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Retapamulin (also known as SB-275833) is a novel and potent topical antibiotic of the pleuromutilin class approved by the FDA for treatment of impetigo in children. It binds to both E. coli and S. aureus ribosomes with similar potencies with Kd of 3 nM. It has 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.
Physicochemical Properties
| Molecular Formula | C30H47NO4S | |
| Molecular Weight | 517.76 | |
| Exact Mass | 517.322 | |
| Elemental Analysis | C, 69.59; H, 9.15; N, 2.71; O, 12.36; S, 6.19 | |
| CAS # | 224452-66-8 | |
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| PubChem CID | 6918462 | |
| Appearance | White to off-white solid powder. | |
| Density | 1.2±0.1 g/cm3 | |
| Boiling Point | 594.9±50.0 °C at 760 mmHg | |
| Flash Point | 313.6±30.1 °C | |
| Vapour Pressure | 0.0±3.8 mmHg at 25°C | |
| Index of Refraction | 1.571 | |
| LogP | 5.45 | |
| Hydrogen Bond Donor Count | 1 | |
| Hydrogen Bond Acceptor Count | 6 | |
| Rotatable Bond Count | 6 | |
| Heavy Atom Count | 36 | |
| Complexity | 895 | |
| Defined Atom Stereocenter Count | 10 | |
| SMILES | S(C([H])([H])C(=O)O[C@]1([H])C([H])([H])[C@](C([H])=C([H])[H])(C([H])([H])[H])[C@]([H])([C@]([H])(C([H])([H])[H])[C@]23C([H])([H])C([H])([H])C([C@@]2([H])[C@@]1(C([H])([H])[H])[C@]([H])(C([H])([H])[H])C([H])([H])C3([H])[H])=O)O[H])C1([H])C([H])([H])[C@]2([H])C([H])([H])C([H])([H])[C@]([H])(C1([H])[H])N2C([H])([H])[H] |
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| 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 | |
| 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 | |
| Synonyms | SB-275833; SB 275833; SB275833; Retapamulin, trade names Altabax and Altargo. | |
| HS Tariff Code | 2934.99.9001 | |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: This product requires protection from light (avoid light exposure) during transportation and storage. |
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| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
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| Toxicity/Toxicokinetics |
Effects During Pregnancy and Lactation ◉ Summary of Use during Lactation No information is available on the use of retapamulin during breastfeeding. Because retapamulin is poorly absorbed after topical application, it is not likely to reach the bloodstream of the infant or cause any adverse effects in breastfed infants after maternal application away from the breast. Only water-miscible cream or gel products should be applied to the breast, because ointments may expose the infant to high levels of mineral paraffins via licking. ◉ Effects in Breastfed Infants Relevant published information was not found as of the revision date. ◉ Effects on Lactation and Breastmilk Relevant published information was not found as of the revision date. |
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| References | Antimicrob Agents Chemother.2006 Nov;50(11):3875-81. Epub 2006 Aug 28. | ||
| Additional Infomation |
Retapamulin is a carbotricyclic compound, a carboxylic ester and a cyclic ketone. Retapamulin is a Pleuromutilin Antibacterial. See also: Retapamulin (annotation moved to). |
Solubility Data
| Solubility (In Vitro) |
DMSO : 104~110 mg/mL ( 200.86~212.45 mM ) Ethanol : ~104 mg/mL |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.75 mg/mL (5.31 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 27.5 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.75 mg/mL (5.31 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 27.5 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 2.75 mg/mL (5.31 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 27.5 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. Solubility in Formulation 4: 10% DMSO+40% PEG300+5% Tween-80+45% Saline: ≥ 2.75 mg/mL (5.31 mM) (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.9314 mL | 9.6570 mL | 19.3140 mL | |
| 5 mM | 0.3863 mL | 1.9314 mL | 3.8628 mL | |
| 10 mM | 0.1931 mL | 0.9657 mL | 1.9314 mL |