Antimycotics. November 14, Jan Strojil. Ústav farmakologie LF UP
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1 Ústav farmakologie LF UP November 14, 2005
2 Introduction Polyens Azoles Alylamines Other Outline Introduction Polyens Azoles Alylamines and morfolines Other
3 Introduction Polyens Azoles Alylamines Other Mycoses Systemic mycoses systemic candidiasis cryptococal meningitis or endocarditis pulmonary aspergillosis rhinocerebral mucormycosis Superficial mycoses dermatomycoses (tinea) trichophyton microsporum epidermophyton superficial candidiasis aspergilloma tinea pedis
4 Introduction Polyens Azoles Alylamines Other Physiology membrane pores polyens cell wall reductase demethylase ergosterol demethyl lanosterol lanosterol ergosterol synthesis inhibitors morfolines: amorolfine azoles: ketoconazole epoxidase squalene epoxide squalene DNA/RNA alylamines: naftifine microtubules inhibitors griseofulvin antimetabolite fluorouracil flucytosine cytosindeaminase
5 Introduction Polyens Azoles Alylamines Other Polyens Introduction Polyens Azoles Alylamines and morfolines Other
6 Introduction Polyens Azoles Alylamines Other Polyens Amphotericin B antibiotic macrolide structure binds to ergosterol in membrane creates pores loss of K + combination with flucytosine Indications severe systemic mycoses amphotericin B candidosis(endocarditis, pneumonia, systemic candidosis) aspergillosis and mucormycoses drug of choice cryptococcocal infections, including meningitis coccidiomycosis, histoplasmosis, blastomycosis
7 Introduction Polyens Azoles Alylamines Other Polyens Amphotericin B Characteristics not absorbed from GIT fungistatic toxic lipid complexes, β cyclodextrin, liposomes, nanospheres normally does not cross BBB Side effects nephrotoxic renal impairment in 80% of patients hypokalaemia, hypomagnesaemia nausea, chills, fever, headache local reaction slow i.v. infusion
8 Introduction Polyens Azoles Alylamines Other Polyens Nystatin similar to Amphotericin B no absorption highly toxic only local Natamycin (pimaricin) similar to nystatin local therapy
9 Introduction Polyens Azoles Alylamines Other Azoles Introduction Polyens Azoles Alylamines and morfolines Other
10 Introduction Polyens Azoles Alylamines Other Physiology membrane pores polyens cell wall ergosterol ergosterol synthesis inhibitors reductase morfolines: amorolfine demethyl lanosterol demethylase lanosterol azoles: ketoconazole cell membrane epoxidase squalene epoxide squalene alylamines: naftifine microtubules inhibitors griseofulvin DNA/RNA antimetabolite fluorouracil flucytosine cytosindeaminase
11 Introduction Polyens Azoles Alylamines Other Azoles General characteristics & action synthetic fungistatic inhibit fungal CYP450 3A alter fluidity of membrane inhibit replication imidazoles and triazoes Indications topical use (some also have antibacterial activity) systemic use local and systemic mycoses clotrimazole
12 Introduction Polyens Azoles Alylamines Other Azoles Miconazole obsolete Ketoconazole first azole for oral administration Indications systemic candidosis, coccidiomycosis, histoplasmosis, skin mycosis Side effects nausea, vomiting, hepatopathy, inhibition of steroid hormones production Interactions CYP 3A, needs acid for absorption
13 Introduction Polyens Azoles Alylamines Other Azoles Fluconazole triazole reaches high concentrations in CSF can reach fungicidal concentrations Indications first choice for fungal meningitis Side effects better tolerated, GIT, does not inhibit steroids Interactions lower afinity to human CYP 3A
14 Introduction Polyens Azoles Alylamines Other Azoles Itraconazole triazole, lipid soluble variable absorption β cyclodextrin coated particles for IV Indications first choice for fungal meningitis Side effects well tolerated, skin lesions, does not inhibit steroids Interactions CYP 3A inhibition, needs acid (Coca Cola )
15 Introduction Polyens Azoles Alylamines Other Azoles other voriconazole wider spectrum more expensive (VFEND ) posaconazole even wider spectrum even more expensive (Noxafil ) ravuconazole in clinical trials
16 Introduction Polyens Azoles Alylamines Other Alylamines and morfolines Introduction Polyens Azoles Alylamines and morfolines Other
17 Introduction Polyens Azoles Alylamines Other Physiology membrane pores polyens cell wall reductase demethylase ergosterol demethyl lanosterol lanosterol ergosterol synthesis inhibitors morfolines: amorolfine azoles: ketoconazole epoxidase squalene epoxide squalene DNA/RNA alylamines: naftifine microtubules inhibitors griseofulvin antimetabolite fluorouracil flucytosine cytosindeaminase
18 Introduction Polyens Azoles Alylamines Other Alylamines and morfolines naftifine local, fingicidal, wide spectrum antiflogistic effect terbinafine similar to naftifine, also oral form, keratinophilic amorolfine good penetration into nails used in the form of a lacquer
19 Introduction Polyens Azoles Alylamines Other Other Introduction Polyens Azoles Alylamines and morfolines Other
20 Introduction Polyens Azoles Alylamines Other Physiology membrane pores polyens cell wall reductase demethylase ergosterol demethyl lanosterol lanosterol ergosterol synthesis inhibitors morfolines: amorolfine azoles: ketoconazole epoxidase squalene epoxide squalene DNA/RNA alylamines: naftifine microtubules inhibitors griseofulvin antimetabolite fluorouracil flucytosine cytosindeaminase
21 Introduction Polyens Azoles Alylamines Other Others griseofulvin local infections, given systemically obsolete, treatment needs to be very long flucytosine cytosindeaminase inhibitor (cytosine > uracil) good efect on candida 10g daily well tolerated, mild side effects beneficial combination with amphotericin B
22 Introduction Polyens Azoles Alylamines Other Others caspofungin inhibits cell wall synthesis wide spectrum poor oral absorption long half life 1 dose/day other pradimicin, nikkomycins sordarins GCSFs vaccines?
23 thank you for your attention
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