Retapamulin

Retapamulin
Clinical data
Trade names	Altabax, Altargo
AHFS/Drugs.com	Monograph
MedlinePlus	a607049
License data	EU EMA: by INN; US FDA: Retapamulin;
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 ;
PubChem CID	6918462;
DrugBank	DB01256 ;
ChemSpider	25064484 ;
UNII	4MG6O8991R;
KEGG	D05720 ;
ChEMBL	ChEMBL566434 ;
CompTox Dashboard (EPA)	DTXSID00870265 ;
ECHA InfoCard	100.167.142
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 ; Key:STZYTFJPGGDRJD-NHUWBDDWSA-N ;
	(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.^[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.

[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.

[1]