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MedKoo Cat#: 300270 | Name: Retapamulin
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Retapamulin, also known as SB-275833, is a newer topical agent of pleuromutilin class approved by the Food and Drug Administration for treatment of impetigo in children. It has been demonstrated to have low potential for the development of antibacterial resistance and a high degree of potency against poly drug resistant Gram-positive bacteria found in skin infections including Staphylococcus aureus strains. The drug is safe owing to low systemic absorption and has only minimal side-effect of local irritation at the site of application.

Chemical Structure

Retapamulin
Retapamulin
CAS#224452-66-8

Theoretical Analysis

MedKoo Cat#: 300270

Name: Retapamulin

CAS#: 224452-66-8

Chemical Formula: C30H47NO4S

Exact Mass: 517.3226

Molecular Weight: 517.76

Elemental Analysis: C, 69.59; H, 9.15; N, 2.71; O, 12.36; S, 6.19

Price and Availability

Size Price Availability Quantity
25mg USD 90.00 Ready to ship
50mg USD 150.00 Ready to ship
100mg USD 250.00 Ready to ship
200mg USD 425.00 Ready to ship
500mg USD 900.00 Ready to ship
1g USD 1,450.00 Ready to ship
2g USD 2,450.00 Ready to ship
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Related CAS #
No Data
Synonym
SB-275833; SB 275833; SB275833; Retapamulin, brand names Altabax and Altargo.
IUPAC/Chemical Name
(3aR,4S,5R,7S,8S,9R,9aS,12R)-8-hydroxy-4,7,9,12-tetramethyl-3-oxo-7-vinyldecahydro-4,9a-propanocyclopenta[8]annulen-5-yl 2-(((1R,3s,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl)thio)acetate
InChi Key
STZYTFJPGGDRJD-QPCPVAGTSA-N
InChi Code
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
SMILES Code
O=C(O[C@@H]1C[C@](C=C)(C)[C@@H](O)[C@H](C)[C@]2(CCC3=O)[C@]3([H])[C@]1(C)[C@H](C)CC2)CS[C@@H]4C[C@@](N5C)([H])CC[C@@]5([H])C4
Appearance
White to off-white solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO and ethanol
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO and ethanol
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Biological target:
Retapamulin(SB-275833) is a topical antibiotic, which binds to both E. coli and S. aureus ribosomes with similar potencies with Kd of 3 nM.
In vitro activity:
The purpose of this study was to determine the in vitro activity of retapamulin against methicillin-susceptible Staphylococcus aureus (MSSA), methicillin-resistant S. aureus (MRSA), and linezolid and methicillin-resistant S. aureus.The minimum inhibitory concentrations (MICs) were determined on Mueller-Hinton agar. Retapamulin inhibited all the isolates of MSSA and MRSA at 0.125 mg/L, but the 18 linezolid-resistant-MRSA strains proved resistant, with MICs over 32 mg/L. Retapamulin demonstrated excellent in vitro activity against MSSA and MRSA strains, but not against MRSA isolates harbouring the cfr gene. The results of this in vitro study support cut-off values for retapamulin of ≤ 0.5, 1, and ≥ 2 mg/L for susceptible, intermediate, and resistant strains, respectively. Reference: Rev Esp Quimioter. 2011 Sep;24(3):127-30. https://pubmed.ncbi.nlm.nih.gov/21947094/
In vivo activity:
The purpose of this study was to evaluate the effect of topically applied retapamulin ointment using various dosing regimens in the Staphylococcus aureus and Streptococcus pyogenes wound infection model. Therapy was administered topically (0.1 ml/mouse) b.i.d. (beginning at 1 and 7 h postinfection) or t.i.d. (beginning at 1, 4, and 7 h postinfection) and continued for 3, 4, or 6 days (4, 5, or 7 days of therapy). Additional groups of mice received petrolatum ointment or remained untreated to act as placebo or infected controls. Following infection with S. aureus J1225 (5 days postinfection), bacterial numbers from untreated control animals were 6.3 ± 0.3 log10 CFU/wound. Retapamulin administered t.i.d. for 4 days demonstrated significant efficacy (P ≤ 0.01) compared with untreated animals at all concentrations tested. A maximum 4.6 log10 reduction in bacterial counts was achieved at 2% (wt/wt) (1.7 ± 0.1 log10 CFU/wound; 7/8 wounds cleared to the limit of detection). All retapamulin concentrations evaluated produced a potent effect compared with untreated or placebo-treated animals (P ≤ 0.01). The effect obtained with 4-day t.i.d. application of 0.5%, 1%, and 2% wt/wt were similar, reducing bacterial counts by >5 log10 (1.9 ± 0.4, 2.3 ± 1.3, and 2.3 ± 1.5 log10 CFU/wound, respectively). Overall, these results demonstrate the potential benefit of retapamulin over existing topical antibiotics, particularly against isolates resistant to currently used agents. Reference: Antimicrob Agents Chemother. 2006 Nov; 50(11): 3886–3888. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1635196/
Solvent mg/mL mM
Solubility
DMSO 30.0 57.90
Ethanol 30.0 57.90
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 517.76 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. 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. PMID: 23796931; PMCID: PMC3754297. 2. Candel FJ, Morales G, Picazo JJ. In vitro activity of retapamulin against linezolid and methicillin-resistant Staphylococcus aureus isolates. Rev Esp Quimioter. 2011 Sep;24(3):127-30. PMID: 21947094. 3. Guo Y, Ramos RI, Cho JS, Donegan NP, Cheung AL, Miller LS. In vivo bioluminescence imaging to evaluate systemic and topical antibiotics against community-acquired methicillin-resistant Staphylococcus aureus-infected skin wounds in mice. Antimicrob Agents Chemother. 2013 Feb;57(2):855-63. doi: 10.1128/AAC.01003-12. Epub 2012 Dec 3. PMID: 23208713; PMCID: PMC3553733. 4. Rittenhouse S, Singley C, Hoover J, Page R, Payne D. Use of the surgical wound infection model to determine the efficacious dosing regimen of retapamulin, a novel topical antibiotic. Antimicrob Agents Chemother. 2006 Nov;50(11):3886-8. doi: 10.1128/AAC.00183-06. PMID: 17065626; PMCID: PMC1635196.
In vitro protocol:
1. 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. PMID: 23796931; PMCID: PMC3754297. 2. Candel FJ, Morales G, Picazo JJ. In vitro activity of retapamulin against linezolid and methicillin-resistant Staphylococcus aureus isolates. Rev Esp Quimioter. 2011 Sep;24(3):127-30. PMID: 21947094.
In vivo protocol:
1. Guo Y, Ramos RI, Cho JS, Donegan NP, Cheung AL, Miller LS. In vivo bioluminescence imaging to evaluate systemic and topical antibiotics against community-acquired methicillin-resistant Staphylococcus aureus-infected skin wounds in mice. Antimicrob Agents Chemother. 2013 Feb;57(2):855-63. doi: 10.1128/AAC.01003-12. Epub 2012 Dec 3. PMID: 23208713; PMCID: PMC3553733. 2. Rittenhouse S, Singley C, Hoover J, Page R, Payne D. Use of the surgical wound infection model to determine the efficacious dosing regimen of retapamulin, a novel topical antibiotic. Antimicrob Agents Chemother. 2006 Nov;50(11):3886-8. doi: 10.1128/AAC.00183-06. PMID: 17065626; PMCID: PMC1635196.
1: Zha M, Usatine R. Common Skin Conditions in Children and Adolescents: Bacterial Infections. FP Essent. 2024 Jun;541:14-19. PMID: 38896826. 2: García-Castillo M, Hernández-García M, Correa A, Coppi M, Griener T, Fritsche T, Pitart C, Sampaio J, Seifert H, Wake K, Wootton M, Vila J, Cantón R. In vitro activity of ozenoxacin against Staphylococcus aureus and Streptococcus pyogenes clinical isolates recovered in a worldwide multicentre study (2020-2022). JAC Antimicrob Resist. 2024 Jun 13;6(3):dlae088. doi: 10.1093/jacamr/dlae088. PMID: 38872714; PMCID: PMC11170484. 3: Fijalkowski I, Snauwaert V, Van Damme P. Proteins à la carte: riboproteogenomic exploration of bacterial N-terminal proteoform expression. mBio. 2024 Apr 10;15(4):e0033324. doi: 10.1128/mbio.00333-24. Epub 2024 Mar 21. PMID: 38511928; PMCID: PMC11005335. 4: Bello SO, Imam MU, Bello MB, Yunusa A, Ahmed Adamu A, Shuaibu A, Igumbor EU, Habib ZG, Popoola MA, Ochu CL, Yahaya Bello A, Deeni YY, Okoye I. Erythromycin, retapamulin, pyridoxine, folic acid, and ivermectin inhibit cytopathic effect, papain-like protease, and MPRO enzymes of SARS-CoV-2. Front Cell Infect Microbiol. 2023 Nov 27;13:1273982. doi: 10.3389/fcimb.2023.1273982. PMID: 38089816; PMCID: PMC10711598. 5: Sun P, Cui M, Jing J, Kong F, Wang S, Tang L, Leng J, Chen K. Deciphering the molecular and cellular atlas of immune cells in septic patients with different bacterial infections. J Transl Med. 2023 Nov 2;21(1):777. doi: 10.1186/s12967-023-04631-4. PMID: 37919720; PMCID: PMC10621118. 6: Sweeney DT, Zárate-Pérez F, Stokowa-Sołtys K, Hackett JC. Induced Fit Describes Ligand Binding to Membrane-Associated Cytochrome P450 3A4. Mol Pharmacol. 2023 Oct;104(4):154-163. doi: 10.1124/molpharm.123.000698. Epub 2023 Aug 3. PMID: 37536953; PMCID: PMC10506697. 7: Zhang C, Li J, Lu R, Wang S, Fu Z, Yao Z. Efficacy of a Novel Antibacterial Agent Exeporfinium Chloride, (XF-73), Against Antibiotic-Resistant Bacteria in Mouse Superficial Skin Infection Models. Infect Drug Resist. 2023 Jul 25;16:4867-4879. doi: 10.2147/IDR.S417231. PMID: 37520450; PMCID: PMC10386860. 8: Yong C, Yu J, Wu C, Zhang X, Li Y, Xie C, He X, Liu D, Wang Z, Lai P, Zhang Y. Design, Synthesis, and Biological Activity of Thioguanine-Modified Pleuromutilin Derivatives. ACS Med Chem Lett. 2023 May 10;14(6):737-745. doi: 10.1021/acsmedchemlett.3c00004. PMID: 37312858; PMCID: PMC10258896. 9: Drugs and Lactation Database (LactMed®) [Internet]. Bethesda (MD): National Institute of Child Health and Human Development; 2006–. Retapamulin. 2023 Apr 15. PMID: 30000967. 10: Bello SO, Yunusa A, Adamu AA, Imam MU, Bello MB, Shuaibu A, Igumbor EU, Habib ZG, Popoola MA, Ochu CL, Bello AY, Deeni YY, Okoye I. Innovative, rapid, high-throughput method for drug repurposing in a pandemic-A case study of SARS- CoV-2 and COVID-19. Front Pharmacol. 2023 Mar 1;14:1130828. doi: 10.3389/fphar.2023.1130828. PMID: 36937851; PMCID: PMC10014809. 11: Schafhauser T, Wibberg D, Binder A, Rückert C, Busche T, Wohlleben W, Kalinowski J. Genome Assembly and Genetic Traits of the Pleuromutilin-Producer Clitopilus passeckerianus DSM1602. J Fungi (Basel). 2022 Aug 16;8(8):862. doi: 10.3390/jof8080862. PMID: 36012850; PMCID: PMC9410065. 12: Laczkovich I, Mangano K, Shao X, Hockenberry AJ, Gao Y, Mankin A, Vázquez- Laslop N, Federle MJ. Discovery of Unannotated Small Open Reading Frames in Streptococcus pneumoniae D39 Involved in Quorum Sensing and Virulence Using Ribosome Profiling. mBio. 2022 Aug 30;13(4):e0124722. doi: 10.1128/mbio.01247-22. Epub 2022 Jul 19. PMID: 35852327; PMCID: PMC9426450. 13: Chai F, Wang J, Zhou KX, Wang SK, Liu YH, Jin Z, Tang YZ. Design, synthesis and biological evaluation of novel pleuromutilin derivatives possessing 4-aminothiophenol linker as promising antibacterial agents. Bioorg Chem. 2022 Sep;126:105859. doi: 10.1016/j.bioorg.2022.105859. Epub 2022 May 10. PMID: 35605553. 14: Ding R, Wang X, Fu J, Chang Y, Li Y, Liu Y, Liu Y, Ma J, Hu J. Design, synthesis and antibacterial activity of novel pleuromutilin derivatives with thieno[2,3-d]pyrimidine substitution. Eur J Med Chem. 2022 Jul 5;237:114398. doi: 10.1016/j.ejmech.2022.114398. Epub 2022 Apr 19. PMID: 35468515. 15: Hsu MH, Johnson EF. Structural characterization of the homotropic cooperative binding of azamulin to human cytochrome P450 3A5. J Biol Chem. 2022 May;298(5):101909. doi: 10.1016/j.jbc.2022.101909. Epub 2022 Apr 6. PMID: 35398097; PMCID: PMC9079302. 16: Gahlawat G, Tesfaye W, Bushell M, Abrha S, Peterson GM, Mathew C, Sinnollareddy M, McMillan F, Samarawickrema I, Calma T, Chang AY, Engelman D, Steer A, Thomas J. Emerging Treatment Strategies for Impetigo in Endemic and Nonendemic Settings: A Systematic Review. Clin Ther. 2021 Jun;43(6):986-1006. doi: 10.1016/j.clinthera.2021.04.013. Epub 2021 May 27. PMID: 34053699. 17: Deshpande L, Cantrell L, Romero JR, Carvalhaes C, Sader HS, Mendes RE. Characterization of a vga gene variant recovered from a Staphylococcus saprophyticus causing a community-acquired urinary tract infection: report from the SENTRY Antimicrobial Surveillance Program 2017. Diagn Microbiol Infect Dis. 2021 Aug;100(4):115398. doi: 10.1016/j.diagmicrobio.2021.115398. Epub 2021 Apr 20. PMID: 34030104. 18: Meydan S, Klepacki D, Mankin AS, Vázquez-Laslop N. Identification of Translation Start Sites in Bacterial Genomes. Methods Mol Biol. 2021;2252:27-55. doi: 10.1007/978-1-0716-1150-0_2. PMID: 33765270; PMCID: PMC8672441. 19: Galindo E, Hebert AA. A comparative review of current topical antibiotics for impetigo. Expert Opin Drug Saf. 2021 Jun;20(6):677-683. doi: 10.1080/14740338.2021.1902502. Epub 2021 Apr 13. PMID: 33726585. 20: Cai X, Wang Q, Fang Y, Yao D, Zhan Y, An B, Yan B, Cai J. Attenuator LRR - a regulatory tool for modulating gene expression in Gram-positive bacteria. Microb Biotechnol. 2021 Nov;14(6):2538-2551. doi: 10.1111/1751-7915.13797. Epub 2021 Mar 15. PMID: 33720523; PMCID: PMC8601186.