Retapamulin

Retapamulin
Names
Trade namesAltabax, Altargo
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
Clinical data
WHO AWaReUnlinkedWikibase error: ⧼unlinkedwikibase-error-statements-entity-not-set⧽
Pregnancy
category
  • US: B (No risk in non-human studies)
    Routes of
    use    		Topical (ointment)
    External links
    AHFS/Drugs.comMonograph
    MedlinePlusa607049
    Legal
    License data
    Legal status
    Pharmacokinetics
    BioavailabilityLow
    Protein binding94%
    MetabolismLiver, CYP3A4-mediated
    Elimination half-lifeUndetermined
    ExcretionUndetermined
    Chemical and physical data
    FormulaC30H47NO4S
    Molar mass517.77 g·mol−1
    3D model (JSmol)
    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

    Retapamulin, sold as the brand name Altabax among others, is a antibiotic which is applied to the skin to threat impetigo, a bacterial skin infection.[1] It is not useful against MRSA.[1]

    Common side effects include irritation at the site it is used.[1] Other side effects may include allergic reactions such as angioedema.[1] It generally works by stopping bacterial growth by inhibiting the bacterial ribosome.[1]

    Retapamulin was approved for medical use in the United States and Europe in 2007.[1][2] It; however, was withdrawn from the market in 2019 in Europe.[2] In the United States 15 grams of 1% cream costs about 325 USD as of 2021.[3] It was original made from a fungus.[4]

    Medical uses

    Retapamulin is used for the topical treatment of impetigo due to Staphylococcus aureus (methicillin-susceptible only) or Streptococcus pyogenes.[5]

    Dosage

    It is used twice per day for 5 days.[4]

    Contraindications

    None yet reported.[5]

    Side effects

    The most common reported adverse reaction was irritation at the application site.[5]

    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.[5]

    Pharmacokinetics

    Systemic exposure following topical application through intact skin is low.[5]

    History

    It is the first drug in the new class of pleuromutilin antibiotics to be approved for human use.

    It was withdrawn from the market in 2019 by Glaxo Group as they did not consider it commercially viable.[6]

    References

    1. 1 2 3 4 5 6 "Retapamulin Monograph for Professionals". Drugs.com. Archived from the original on 6 August 2020. Retrieved 21 July 2021.
    2. 1 2 "Altargo". Archived from the original on 9 April 2021. Retrieved 21 July 2021.
    3. ↑ "Retapamulin Prices, Coupons & Savings Tips - GoodRx". GoodRx. Retrieved 21 July 2021.
    4. 1 2 Hartman-Adams, Holly; Banvard, Christine; Juckett, Gregory (15 August 2014). "Impetigo: Diagnosis and Treatment". American Family Physician. 90 (4): 229–235. ISSN 0002-838X. Archived from the original on 24 May 2021. Retrieved 21 July 2021.
    5. 1 2 3 4 5 Borrza, S.; Philippi, E., eds. (2007). Physicians' Desk Reference (62nd ed.). pp. 1318–20. ISBN 978-1-56363-660-8.
    6. ↑ "Altargo Withdrawal of the marketing authorisation in the European Union" (PDF). Archived (PDF) from the original on 18 March 2019. Retrieved 21 July 2021.
    Identifiers:
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