Lipoxamycin hemisulfate

Cas No.:	11075-87-9
Chemical Name:	Lipoxamycin hemisulfate
SMILES:	OC[C@@H](C(N(CCC(CCCCCCC(CCCC(C)C)=O)=O)O)=O)N.OC[C@H](N)C(N(CCC(CCCCCCC(CCCC(C)C)=O)=O)O)=O.OS(O)(=O)=O
Formula:	C19H36N2O5.1/2H2O4S
M.Wt:	421.54
Purity:	>98%
Sotrage:	Powder-20°C3 years4°C2 yearsIn solvent-80°C6 months-20°C1 month
Publication:	[1]. S M Mandala, et al. Inhibition of Serine Palmitoyl-Transferase Activity by Lipoxamycin. J Antibiot (Tokyo). 1994 Mar;47(3):376-9. [2]. H A Whaley. The Structure of Lipoxamycin, a Novel Antifungal Antibiotic. J Am Chem Soc. 1971 Jul 28;93(15):3767-9.

Description:	Lipoxamycin hemisulfate is an antifungal antibiotic and a potent serine palmitoyltransferase inhibitor with an IC50 of 21 nM[1][2].
Target:	Serine palmitoyltransferase[1]
In Vivo:	Lipoxamycin is highly toxic in mice when applied subeutaneously or topically. Toxicity may be mechanism based, since studies with a Chinese hamster ovary cell mutant have shown that the serine palmitoyltransferase is an essential enzymein mammalian cells[1].
In Vitro:	Lipoxamycin has antifungal activity against a panel of humanpathogenic fungi with better potency against some of the Candida species (MIC values, 0.25-16 µg/mL). Cryptococcus neoformans is the most sensitive organism, followed by various species of Candida. Other filamentous fungi are sensitive to the Lipoxamycin in disk diffusion assays[1]. Lipoxamycin has a long alkyl chain and an amino-containing polar head group. Lipoxamycin is on the same order of potency as the sphingofungins and also have potent activity against the mammalianenzyme[1].
References:	[1]. S M Mandala, et al. Inhibition of Serine Palmitoyl-Transferase Activity by Lipoxamycin. J Antibiot (Tokyo). 1994 Mar;47(3):376-9. [2]. H A Whaley. The Structure of Lipoxamycin, a Novel Antifungal Antibiotic. J Am Chem Soc. 1971 Jul 28;93(15):3767-9.