Antimicotici

<p>Micafungin, as one of three echinocandina, has been proven to be a successful antifungal therapeutic in treating general Candida fungus infections. The treatment of immunocompromised patients is particularly important as Candida infections cause high mortality rates in patients in intensive care units, receiving chemotherapy, or stem cell transplants. This product acts as an anti-fungal by inhibiting the 1,3-beta-D-glucan synthase enzyme. As a result the production of 1,3-beta-D-glucan, which is crucial to the fungal cell wall, is hindered. Thus, the fungal cell wall loses integrity allowing for osmotic instability and cell lysis to occur.</p>

<p>Voriconazole is a synthetic, lipophilic molecule that is used in the treatment of fungal infections. Voriconazole binds to ergosterol which is the major sterol in the cell wall of fungi and inhibits its synthesis, leading to cell death. This drug binds to the enzyme 14α-demethylase allowing the conversion of lanosterol into ergosterol. As a result, this binding leads to the inhibition of ergosterol synthesis, as well as other sterols that are necessary for fungal growth (e.g., squalene).</p>

<p>Posaconazole is an antifungal agent that inhibits the 14-alpha demethylase enzyme which is responsible for the synthesis of the fungal cell wall component, ergosterol. This demethylase enzyme synthesizes ergosterol through converting lanosterol to ergosterol. Therefore Posaconazole prevents the formation of fungal cell walls with the appropriate membrane permeability thus leading to fungal cell lysis. Posaconazole can be used as an antifungal drug to treat opportunistic fungal infections in immunocompromised individuals such as HIV patients. Moreover it is shown to inflict its inhibitory activity against common pathogenic fungus such as Candida and Aspergillus species but also Mucorales and some Fusarium species, which are less common.</p>

<p>Anti-fungal; lanosterol 14α-demethylase inhibitor</p>

<p>2-Methyl-4-isothiazolin-3-one HCl , also known as MIT hydrochloride is often used as a preservative in personal care products and other industrial applications. The product has shown to act as an antimicrobial and antifungal agent.</p>

<p>Inhibitor of squalene epoxidase</p>

<p>Lucimycin is an antibiotic, which is derived from the fermentation of specific Streptomyces bacterial strains. This compound exerts its antibacterial effects by binding to the 50S subunit of the bacterial ribosome, thereby inhibiting protein synthesis and effectively halting bacterial growth. Lucimycin is particularly effective against Gram-positive bacteria and some Gram-negative species, making it a valuable tool in both clinical and research settings.</p>

<p>Inhibitor of glucan synthase; antifungal compound</p>

<p>Pan-histone demethylase inhibitor; anti-fungal; iron-chelator</p>

<p>Fungicide</p>

<p>Anthelmintic; inhibitor of tubulin polymerization</p>

<p>Fluconazole is an antifungal drug used to treat a wide range of fungal infections. Fluconazole is a cytochrome demethylase system inhibitor that acts by interfering with β-glucan biosynthesis. It has been shown to be effective in treating candidemia, a life-threatening form of candidiasis caused by the fungus Candida albicans. Fluconazole seems to be more effective than amphotericin B in treating some isolates of C. albicans, making it a valuable tool in the fight against this deadly fungal infection, although due to the increase of antimicrobial resistance, fluconazole has been studied in combination with other drugs (e.g. farnesol).</p>

<p>Posaconazole is a triazole antifungal agent that inhibits the 14-alpha demethylase enzyme. This drug prevents the formation of fungal cell walls thus leading to fungal cell lysis. Posaconazole is shown to inflict its inhibitory activity against common pathogenic fungus such as Candida and Aspergillus species in severely immunocompromised patients.</p>

<p>Clotrimazole is an azole antifungal medication with action on fungal cell membrane disruption and is used for treating fungal infections like athlete's foot, ringworm, and vaginal yeast infections.</p>

<p>Anti-fungal; glucan synthase inhibitor</p>

<p>A fungicide</p>

<p>Caspofungin is an echinocandin that belongs to the class of antifungal agents. It is used to treat Aspergillus and Candida infections. It works by inhibiting the synthesis of beta-(1,3)-D-glucan, an essential component of the cell wall of Aspergillus species and Candida species.</p>

<p>Isoconazole is an azole antifungal compound with a mode of action that inhibits ergosterol synthesis, disrupting fungal cell membranes. It is used for treating fungal infections of the skin and nails.</p>

<p>Posaconazole is an antifungal agent that inhibits the 14-alpha demethylase enzyme which is responsible for the synthesis of the fungal cell wall component, ergosterol. This demethylase enzyme synthesizes ergosterol through converting lanosterol to ergosterol. Therefore Posaconazole prevents the formation of fungal cell walls with the appropriate membrane permeability thus leading to fungal cell lysis. Posaconazole can be used as an antifungal drug to treat opportunistic fungal infections in immunocompromised individuals such as HIV patients. Moreover it is shown to inflict its inhibitory activity against common pathogenic fungus such as Candida and Aspergillus species but also Mucorales and some Fusarium species, which are less common.</p>

<p>Terconazole is an azole antifungal agent with action on fungal cell membranes by inhibiting ergosterol biosynthesis and is used for treating vaginal yeast infections.</p>

<p>Ketoconazole is an azole antifungal compound with a mode of action that inhibits ergosterol synthesis, disrupting fungal cell membranes. It is used for treating fungal infections of the skin and scalp.</p>

<p>Oxiconazole is an anti-fungal agent that is used for the treatment of various dermatophyte infections. It can be used to treat athlete’s foot, ringworm and jock itch. This drug inhibits ergosterol biosynthesis and acts to destabilize the fungal cytochrome enzyme P450 51. Additionally, this drug has shown to inhibit DNA synthesis and suppress concentrations of ATP.</p>

<p>Atovaquone is an antimicrobial drug that is used for the treatment of Pneumocystis jirovecii pneumonia. This drug is an analog of ubiquinone and has good in vitro activity against Toxoplasma gondii.</p>

<p>Fengycin A analogue is an antifungal lipopeptide, which is a cyclic compound derived from microbial sources, specifically produced by Bacillus subtilis strains. It functions primarily by disrupting the cell membranes of pathogenic fungi, leading to altered membrane permeability and subsequent cell death. The unique structure of fengycin allows it to interact with membrane lipids, compromising membrane integrity and inhibiting fungal growth.</p>

<p>Efinaconazole is a triazole antifungal agent with action on fungal 14α-demethylase to inhibit ergosterol synthesis and is used for treating onychomycosis (fungal nail infections).</p>

<p>Filipin is a polyene macrolide antifungal agent with action on cholesterol in cell membranes and is used for histochemical staining and research on cholesterol metabolism.</p>

<p>Ipconazole is a fungicide with a mode of action that inhibits ergosterol biosynthesis, disrupting fungal cell membranes. It is used for seed treatment to protect crops like cereals and vegetables from fungal diseases. It's sold as a mixture of two isomers.</p>

<p>Posaconazole is an antifungal agent that inhibits the 14-alpha demethylase enzyme which is responsible for the synthesis of the fungal cell wall component, ergosterol. This demethylase enzyme synthesizes ergosterol through converting lanosterol to ergosterol. Therefore Posaconazole prevents the formation of fungal cell walls with the appropriate membrane permeability thus leading to fungal cell lysis. Posaconazole can be used as an antifungal drug to treat opportunistic fungal infections in immunocompromised individuals such as HIV patients. Moreover it is shown to inflict its inhibitory activity against common pathogenic fungus such as Candida and Aspergillus species but also Mucorales and some Fusarium species, which are less common.</p>

<p>Impurity of Micafungin; anti-fungal</p>

<p>Terbinafine is an antifungal drug that is used in the treatment of dermatophyte infections of the toenails and fingernails. Terbinafine also treats other skin infections. This drug works by inhibiting ergosterol synthesis which in return inhibits fungal squalene monooxygenase. This results in a disruption of fungal cell wall synthesis.</p>

<p>Fenticonazole nitrate is an imidazole antifungal agent with action on fungal cell membrane disruption and is used for treating fungal infections like vaginal thrush and athlete's foot.</p>

<p>Itraconazole is an anti-fungal drug that inhibits the synthesis of ergosterol, a component of the fungal cell membrane. Itraconazole is in a class of antifungals called triazoles. The drug binds to ergosterol in the fungal cell membrane and prevents it from being inserted into the membrane. This decreases the permeability of the plasma membrane, causing leakage of cellular contents. Additionally, it has been shown to have a glucose-lowering effect in the treatment of acute leukaemia and may be used for research in aiding to diagnose hematopoietic stem cell or leukaemia.</p>

<p>Activator of the two-pore domain potassium channel TASK3</p>

<p>Miconazole is an antifungal drug that is used for the treatment of fungal infections. This drug has broad-spectrum activity and works by inhibiting fungal CYP450 14α-lanosterol demethylase activity. This leads to altered ergosterol production and an impaired cell membrane.</p>

<p>Butenafine hydrochloride is an antifungal agent and is used for the treatment of fungal infections. It inhibits the synthesis of ergosterol, a key component of fungal cell membranes.</p>

<p>Pafuramidine is an antiprotozoal prodrug with action on protozoal DNA synthesis inhibition and is used for treating African sleeping sickness and Pneumocystis pneumonia.</p>

<p>Ciclopirox is a broad-spectrum antifungal agent that is used to treat onychomycosis of fingernails and toenails in immunocomprised patients. Ciclopirox has been shown to work by binding to polyvalent metal cations such Al3+ and Fe3+. These cations interfere with cellular processes including mitochondrial electron transport and energy synthesis by inhibiting numerous enzymes, including cytochromes. Additionally, the plasma membrane of fungi appears to be altered by ciclopirox as well, leading to the disorder of internal structures.</p>

<p>Bifonazole is an antifungal drug that is used for the treatment of fungal infections. This drug inhibits the production of ergosterol and destabilizes the fungal cytochrome p450 51 enzyme.</p>

<p>Delafloxacin is a fluoroquinolone antibiotic with action on bacterial DNA gyrase and topoisomerase IV and is used for treating acute bacterial skin and skin structure infections.</p>

<p>2-Methyl-4-isothiazolin-3-one or MIT is a powerful antimicrobial and antifungal agent which is widely used in personal care products. It is also used in industrial applications as a preservative and antifouling agent.</p>

<p>Amphotericin A is a polyene macrolide antibiotic, which is derived primarily from the soil bacterium *Streptomyces nodosus*. This compound functions by binding to ergosterol, an essential component of fungal cell membranes. This binding creates pores in the membrane, increasing its permeability and ultimately leading to cell death. Unlike its more widely used counterpart Amphotericin B, Amphotericin A is less frequently utilized but is critical in the study and understanding of antifungal activity.</p>

<p>Exalamide is an arenecarboxamide antifungal agent with action on fungal growth inhibition and is used for research on fungal infections.</p>

<p>Butoconazole nitrate is an antifungal agent and is used for the treatment of vaginal yeast infections. It inhibits the synthesis of ergosterol, disrupting the fungal cell membrane.</p>

<p>Folpet-d4 is a deuterated compound of Folpet. Folpet has a CAS number of 133-07-3. Folpet,a widely used dicarboximide fungicide,induces tumors in the mouse gastrointestinal tract,primarily in the duodenum,and is also cytotoxic effect on human bronchial epithelial cells.</p>

<p>Applications o-Tolylglyoxylic Acid Methyl Ester is an intermediate in the synthesis of Trifloxystrobin (T778900), a broad-spectrum foliar fungicide used in plant protection.<br></p>

<p>Applications 4-(4-Chlorophenyl)-1-(4H-1,2,4-triazol-4-yl)butan-2-one is an impurity in the synthesis of 5-(4-Chlorophenyl)-2,2-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)-1,3-pentanediol (C377885), which is a hydroxy tebuconazole conjugate. Tebuconazole (T013000) is an ergosterol biosynthesis inhibitor. Fungicide.<br>References Gent, D., et al.: Plant Dis., 87, 591 (2003), Wang, C., et al.: Pestic. Biochem. Physiol., 87, 1 (2007),<br></p>

<p>Applications R406 is a potent Syk inhibitor which affects Dectin-1-mediated signalling in mammilian cells. R406 thus acts an anti-fungal agent. Also a potential anti-leukemia agent, through modulation of sphingosine-1 phosphate receptor 1 (S1PR1).<br>References Borge, M. et al.: J. Immunol., 193, 3165 (2014); Kimura, Y. et al.: J. Biol. Chem., 289, 31565 (2014);<br></p>

<p>Applications 3-Methyl-3-phenylamino-1-butyne is an intermediate in the synthesis of Endophenazine A which is a new phenazine antibiotic isolated from the arthropod associated endosymbiont Streptomyces anulatus and shows antimicrobial activities against Gram-positive bacteria and some filamentous fungi, and herbicidal activity against Lemna minor (duckweed).<br>References Gebhardt, K., et al.: J. Antibiot., 55, 794 (2002)<br></p>

<p>Applications 2-[[[1-(4-Chlorophenyl)-1H-pyrazol-3-yl]oxy]methyl]benzenamine is an intermediate used in the synthesis of (P840402), which is an isotope labelled Pyraclostrobin, a fungicide for use in seed grass and food crops.<br>References Gyldenkaerne, S., et al.: Pestic Sci., 55, 1210 (1999), Pennington, D., et al.: Environ. Sci. Technol., 39, 1119 (2005), Wang, S., et al.: Food Control., 18, 731 (2007),<br></p>

<p>Applications (5E)-5-(3-Bromopropylidene)-5,11-dihydro-10H-dibenzo[a,d]cyclohepten-10-one is an intermediate in the synthesis of 10-Hydroxy (E)-Amitriptyline (D462790). (5E)-5-[3-(dimethylamino)propylidene]-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-10-ol is a metabolite of amitriptyline (A633350) which is a dibenzocycloheptadiene derivative and an antidepressant (1). Amitriptyline is also a TrkA and TrkB receptor agonist and exhibits neurotrophic and anti-inflammatory activities (2,3). Drinking water contaminant candidate list 3 (CCL 3) compound as per United States Environmental Protection Agency (EPA).<br></p>

<p>Applications 5-​(2-​Chlorophenyl)​-​3-​cyclopropyl-​4,​5-​dihydro-1H-​pyrazole is an intermediate in synthesizing Sedaxane (S242000), a broad-spectrum seed treatment fungicide used for control of seed- and soil-borne diseases in a broad range of crops. It inhibits fungal respiration by binding to the succinate dehydrogenase complex in the fungal mitochondrium.<br>References Zeun, R., et al.: Pest Manag. Sci., 69, 527 (2013); Oostendorp, M., et al.: Phytopathology, 101, S133 (2011); Olaya, G., et al.: Phytopathology, 101, S132 (2011)<br></p>

<p>Applications Methyl 2-[2-[(2,5-Dimethylphenoxy)methyl]phenyl]-2-(hydroxy)acetic Acid Ester is an intermediate used in the synthesis of Mandestrobin (M162555), which is a novel fungicide having a methoxyacetamid structure. Mandestrobin also shows safer profiles for human health and the environment.<br>References Hirotomi, D., &amp; Kiguchi, S.: PCT Int. Appl., WO 2017026526 A1 20170216 (2017)<br></p>

<p>Applications 2-[(6-Chloro-4-pyrimidinyl)oxy]-α-(dimethoxymethyl)benzeneacetic Acid Methyl Ester is an impurity of Azoxystrobin (A965150), an strobilurin fungicide.<br>References Liu H.J., et al.: J. Chin. Chem. Soc., 60, 27 (2013);<br></p>

<p>Applications 2-Demethyl Mandestrobin is an intermediate used in the synthesis of Mandestrobin (M162555), which is a novel fungicide having a methoxyacetamid structure. Mandestrobin also shows safer profiles for human health and the environment.<br>References Hirotomi, D., &amp; Kiguchi, S.: PCT Int. Appl., WO 2017026526 A1 20170216 (2017)<br></p>

<p>Applications A bactericidal and fungicidal.<br>References Schoppelrei, J., et al.: J. Phys. Chem., 100, 14343 (1996), Kolb, H., et al.: Drug Discovery Today, 8, 1128 (2003),<br></p>

<p>Applications (5E)-5-(3-Bromopropylidene)-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-10-ol is an intermediate in the synthesis of 10-Hydroxy (E)-Amitriptyline (D462790). (5E)-5-[3-(dimethylamino)propylidene]-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-10-ol is a metabolite of amitriptyline (A633350) which is a dibenzocycloheptadiene derivative and an antidepressant (1). Amitriptyline is also a TrkA and TrkB receptor agonist and exhibits neurotrophic and anti-inflammatory activities (2,3). Drinking water contaminant candidate list 3 (CCL 3) compound as per United States Environmental Protection Agency (EPA).<br></p>

<p>Applications Rhein Methylate 3-(2,3,4,6-Tetraacetate β-D-Glucopyranose) is an intermediate in synthesizing Rhein 8-Glucoside (R318520), which has been seen to exhibit cytotoxic and DNA-damaging properties towards tumor and normal human cells. In addition it has been shown to be an inhibitor of PTP1B (Human Protein Tyrosine Kinase 1B) in vitro. It is an analog of Rhein (318500) which is found in the free state and as glucoside in Rheum spp, Polygonaceae (rhubarb) and in Senna leaves. It is a potential antioxidant resource: endophytic fungi from medicinal plants.<br>References Wanitschke, Pharmacology, 20, Suppl. 1, 21 (1980); Raimondi, L., et al.: Pharmacol. Res. Commun., 14, 103 (1982); Franchi-Micheli, S., et al.: J. Pharm. Pharmacol., 35, 262 (1983); Li, S. et al.: J. Asian Nat. Prod. Res., 8, 281 (2006); Shi, Y.Q. et al.: Anticancer. Res., 21, 2847 (2001)<br></p>

<p>Antifungal agent 20 effectively combats various fungi, like Colletotrichum spp., Rhizoctonia, Phytophthora, Diplodia, and Fusarium.</p>

<p>Tecnazene is a giant myofibrillar protein. It also presents in invertebrate striated muscle.</p>

<p>Benzyl 2-hydroxy-6-methoxybenzoate exhibits potent antifungal activity, demonstrating an IC 50 of 25–26 μg/mL against fungal strains.</p>

<p>Amphotericin X1, Amphotericin B derivative, has potent antifungal effects against various fungi (MICs: 1-8 μg/mL).</p>

<p>Butenafine hydrochloride, a squalene epoxidase inhibitor, disrupts ergosterol synthesis, increasing cell membrane permeability.</p>

<p>Dicloran is an aromatic fungicide that delays spore germination and inhibits hyphal growth, effective against Botrytis, Monilinia, Rhizopus, Sclerotinia.</p>

<p>Antifungal agent 76 has broad-spectrum antifungal activity with a MIC value of 0.25-16 μg/mL.Antifungal agent 76 may act by disrupting fungal cell membranes and can be used to study fungal infections.</p>

<p>Anti-fungal; sterol demethylase inhibitor</p>

<p>Broad spectrum imidazole antifungal</p>

<p>Abafungin is an antifungal agent and is used for treating fungal infections.</p>

<p>(+)-Xylariamide A is a probe used for mycobacterial and fungal carbonic anhydrase.</p>

<p>Flusilazole (DPX6573) is an organosilicon fungicide with broad spectrum antifungal effects.</p>

<p>Prothioconazole (Proline 480 SC Fungicide) is a chiral triazole fungicide in plant pathogen control.</p>

<p>Pyrifenox is a pesticide and azole inhibitor.</p>

<p>Enoxastrobin is a reagent biochemical.</p>

<p>Triforine is an agent of biochemical.</p>

<p>Butoconazole (1-[4-(4-chlorophenyl)-2-[(2,6-dichlorophenyl)thio]butyl]-1H-imidazole) is an imidazole antifungal agent</p>

<p>Demethoxyencecalin is extracted from Helianthus annuus with antifungal activities.</p>

<p>Bitertanol (KWG 0599) is a triazole fungicide. Bitertanol inhibits demethylation, disrupts membrane function, and prevents sterol synthesis.</p>

<p>Applications A new N-halamine monomer was synthesized and used to prepare water-based polymeric N-halamines by emulsion polymn. Also, the compound was tested for antibacterial activity against Candida albicans, Staphylococcus aureus, and Escherichia coli.<br>References Kohl, H., et al.: J. Pharm. Sci., 69, 1292 (1980), Greenberger, P., et al.: Clin. Allergy Immunol., 16, 449 (2002), Gant, V., et al.: J. Antimicrob. Chemother., 60, 294 (2007), Pestka, J., et al.: Toxicol. Sci., 104, 4 (2008),<br></p>

<p>Applications Curvulin is a phototoxin that inhibits microtuble assembly.<br></p>

<p>Applications Dictamnine is an herbal extract from the root of Dictamnus dasycarpus, and exhibits anti-microbial activity against bacteria and fungi. Phytotoxic agent.<br>References Guo, N. et al.: Yeast., 25, 631 (2008); Schempp, C. et al.: Planta. Med., 72, 941 (2006);<br></p>

<p>Applications Benzotriazol-1-ylacetic Acid is used as a reagent in the synthesis of benzotriazole imidazoline compounds which are used as metal corrosion inhibitors. Benzotriazol-1-ylacetic Acid is also a reagent in the synthesis of N-(benzo[1,2,3]triazol-1-yl)-N-((benzyl)acetamido)phenyl carboxamides which are used as severe acute respiratory syndrome coronavirus (SARS-CoV) 3CLpro inhibitors.<br>References Turlington, M., et al.: Bioorg, Med. Chem. Lett., 23, 6172 (2013); Chen, Y., et al.: Faming Zhuanli Shenqing. CN 103664902 A 20140326. Mar 26, 2014<br></p>

<p>Applications 5-Mercapto-1H-1,2,3-triazole Sodium Salt is used as a reactant in the preparation of cephem derivatives as anti-Helicobacter pylori agents in relation to lability towards β-lactamase and potential for causing diarrhea.<br>References Yoshida, Y., et al.: Bioorg. Med. Chem., 8, 2317 (2000);<br></p>

<p>Applications 5,6-Dehydromethysticin is a proposed intermediate in the synthesis of 3-Hydroxyhispidin (H943133), a derivative of Hispidin. Hispidin (H436450) is a naturally occuring precursor to fungal luciferin responsible for luminosity in mushrooms.<br>References Lee, Y. et al.: Biol. Pharm. Bull., 31, 10 (1968); Purtov, K. et al.: Angew. Chem. Int. Ed., 54, 8124 (2014);<br></p>

<p>Applications 1,4-Bis([1,1'-biphenyl]-4-ylphenylmethyl)-1H-imidazole is derived from 5-([1,1’-Biphenyl]-4-ylphenylmethyl)-1H-imidazole (B397925), which is a structural isomer of Bifonazole (B383400) that is an anti-fungal agent used in the treatment of skin diseases. Bifonazole causes an increase in Ca2+ concentration and triggers cell death in PC3 human prostate cancer cells.<br>References Cheng, J. et al.: J. Recep. Sign. Transduct., 34, 493 (2014); Chen, Z. et al.: Mol. Pharm., 12, 590 (2015);<br></p>