{{Drugbox
, IUPAC_name = ''N''-
{(6''R'',9''S'',10''R'',13''S'',15a''S'',18''R'',22''S'',24a''S'')-18-
{
3''S'')-1-azabicyclo[2.2.2ct-3-ylthio.html" ;"title=".2.2.html" ;"title="3''S'')-1-azabicyclo[2.2.2">3''S'')-1-azabicyclo[2.2.2ct-3-ylthio">.2.2.html" ;"title="3''S'')-1-azabicyclo[2.2.2">3''S'')-1-azabicyclo[2.2.2ct-3-ylthioethyl}-22-[4-(dimethylamino)benzyl]-
6-ethyl-10,23-dimethyl-5,8,12,15,17,21,24-heptaoxo-13-phenyldocosahydro-12''H''-
pyrido[2,1-''f'']pyrrolo-[2,1-''l''][1,4,7,10,13,16] oxapentaazacyclononadecin-9-yl}-3-
hydroxypyridine-2-carboxamide
, image = Quinupristin.png
, CAS_number = 120138-50-3
, UNII_Ref = {{fdacite, correct, FDA
, UNII = 23OW28RS7P
, ATC_prefix =
, ATC_suffix =
, PubChem = 5388937
, DrugBank =
, ChEMBL = 1200649
, ChemSpiderID = 4470884
, smiles = CC
@@HC(=O)N2CCC
@HC(=O)N(
@HC(=O)N3C
@HC(=O)C
@HC(=O)N
@HC(=O)O
@@H @@HC(=O)N1)NC(=O)C4=C(C=CC=N4)O)C)C5=CC=CC=C5)CS
@@HCN7CCC6CC7)CC8=CC=C(C=C8)N(C)C)C
, StdInChI = 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
, StdInChIKey = WTHRRGMBUAHGNI-LCYNINFDSA-N
, C=53, H=67, N=9, O=10, S=1
, bioavailability =
, protein_bound =
, metabolism =
, elimination_half-life = 3.1 hours
, excretion =
, pregnancy_AU =
, pregnancy_US =
, pregnancy_category=
, legal_AU =
, legal_CA =
, legal_UK =
, legal_US =
, legal_status =
, routes_of_administration =
Quinupristin is a
streptogramin B antibiotic, used in combination with
dalfopristin
Dalfopristin is a semi-synthetic streptogramin antibiotic analogue of ostreogyrcin A ( virginiamycin M, pristinamycin IIA, streptogramin A). The combination quinupristin/dalfopristin (marketed under the trade name Synercid) was brought to th ...
under the trade name
Synercid. It has activity against
Gram-positive
In bacteriology, gram-positive bacteria are bacteria that give a positive result in the Gram stain test, which is traditionally used to quickly classify bacteria into two broad categories according to their type of cell wall.
Gram-positive bact ...
and
atypical bacteria but not
Gram-negative bacteria
Gram-negative bacteria are bacteria that do not retain the crystal violet stain used in the Gram staining method of bacterial differentiation. They are characterized by their cell envelopes, which are composed of a thin peptidoglycan cell wall ...
. It inhibits bacterial protein synthesis. The combination of quinupristin and dalfopristin is not active against ''
Enterococcus faecalis
''Enterococcus faecalis'' – formerly classified as part of the group D ''Streptococcus'' system – is a Gram-positive, commensal bacterium inhabiting the gastrointestinal tracts of humans. Like other species in the genus ''Enterococcus'', ''E ...
'' and needs to be given in combination with other antibacterials for mixed infections that involve Gram-negative organisms.
Antibiotics