Candicidin Struktur

Candicidin

Bezeichnung:Candicidin

CAS-Nr1403-17-4

Englisch Name:Candicidin

CBNumberCB6501392

SummenformelC21H36O5

Molgewicht368.51

MOL-Datei1403-17-4.mol

Synonyma

Candicidin

Candicidin physikalisch-chemischer Eigenschaften

Siedepunkt	878.79°C (rough estimate)
Dichte	1.1100 (rough estimate)
Brechungsindex	1.6200 (estimate)
storage temp.	Store at -20°C
Löslichkeit	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
Biologische Quelle	Streptomyces griseus
Wasserlöslichkeit	13.47g/L(21 ºC)

Sicherheit

Toxizität

LD50 i.p. in mice: 14 mg/kg (Vining)

Candicidin Chemische Eigenschaften,Einsatz,Produktion Methoden

Originator
Candeptin,Schmidt,US,1964
Verwenden
Candicidin 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.
Definition
ChEBI: 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.
Manufacturing Process
Hubert Lechevalier et al were the first to describe "Candicidin, a New Antifungal Antibiotic," in Mycologia XLV, No. 2, 155-171, March-April 1953. They produced candicidin by growing a culture of the organism streptomyces griseus No. 3570 on a yeast-glucose medium, isolating a "crude candicidin" from the resulting broth and purifying it. An improved extraction and purification method is described in US Patent 2,872,373 and is shown in the flow diagram below.
Another extraction and separation process is described in US Patent 2,992,162.
Trademarks
Vanobid (Sanofi Aventis).
Therapeutic Function
Topical antifungal

Candicidin Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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