Catalog Number | R003447 |
CAS Number | 6834-98-6 |
Molecular Formula | C35H58O12
|
Purity | 95% |
Target | Antibiotic |
Solubility | Soluble in DMSO |
Storage | -20°C |
Overview of Clinical Research | <span style="color:#000000;"><span style="font-family:arial,helvetica,sans-serif;"><span style="font-size:12px;">Lagosin( Pentamycin) acts as a c<span style="font-variant-ligatures: normal; orphans: 2; widows: 2;">ell membrane permeability enhancer. The p</span><span style="font-variant-ligatures: normal; orphans: 2; widows: 2;">reclinical study for Vaginitis (LMV 602) in Switzerland (Vaginal) discontinued in 2015. </span></span></span></span>
<h1 class="document__title hotspot-element" id="drugNameID" style="font-size: 3rem; margin: 7px 0px 14px; font-family: Georgia, "New Century Schoolbook", "Nimbus Roman No9 L", serif; font-weight: normal; letter-spacing: 0.02em; line-height: 1.2; word-break: break-word; color: rgb(51, 51, 51); font-variant-ligatures: normal; orphans: 2; widows: 2;">
</h1>
|
IUPAC Name | (3R,4S,6S,8S,10R,12R,14R,15R,16R,17E,19E,21E,23E,25E,27S,28R)-4,6,8,10,12,14,15,16,27-nonahydroxy-3-[(1R)-1-hydroxyhexyl]-17,28-dimethyl-1-oxacyclooctacosa-17,19,21,23,25-pentaen-2-one |
InChI | InChI=1S/C35H58O12/c1-4-5-11-16-29(41)32-30(42)20-26(38)18-24(36)17-25(37)19-27(39)21-31(43)34(45)33(44)22(2)14-12-9-7-6-8-10-13-15-28(40)23(3)47-35(32)46/h6-10,12-15,23-34,36-45H,4-5,11,16-21H2,1-3H3/b7-6+,10-8+,12-9+,15-13+,22-14+/t23-,24+,25-,26+,27-,28+,29-,30+,31-,32-,33-,34-/m1/s1 |
InChIKey | AGJUUQSLGVCRQA-SWOUQTJZSA-N |
SMILES | CCCCCC(C1C(CC(CC(CC(CC(CC(C(C(C(=CC=CC=CC=CC=CC(C(OC1=O)C)O)C)O)O)O)O)O)O)O)O)O |
Reference | 1. Proc Natl Acad Sci U S A. 1972 Dec;69(12):3795-9.<br />
Fluorescence studies of the binding of the polyene antibiotics filipin 3, amphotericin B, nystatin, and lagosin to cholesterol.<br />
Bittman R, Fischkoff SA.<br />
The interactions of filipin III, amphotericin B, nystatin, and lagosin with sterols in aqueous suspension and in vesicles were followed by fluorescence excitation spectra and by measurement of polarized fluorescence intensities. The equilibrium constants for association of the polyene antibiotics with aqueous suspensions of cholesterol follow the order filipin III > amphotericin B > nystatin > lagosin, in agreement with the order reported for the extent of damage these antibiotics cause in natural and model membranes. Fluorescence polarization measurements show that hydrophobic forces are primarily responsible for the formation of the complexes. Filipin III undergoes a large enhancement in fluorescence polarization on binding to aqueous suspensions of cholesterol and epi-cholesterol, and to vesicles of lecithin-cholesterol, lecithin-beta-cholestanol, and lecithinergosterol. Small increases in polarization occur on interaction of filipin III with vesicles derived from lecithin and epi-cholesterol, thiocholesterol, and androstan-3beta-ol. Amphotericin B undergoes a relatively constant enhancement in fluorescence polarization on interaction with the various lecithin-sterol vesicles used and does not display the selectivity exhibited by filipin III. It is suggested that filipin III serves as a probe of lecithin-sterol interaction.<br />
<br />
2. J Antibiot (Tokyo). 1982 Aug;35(8):988-96.<br />
Physicochemical and biological comparison of polyene macrolide antibiotics fungichromin, lagosin and cogomycin.<br />
Pandey RC, Guenther EC, Aszalos AA, Brajtburg J.<br />
The three polyene macrolide antibiotics, fungichromin, lagosin, and cogomycin, previously described as having some stereochemical differences at one or more centers, are shown by countercurrent distribution, high-performance liquid chromatography, carbon-13 nuclear magnetic resonance spectroscopy, circular dichroism, and biological studies to be identical in all respects, including stereochemical aspects. The differences observed earlier in their properties have now been ascribed to varying amounts of impurities, which are separable by high-performance liquid chromatography. All three antibiotics contain one major and several minor components.
|