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Cilofungin

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Cilofungin
Names
IUPAC name N--11,20,21,25-tetrahydroxy-3,15-bis(1-hydroxyethyl)-26-methyl-2,5,8,14,17,23-hexaoxo-1,4,7,13,16,22-hexaazatricycloheptacosan-18-yl]-4-(octyloxy)benzamide
Other names 1--L-ornithine]echinocandin B
(4R,5R)-4,5-Dihydroxy-N--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
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
MeSH Cilofungin
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C49H71N7O17/c1-5-6-7-8-9-10-19-73-31-17-13-28(14-18-31)42(65)50-32-21-34(61)45(68)54-47(70)38-39(62)24(2)22-56(38)49(72)36(26(4)58)52-46(69)37(41(64)40(63)27-11-15-29(59)16-12-27)53-44(67)33-20-30(60)23-55(33)48(71)35(25(3)57)51-43(32)66/h11-18,24-26,30,32-41,45,57-64,68H,5-10,19-23H2,1-4H3,(H,50,65)(H,51,66)(H,52,69)(H,53,67)(H,54,70)/t24-,25+,26+,30+,32-,33-,34+,35-,36-,37-,38-,39-,40-,41-,45+/m0/s1Key: ZKZKCEAHVFVZDJ-MTUMARHDSA-N
  • InChI=1/C49H71N7O17/c1-5-6-7-8-9-10-19-73-31-17-13-28(14-18-31)42(65)50-32-21-34(61)45(68)54-47(70)38-39(62)24(2)22-56(38)49(72)36(26(4)58)52-46(69)37(41(64)40(63)27-11-15-29(59)16-12-27)53-44(67)33-20-30(60)23-55(33)48(71)35(25(3)57)51-43(32)66/h11-18,24-26,30,32-41,45,57-64,68H,5-10,19-23H2,1-4H3,(H,50,65)(H,51,66)(H,52,69)(H,53,67)(H,54,70)/t24-,25+,26+,30+,32-,33-,34+,35-,36-,37-,38-,39-,40-,41-,45+/m0/s1Key: ZKZKCEAHVFVZDJ-MTUMARHDBF
SMILES
  • O=C2N5(C(=O)N(O)(O)C(NC(=O)c1ccc(OCCCCCCCC)cc1)C(=O)N(C(=O)N4(C(=O)N(C(=O)N2(O)C)(O)(O)c3ccc(O)cc3)C(O)C4)(O)C)(O)(C)C5
Properties
Chemical formula C49H71N7O17
Molar mass 1030.12474
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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. It accomplishes this by interfering with an invading fungus' ability to synthesize the cell wall (specifically, it inhibits the synthesis of (1→3)-β-D-glucan).

References

  1. ^ "International Nonproprietary Names for Pharmaceutical Substances (INN). Recommended International Nonproprietary Names (Rec. INN): List 29" (PDF). World Health Organization.
  2. Hudler, George (1998). Magical Mushrooms, Mischievous Molds. Princeton, New Jersey: Princeton University Press. pp. 112. ISBN 978-0-691-07016-2.
Antifungals (D01 and J02)
Wall/
membrane
Ergosterol
inhibitors
Azoles (lanosterol 14α-
demethylase inhibitors)
Imidazoles
  • Systemic: ketoconazole
Triazoles
Thiazoles
Polyene antimycotics
(ergosterol binding)
Squalene monooxygenase
inhibitors
Allylamines
Benzylamines
Others
β-glucan synthase
inhibitors
Intracellular
Pyrimidine analogues/
thymidylate synthase inhibitors
Mitotic inhibitors
Aminoacyl tRNA synthetase inhibitors
Others
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