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.


Price and Availability

Size Price Shipping out time Quantity
50mg USD 150 Same day
100mg USD 250 Same day
200mg USD 450 Same day
500mg USD 750 Same day
1g USD 1250 Same day
2g USD 1950 Same day
5g USD 2950 2 Weeks
10g USD 3950 2 Weeks
20g USD 6850 2 Weeks
Inquire bulk and customized quantity

Pricing updated 2020-10-26. Prices are subject to change without notice.

Retapamulin, purity > 98%, is in stock. The same day shipping out after order is received. Note: the estimated shipping out time for order > 2g may be 2 weeks.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 300270
Name: Retapamulin
CAS#: 224452-66-8
Chemical Formula: C30H47NO4S
Exact Mass: 517.32258
Molecular Weight: 517.76
Elemental Analysis: C, 69.59; H, 9.15; N, 2.71; O, 12.36; S, 6.19


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


Technical Data

Appearance:
White to off-white solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Certificate of Analysis:

Safety Data Sheet (SDS):

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.

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

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


References

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.