Quinupristin/dalfopristin: Difference between revisions

Quinupristin/dalfopristin
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;
Chemical and physical data
Formula	C53H67N9O10S
Molar mass	1022.24 g/mol g·mol−1

Quinupristin/dalfopristin
Combination of
Quinupristin	Antibiotic
Dalfopristin	Antibiotic
Clinical data
Pregnancy; category	B (U.S.);
Routes of; administration	IV
ATC code	J01FG02 (WHO) ;
Legal status
Legal status	℞-only (U.S.);
Identifiers
CAS Number	126602-89-9;
PubChem CID	23724510;
ChemSpider	21106373 ;
ChEMBL	ChEMBL1200649 ;
Chemical and physical data
	InChI InChI=1S/C53H67N9O10S.C34H50N4O9S/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;1-7-37(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/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);9-12,18,21-22,24-25,28,31-32,39H,7-8,13-17,19-20H2,1-6H3,(H,35,41)/b;10-9+,12-11+,23-18+/t31-,35+,37-,38+,39+,40+,43-,44+,45+;24-,25-,28-,31-,32-/m11/s1 ; Key:PPKJUHVNTMYXOD-PZGPJMECSA-N ;
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Revision as of 04:13, 7 August 2011

Quinupristin/dalfopristin (trade name Synercid) is a combination of two antibiotics used to treat infections by staphylococci and by vancomycin-resistant Enterococcus faecium.

Quinupristin and dalfopristin are both streptogramin antibiotics, derived from pristinamycin. Quinupristin is derived from pristinamycin IA; dalfopristin from pristinamycin IIA. They are combined in a weight-to-weight ratio of 30% quinupristin to 70% dalfopristin.

Administration

Intravenous, usually 7.5 mg/kg every 8–12 hours

Mechanism of action

Quinupristin and dalfopristin are protein synthesis inhibitors in a synergestic manner. While each of the two is only a bacteriostatic agent, the combination shows bactericidal activity.

Dalfopristin binds to the 23S portion of the 50S ribosomal subunit, and changes the conformation of it, enhancing the binding of quinupristin^[1] by a factor of about 100. In addition, it inhibits peptidyl transfer.^[1]
Quinupristin binds to a nearby site on the 50S ribosomal subunit and prevents elongation of the polypeptide,^[1] as well as causing incomplete chains to be released.^[1]

Pharmacokinetics

Clearance by the liver, half-life 1–3 hours (with persistence of effects for 9–10 hours).

Side effects

Joint aches (arthralgia) or muscle aches (myalgia)
Nausea, diarrhea or vomiting
Rash or itching
Headache
Phlebitis
Hyperbilirubinemia

Drug interactions

Inhibits P450 and enhances the effects of terfenadine, astemizole, indinavir, midazolam, Ca channel blockers, warfarin, cisapride and cyclosporine.

References

^ ^a ^b ^c ^d Page 212 in: Title: Hugo and Russell's pharmaceutical microbiology Authors: William Barry Hugo, Stephen P. Denyer, Norman A. Hodges, Sean P. Gorman Edition: 7, illustrated Publisher: Wiley-Blackwell, 2004 ISBN: 0632064676, 9780632064670 Length: 481 pages

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 | ATC_suffix        = FG02
 | PubChem           = 23724510
+| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
 | DrugBank          =
 | pregnancy_AU      =  <!-- A / B1 / B2 / B3 / C / D / X -->