Quinupristin/dalfopristin (Synercid)

Synonym(s): RP 59500

Class: Streptogramin

Spectrum of activity:	Gram-positive
Details of activity:	Binds to the bacterial 50S ribosomal subunit and inhibits the elongation process of protein synthesis; against M. pneumoniae, activity was similar to erythromycin, roxithromycin and clarithromycin
Description:	Pristinamycin-derivative. Intravenous application. Mixture of 30% quinupristin (derived from pristinamycin IA) to 70% dalfopristin (derived from pristinamycin IIA);Georgopoulos A, Breyer S, Feistauer S, et al. Bactericidal effect of RP 59500 against staphylococci wth different pheotypes in a diffusion chamber model in rabbits. 32nd-Intersci-Conf-Antimicrobial-Agents-Chemother 1992; 329; off-patent
Institute where first reported:	Rhone-Poulenc Rorer, Collegeville, Penn; St Marianna University
Year first mentioned:	1989
Highest developmental phase:	Approved by FDA in 1999
Development status:	Approved
Reason Dropped:	Discontinued in most countries

Chemical structure(s):
Canonical SMILES:	CCN(CC)CCS(=O)(=O)[C@@H]1CCN2C1C(=O)O[C@H](C(C)C)[C@H](C)/C=C/C(=O)NC/C=C/C(=C/[C@H](CC(=O)CC3=NC(=CO3)C2=O)O)/C
Isomeric SMILES:	CCN(CC)CCS(=O)(=O)[C@@H]1CCN2C1C(=O)O[C@@H]([C@@H](/C=C/C(=O)NC/C=C/C(=C/[C@H](CC(=O)CC3=NC(=CO3)C2=O)O)/C)C)C(C)C
InChI:	InChI=1S/C34H50N4O9S/c1-7-37(8-2)16-17-48(44,45)28-13-15-38-31(28)34(43)47-32(22(3)4)24(6)11-12-29(41)35-14-9-10-23(5)18-25(39)19-26(40)20-30-36-27(21-46-30)33(38)42/h9-12,18,21-22,24-25,28,31-32,39H,7-8,13-17,19-20H2,1-6H3,(H,35,41)/b10-9+,12-11+,23-18+/t24-,25-,28-,31?,32-/m1/s1
InChI Key:	SUYRLXYYZQTJHF-RJUFQJKESA-N
Canonical SMILES:	CC[C@@H]1C(=O)N2CCC[C@H]2C(=O)N(C)[C@@H](CC3=CC=C(C=C3)N(C)C)C(=O)N4CC(CS[C@@H]5CN6CCC5CC6)C(=O)CC4C(=O)N[C@@H](C7=CC=CC=C7)C(=O)O[C@H](C)[C@@H](C(=O)N1)NC(=O)C8=NC=CC=C8O
Isomeric SMILES:	CC[C@@H]1C(=O)N2CCC[C@H]2C(=O)N([C@H](C(=O)N3CC(C(=O)CC3C(=O)N[C@H](C(=O)O[C@@H]([C@@H](C(=O)N1)NC(=O)C4=C(C=CC=N4)O)C)C5=CC=CC=C5)CS[C@@H]6CN7CCC6CC7)CC8=CC=C(C=C8)N(C)C)C
InChI:	InChI=1S/C53H67N9O10S/c1-6-37-50(68)61-23-11-14-38(61)51(69)59(5)40(26-32-16-18-36(19-17-32)58(3)4)52(70)62-28-35(30-73-43-29-60-24-20-33(43)21-25-60)42(64)27-39(62)47(65)57-45(34-12-8-7-9-13-34)53(71)72-31(2)44(48(66)55-37)56-49(67)46-41(63)15-10-22-54-46/h7-10,12-13,15-19,22,31,33,35,37-40,43-45,63H,6,11,14,20-21,23-30H2,1-5H3,(H,55,66)(H,56,67)(H,57,65)/t31-,35?,37-,38+,39?,40+,43-,44+,45+/m1/s1
InChI Key:	WTHRRGMBUAHGNI-MJWHERSYSA-N
Structure link:	https://pubchem.ncbi.nlm.nih.gov/compound/23724510

External links:
Guide to Pharmacology:	dalfopristin
Main Source:	https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1312217/
Citation:	https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4135883/