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Echinocandin B information


Echinocandin B
Names
IUPAC name
(9Z,12Z)-N-{(2R,6S,9R,11R,12R,14aS,16R,20S,23S,25aS)-23-[(1S,2S)-1,2-Dihydroxy-2-(4-hydroxyphenyl)ethyl]-2,11,12-trihydroxy-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}-9,12-octadecadienamide
Identifiers
CAS Number
  • 54651-05-7 checkY
3D model (JSmol)
  • Interactive image
ChemSpider
  • 28296438 ☒N
ECHA InfoCard 100.184.852 Edit this at Wikidata
MeSH echinocandin+B
PubChem CID
  • 6436199
UNII
  • CNW0ZW8ZTQ checkY
CompTox Dashboard (EPA)
  • DTXSID301027535 Edit this at Wikidata
InChI
  • InChI=1S/C52H81N7O15/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-40(65)53-36-27-39(64)49(71)57-48(70)37-25-30(2)28-58(37)51(73)42(32(4)61)55-50(72)43(45(67)44(66)33-21-23-34(62)24-22-33)56-47(69)38-26-35(63)29-59(38)52(74)41(31(3)60)54-46(36)68/h9-10,12-13,21-24,30-32,35-39,41-45,49,60-64,66-67,71H,5-8,11,14-20,25-29H2,1-4H3,(H,53,65)(H,54,68)(H,55,72)(H,56,69)(H,57,70)/b10-9-,13-12-/t30-,31-,32-,35-,36-,37+,38+,39-,41+,42+,43+,44+,45+,49-/m1/s1 ☒N
    Key: VEYRWWIYQJAHTA-LUIZREEVSA-N ☒N
SMILES
  • CCCCC/C=C\C/C=C\CCCCCCCC(=O)N[C@@H]1C[C@H]([C@H](NC(=O)[C@@H]2C[C@H](CN2C(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H]3C[C@H](CN3C(=O)[C@@H](NC1=O)[C@@H](C)O)O)[C@@H]([C@H](c4ccc(cc4)O)O)O)[C@@H](C)O)C)O)O
Properties
Chemical formula
C52H81N7O16
Molar mass 1060.24 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Echinocandin B, a lipopeptide, is a naturally occurring cyclic hexapeptide with a linoleoyl side chain. It belongs to a class of antifungal agents called echinocandins, which inhibits the synthesis of glucan, a major component of the fungal cell wall, via noncompetitive inhibition of a crucial enzyme, β-(1→3)-D-glucan synthase. Echinocandin B is a fermentation product of Aspergillus nidulans and the closely related species, A. rugulosus;[1] discovered in 1974 in A. nidulans var. echinulatus strain A 32204 in Germany,[2] it was the first of the echinocandin class of antifungals.

Echinocandin B can undergo deacylation (removal of the lipid side chain) by the action of a deacylase enzyme from the filamentous bacterium Actinoplanes utahensis, which catalyzes the cleavage of the linoleoyl side chain;[3] in three subsequent synthetic steps, including a chemical reacylation, the antifungal drug anidulafungin is synthesized.[4]

  1. ^ Denning DW (1997). "Echinocandins and pneumocandins - a new antifungal class with a novel mode of action". J Antimicrob Chemother. 40 (5): 611–614. doi:10.1093/jac/dkf045. PMID 9421307.
  2. ^ Nyfeler R, Keller-Schierlein W (1974). "Metabolites of microorganisms. 143. Echinocandin B, a novel polypeptide-antibiotic from Aspergillus nidulans var. echinulatus: isolation and structural components". Helv Chim Acta. 57 (8): 2459–2477. doi:10.1002/hlca.19740570818. PMID 4613708.
  3. ^ Lei Shao; Jian Li; Aijuan Liu; Qing Chang; Huimin Lin; Daijie Chen (2013). "Efficient Bioconversion of Echinocandin B to Its Nucleus by Overexpression of Deacylase Genes in Different Host Strains". Applied and Environmental Microbiology. 79 (4): 1126–1133. Bibcode:2013ApEnM..79.1126S. doi:10.1128/AEM.02792-12. PMC 3568618. PMID 23220968.
  4. ^ "Anidulafungin EMA Europa" (PDF). Archived from the original (PDF) on 2018-06-19.

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Echinocandin

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Echinocandins are a class of antifungal drugs that inhibit the synthesis of β-glucan in the fungal cell wall via noncompetitive inhibition of the enzyme...

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Echinocandin B

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Echinocandin B, a lipopeptide, is a naturally occurring cyclic hexapeptide with a linoleoyl side chain. It belongs to a class of antifungal agents called...

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Aspergillus nidulans

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ascospores. Anidulafungin is a semisynthetic lipopeptide antifungal drug of echinocandin B subclass, derived from a fermentation product of A. nidulans var. echinulatus...

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Anidulafungin

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Anidulafungin (INN): 42  (trade names Eraxis, Ecalta) is a semisynthetic echinocandin used as an antifungal drug. It was previously known as LY303366. It may...

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Aspergillus cleistominutus

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arugosin A, arugosin B, arugosin C, asperthecin, aspertetronin A, aspertetronin B, echinocandin B, echinocandin C, echinocandin D, epishamixanthone, shamixanthone...

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Aspergillus microthecius

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sterigmatocystin, versicolourin, desferritriacetylfusigen, echinocandin B, echinocandin E, emericellin, emestrin, aurantioemestrin, dethiosecoemestrin...

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Aspergillus quadrilineatus

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sterigmatocystin, versicolourin, desferritriacetylfusigen, echinocandin B & E, variacoxanthone B, emestrin, aurantioemestrin, dethiosecoemestrin, emindol...

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Aspergillus navahoensis

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acid, 6,7,8-trihydroxy-3-methylisocoumarin, desferritriacetylfusigen, echinocandin B, and sterigmatocystin. A. navahoensis has been cultivated on both Czapek...

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Aspergillus rugulosus

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methylbenzaldehyde, 2,4-dihydroxy-6-(hydroxymethyl)-benzaldehyde, echinocandin B, echinocandin C, echinocandin D, epishamixanthone, shamixanthone, 14-Hydroxytajixanthone...

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Pneumocandin B0

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Pneumocandin B0, also known as pneumocandin B0, pneumocandin B(0), and hydroxy echinocandin, is an organic chemical compound with the formula C50H80N8O17...

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Papulacandin B

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Papulacandin B is a papulacandin isolated from a strain of Papularia sphaerosperma. It is a molecule with antifungal activity. Echinocandin Traxler, P.;...

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Candida tropicalis

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peripheral organs. For invasive disease, treatments include amphotericin B, echinocandins, or extended-spectrum triazole antifungals. In the history of fungi...

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Antifungal

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synthesis. Examples include butenafine, naftifine, and terbinafine. Echinocandins inhibit the creation of glucan in the fungal cell wall by inhibiting...

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Invasive candidiasis

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treatment is an echinocandin class antifungal (caspofungin, micafungin, or anidulafungin) given intravenously. Fluconazole, amphotericin B, and other antifungals...

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Aminocandin

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Aminocandin is an echinocandin antifungal. It works by targeting the glucan in fungal cell walls. Andes D, Marchillo K, Lowther J, Bryskier A, Stamstad...

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Fluconazole

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antifungal drugs of class echinocandins, recommended as the first method of treatment against invasive candidiasis. The three echinocandins currently licensed...

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Cilofungin

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Cilofungin (INN) is the first clinically applied member of the echinocandin family of antifungal drugs. It was derived from a fungus in the genus Aspergillus...

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Coccidioides immitis

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structure to fluconazole) and caspofungin (glucan synthesis inhibitor of the echinocandin structural class). However, these drugs have not been FDA approved, and...

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Caspofungin

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Merck & Co., Inc.. It is a member of a class of antifungals termed the echinocandins.[medical citation needed] It works by inhibiting the enzyme (1→3)-β-D-glucan...

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Glucan

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important. They represent a drug target for antifungal medications of the echinocandin class. The following are glucans (The α- and β- and numbers clarify the...

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Candidiasis

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widespread disease, an echinocandin such as caspofungin or micafungin is used. A number of weeks of intravenous amphotericin B may be used as an alternative...

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Ibrexafungerp

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in vivo, against multidrug-resistant pathogens, including azole- and echinocandin-resistant strains. Ibrexafungerp is a triterpenoid antifungal agent....

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Fungemia

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vs non-neutropenic candidemia is treated differently. An intravenous echinocandin such as anidulafungin, caspofungin or micafungin is recommended as first-line...

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Candida auris

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to 35% were reported resistant to amphotericin B; however, most isolates are susceptible to echinocandins. Treatment is complicated because C. auris is...

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Pichia kudriavzevii

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kudriavzevii can be successfully treated with voriconazole, amphotericin B, and echinocandins (micafungin, caspofungin, and anidulafungin).[citation needed] Cacao...

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Mechanism of action

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"New developments and directions in the clinical application of the echinocandins". Archives of Toxicology. 91 (4): 1613–1621. doi:10.1007/s00204-016-1916-3...

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Nakaseomyces glabratus

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resistant to common treatments like fluconazole. N. glabratus resistance to Echinocandin is also increasing, leaving expensive and toxic antifungal treatments...

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Aspergillus pachycristatus

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isolated from soil in Xinjiang in China. It has been reported to produce echinocandins. A. pachycristatus has been cultivated on both Czapek yeast extract...

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