Structure via PubChem · Public domain (PubChem)
cilofungin
Sign in to saveAlso known as LY-121019, LY121019
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).
Chemical data
- Formula
- C49H71N7O17
- Molecular weight
- 1030.1 g/mol
- IUPAC name
- 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-hexazatricyclo[22.3.0.09,13]heptacosan-18-yl]-4-octoxybenzamide
- SMILES
- CCCCCCCCOC1=CC=C(C=C1)C(=O)N[C@H]2C[C@H]([C@H](NC(=O)[C@@H]3[C@H]([C@H](CN3C(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H]4C[C@H](CN4C(=O)[C@@H](NC2=O)[C@@H](C)O)O)[C@@H]([C@H](C5=CC=C(C=C5)O)O)O)[C@@H](C)O)C)O)O)O
- InChIKey
- ZKZKCEAHVFVZDJ-MTUMARHDSA-N
- XLogP
- 0.7
- Polar surface area
- 377 Ų
- H-bond donors
- 14
- H-bond acceptors
- 17
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
98 papers- Cilofungin (LY121019) shows nonlinear plasma pharmacokinetics and tissue penetration in rabbits.Antimicrobial agents and chemotherapy · 1990
- Cilofungin (LY121019) inhibits Candida albicans (1-3)-beta-D-glucan synthase activity.Antimicrobial agents and chemotherapy · 1988
- Echinocandin antifungal drugs.Lancet (London, England) · 2003
- Use of cilofungin as direct fluorescent probe for monitoring antifungal drug-membrane interaction.Antimicrobial agents and chemotherapy · 1994
- In-vitro activity of cilofungin (LY121019) in comparison with amphotericin B.The Journal of antimicrobial chemotherapy · 1989
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 1029.491
Show 6 more facts
- chemical formula
- C₄₉H₇₁N₇O₁₇
- canonical SMILES
- CCCCCCCCOC1=CC=C(C=C1)C(=O)NC2CC(C(NC(=O)C3C(C(CN3C(=O)C(NC(=O)C(NC(=O)C4CC(CN4C(=O)C(NC2=O)C(C)O)O)C(C(C5=CC=C(C=C5)O)O)O)C(C)O)C)O)O)O
- isomeric SMILES
- CCCCCCCCOC1=CC=C(C=C1)C(=O)N[C@H]2C[C@H]([C@H](NC(=O)[C@@H]3[C@H]([C@H](CN3C(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H]4C[C@H](CN4C(=O)[C@@H](NC2=O)[C@@H](C)O)O)[C@@H]([C@H](C5=CC=C(C=C5)O)O)O)[C@@H](C)O)C)O)O)O
- World Health Organisation international non-proprietary name
- cilofungin
- subject has role
- antifungal
- Commons category
- Cilofungin
Sources (1)
via Wikidata · CC0
~1 min read
Encyclopedic overview
1 sectionsContents
- References
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 ==
Excerpted from Wikipedia’s “cilofungin” article, available under the CC BY-SA 4.0 licence.