Difficidin

Class: Protein synthesis inhibitor

Spectrum of activity:	Gram-positive  &  Gram-negative
Details of activity:	Broad Spectrum against Aerobic and Anaerobic bacteria (2)
Description:	macrocyclic polyene lactone phosphate ester
Institute where first reported:	Merck & Co., USA
Year first mentioned:	1986
Highest developmental phase:	Preclinical
Development status:	Inactive
Reason Dropped:	Unstable at different pH's and easily oxidated (1). Additionally, little in vivo activity in mice model when administered subcutaneously but was effective through intraperitoneal injection suggesting metabolism of compound and hence preventing its transloction to site of infection (2).

Chemical structure(s):
Canonical SMILES:	C=C/C=C(\C)/CCC1C/C=C/C=C(\C)/C(CCC/C=C\C=C/C=C/CC(C)C(=C)CC(=O)O1)OP(=O)(O)O
Isomeric SMILES:	CC1C/C=C/C=C\C=C/CCCC(/C(=C/C=C/CC(OC(=O)CC1=C)CC/C(=C/C=C)/C)/C)OP(=O)(O)O
InChI:	InChI=1S/C31H45O6P/c1-6-17-25(2)22-23-29-20-16-15-19-27(4)30(37-38(33,34)35)21-14-12-10-8-7-9-11-13-18-26(3)28(5)24-31(32)36-29/h6-11,13,15-17,19,26,29-30H,1,5,12,14,18,20-24H2,2-4H3,(H2,33,34,35)/b9-7-,10-8-,13-11+,16-15+,25-17+,27-19+
InChI Key:	ZUWUQYGHRURWCL-XUIVTPDHSA-N
Structure link:	https://pubchem.ncbi.nlm.nih.gov/compound/6438594

External links:
Guide to Pharmacology:	difficidin
Citations:	https://www.jstage.jst.go.jp/article/antibiotics1968/40/12/40_12_1682/_pdf http://www.ncbi.nlm.nih.gov/pubmed/3123448