Chemistry:Pristinamycin

From HandWiki
Short description: Group of chemical compounds
Pristinamycin
Pristinamycin IA.png
Streptogramin A.svg
Combination of
Pristinamycin IAantibiotic
Pristinamycin IIAantibiotic
Clinical data
AHFS/Drugs.comInternational Drug Names
MedlinePlusa603007
ATC code
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
 ☒N☑Y (what is this?)  (verify)

Pristinamycin (INN), also spelled pristinamycine, is an antibiotic used primarily in the treatment of staphylococcal infections, and to a lesser extent streptococcal infections. It is a streptogramin group antibiotic, similar to virginiamycin, derived from the bacterium Streptomyces pristinaespiralis. It is marketed in Europe by Sanofi-Aventis under the trade name Pyostacine.

Pristinamycin is a mixture of two components that have a synergistic antibacterial action. Pristinamycin IIA is a macrolide , and results in pristinamycin's having a similar spectrum of action to erythromycin. Pristinamycin IA (streptogramin B) is a depsipeptide.[1] PI and PII are coproduced by S. pristinaespiralis in a ratio of 30:70. Each compound binds to the bacterial 50 S ribosomal subunit and inhibits the elongation process of the protein synthesis, thereby exhibiting only a moderate bacteriostatic activity. However, the combination of both substances acts synergistically and leads to a potent bactericidal activity that can reach up to 100 times that of the separate components.

The pristinamycin biosynthetic gene cluster is the largest antibiotic supercluster known so far, with a size of ~210 kb, wherein the PI and PII biosynthetic genes are not clustered individually but are scattered across the complete sequence region.[2] Furthermore, this biosynthetic gene region is interrupted by a cryptic type II PKS gene cluster.

Clinical use

Despite the macrolide component, it is effective against erythromycin-resistant staphylococci and streptococci.[3][4] It is active against methicillin-resistant Staphylococcus aureus (MRSA). Its usefulness for severe infections, however, may be limited by the lack of an intravenous formulation owing to its poor solubility.[5] Nevertheless, it is sometimes used as an alternative to rifampicin+fusidic acid or linezolid for the treatment of MRSA.

The lack of an intravenous formulation led to the development of the pristinamycin-derivative quinupristin/dalfopristin (i.e., Synercid), which may be administered intravenously for more severe MRSA infections.

See also

Footnotes

  1. "From foreign pharmacopoeias: 'new' antibiotics from old?". The Journal of Antimicrobial Chemotherapy 27 (6): 702–705. June 1991. doi:10.1093/jac/27.6.702. PMID 1938680. 
  2. "Characterization of the 'pristinamycin supercluster' of Streptomyces pristinaespiralis". Microbial Biotechnology 4 (2): 192–206. March 2011. doi:10.1111/j.1751-7915.2010.00213.x. PMID 21342465. 
  3. "[Streptococcus pneumoniae: lack of emergence of pristinamycin resistance]". Pathologie-Biologie 49 (10): 840–845. December 2001. doi:10.1016/S0369-8114(01)00255-3. PMID 11776696. 
  4. "[In vitro activity of the pristinamycin against the isolated staphylococci in the french hospitals in 1999-2000]". Pathologie-Biologie 51 (7): 400–404. September 2003. doi:10.1016/S0369-8114(03)00054-3. PMID 12948760. 
  5. Sean C. Sweetman, ed (November 30, 2004). Martindale: The complete drug reference (34th ed.). London: Pharmaceutical Press. ISBN 0-85369-550-4.