Filipin

Title: Filipin
CAS Registry Number: 11078-21-0
Additional Names: Filimarisin
Manufacturers' Codes: U-5956; NSC-3364
Literature References: Polyene antibiotic complex containing at least eight pentaene compounds, which has been resolved into three pure components, filipin II, III (major), and IV, which differ in the number of hydroxyl groups present (8, 9, 9, resp.) and filipin I, a mixture of at least 5 components. Described as a single entity in the earlier literature. Initial isolation from Streptomyces filipenensis in Philippine soil: Whitfield et al., J. Am. Chem. Soc. 77, 4799 (1955). Early structural work: Dhar et al., Proc. Chem. Soc. London 1960, 310; Djerassi et al., Tetrahedron Lett. 1961, 383; Golding, Rickards, ibid. 1964, 2615; Dhar et al., J. Chem. Soc. 1964, 842; Ceder, Ryhage, Acta Chem. Scand. 18, 588 (1964). Separation of filipin complex into components: Bergy, Eble, J. Antibiot. 23, 414 (1970); see also Rickards et al., ibid. 603. Mechanism of action: R. W. Holz in Antibiotics vol. 5, pt. 2, F. E. Hahn, Ed. (Springer-Verlag, New York, 1979) pp 313-340. Filipin also interacts specifically with 3b-hydroxysterols (e.g. cholesterol): P. M. Elias et al., J. Histochem. Cytochem. 27, 1247 (1979); see also N. J. Severs, H. J. Simons, Nature 303, 637 (1983).
Properties: Yellow, feathery needles from chloroform, mp 195-205°. Sensitive to air. [a]D22 -148.3° (c = 0.89 in methanol). uv max (methanol): 322, 338, 355 nm (E1%1cm 910, 1360, 1330). Freely sol in DMF, pyridine. Also sol in 95% ethanol, methanol, butanol, isopropanol, glacial acetic acid, ether. Practically insol in water, chloroform.
Melting point: mp 195-205°
Optical Rotation: [a]D22 -148.3° (c = 0.89 in methanol)
Absorption maximum: uv max (methanol): 322, 338, 355 nm (E1%1cm 910, 1360, 1330)
Derivative Type: Filipin III
CAS Registry Number: 480-49-9
Additional Names: 4,6,8,10,12,14,16,27-Octahydroxy-3- (1-hydroxyhexyl)-17,28-dimethyloxacyclooctacosa-17,19,21,23,25-pentaen-2-one; 15-deoxylagosin
Molecular Formula: C35H58O11
Molecular Weight: 654.83
Percent Composition: C 64.20%, H 8.93%, O 26.88%
Properties: Isomeric with filipin IV. Crystals from propanol, mp 163-180° (Bergy, Eble). [a]D25 -245° (c = 0.8 in DMF). uv max (methanol): 243, 308, 321, 337, 354 nm (E1%1cm 62, 413, 851, 1368, 1343).
Melting point: mp 163-180° (Bergy, Eble)
Optical Rotation: [a]D25 -245° (c = 0.8 in DMF)
Absorption maximum: uv max (methanol): 243, 308, 321, 337, 354 nm (E1%1cm 62, 413, 851, 1368, 1343)
Use: Produces arthritis rapidly in rabbits: Pras, Weissman, Drug Trade News, July 4, 1966, p 40; as a sterol probe in freeze-fracture cytochemistry.
Therap-Cat: Antifungal.
Keywords: Antifungal (Antibiotics); Polyenes.
Filixic Acids Finasteride Fingolimod Fipexide Firefly Luciferin

Filipin
FilipinIII.png
Identifiers
CAS number 480-49-9 YesY
PubChem 6433194
ChemSpider 21106312 YesY
KEGG D04186 YesY
MeSH Filipin
Jmol-3D images Image 1
Properties
Molecular formula C35H58O11
Molar mass 654.83 g mol−1
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Filipin is a chemical compound. It was isolated by chemists at the Upjohn company in 1955 from the mycelium and culture filtrates of a previously unknown actinomycete, Streptomyces filipinensis, that was discovered in a soil sample collected in the Philippine Islands. Thus the name Filipin. The isolate possessed potent antifungal activity. It was identified as a polyene macrolide based on its characteristic UV-Vis and IR spectra.