Pirlimycin

Synonym(s): U-57930E  |  U57930E  |  U 57930E

Class: Lincosamide

Spectrum of activity:	Gram-positive
Details of activity:	Active against Staphylococcus aureus, Streptococcus pyogenes, Streptococcus pneumoniae, beta-haemolytic Streptococcus, and Enterococcus spp.; protein synthesis inhibitor
Description:	Semi-synthetic compound; analogue of clindamycin; shows superior activity to clindamycin in mice infected with Staphylococcus aureus, Streptococcus pyogenes, or Streptococcus pneumoniae
Institute where first reported:	The Upjohn Co., Kalamazoo, Michigan
Year first mentioned:	1982
Development status:	Experimental

Chemical structure(s):
Canonical SMILES:	CC[C@@H]1CCN[C@@H](C1)C(=O)N[C@H]([C@H](C)Cl)[C@@H]2[C@@H]([C@@H]([C@H]([C@H](O2)SC)O)O)O
Isomeric SMILES:	CC[C@@H]1CCN[C@@H](C1)C(=O)N[C@@H]([C@@H]2[C@@H]([C@@H]([C@H]([C@H](O2)SC)O)O)O)[C@H](C)Cl
InChI:	InChI=1S/C17H31ClN2O5S/c1-4-9-5-6-19-10(7-9)16(24)20-11(8(2)18)15-13(22)12(21)14(23)17(25-15)26-3/h8-15,17,19,21-23H,4-7H2,1-3H3,(H,20,24)/t8-,9+,10-,11+,12-,13+,14+,15+,17+/m0/s1
InChI Key:	HBJOXQRURQPDEX-MHXMMLMNSA-N
Structure link:	https://pubchem.ncbi.nlm.nih.gov/compound/157385

External links:
Guide to Pharmacology:	pirlimycin
Main Source:	https://journals.asm.org/doi/10.1128/aac.21.6.902
Citation:	https://journals.asm.org/doi/10.1128/aac.22.2.334