Structure via PubChem · Public domain (PubChem)
retapamulin
Sign in to saveAlso known as SB-275833, {(1S,2R,3S,4S,6R,7R,8R,14R)-4-ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxo-6-tricyclo[5.4.3.01,8]tetradecanyl} 2-({(1R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl}sulfanyl)acetate
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.
Chemical data
- Formula
- C30H47NO4S
- Molecular weight
- 517.8 g/mol
- IUPAC name
- [(1S,2R,3S,4S,6R,7R,8R,14R)-4-ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxo-6-tricyclo[5.4.3.01,8]tetradecanyl] 2-[(8-methyl-8-azabicyclo[3.2.1]octan-3-yl)sulfanyl]acetate
- 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)CSC4CC5CCC(C4)N5C)C
- InChIKey
- STZYTFJPGGDRJD-OSBNDYPUSA-N
- XLogP
- 6.1
- Polar surface area
- 92.1 Ų
- H-bond donors
- 1
- H-bond acceptors
- 6
- Formal charge
- 0
via PubChem
Wikidata facts
- Subclass of
- medication
- Mass
- 517.322571
Show 4 more facts
- chemical formula
- C₃₀H₄₇NO₄S
- World Health Organisation international non-proprietary name
- retapamulin
- canonical SMILES
- CC1CCC23CCC(=O)C2C1(C(CC(C(C3C)O)(C)C=C)OC(=O)CSC4CC5CCC(C4)N5C)C
- isomeric 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
Sources (2)
via Wikidata · CC0
~3 min read
Encyclopedic overview
7 sectionsContents
- Indications
- Pharmacology
- Mechanism of action
- Pharmacokinetics
- Contraindications
- Adverse reactions
- References
{{Drugbox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 464381219 | 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 | image = Retapamulin.svg | image_class = skin-invert-image | image2 = Retapamulin 3D sticks.png | image_class2 = bg-transparent
| tradename = Altabax, Altargo | Drugs.com = | MedlinePlus = a607049 | licence_EU = yes | licence_US = Retapamulin | pregnancy_AU = | pregnancy_US = B | pregnancy_category = | legal_AU = | legal_CA = | legal_UK = POM | legal_US = Rx-only | legal_status = | routes_of_administration = Topical (ointment)
Excerpted from Wikipedia’s “retapamulin” article, available under the CC BY-SA 4.0 licence.