Chemistry:Quinupristin

Quinupristin

Pharmacokinetic data
Elimination half-life	3.1 hours
Identifiers
IUPAC name N-{(6R,9S,10R,13S,15aS,18R,22S,24aS)-18- {[(3S)-1-azabicyclo[2.2.2]oct-3-ylthio]methyl}-22-[4-(dimethylamino)benzyl]- 6-ethyl-10,23-dimethyl-5,8,12,15,17,21,24-heptaoxo-13-phenyldocosahydro-12H- pyrido[2,1-f]pyrrolo-[2,1-l][1,4,7,10,13,16] oxapentaazacyclononadecin-9-yl}-3- hydroxypyridine-2-carboxamide
CAS Number	120138-50-3
PubChem CID	5388937
ChemSpider	4470884
UNII	23OW28RS7P
ChEMBL	ChEMBL1200649
Chemical and physical data
Formula	C53H67N9O10S
Molar mass	1022.23 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC[C@@H]1C(=O)N2CCC[C@H]2C(=O)N([C@H](C(=O)N3C[C@H](C(=O)C[C@H]3C(=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 Key:WTHRRGMBUAHGNI-LCYNINFDSA-N

Quinupristin is a streptogramin B antibiotic, used in combination with dalfopristin under the trade name Synercid. It has activity against Gram-positive and atypical bacteria but not Gram-negative bacteria. It inhibits bacterial protein synthesis. The combination of quinupristin and dalfopristin is not active against Enterococcus faecalis and needs to be given in combination with other antibacterials for mixed infections that involve Gram-negative organisms.