Candicidin
Grundinformationen
- CAS
1403-17-4- Standard-SMILES
CC1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/C(OC2O[C@H](C)[C@@H](O)[C@H](N)[C@@H]2O)CC(O)C(C(=O)O)C(O)CC(=O)CC(O)CC(O)CC(O)CC(=O)CCCC(=O)CC(=O)OC1C(C)CC(C)C(O)CC(=O)c1ccc(N)cc1- InChIKey
OPGSFDUODIJJGF-JBUZINEHSA-N- Summenformel
- C59H84N2O18
- Durchschnittliche Molmasse
- 1.109,3 g/mol
- Monoisotopische Masse
- 1.108,57191383
Überblick
Candicidin D is a 38-membered ring lactone containing seven (E)-double bonds between positions 22 and 35 and substituted by hydroxy groups at positions 9, 11, 13, 17 and 19, oxo groups at positions 3, 7 and 15, a carboxy group at position 18, a 3-amino-3,6-dideoxymannopyranosyloxy group at position 21, a methyl group at position 36 and a 7-(4-aminophenyl)-5-hydroxy-4-methyl-7-oxoheptan-2-yl group at position 37. It is the major component of candicidin, a mixture of antifungal heptaene macrolides obtained from a strain of Streptomyces griseus. It has a role as a bacterial metabolite and an antifungal drug. It is a macrolide antibiotic and a polyene antibiotic.
Namen und Bezeichner
- Bevorzugter Name
- Candicidin
- IUPAC
- (23E,25E,27E,29E,31E,33E,35E)-22-[(3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-38-[7-(4-aminophenyl)-5-hydroxy-4-methyl-7-oxoheptan-2-yl]-10,12,14,18,20-pentahydroxy-37-methyl-2,4,8,16-tetraoxo-1-oxacyclooctatriaconta-23,25,27,29,31,33,35-heptaene-19-carboxylic acid
- Lokaler Name
- Candicidin
- Englischer Name
- Candicidin
- Summenformel
- C21H36O5
- Molmasse
- 368.51
Namen und Synonyme
CANDICIDINCandeptin1403-17-4CandizidinCandicidinaCandicidineCandicidinum48N2IYJ202DTXSID301014435RefChem:56983G01AA04CHEBI:354984
Weitere Namen anzeigen
Candicidin complexcandimonCARBOPRSTLevorinumNSC 94219Canitracin
DTXCID301437025NSC94219NSC-94219215-763-7NSC-759868VanobidCandicidin D1(23E,25E,27E,29E,31E,33E,35E)-22-[(3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-38-[7-(4-aminophenyl)-5-hydroxy-4-methyl-7-oxoheptan-2-yl]-10,12,14,18,20-pentahydroxy-37-methyl-2,4,8,16-tetraoxo-1-oxacyclooctatriaconta-23,25,27,29,31,33,35-heptaene-19-carboxylic acid
Datenbank-Bezeichner
- CAS
1403-17-4- PubChem CID
- 10079874
- DTXSID
DTXSID301014435- ChEMBL
CHEMBL1200647- ChEBI
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 1,8
- Polarare Oberfläche (TPSA)
- 364 Ų
- H-Brücken-Donoren
- 11
- H-Brücken-Akzeptoren
- 20
- Frei drehbare Bindungen
- 10
- Schwere Atome
- 79
- Formalladung
- 0
- Komplexität
- 2.130
Experimentelle und physikochemische Eigenschaften
DrugsPharmaceuticals -> Antibiotics
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Physikochemische Eigenschaften
- Siedepunkt
- 878.79 °C · 878.79°C (rough estimate)
- Dichte
- 1.11 · 1.1100 (rough estimate)
- Brechungsindex
- 1.62 · 1.6200 (estimate)
- storage temp.
- -20 °C · Store at -20°C
- Löslichkeit
- 4.9 · DMSO:4.9(Max Conc. mg/mL);10.08(Max Conc. mM)Ethanol:12.5(Max Conc. mg/mL);25.72(Max Conc. mM)
- Aggregatzustand
- A solid
- Farbe
- Light yellow to light brown
- Biologische Quelle
- Streptomyces griseus
- Wasserlöslichkeit
- 13.47 g/L · 13.47g/L(21 ºC)
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
Sicherheitsdaten
- wgk
- WGK 3
- Toxizität
- LD50 i.p. in mice: 14 mg/kg (Vining)
- Speicherklasse
- 11 - Combustible Solids
Chemie und Industrie
Pharmakologische Informationen
ATC Code
G - Genito urinary system and sex hormones
QG - Genito urinary system and sex hormones
Pharmacodynamics
Candicidin is a polyene antifungal antibiotic produced by a strain of <i>Streptomyces griseus</i>. It is especially effective against <i>Candida albicans</i> (more effective than amphotericin B), and is administered intravaginally in the treatment of vulvovaginal candidiasis.
Mechanism of Action
Ergosterol, the principal sterol in the fungal cytoplasmic membrane, is the target site of action of Candicidin. Candicidin binds irreversibly to ergosterol, resulting in disruption of membrane integrity and ultimately cell death. There is some evidence that the binding site in the cell wall may be to fatty acids or fatty acid esters and that this binding capacity must be satisfied before candicidin can bring about its lethal effect by binding to sterol in the cell membrane.
MeSH Pharmacological Classification
Substances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues.
Substances that inhibit the growth or reproduction of BACTERIA.
Anwendungen
VerwendenCandicidin is a macrocyclic heptaene antifungal complex produced by Streptomyces griseus and isolated by Lechevalier and colleagues in 1953. The candicidin complex comprises analogues A, B, C and D, with candicidin D as the major component. Candicidin is active against fungi, in particular Candida albicans, and is used clinically to treat vaginal candidiasis. Like all polyene antifungal metabolites, candicidin acts by binding to ergosterol and disrupting the fungal membrane.
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