Retapamulin

Pharmaceutical drug
  • EU EMA: by INN
  • US FDA: Retapamulin
Routes of
administrationTopical (ointment)ATC code
  • D06AX13 (WHO)
Legal statusLegal status
  • UK: POM (Prescription only)
  • US: ℞-only
Pharmacokinetic dataBioavailabilityLowProtein binding94%MetabolismHepatic, CYP3A4-mediatedElimination half-lifeUndeterminedExcretionUndeterminedIdentifiers
  • (3aS,4R,5S,6S,8R,9R,9aR,10R)-6-ethenyl-5-hydroxy-4,6,9,10-tetramethyl-1-oxodecahydro-3a,9-propano-3aH-cyclopenta[8]annulen-8-yl{[(1R,3s,5S)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl]sulfanyl}acetate
CAS Number
  • 224452-66-8 checkY
PubChem CID
  • 6918462
DrugBank
  • DB01256 checkY
ChemSpider
  • 25064484 ☒N
UNII
  • 4MG6O8991R
KEGG
  • D05720 checkY
ChEMBL
  • ChEMBL566434 ☒N
CompTox Dashboard (EPA)
  • DTXSID00870265 Edit this at Wikidata
ECHA InfoCard100.167.142 Edit this at WikidataChemical and physical dataFormulaC30H47NO4SMolar mass517.77 g·mol−13D model (JSmol)
  • Interactive image
  • C[C@@H]1CC[C@@]23CCC(=O)[C@H]2[C@@]1([C@@H](C[C@@]([C@H]([C@@H]3C)O)(C)C=C)OC(=O)CS[C@@H]4C[C@H]5CC[C@@H](C4)N5C)C
  • InChI=1S/C30H47NO4S/c1-7-28(4)16-24(35-25(33)17-36-22-14-20-8-9-21(15-22)31(20)6)29(5)18(2)10-12-30(19(3)27(28)34)13-11-23(32)26(29)30/h7,18-22,24,26-27,34H,1,8-17H2,2-6H3/t18-,19+,20-,21+,22-,24-,26+,27+,28-,29+,30+/m1/s1 ☒N
  • Key:STZYTFJPGGDRJD-NHUWBDDWSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

Retapamulin is a topical antibiotic developed by GlaxoSmithKline. It is the first drug in the new class of pleuromutilin antibiotics to be approved for human use. It is marketed as an ointment under the brand names Altabax and Altargo.

Retapamulin was approved by the United States Food and Drug Administration in April 2007 for the treatment of bacterial skin infections such as impetigo. In May 2007, retapamulin received approval in the EU from the European Medicines Agency for the same indication.[citation needed]

Clinical trials have demonstrated its efficacy against certain Gram-positive bacteria including MRSA.[1]

Indications

Retapamulin is indicated for the topical treatment of impetigo due to Staphylococcus aureus (methicillin-susceptible only) or Streptococcus pyogenes.[2]

Pharmacology

Mechanism of action

Retapamulin is an antibacterial agent, specifically a protein synthesis inhibitor. The medication selectively inhibits bacterial protein synthesis by interacting at a site on the 50S subunit of the bacterial ribosome through an interaction that differs from other antibiotics.[2]

Pharmacokinetics

Systemic exposure following topical application through intact skin is low.[2]

Contraindications

None yet reported.[2]

Adverse reactions

The most common reported adverse reaction was irritation at the application site.[2]

References

  1. ^ Jones R, Fritsche T, Sader H, Ross J (2006). "Activity of retapamulin (SB-275833), a novel pleuromutilin, against selected resistant gram-positive cocci". Antimicrob Agents Chemother. 50 (7): 2583–6. doi:10.1128/AAC.01432-05. PMC 1489758. PMID 16801451.
  2. ^ a b c d e Borrza, S.; Philippi, E., eds. (2007). Physicians' Desk Reference (62nd ed.). pp. 1318–20. ISBN 978-1-56363-660-8.
  • v
  • t
  • e
30S
Aminoglycosides
(initiation inhibitors)
-mycin (Streptomyces)
-micin (Micromonospora)
other
Tetracycline antibiotics
(tRNA binding)
Tetracyclines
Glycylcyclines
50S
Oxazolidinone
(initiation inhibitors)
Peptidyl transferase
Amphenicols
Pleuromutilins
MLS (transpeptidation/translocation)
Macrolides
Ketolides
Lincosamides
Streptogramins
EF-G
Steroid antibacterials