Retapamulin

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
Clinical data
Trade namesAltabax, Altargo
AHFS/Drugs.comMonograph
MedlinePlusa607049
License data
Routes of
administration		Topical (ointment)
ATC code
Legal status
Legal status
Pharmacokinetic data
BioavailabilityLow
Protein binding94%
MetabolismHepatic, CYP3A4-mediated
Elimination half-lifeUndetermined
ExcretionUndetermined
Identifiers
IUPAC name
  • (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
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.167.142
Chemical and physical data
FormulaC30H47NO4S
Molar mass517.77 g·mol−1
3D model (JSmol)
SMILES
  • 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
  • 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
 NY (what is this?)  (verify)

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.

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. Borrza, S.; Philippi, E., eds. (2007). Physicians' Desk Reference (62nd ed.). pp. 1318–20. ISBN 978-1-56363-660-8.
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