Retapamulin
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MedKoo CAT#: 300270

CAS#: 224452-66-8

Description: 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

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Retapamulin
CAS# 224452-66-8
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 300270
Name: Retapamulin
CAS#: 224452-66-8
Chemical Formula: C30H47NO4S
Exact Mass: 517.32
Molecular Weight: 517.760
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 Ready to ship
50mg USD 150 Ready to ship
100mg USD 250 Ready to ship
200mg USD 425 Ready to ship
500mg USD 900 Ready to ship
1g USD 1450 Ready to ship
2g USD 2450 Ready to ship
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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/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 30.0 57.90
Ethanol 30.0 57.90

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.

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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.

2: Retapamulin. Aust Prescr. 2015 Feb;38(1):33-4. Epub 2014 Nov 6. Review. PubMed PMID: 26648610; PubMed Central PMCID: PMC4654036.

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.

4: 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.

5: 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.

6: 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.

7: 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.

8: 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.

9: 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 Jun 24. [Epub ahead of print] PubMed PMID: 23796931; PubMed Central PMCID: PMC3754297.

10: Dhingra D, Parakh A, Ramachandran S. Retapamulin: a newer topical antibiotic. J Postgrad Med. 2013 Apr-Jun;59(2):127-30. doi: 10.4103/0022-3859.113842. PubMed PMID: 23793314.

11: Nalwade S, Reddy VR. A validated stability-indicating liquid chromatographic method for the determination of retapamulin in topical dosage form. J Chromatogr Sci. 2014 Mar;52(3):238-45. doi: 10.1093/chromsci/bmt018. Epub 2013 Mar 19. PubMed PMID: 23510782.

12: Tomayko JF, Li G, Breton JJ, Scangarella-Oman N, Dalessandro M, Martin M. The safety and efficacy of topical retapamulin ointment versus placebo ointment in the treatment of secondarily infected traumatic lesions: a randomized, double-blind superiority study. Adv Skin Wound Care. 2013 Mar;26(3):113-21. doi: 10.1097/01.ASW.0000427922.12498.c4. PubMed PMID: 23426412.

13: Kircik LH. Efficacy and tolerability of retapamulin 1% ointment for the treatment of infected atopic dermatitis: a pilot study. J Drugs Dermatol. 2012 Jul;11(7):858-60. PubMed PMID: 22777229.

14: 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. PubMed PMID: 21947094.

15: Pérez-Trallero E, Tamayo E, Montes M, García-Arenzana JM, Iriarte V. In vitro activities of retapamulin and 16 other antimicrobial agents against recently obtained Streptococcus pyogenes isolates. Antimicrob Agents Chemother. 2011 May;55(5):2406-8. doi: 10.1128/AAC.01665-10. Epub 2011 Feb 22. PubMed PMID: 21343452; PubMed Central PMCID: PMC3088200.

16: Farrell DJ, Robbins M, Rhys-Williams W, Love WG. Investigation of the potential for mutational resistance to XF-73, retapamulin, mupirocin, fusidic acid, daptomycin, and vancomycin in methicillin-resistant Staphylococcus aureus isolates during a 55-passage study. Antimicrob Agents Chemother. 2011 Mar;55(3):1177-81. doi: 10.1128/AAC.01285-10. Epub 2010 Dec 13. PubMed PMID: 21149626; PubMed Central PMCID: PMC3067113.

17: Weinberg JM, Tyring SK. Retapamulin: an antibacterial with a novel mode of action in an age of emerging resistance to Staphylococcus aureus. J Drugs Dermatol. 2010 Oct;9(10):1198-204. PubMed PMID: 20941943.

18: Schram SE, Warshaw EM. Retapamulin: an emerging antimicrobial allergen. Dermatitis. 2010 May-Jun;21(3):160-1. PubMed PMID: 20487660.

19: Dubois EA, Cohen AF. Retapamulin. Br J Clin Pharmacol. 2010 Jan;69(1):2-3. doi: 10.1111/j.1365-2125.2009.03505.x. PubMed PMID: 20078606; PubMed Central PMCID: PMC2830591.

20: Moody MN, Morrison LK, Tyring SK. Retapamulin: what is the role of this topical antimicrobial in the treatment of bacterial infections in atopic dermatitis? Skin Therapy Lett. 2010 Jan;15(1):1-4. Review. PubMed PMID: 20066388.