224452-66-8
Retapamulin
CAS: 224452-66-8
Molecular Formula: C30H47NO4S
224452-66-8 - Names and Identifiers
| Name | Retapamulin |
| Synonyms | SB-275833 tetapaMulin RETAPAMULIN Rebapamulin Retapamulin RetapaMulin API RetapaMulin (SB-275833) (3Ar,4R,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 (3aS,4R,5S,6S,8R,9R,9aR,10R)-2-(exo-8-Methyl-8-azabicyclo[3.2.1]octan-3-ylsulfanyl)acetic acid 5-hydroxy-4,6,9,10-tetraMethyl-1-oxo-6-vinylperhydro-3a,9-propanocyclopentacycloocten-8-yl ester 3a,9-propano-3aH-cyclopentacyclooctene-8-acetic acid, 6-ethenyldecahydro-5-hydroxy-4,6,9,10-tetramethyl-α-[[(3-endo)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl]thio]-1-oxo-, ion(1-), (3aS,4R,5S,6S,8R,9R,9aR,10R)- |
| CAS | 224452-66-8 |
| EINECS | 639-491-7 |
| InChI | InChI=1/C30H47NO4S/c1-7-28(4)16-22(24(27(34)35)36-21-14-19-8-9-20(15-21)31(19)6)29(5)17(2)10-12-30(18(3)26(28)33)13-11-23(32)25(29)30/h7,17-22,24-26,33H,1,8-16H2,2-6H3,(H,34,35)/p-1/t17-,18+,19-,20+,21+,22+,24?,25+,26+,28-,29+,30+/m1/s1 |
224452-66-8 - Physico-chemical Properties
| Molecular Formula | C30H47NO4S |
| Molar Mass | 517.76 |
| Density | 1.16±0.1 g/cm3(Predicted) |
| Boling Point | 594.9±50.0 °C(Predicted) |
| Flash Point | 331°C |
| Solubility | DMSO 104 mg/mL ;Water <1 mg/mL;Ethanol 104 mg/mL |
| Vapor Presure | 3.57E-18mmHg at 25°C |
| pKa | 14.65±0.70(Predicted) |
| Storage Condition | 2-8°C |
| Use | A broad spectrum antibiotic with no cross resistance to existing classes |
| In vitro study | Retapamulin, a potent inhibitor of protein synthesis, was derived from lysates prepared from erythromycin-sensitive Escherichia coli cells with an IC50 of 0.33 μm. The intracellular components of rabbit reticulocytes are necessary for protein synthesis in mammals, and Retapamulin (100 μm) was not effective in inhibiting the translation process in eukaryotic cells tested with its lysate system. Retapamulin binds to the Erys ribosome and completely displaces the labeled ligand base with an IC50 of 26.1 nM. Retapamulin partially inhibits the ability of charged, N-blocked tRNA to bind to the ribosomal P site of Escherichia Coli with an IC50 of 17.4 nM (maximum inhibition is 80%). Retapamulin inhibits Staphylococcus aureus and Streptococcus pyogenes with MIC90 of 0.12 μg/ml and ≤ 0.03 μg/ml, respectively. Retapamulin inhibited S. Aureus subpopulation with a MIC50/90 value of 0.06/0.12 μg/ml. Retapamulin showed good inhibitory activity against these strains and the required MIC was 0.06 μg/ml. Retapamulin was effective against Streptococcus pyogenes strains with a tested MIC90 of 0.016 μg/ml, which was 32-fold and> 1,024-fold more effective than mupirocin and fusidic acid, respectively, based on MIC90s. Retapamulin binds to specific sites of bacterial ribosomes with its novel mode of action. Retapamulin (<2 mg/L) inhibited 37/52 (71%) of Bacteroides fragilis strains and 85/87 (98%) of other Gram-negative bacilli. Retapamulin was more effective against Propionibacterium acnes and anaerobic Gram-positive cocci than clindamycin, metronidazole, and ceftriaxone. Retapamulin inhibited total viable cell (TVC), protein synthesis, and 50s subunit synthesis, with IC50 of 12 ng/ml, respectively, in the wild-type (wt) S. Aureus strain RN1786, 5 ng/ml and 27 ng/ml. |
224452-66-8 - Introduction
Retapamulin is a local antibiotic that can bind Escherichia coli and Staphylococcus aureus ribosomes with similar effects, with a Kd value of 3 nM.
Last Update：2022-10-16 17:15:04
224452-66-8 - Reference Information
| biological activity | Retapamulin (SB-275833) is a local antibiotic that can bind Escherichia coli and Staphylococcus aureus ribosomes with similar effects, with a Kd value of 3 nM. |
| Target | Value |
| ribosome | 3 nM(Kd) |
Last Update：2024-04-09 21:46:18
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