Chemistry:Retapamulin

Short description: Pharmaceutical drug

Retapamulin

Clinical data
Trade names	Altabax, Altargo
AHFS/Drugs.com	Monograph
MedlinePlus	a607049
License data	EU EMA: by INN US FDA: Retapamulin
Pregnancy category	US: B (No risk in non-human studies)
Routes of administration	Topical (ointment)
ATC code	D06AX13 (WHO)
Legal status
Legal status	UK: POM (Prescription only) US: ℞-only
Pharmacokinetic data
Bioavailability	Low
Protein binding	94%
Metabolism	Hepatic, CYP3A4-mediated
Elimination half-life	Undetermined
Excretion	Undetermined
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	224452-66-8 Y
PubChem CID	6918462
DrugBank	DB01256 Y
ChemSpider	25064484 N
UNII	4MG6O8991R
KEGG	D05720 Y
ChEMBL	ChEMBL566434 N
Chemical and physical data
Formula	C30H47NO4S
Molar mass	517.77 g·mol−1
3D model (JSmol)	Interactive image
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 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.

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

Indications

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

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.

Pharmacokinetics

Systemic exposure following topical application through intact skin is low.

Contraindications

None yet reported.

Adverse reactions

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