Retapamulin

Pleuromutilin antibiotic,protein synthesis inhibitor CAS# 224452-66-8

Retapamulin

Catalog No. BCC4837----Order now to get a substantial discount!

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Chemical structure

Retapamulin

3D structure

Chemical Properties of Retapamulin

Cas No. 224452-66-8 SDF Download SDF
PubChem ID 23725003 Appearance Powder
Formula C30H47NO4S M.Wt 517.76
Type of Compound N/A Storage Desiccate at -20°C
Synonyms SB-275833
Solubility DMSO : ≥ 52 mg/mL (100.43 mM)
*"≥" means soluble, but saturation unknown.
SMILES CC1CCC23CCC(=O)C2C1(C(CC(C(C3C)O)(C)C=C)OC(=O)CSC4CC5CCC(C4)N5C)C
Standard InChIKey STZYTFJPGGDRJD-NJUFAHRVSA-N
Standard 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
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of Retapamulin

DescriptionRetapamulin(SB-275833) is a topical antibiotic, which binds to both E. coli and S. aureus ribosomes with similar potencies with Kd of 3 nM. IC50 Value: 3 nM(Kd, E.coli) Target: Antibacterial Retapamulin is a topical antibiotic developed by GlaxoSmithKline. Retapamulin(SB-275833) is the first drug in the new class of pleuromutilin antibiotics to be approved for human use.Retapamulin(SB-275833) is marketed as an ointment under the brand names Altabax and Altargo. Retapamulin(SB-275833) is useful for Antibiotics.

References:
[1]. Kircik LH. Efficacy and tolerability of retapamulin 1% ointment for the treatment of infected atopic dermatitis: a pilot study. J Drugs Dermatol. 2012 Jul 1;11(7):858-60. [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. [3]. 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. [4]. 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. [5]. Retapamulin: focus on its use in the treatment of uncomplicated superficial skin infections and impetigo By Jacobs, Michael R.From Expert Review of Dermatology (2010), 5(5), 505-517.

Retapamulin Dilution Calculator

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Retapamulin Molarity Calculator

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Preparing Stock Solutions of Retapamulin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.9314 mL 9.657 mL 19.314 mL 38.6279 mL 48.2849 mL
5 mM 0.3863 mL 1.9314 mL 3.8628 mL 7.7256 mL 9.657 mL
10 mM 0.1931 mL 0.9657 mL 1.9314 mL 3.8628 mL 4.8285 mL
50 mM 0.0386 mL 0.1931 mL 0.3863 mL 0.7726 mL 0.9657 mL
100 mM 0.0193 mL 0.0966 mL 0.1931 mL 0.3863 mL 0.4828 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Retapamulin

Retapamulin is a pleuromutilin antibiotic [1].

Retapamulin is developed for topical treatment of skin infections which is mainly caused by gram-positive organisms, β-hemolytic streptococci and coagulase-negative staphylococci. Retapamulin is especially used against those drug resistance strains. In the in vitro studies, retapamulin demonstrates potent activity and a broad spectrum. It shows excellent antimicrobial activities against S. aureus, S. epidermidis, S. saprophyticus, S. pyogenes, S. agalactiae and Viridans group streptococci with MIC50 values of 0.06μg/ml, 0.06μg/ml, 0.12μg/ml, 0.008μg/ml, 0.016μg/ml and 0.03μg/ml, respectively. Retapamulin plays its antibiotic role through binding to a unique site of the bacterial ribosome [1, 2].

References:
[1] Jones R N, Fritsche T R, Sader H S, et al. Activity of retapamulin (SB-275833), a novel pleuromutilin, against selected resistant gram-positive cocci. Antimicrobial agents and chemotherapy, 2006, 50(7): 2583-2586.
[2] Rittenhouse S, Biswas S, Broskey J, et al. Selection of retapamulin, a novel pleuromutilin for topical use. Antimicrobial agents and chemotherapy, 2006, 50(11): 3882-3885.

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References on Retapamulin

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.[Pubmed:25396674]

Adv Skin Wound Care. 2014 Dec;27(12):548-59.

OBJECTIVE: To evaluate the clinical and bacteriological efficacy of topical Retapamulin ointment 1% versus oral linezolid in the treatment of patients with secondarily infected traumatic lesions (SITLs; excluding abscesses) or impetigo due to methicillin-resistant Staphylococcus aureus (MRSA). DESIGN: A randomized, double-blind, double-dummy, multicenter, comparative study (NCT00852540). SETTING: Patients recruited from 36 study centers in the United States. PATIENTS: Patients 2 months or older with SITL (including secondarily infected lacerations or sutured wounds) or impetigo (bullous and nonbullous) suitable for treatment with a topical antibiotic, with a total Skin Infection Rating Scale score of 8 or greater, including a pus/exudate score of 3 or greater. INTERVENTIONS: Patients received Retapamulin ointment 1% (plus oral placebo), twice daily for 5 days or oral linezolid (plus placebo ointment) 2 or 3 times daily for 10 days. MAIN OUTCOME MEASURE: Primary end point: clinical response (success/failure) at follow-up in patients with MRSA at baseline (per-protocol population). Secondary efficacy end points: clinical and microbiologic response and outcome at follow-up and end of therapy; therapeutic response at follow-up. MAIN RESULTS: The majority of patients had SITL (70.4% [188/267] and 66.4% [91/137] in the Retapamulin and linezolid groups, respectively; intent-to-treat clinical population). Clinical success rate at follow-up was significantly lower in the Retapamulin versus the linezolid group (63.9% [39/61] vs 90.6% [29/32], respectively; difference in success rate -26.7%; 95% CI, -45.7 to -7.7). CONCLUSIONS: Clinical success rate at follow-up in the per-protocol MRSA population was significantly lower in the Retapamulin versus the linezolid group. It could not be determined whether this was related to study design, bacterial virulence, or Retapamulin activity.

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.[Pubmed:26666950]

Antimicrob Agents Chemother. 2015 Dec 14;60(3):1298-303.

Mupirocin is a topical antimicrobial used to decolonize patients who carry methicillin-resistant Staphylococcus aureus (MRSA), and the topical agent Retapamulin may be a potential alternative therapy. The goal of this study was to determine the in vitro activity of Retapamulin as well as a panel of 15 antimicrobial agents, including mupirocin, for 403 MRSA isolates collected longitudinally from a naive population at the Veterans Affairs Puget Sound Health Care System. The MICs for Retapamulin had a unimodal distribution, ranging from 0.008 to 0.5 mug/ml. One isolate had an MIC of >16 mug/ml, was also resistant to clindamycin and erythromycin, and was recovered from the nares of a patient undergoing hemodialysis. Twenty-four isolates (6%) and 11 isolates (3%) demonstrated low-level resistance (MICs of 8 to 64 mug/ml) and high-level resistance (MICs of >/= 512 mug/ml), respectively, to mupirocin. Isolates were recovered from 10 patients both before and after mupirocin therapy. Of those, isolates from 2 patients demonstrated MIC changes postmupirocin therapy; in both cases, however, strain typing demonstrated that the pre- and postmupirocin strains were different. A total of 386 isolates (96%) had vancomycin MICs of Retapamulin (0.25%) Although the use of mupirocin is currently the standard therapy for decolonization practices, the activity of Retapamulin warrants its consideration as an alternative therapy in MRSA decolonization regimens.

In Vitro Antimicrobial Activities of Fusidic Acid and Retapamulin against Mupirocin- and Methicillin-Resistant Staphylococcus aureus.[Pubmed:26512169]

Ann Dermatol. 2015 Oct;27(5):551-6.

BACKGROUND: The in vitro activities of Retapamulin and fusidic acid against clinical isolates of mupirocin-resistant and methicillin-resistant Staphylococcus aureus (MRSA) from Korea are not well understood. OBJECTIVE: This study aimed to determine the activities of Retapamulin and fusidic acid against clinical isolates of mupirocin-resistant MRSA. METHODS: Clinical isolates of mupirocin-resistant MRSA were collected from two tertiary hospitals. The minimal inhibitory concentrations of mupirocin, fusidic acid, and Retapamulin were determined using agar dilution method. Polymerase chain reaction was used to confirm the identity of the species and the presence of resistance genes. Pulsed-field gel electrophoresis (PFGE) patterns of chromosomal DNA were used to determine the genetic similarity of high-level mupirocin-resistant isolates. RESULTS: Of the 497 MRSA isolates tested, 22 (4.4%) were mupirocin-resistant. Of these, 9 (1.8%) and 13 (2.6%) had high-level and low-level mupirocin resistance, respectively. Analysis of the PFGE patterns of the high-level mupirocin-resistant MRSA isolates identified five clusters. All 13 of the low-level mupirocin-resistant isolates were resistant to fusidic acid but susceptible to Retapamulin. However, among the 9 high-level mupirocin-resistant isolates, 56% were resistant to fusidic acid, and all were susceptible to Retapamulin. CONCLUSION: Retapamulin is highly active in vitro against Korean clinical isolates of high-level mupirocinand methicillin-resistant Staphylococcus aureus with different genetic backgrounds. Fusidic acid is more active against high-level mupirocin-resistant MRSA than low-level mupirocin-resistant MRSA.

Description

Retapamulin(SB-275833) is a topical antibiotic, which binds to both E.

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