Lefamulin CAS#: 1061337-51-6; ChemWhat Code: 1417556
Identification
| Product Name | Lefamulin |
| IUPAC Name | [(1S,2R,3S,4S,6R,7R,8R,14R)-4-ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxo-6-tricyclo[5.4.3.01,8]tetradecanyl] 2-[(1R,2R,4R)-4-amino-2-hydroxycyclohexyl]sulfanylacetate |
| Molecular Structure |  |
| CAS Registry Number | 1061337-51-6 |
| MDL Number | MFCD28963989 |
| Synonyms | Lefamulin 1061337-51-6 BC-3781 CHEMBL3291398 Xenleta 1061337-51-6 (free base) (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,2R,4R)-4-amino-2-hydroxycyclohexyl)thio)acetate BC3781 compound 7 [PMID: 24874438] Lefamulin (USAN/INN) Lefamulin(BC-3781) Lefamulin(BC-3781)? SCHEMBL19766421 GTPL10824 DTXSID101027896 Acetic acid, 2-[[(1R,2R,4R)-4-amino-2-hydroxycyclohexyl]thio]-, (3aS,4R,5S,6S,8R,9R,9aR,10R)-6-ethenyldecahydro-5-hydroxy-4,6,9,10-tetramethyl-1-oxo-3a,9-propano-3aH-cyclopentacycloocten-8-yl ester EX-A3600 BDBM50019649 AKOS040759180 HY-16908 TS-09691 CS-0012945 NS00073375 D11631 Q27253537 (3aS,4R,5S,6S,8R,9R,9aR,10R)-6-ethenyl-5-hydroxy-4,6,9,10-tetramethyl-1-oxodecahydro-3a,9-propanocyclopenta[8]annulen-8-yl {[(1R,2R,4R)-4-amino-2-hydroxycyclohexyl]sulfanyl}acetate [(1S,2R,3S,4S,6R,7R,8R,14R)-4-ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxo-6-tricyclo[5.4.3.01,8]tetradecanyl] 2-[(1R,2R,4R)-4-amino-2-hydroxycyclohexyl]sulfanylacetate 62B |
| Molecular Formula | C28H45NO5S |
| Molecular Weight | 507.7 |
| InChI | InChI=1S/C28H45NO5S/c1-6-26(4)14-22(34-23(32)15-35-21-8-7-18(29)13-20(21)31)27(5)16(2)9-11-28(17(3)25(26)33)12-10-19(30)24(27)28/h6,16-18,20-22,24-25,31,33H,1,7-15,29H2,2-5H3/t16-,17+,18-,20-,21-,22-,24+,25+,26-,27+,28+/m1/s1 |
| InChI Key | KPVIXBKIJXZQJX-FCEONZPQSA-N |
| Canonical SMILES | C[C@@H]1CC[C@@]23CCC(=O)[C@H]2[C@@]1([C@@H](C[C@@]([C@H]([C@@H]3C)O)(C)C=C)OC(=O)CS[C@@H]4CC[C@H](C[C@H]4O)N)C |
| Patent Information | ||
| Patent ID | Title | Publication Date |
| EP4338732 | LEFAMULIN AND ITS DERIVATIVES FOR USE IN THE TREATMENT OF TULAREMIA | 2024 |
| WO2021/209174 | THERAPEUTIC USE OF PLEUROMUTILINS | 2021 |
| EP1972618 | Pleuromutilin derivatives for the treatment of diseases mediated by microbes | 2008 |
Physical Data
| Appearance | Solid |
Spectra
| Nucleus (NMR Spectroscopy) | Solvents (NMR Spectroscopy) | Frequency (NMR Spectroscopy), MHz |
| 1H | chloroform-d1 | 400 |
| Description (UV/VIS Spectroscopy) |
| Absorption maxima |
Route of Synthesis (ROS)
| Conditions | Yield |
| Stage #1: 14-O-{(1R,2R,4R)-[(2,2,2-trifluoroacetyl)-amino-2-hydroxy-cyclohexyl-sulfanyl]-acetyl}-mutilin With water; potassium carbonate In methanol at 40 – 45℃; for 5h; Industry scale; Stage #2: With potassium carbonate In dichloromethane; water; isopropyl alcohol at 0 – 25℃; for 1.5h; Industry scale; Experimental Procedure Example 714-0-{[(lR,2R,4R)-4-Amino-2-hydroxy-cyclohexylsuIfanyl]-acetyl}-mutilin, crystalline Form 2; 72.7 g of crude 14-O-{[(l/?,2 ?,4i?)-4-[(2,2,2-Trifluoro-acetyl)-amino-2-hydroxy-cyclohexyl- sulfanyl] -acetyl} -mutilin, 419.9 ml of methanol and 168 ml of water were charged to a flask and the mixture obtained was warmed to 40 to 45°C. To the mixture obtained 67.3 g ofK2CO3 was added and the mixture obtained was stirred at 40 to 45 °C for 5 h. The reaction was followed by HPLC until completion. Upon completion of the reaction, the mixture obtained was cooled to 20 to 25 °C, 588 ml of CH2C12 and 588 ml of 2 M phosphoric acid were added and the mixture obtained was stirred at 20 to 25 °C for 15 min. The mixture obtained was filtered biphasically, separated, and the organic layer obtained was extracted with 588 ml of 1 M phosphoric acid. The phases obtained were separated and to the combined aqueous (product) layers obtained was added 588 ml of CH2C12 and the mixture obtained was cooled to 10 to 15 °C. To the mixture obtained 6 M NaOH was added drop wise at <25 °C until a pH of >9 was reached (275 ml required). The mixture obtained was filtered biphsaically and the layers obtained were separated. The organic (product) layer obtained was concentrated to approximately 5 volumes in vacuo at <40°C, 176 ml of CH2CI2 was added and the mixture obtained was concentrated once more to 2 vols in vacuo at <40°C. To the concentrate obtained 323.5 ml of n-butanol was added dropwise, the mixture obtained was concentrated to 5 volumes in vacuo at <40°C and the concentrate obtained was stirred at 20 to 25 °C for 2 h. The mixture obtained was filtered, the precipitate obtained was washed with 117.6 ml of w-butanol and the solid obtained was dried overnight in vacuo at 40°C producing 44.2 g of 14-0-{[(lR,2R,4R)-4-amino-2-hydroxy-cyclohexylsulfanyl]-acetyl}- mutilin in crystalline Form 2. 44.2 g of crude 14-0-{[(lR,2R,4R)-4-amino-2-hydroxy-cyclohexylsulfanyl]-acetyl}-mutilin was charged to a clean vessel and 221 ml of w-butanol was added. The mixture obtained was heated to 88 to 92 °C, stirred for 40 min, allowed to cool at a steady rate over 3 h to 40 to 45 °C and stirred for a further 2 h. The mixture obtained was filtered, washed with 44.2 ml of «-butanol followed by 44.2 ml of MTBE and dried in vacuo at <40°C.37.6 g of crystalline 14-O-{[(l ?,2J?,4i?)-4-amino-2-hydroxy-cyclohexylsulfanyl]-acetyl}- mutilin in crystalline Form 2 was obtained in the form of a white crystalline solid.The 1H NMR pattern confirms the structure of 14-O-{[(li?,2i?,4i?)-4-amino-2-hydroxy- cyclohexylsulfanyl] -acetyl }-mutilin. The NMR pattern for 14-O-{[(lif,2 ?,4i?)-4-amino-2- hydroxy-cyclohexylsulfanyl]-acetyl}-mutilin is described in example 4. |
Safety and Hazards
| Pictogram(s) |     |
| Signal | Danger |
| GHS Hazard Statements | H302 (50%): Harmful if swallowed [Warning Acute toxicity, oral] H315 (50%): Causes skin irritation [Warning Skin corrosion/irritation] H317 (50%): May cause an allergic skin reaction [Warning Sensitization, Skin] H318 (50%): Causes serious eye damage [Danger Serious eye damage/eye irritation] H330 (50%): Fatal if inhaled [Danger Acute toxicity, inhalation] H411 (50%): Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard] |
| Precautionary Statement Codes | P260, P261, P264, P264+P265, P270, P271, P272, P273, P280, P284, P301+P317, P302+P352, P304+P340, P305+P354+P338, P316, P317, P320, P321, P330, P332+P317, P333+P317, P362+P364, P391, P403+P233, P405, and P501 (The corresponding statement to each P-code can be found at the GHS Classification page.) |
Other Data
| HS Code | |
| Storage | Under room temperature away from light |
| Shelf Life | 2 years |
| Market Price |
| Druglikeness | |
| Lipinski rules component | |
| Molecular Weight | 507.735 |
| logP | -0.043.512 |
| HBA | 6 |
| HBD | 3 |
| Matching Lipinski Rules | 3 |
| Veber rules component | |
| Polar Surface Area (PSA) | 135.15 |
| Rotatable Bond (RotB) | 6 |
| Matching Veber Rules | 2 |
| Use Pattern |
| Lefamulin CAS#: 1061337-51-6 is a pleuromutilin class antibiotic used to treat community-acquired bacterial pneumonia (CABP) in adult patients caused by susceptible microorganisms. To minimize the emergence of resistant bacteria and preserve the efficacy of Lefamulin and other antibiotics, it should be used only for the treatment or prevention of confirmed or highly suspected bacterial infections. |
Buy Reagent | |
| No reagent supplier? | Send quick inquiry to ChemWhat |
| Want to be listed here as a reagent supplier? (Paid service) | Click here to contact ChemWhat |
Approved Manufacturers | |
| Want to be listed as an approved manufacturer (Requires approvement)? | Please download and fill out this form and send back to approved-manufacturers@chemwhat.com |
Contact Us for Other Help | |
| Contact us for other information or services | Click here to contact ChemWhat |