- Retapamulin
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Retapamulin 
Systematic (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}acetateClinical data AHFS/Drugs.com monograph MedlinePlus a607049 Licence data EMA:Link, US FDA:link Pregnancy cat. B(US) Legal status POM (UK) ℞-only (US) Routes Topical (ointment) Pharmacokinetic data Bioavailability Low Protein binding 94% Metabolism Hepatic, CYP3A4-mediated Half-life Undetermined Excretion Undetermined Identifiers CAS number 224452-66-8 
ATC code D06AX13 PubChem CID 6918462 DrugBank DB01256 ChemSpider 5293659 UNII 4MG6O8991R 
KEGG D05720 ChEMBL CHEMBL566434 Chemical data Formula C30H47NO4S Mol. mass 517.77 g/mol SMILES eMolecules & PubChem - 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-FJJJPKKESA-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]
Contents
Pharmacological specifications
Mechanism of action (pharmacodynamics)
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]
Acceptance and repartition in the body (pharmakinetics)
Systemic exposure following topical application through intact skin was low [2]
Clinical use
Indications
Retapamulin is indicated for the topical treatment of impetigo due to Staphylococcus aureus (methicillin-susceptible only) or Streptococcus pyogenes.[2]
Contraindications
None yet reported.[2]
Adverse reactions
The most common reported adverse reaction was irritation at the application site.[2]
References
- ^ 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. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=1489758. Full text at PMC: 1489758
- ^ a b c d e Physicans' Desk Reference(ISBN 1-56363-660-3) (62 ed.). 2007. pp. 1318–20.
Antibacterials: protein synthesis inhibitors (J01A, J01B, J01F, J01G, QJ01XQ) 30S -mycin (Streptomyces)Neomycin# (Framycetin, Paromomycin, Ribostamycin)
Kanamycin# (Amikacin, Arbekacin, Bekanamycin, Dibekacin, Tobramycin)
Paromomycin-micin (Micromonospora)Tetracyclines50S Linezolid • Torezolid • Eperezolid • Posizolid • RadezolidPleuromutilinsRetapamulin • Tiamulin • ValnemulinErythromycin# • Azithromycin# • Spiramycin • Midecamycin • Oleandomycin • Roxithromycin • Josamycin • Troleandomycin • Clarithromycin • Miocamycin • Rokitamycin • Dirithromycin • Flurithromycin • Ketolide (Telithromycin, Cethromycin, Solithromycin)EF-G Steroid antibacterials
This systemic antibacterial-related article is a stub. You can help Wikipedia by expanding it. - 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
