacokinetics and dose proportionality of ketoconazole in normal volunteers , 1986, Antimicrobial Agents and Chemotherapy.

[116]  H. van den Bossche,et al.  Anticandidal activities of terconazole, a broad-spectrum antimycotic , 1986, Antimicrobial Agents and Chemotherapy.

[117]  J. Cutsem,et al.  The in vivo antifungal activity of broad-spectrum azoles , 1986 .

[118]  R. Heel,et al.  Tioconazole. A review of its antimicrobial activity and therapeutic use in superficial mycoses. , 1986, Drugs.

[119]  G. Cauwenbergh.  New and prospective developments in antifungal drugs. , 1986, Acta dermato-venereologica. Supplementum.

[120]  F. Odds,et al.  Suppression of ATP in Candida albicans by imidazole and derivative antifungal agents. , 1985, Sabouraudia.

[121]  W. Raab.  Terconazol, ein neues Triazolderivat zur Behandlung vaginaler Mykosen , 1985 .

[122]  B. Foleno,et al.  In vitro studies with terconazole. , 1985, Gynäkologisch-Geburtshilfliche Rundschau.

[123]  H. Vanden Bossche.  Biochemical targets for antifungal azole derivatives: hypothesis on the mode of action. , 1985, Current topics in medical mycology.

[124]  J. Heeres,et al.  ANTIMYCOTIC AZOLES. 7. SYNTHESIS AND ANTIFUNGAL PROPERTIES OF A SERIES OF NOVEL TRIAZOL-3-ONES , 1984 .

[125]  J. Heeres,et al.  Antimycotic azoles. 7. Synthesis and antifungal properties of a series of novel triazol-3-ones. , 1984, Journal of medicinal chemistry.

[126]  A. Espinel-Ingroff,et al.  In vitro studies with R 51,211 (itraconazole) , 1984, Antimicrobial Agents and Chemotherapy.

[127]  P. Marichal,et al.  Molecular basis for the antimycotic and antibacterial activity of N‐substituted imidazoles and triazoles: The inhibition of isoprenoid biosynthesis , 1984 .

[128]  A. Espinel-Ingroff,et al.  In vitro susceptibility studies with oxiconazole (Ro 13-8996). , 1984, Chemotherapy.

[129]  H. Matsumoto,et al.  1-(1-(2-((3-CHLOROBENZYL)OXY)PHENYL)VINYL)-1H-IMIDAZOLE HYDROCHLORIDE, A NEW POTENT ANTIFUNGAL AGENT , 1983 .

[130]  A. Vinnerberg,et al.  Open comparison of the efficacy, toleration and safety of tioconazole and econazole in the 3-day treatment of vaginal candidiasis. , 1983, Gynakologische Rundschau.

[131]  J. Artner,et al.  Open studies of the efficacy, tolerance, systemic absorption and vaginal persistence following a single application of tioconazole ointment in the treatment of patients with vaginal candidiasis. , 1983, Gynakologische Rundschau.

[132]  H. Matsumoto,et al.  1-[1-[2-[(3-Chlorobenzyl)oxy]phenyl]vinyl]-1H-imidazole hydrochloride, a new potent antifungal agent. , 1983, Journal of medicinal chemistry.

[133]  J. Heeres,et al.  Antimycotic azoles. 6. Synthesis and antifungal properties of terconazole, a novel triazole ketal. , 1983, Journal of medicinal chemistry.

[134]  J. V. van Cutsem,et al.  Terconazole - a new broad-spectrum antifungal. , 1983, Chemotherapy.

[135]  B. Farkas,et al.  [Results of isoconazol nitrate treatment of vaginal mycoses]. , 2009, Mykosen.

[136]  T. Arai,et al.  Effect of ketoconazole on isolated mitochondria from Candida albicans , 1982, Antimicrobial Agents and Chemotherapy.

[137]  A. Costa,et al.  “In vitro” Antimycotic Activity of Fenticonazole (Rec 15/1476): Die antimykotische Wirkung von Fenticonazole (Rec 15/1476) , 1982, Mykosen.

[138]  D. Feingold,et al.  Mechanisms of action of the antimycotic imidazoles. , 1981, The Journal of investigative dermatology.

[139]  C. Niemegeers,et al.  Inhibition and induction of microsomal enzymes in rat. A comparative study of four antimycotics: miconazole, econazole, clotrimazole and ketoconazole. , 1981, Archives internationales de pharmacodynamie et de therapie.

[140]  D. Barzaghi,et al.  Fenticonazole, a new imidazole derivative with antibacterial and antifungal activity. In vitro study. , 1981, Arzneimittel-Forschung.

[141]  P. Cazzulani,et al.  Toxicological and pharmacological properties of fenticonazole, a new topical antimycotic. , 1981, Arzneimittel-Forschung.

[142]  R. Cappelletti,et al.  Physico-chemical, structural and analytical studies on fenticonazole, a new drug with antimycotic properties. , 1981, Arzneimittel-Forschung.

[143]  D. Barzaghi,et al.  Antifungal activity of fenticonazole in experimental dermatomycosis and candidiasis. , 1981, Arzneimittel-Forschung.

[144]  F. Odds.  Laboratory evaluation of antifungal agents: a comparative study of five imidazole derivatives of clinical importance. , 1980, The Journal of antimicrobial chemotherapy.

[145]  M. De Brabander,et al.  The activity of ketoconazole in mixed cultures of leukocytes and Candida albicans. , 1980, Sabouraudia.

[146]  J. Graybill,et al.  Suppression of cryptococcosis and histoplasmosis by ketoconazole in athymic nude mice. , 1980, The Journal of infectious diseases.

[147]  D. Stevens,et al.  Ketoconazole, an oral antifungal: laboratory and clinical assessment of imidazole drugs. , 1979, Postgraduate medical journal.

[148]  J. Heeres,et al.  Antimycotic imidazoles. part 4. Synthesis and antifungal activity of ketoconazole, a new potent orally active broad-spectrum antifungal agent. , 1979, Journal of medicinal chemistry.

[149]  M. Leeming,et al.  Antifungal Activity of Tioconazole (UK-20,349), a New Imidazole Derivative , 1979, Antimicrobial Agents and Chemotherapy.

[150]  E. Herms,et al.  [Comparative clinical investigations with the new antimycotic agent isoconazole nitrate and its combination with diflucortolone-21-valerate in the case of inflammatory and eczematised dermatomycoses]. , 1979, Mykosen.

[151]  H. B. Levine,et al.  Oral therapy for experimental coccidioidomycosis with R41 400 (ketoconazole), a new imidazole. , 1978, The American review of respiratory disease.

[152]  R. E. Jones,et al.  1-[4-(4-Chlorophenyl)-2-(2,6-dichlorophenylthio)-n-butyl]-1H-imidazole nitrate, a new potent antifungal agent. , 1978, Journal of medicinal chemistry.

[153]  K. Uchida,et al.  Studies on Antifungal Activities of Econazole , 1978 .

[154]  J. Heeres,et al.  Antimycotic imidazoles. 3. Synthesis and antimycotic properties of 1-[2-(aryloxyalkyl)-2-phenylethyl]-1H-imidazoles. , 1977, Journal of medicinal chemistry.

[155]  M. Borgers,et al.  Cytochemical and Biochemical Studies of Yeasts After In Vitro Exposure to Miconazole , 1977, Antimicrobial Agents and Chemotherapy.

[156]  M. E. Goldberg.  Pharmacological and biochemical properties of drug substances , 1977 .

[157]  E. Drouhet,et al.  Treatment of pityriasis capitis (dandruff) with econazole nitrate. , 1977, Acta dermato-venereologica.

[158]  C. Niemegeers,et al.  Bilogical and toxicological properties of econazole, a broad-spectrum antimycotic. , 1975, Arzneimittel-Forschung.

[159]  J. V. van Cutsem,et al.  Miconazole, a broad-spectrum antimycotic agent with antibacterial activity. , 1972, Chemotherapy.

[160]  J. Heeres,et al.  The preparation and antimycotic properties of derivatives of 1-phenethylimidazole. , 1969, Journal of medicinal chemistry.

[161]  E. F. Godefroi.  Reductive ring cleavage of 1,3-disubstituted imidazolium iodides by sodium borohydride , 1968 .

[162]  V. D. Bossche.  34000 , A Dioxolane lmidazole in the Therapy for Experimental Coccidioidomycosis * , 2022 .