Compound ID | 1994

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Retapamulin

Synonym(s): SB-275833  |  SB275833

Class: Pleuromutilin

Spectrum of activity: Gram-positive
Details of activity: Binds to the peptidyl transferase component of the 50S subunit of the bacterial tRNA complex, thus inhibiting peptide bond formation. It is active against Gram-positive bacteria.
Description: Synthetic pleuromutilin derivative for topical use. GSK brands no longer authorised by the European Medicine Agency (EMA) and other agencies.
Year first mentioned: 2005
Development status: Approved, off-patent
Chemical structure(s):
Click here for structure editor
Molecular weight: 517.77
Iso. 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)CSC4C[C@H]5CC[C@@H](C4)N5C)C
InChI Key: STZYTFJPGGDRJD-FJJJPKKESA-N
Can. SMILES: C=C[C@]1(C)C[C@H]([C@]2(C)[C@H](C)CC[C@]3(CCC(=O)[C@@H]23)[C@@H](C)[C@@H]1O)OC(=O)CSC4C[C@H]5CC[C@@H](C4)N5C
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
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/6918462
Guide to Pharmacology: retapamulin
Citations:
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1489758/
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8713557/

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