Natural Product (NP) Details

General Information of the NP (ID: NP9882)
Name
Anidulafungin
Synonyms
Anidulafungin; Eraxis; 166663-25-8; Ecalta; UNII-9HLM53094I; Anidulafungin (LY303366); VER-002; CHEBI:55346; LY-303366; 9HLM53094I; LY303366; V-Echinocandin; Anidulafungina; Anidulafungine; Anidulafunginum; Anidulafungin [USAN:INN:BAN]; C58H73N7O17; SCHEMBL38292; (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; CHEMBL264241; VER002; BDBM50417554; MFCD00917070; s4286; CCG-270647; DB00362; NCGC00386349-01; AT-36943; SW222238-1; A13436; D70013; Z-3192; 663A258; J-010304; Q4764531; Echinocandin B, 1-((4R,5R)-4,5-dihydroxy-N2-((4''-(pentyloxy)(1,1':4',1''-terphenyl)-4-yl)carbonyl)-L-ornithine); N-[(3S,6S,9S,11R,15S,18S,20R,21R,24S,25S,26S)-6-[(1S,2S)-1,2-dihydroxy-2-(4-hydroxyphenyl)ethyl]-11,20,21,25-tetrahydroxy-3,15-bis[(1R)-1-hydroxyethyl]-26-methyl-2,5,8,14,17,23-hexaoxo-1,4,7,13,16,22-hexaazatricyclo[22.3.0.0^{9,13}]heptacosan-18-yl]-4-{4-[4-(pentyloxy)phenyl]phenyl}benzamide; N-[[(1S,2S)-1,2-dihydroxy-2-(4-hydroxyphenyl)ethyl]-tetrahydroxy-bis[(1R)-1-hydroxyethyl]-methyl-hexaoxo-[?]yl]-4-[4-(4-pentoxyphenyl)phenyl]benzamide; N-{(2R,6S,9S,11R,12R,14aS,15S,16S,20S,23S,25aS)-23-[(1S,2S)-1,2-dihydroxy-2-(4-hydroxyphenyl)ethyl]-2,11,12,15-tetrahydroxy-6,20-bis[(1R)-1-hydroxyethyl]-16-methyl-5,8,14,19,22,25-hexaoxotetracosahydro-1H-dipyrrolo[2,1-c:2',1'-l][1,4,7,10,13,16]hexaazacyclohenicosin-9-yl}-4''-(pentyloxy)-1,1':4',1''-terphenyl-4-carboxamide
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Species Origin Aspergillus nidulans ...     Click to Show/Hide
Aspergillus nidulans
Kingdom: Fungi
Phylum: Ascomycota
Class: Eurotiomycetes
Order: Eurotiales
Family: Aspergillaceae
Genus: Aspergillus
Species: Aspergillus nidulans
Disease Epilepsy/seizure [ICD-11: 8A60] Approved [1]
Structure
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2D MOL

3D MOL

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Formula
C58H73N7O17
PubChem CID
166548
Canonical SMILES
CCCCCOC1=CC=C(C=C1)C2=CC=C(C=C2)C3=CC=C(C=C3)C(=O)NC4CC(C(NC(=O)C5C(C(CN5C(=O)C(NC(=O)C(NC(=O)C6CC(CN6C(=O)C(NC4=O)C(C)O)O)C(C(C7=CC=C(C=C7)O)O)O)C(C)O)C)O)O)O
InChI
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
InChIKey
JHVAMHSQVVQIOT-MFAJLEFUSA-N
CAS Number
CAS 166663-25-8
ChEBI ID
CHEBI:55346
TTD Drug ID
D0F9BY
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Efficacy can be Enhanced by This NP
          Voriconazole      Aspergillosis     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Up-regulation Expression CYP51A1  Molecule Info 
Pathway MAP
                    In-vitro Model Aspergillus fumigatus Microorganism model Aspergillus fumigatus
                    Experimental
                    Result(s)		 The combination demonstrated synergy against the VCZ-R clinical isolate as well.
          Posaconazole      Aspergillosis     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [3]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vitro Model Aspergillus fumigatus Microorganism model Aspergillus fumigatus
                    In-vivo Model Six-week-old female Swiss mice were immunosuppressed with a combination of cyclophosphamide and cortisone acetate.
                    Experimental
                    Result(s)		 The PSC and AFG combination therapy was highly effective and should be evaluated in larger-scale experiments.
          Amphotericin B      Fungal infection     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [4]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Experimental
                    Result(s)		 Anidulafungin with amphotericin B results in a synergistic effect against C. albicans and C. glabrata biofilms at serum concentrations of the drugs, but showed no interaction against C. tropicalis and C. parapsilosis complex.
Target and Pathway
Target(s) Fungal 1,3-beta-glucan synthase (Fung GSC2)  Molecule Info  [5]
KEGG Pathway Starch and sucrose metabolism Click to Show/Hide
2 MAPK signaling pathway - yeast
References
Reference 1 Echinocandins: pharmacokinetic and therapeutic issues. Curr Med Res Opin. 2009 Jul;25(7):1741-50.
Reference 2 In vitro efficacy of the combination of voriconazole and anidulafungin against voriconazole-resistant cyp51A mutants of Aspergillus fumigatus. Diagn Microbiol Infect Dis. 2012 Jun;73(2):135-7.
Reference 3 Evaluation of the efficacy of a posaconazole and anidulafungin combination in a murine model of pulmonary aspergillosis due to infection with Aspergillus fumigatus. Diagn Microbiol Infect Dis. 2018 Jan;90(1):40-43.
Reference 4 In vitro activity of anidulafungin in combination with amphotericin B or voriconazole against biofilms of five Candida species. J Antimicrob Chemother. 2016 Dec;71(12):3449-3452.
Reference 5 2006 drug approvals: finding the niche. Nat Rev Drug Discov. 2007 Feb;6(2):99-101.
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