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Quinupristin/dalfopristin

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Revision as of 07:48, 24 October 2011 by CheMoBot (talk | contribs) (Updating {{drugbox}} (changes to verified fields - updated 'UNII_Ref', 'ChEBI_Ref', 'KEGG_Ref', 'CAS_number_Ref') per Chem/Drugbox validation (report errors or bugs))(diff) ← Previous revision | Latest revision (diff) | Newer revision → (diff) Pharmaceutical compound
Quinupristin/dalfopristin
Combination of
QuinupristinAntibiotic
DalfopristinAntibiotic
Clinical data
Pregnancy
category
Routes of
administration		IV
ATC code
Legal status
Legal status
  • ℞-only (U.S.)
Identifiers
CAS Number
PubChem CID
ChemSpider
ChEMBL
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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Pharmaceutical compound
Quinupristin/dalfopristin
Pharmacokinetic data
Elimination half-life3.1 hours
Identifiers
IUPAC name
  • N-{(6R,9S,10R,13S,15aS,18R,22S,24aS)-18-

    {oct-3-ylthio]methyl-22-- 6-ethyl-10,23-dimethyl-5,8,12,15,17,21,24-heptaoxo-13-phenyldocosahydro-12H- pyridopyrrolo- oxapentaazacyclononadecin-9-yl}-3-

    hydroxypyridine-2-carboxamide
CAS Number
PubChem CID
Chemical and physical data
FormulaC53H67N9O10S
Molar mass1022.24 g/mol g·mol

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 by a factor of about 100. In addition, it inhibits peptidyl transfer.
  • Quinupristin binds to a nearby site on the 50S ribosomal subunit and prevents elongation of the polypeptide, as well as causing incomplete chains to be released.

Pharmacokinetics

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

Side effects

  1. Joint aches (arthralgia) or muscle aches (myalgia)
  2. Nausea, diarrhea or vomiting
  3. Rash or itching
  4. Headache
  5. Phlebitis
  6. Hyperbilirubinemia

Drug interactions

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

References

  1. ^ 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

Further reading

  • Allington DR, Rivey MP., "Quinupristin/dalfopristin: a therapeutic review.", Clin Ther. 2001 Jan;23(1):24-44. doi:10.1016/S0149-2918(01)80028-X PMID 11219478.
  • Lamb HM, Figgitt DP, Faulds D., "Quinupristin/dalfopristin: a review of its use in the management of serious gram-positive infections.", Drugs. 1999 Dec;58(6):1061-97. PMID 10651391.
  • Manzella JP., "Quinupristin-dalfopristin: a new antibiotic for severe gram-positive infections.", Am Fam Physician. 2001 Dec 1;64(11):1863-6. PMID 11764864.
  • Paradisi F, Corti G, Messeri D., "Antistaphylococcal (MSSA, MRSA, MSSE, MRSE) antibiotics.", Med Clin North Am. 2001 Jan;85(1):1-17. PMID 11190346.
  • http://www.fda.gov/cder/consumerinfo/druginfo/SYNERCID.HTM
Antibacterials that inhibit protein synthesis (J01A, J01B, J01F, J01G, QJ01XQ)
30S
Aminoglycosides
(initiation inhibitors)
-mycin (Streptomyces)
-micin (Micromonospora)
other
Tetracycline antibiotics
(tRNA binding)
Tetracyclines
Glycylcyclines
50S
Oxazolidinone
(initiation inhibitors)
Peptidyl transferase
Amphenicols
MLS (transpeptidation/translocation)
Macrolides
Ketolides
Lincosamides
Streptogramins
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