Quinupristin/dalfopristin

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Quinupristin/dalfopristin
Systematic (IUPAC) name
quinupristine N-[(6R,9S,10R,13S,15aS,18R,22S,24aS)-22-
[p-(dimethylamino)benzyl]-6-ethyldocosahydro-

10,23-dimethyl-5,8,12,15,17,21,24-heptaoxo-13-phenyl-18-
[["(3S)-3-quinuclidinylthio]methyl]- 12H-pyrido[2,1-f]pyrrolo-[2,1-l][1,4,7,10,13,16] oxapentaazacyclononadecin-9-yl]-3-hydroxypicolinamide

dalfopristin (3R,4R,5E,10E,12E,14S,26R,26aS)-26-
[[2-(diethylamino)ethyl]sulfonyl]-8,9,14,15,24,25,26,26a- octahydro-14-hydroxy-3-
isopropyl-4,12-dimethyl-3H-21,18-nitrilo-1H,22H-pyrrolo[2,1-c][1,8,4,19]- dioxadiazacyclotetracosine-1,7,16,22(4H,17H)-tetrone

Identifiers
CAS number 120138-50-3
112362-50-2
ATC code J01FG02
PubChem 6435782
Chemical data
Formula quinupristin C53H67N9O10S1
dalfopristin C34H50N4O9S
Mol. mass quinupristin 1022.24 g/mol
dalfopristin 690.85 g/mol
Pharmacokinetic data
Bioavailability  ?
Protein binding moderate
Metabolism  ?
Half life quinupristin 3.1 hours
dalfopristin 1 hour
Excretion 75% fecal, 15-19% urinary
Therapeutic considerations
Pregnancy cat.

B (U.S.)

Legal status

℞-only (U.S.)

Routes IV

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Quinupristin/dalfopristin (Synercid®) is a combination of two antibiotics used to treat infections by staphylococci and by vancomycin-resistant Enterococcus faecium. It is not effective against Enterococcus faecalis infections.

Quinupristin and dalfopristin are both streptogramin antibiotics, derived from pristinamycin. Quinupristin is derived from pristinamycin I; 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

Dalfopristin inhibits the early phase of protein synthesis in the bacterial ribosome and quinupristin inhibits the late phase of protein synthesis. The combination of the two components acts synergistically and is more effective in vitro than each component alone.

Pharmacokinetics

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

Side effects

  1. Joint or muscle aches
  2. Nausea, diarrhea or vomiting
  3. Rash or itching
  4. Headache

References

  • Allington DR, Rivey MP., "Quinupristin/dalfopristin: a therapeutic review.", Clin Ther. 2001 Jan;23(1):24-44. 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

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Acknowledgement and Attribution Regarding Sources of Content

Some of the initial content on this page may be incorporated in part from copyleft sources in the public domain including wikis such as Wikipedia and AskDrWiki. Drug information for patients came from the The National Library of Medicine. Infectious disease information may have come from the Centers for Disease Control (CDC). Differential Diagnoses are drawn from clinicians as well as an amalgamation of 3 sources: 1.The Disease Database; 2. Kahan, Scott, Smith, Ellen G. In A Page: Signs and Symptoms. Malden, Massachusetts: Blackwell Publishing, 2004:3; 3. Sailer, Christian, Wasner, Susanne. Differential Diagnosis Pocket. Hermosa Beach, CA: Borm Bruckmeir Publishing LLC, 2002:7 .

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