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Anidulafungin

CAS No:
166663-25-8 Categories: , , ,
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Product Details:

  • Product Name: Anidulafungin
  • CAS #: 166663-25-8
  • Mode of Action:

    Anidulafungin is a semi-synthetic echinocandin with antifungal activity. Anidulafungin inhibits glucan synthase, an enzyme present in fungal, but not mammalian cells. This results in inhibition of the formation of 1, 3-β-D-glucan, an essential component of the fungal cell wall, ultimately leading to osmotic instability and cell death.

  • Pharmacodynamics:

    Anidulafungin is a semi-synthetic lipopeptide synthesized from a fermentation product of Aspergillus nidulans. Anidulafungin is an echinocandin, a class of antifungal drugs that inhibits the synthesis of 1, 3-β-D-glucan, an essential component of fungal cell walls. Anidulafungin is active in vitro against many Candida, as well as some Aspergillus. Like other echinocandins, anidulafungin is not active against Cryptococcus neoformans, Trichosporon, Fusarium, or zygomycetes.

  • Metabolism:

    Hepatic metabolism of anidulafungin has not been observed. Anidulafungin is not a clinically relevant substrate, inducer, or inhibitor of cytochrome P450 (CYP450) isoenzymes. Anidulafungin undergoes slow chemical degradation at physiologic temperature and pH to a ring-opened peptide that lacks antifungal activity.

  • Toxicity:

    During clinical trials a single 400 mg dose of anidulafungin was inadvertently administered as a loading dose. No clinical adverse events were reported. The maximum non-lethal dose of anidulafungin in rats was 50 mg/kg, a dose which is equivalent to 10 times the recommended daily dose for esophageal candidiasis (50mg/day).

  • IUPAC: Echinocandin B, 1-((4R, 5R)-4, 5-dihydroxy-N2-((4''-(pentyloxy)(1, 1':4', 1''-terphenyl)-4-yl)carbonyl)-L-ornithine)
  • ATC: J02AX06
  • PubChem: CID 166548
  • DrugBank: DB00362 (APRD01301)
  • Formula: C58-H73-N7-O17
  • Molecular Mass: 1140.2467
  • Synonyms: (4R,5R)-4,5-Dihydroxy-N(sup 2)-((4'-(pentyloxy)-p-terphenyl-4-yl)carbonyl)-L-ornithyl-L-threonyl-trans-4-hydroxy-L-prolyl-(S)-4-hydroxy-4-(p-hydroxyphenyl)-L-threonyl-L-threonyl-(3S,4S)-3-hydroxy-4-methyl-L-proline cyclic (6-1)-peptide, Anidulafungin, Ecalta, Eraxis, LY303366, UNII-9HLM53094I
  • SMILES: CCCCCOc1ccc(cc1)c2ccc(cc2)c3ccc(cc3)C(=O)N[C@H]4C[C@@H](O)[C@@H](O)NC(=O)[C@@H]5[C@@H](O)[C@@H](C)CN5C(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H]6C[C@@H](O)CN6C(=O)[C@@H](NC4=O)[C@@H](C)O)[C@H](O)[C@@H](O)c7ccc(O)cc7)[C@@H](C)O
  • InChl: 1S/C58H73N7O17/c1-5-6-7-24-82-40-22-18-35(19-23-40)33-10-8-32(9-11-33)34-12-14-37(15-13-34)51(74)59-41-26-43(70)54(77)63-56(79)47-48(71)29(2)27-65(47)58(81)45(31(4)67)61-55(78)46(50(73)49(72)36-16-20-38(68)21-17-36)62-53(76)42-25-39(69)28-64(42)57(80)44(30(3)66)60-52(41)75/h8-23,29-31,39,41-50,54,66-73,77H,5-7,24-28H2,1-4H3,(H,59,74)(H,60,75)(H,61,78)(H,62,76)(H,63,79)/t29-,30+,31+,39+,41-,42-,43+,44-,45-,46-,47-,48-,49-,50-,54+/m0/s1
  • General Reference:
    1. Cappelletty D, Eiselstein-McKitrick K: The echinocandins. Pharmacotherapy. 2007 Mar;27(3):369-88. [PubMed:17316149 ]
    2. Vazquez JA: Anidulafungin: a new echinocandin with a novel profile. Clin Ther. 2005 Jun;27(6):657-73. [PubMed:16117974 ]
    3. Grover ND: Echinocandins: A ray of hope in antifungal drug therapy. Indian J Pharmacol. 2010 Feb;42(1):9-11. doi: 10.4103/0253-7613.62396. [PubMed:20606829 ]
    4. Vazquez JA: The safety of anidulafungin. Expert Opin Drug Saf. 2006 Nov;5(6):751-8. [PubMed:17044802 ]
    5. Menichetti F: Anidulafungin, a new echinocandin: effectiveness and tolerability. Drugs. 2009;69 Suppl 1:95-7. doi: 10.2165/11315570-000000000-00000. [PubMed:19877741 ]
    6. Vazquez JA, Sobel JD: Anidulafungin: a novel echinocandin. Clin Infect Dis. 2006 Jul 15;43(2):215-22. Epub 2006 Jun 9. [PubMed:16779750 ]
    7. Estes KE, Penzak SR, Calis KA, Walsh TJ: Pharmacology and antifungal properties of anidulafungin, a new echinocandin. Pharmacotherapy. 2009 Jan;29(1):17-30. doi: 10.1592/phco.29.1.17. [PubMed:19113794 ]
    8. Morace G, Borghi E, Iatta R, Montagna MT: Anidulafungin, a new echinocandin: in vitro activity. Drugs. 2009;69 Suppl 1:91-4. doi: 10.2165/11315560-000000000-00000. [PubMed:19877740 ]
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