Retapamulin

For research use only. Not for therapeutic Use.

  • CAT Number: A000673
  • CAS Number: 224452-66-8
  • Molecular Formula: C30H47NO4S
  • Molecular Weight: 517.80
  • Purity: ≥95%
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Retapamulin(Cat No.:A000673)is a pleuromutilin antibiotic used primarily for the treatment of skin infections caused by Gram-positive bacteria, including Staphylococcus aureus and Streptococcus pyogenes. It works by inhibiting bacterial protein synthesis through binding to the bacterial ribosome, preventing peptide elongation. Retapamulin is highly effective against both methicillin-resistant and susceptible strains of Staphylococcus aureus. It is typically applied topically, offering an alternative to systemic antibiotics in localized skin infections. Retapamulin is well-tolerated with a low risk of systemic side effects, making it a useful tool in dermatological therapy.


Catalog Number A000673
CAS Number 224452-66-8
Synonyms

224452-66-8; Altabax; Altargo; UNII-4MG6O8991R; Altabax (Glaxo)

Molecular Formula C30H47NO4S
Purity ≥95%
Target Bacterial
Solubility >16.2mg/mL in DMSO
Storage -20°C
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-[[(1S,5R)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl]sulfanyl]acetate
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
InChIKey STZYTFJPGGDRJD-FJJJPKKESA-N
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
Reference

1: Harrington AT, Black JA, Clarridge JE 3rd. In Vitro Activity of Retapamulin
and Antimicrobial Susceptibility Patterns in a Longitudinal Collection of
Methicillin-Resistant Staphylococcus aureus Isolates from a Veterans Affairs
Medical Center. Antimicrob Agents Chemother. 2015 Dec 14;60(3):1298-303. doi:
10.1128/AAC.01568-15. PubMed PMID: 26666950; PubMed Central PMCID: PMC4775979.
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2: Retapamulin. Aust Prescr. 2015 Feb;38(1):33-4. Epub 2014 Nov 6. Review. PubMed
PMID: 26648610; PubMed Central PMCID: PMC4654036.

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3: Park SH, Kim JK, Park K. In Vitro Antimicrobial Activities of Fusidic Acid and
Retapamulin against Mupirocin- and Methicillin-Resistant Staphylococcus aureus.
Ann Dermatol. 2015 Oct;27(5):551-6. doi: 10.5021/ad.2015.27.5.551. Epub 2015 Oct
2. PubMed PMID: 26512169; PubMed Central PMCID: PMC4622889.
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4: Bohaty BR, Choi S, Cai C, Hebert AA. Clinical and bacteriological efficacy of
twice daily topical retapamulin ointment 1% in the management of impetigo and
other uncomplicated superficial skin infections. Int J Womens Dermatol. 2015 Mar
2;1(1):13-20. doi: 10.1016/j.ijwd.2014.12.002. eCollection 2015 Feb. PubMed PMID:
28491950; PubMed Central PMCID: PMC5418665.
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5: Tanus T, Scangarella-Oman NE, Dalessandro M, Li G, Breton JJ, Tomayko JF. A
randomized, double-blind, comparative study to assess the safety and efficacy of
topical retapamulin ointment 1% versus oral linezolid in the treatment of
secondarily infected traumatic lesions and impetigo due to methicillin-resistant
Staphylococcus aureus. Adv Skin Wound Care. 2014 Dec;27(12):548-59. doi:
10.1097/01.ASW.0000456631.20389.ae. PubMed PMID: 25396674.

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6: Gropper S, Albareda N, Chelius K, Kruger D, Mitha I, Vahed Y, Gani M,
García-Alonso F; Ozenoxacin in Impetigo Trial Investigators Group. Ozenoxacin 1%
cream in the treatment of impetigo: a multicenter, randomized, placebo- and
retapamulin-controlled clinical trial. Future Microbiol. 2014;9(9):1013-23. doi:
10.2217/fmb.14.78. PubMed PMID: 25340832.

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7: Haddican M, Linkner RV, Singer G, Jim SC, Gagliotti M, Goldenberg G.
Retapamulin 1% Ointment and Clobetasol Propionate 0.05% Foam is More Efficacious
than Vehicle Ointment and Clobetasol 0.05% Propionate Foam in the Treatment of
Hand/Foot Dermatitis: A Single Center, Randomized, Double-blind Study. J Clin
Aesthet Dermatol. 2014 Jul;7(7):32-6. PubMed PMID: 25053981; PubMed Central
PMCID: PMC4106355.
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8: Mundy LM, Sampson T, Logie JW. Retapamulin prescriptions and monitored
off-label use. Paediatr Drugs. 2014 Aug;16(4):331-6. doi:
10.1007/s40272-014-0077-1. PubMed PMID: 24935401.

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9: McNeil JC, Hulten KG, Kaplan SL, Mason EO. Decreased susceptibilities to
Retapamulin, Mupirocin, and Chlorhexidine among Staphylococcus aureus isolates
causing skin and soft tissue infections in otherwise healthy children. Antimicrob
Agents Chemother. 2014 May;58(5):2878-83. doi: 10.1128/AAC.02707-13. Epub 2014
Mar 10. PubMed PMID: 24614375; PubMed Central PMCID: PMC3993237.
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10: Saravolatz LD, Pawlak J, Saravolatz SN, Johnson LB. In Vitro Activity of
Retapamulin against Staphylococcus aureus Resistant to Various Antimicrobial
Agents. Antimicrob Agents Chemother. 2013 Sep;57(9):4547-4550. doi:
10.1128/AAC.00282-13. Epub 2013 Jun 24. PubMed PMID: 23796931; PubMed Central
PMCID: PMC3754297.

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