Retapamulin

Base Information

• Chemical Name: Retapamulin
• CAS No.: 224452-66-8
• Deprecated CAS: 345632-67-9
• Molecular Formula: C30H47NO4S
• Molecular Weight: 517.773
• Hs Code.: 2933990090
• European Community (EC) Number: 639-491-7
• UNII: 4MG6O8991R
• Nikkaji Number: J2.330.595J
• Wikipedia: Retapamulin
• Wikidata: Q7316645,Q76393594
• NCI Thesaurus Code: C61924
• RXCUI: 642274
• ChEMBL ID: CHEMBL1658
• Mol file: 224452-66-8.mol

Synonyms:acetic acid, 2-(((3-exo)-8-methyl-8-azabicyclo(3.2.1)oct-3-yl)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;Altabax;Altargo;retapamulin;SB 275833;SB-275833;SB275833

Chemical Property of Retapamulin

Chemical Property:

• Vapor Pressure: 3.57E-18mmHg at 25°C
• Boiling Point: 623.8 °C at 760 mmHg
• PKA: 14.65±0.70(Predicted)
• Flash Point: 331 °C
• PSA: 92.14000
• Density: 1.16±0.1 g/cm3(Predicted)
• LogP: 5.18920
• Storage Temp.: 2-8°C
• Solubility.: insoluble in H2O; ≥114.8 mg/mL in EtOH; ≥16.15 mg/mL in DMSO
• XLogP3: 6.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 517.32258015
• Heavy Atom Count: 36
• Complexity: 895

Purity/Quality:

99% min ^*data from raw suppliers

Retapamulin 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC23CCC(=O)C2C1(C(CC(C(C3C)O)(C)C=C)OC(=O)CSC4CC5CCC(C4)N5C)C
• Isomeric 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)CSC4C[C@H]5CC[C@@H](C4)N5C)C
• Recent ClinicalTrials: Treatment of Staphylococcus Aureus Colonization in Hand Eczema
• Recent EU Clinical Trials: A phase III 3 arms, multicenter, randomised, investigator-blind study to assess the efficacy and safety of ozenoxacin 1% cream applied twice daily for 5 days versus placebo in the treatment of patients with impetigo
• Description: Antibacterial retapamulin is a derivative of the natural product pleuromutilin and was developed by Glaxo and approved in the US in 2007 for the treatment of skin infections. It has a unique mechanism of action, inhibiting bacterial protein synthesis by inhibiting the larger subunit of the ribosome, and thus has no cross resistance to other antibacterial agents. Pleuromutilin is a tricyclic diterpenoid that was first isolated in 1951 from the edible mushroom Pleurotus mutilus. The first semisynthetic analogs tiamulin and valnemulin, developed for veterinary use, have been shown to interact uniquely with bacterial ribosomes by high affinity binding to a site on the 50S subunit. Binding to this site interferes with ribosomal peptidyl transferase activity, blocks P-site interactions, and prevents the evolution of active 50S ribosomal subunits. Retapamulin, the first pleuromutilin approved for human use, behaves similarly to selectively inhibit bacterial protein synthesis. This novel mechanism of action has been implicated in the lack of in vitro target-specific cross-resistance with other classes of antibiotics.
• Uses: Retapamulin is a topical antibiotic, which binds to both E. coli and S. aureus ribosomes with similar potencies with Kd of 3 nM Retapamulin is a semi-synthetic pleuormutilin prepared by reacting pleuromutilin tosylate with tropine-3-thiol to give a more hydrophobic analogue with a tertiary amine. This enables formulation as a stable hydrochloride salt. Retapamulin is a broad spectrum antibiotic with no cross resistance to existing antibiotic classes, and is the first pleuromutilin approved for human use. Like all the pleuromutilins, retapamulin inhibits protein synthesis by binding to domain V of 23S rRNA. A broad spectrum antibiotic with no cross resistance to existing classes Retapamulin is a semi-synthetic pleuromutilin prepared by reacting pleuromutilin tosylate with tropine-3-thiol to give a more hydrophobic analogue with a tertiary amine. This enables formulation as a stable hydrochloride salt. Retapamulin is a broad spectrum antibiotic with no cross resistance to existing antibiotic classes, and is the first pleuromutilin approved for human use. Like all the pleuromutilins, retapamulin inhibits protein synthesis by binding to domain V of 23S rRNA.

Technology Process of Retapamulin

There total 12 articles about Retapamulin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.2%

pleuromutilin tosylate (31716-01-5) + C8H15NS*(x)ClH → retapamulin (224452-66-8)

Guidance literature:

With potassium carbonate; In acetone; at 45 ℃; for 20h; Temperature;

Reference yield: 87.3%

pleuromutilin tosylate (31716-01-5) + C8H15NS*H2O4S → retapamulin (224452-66-8)

Guidance literature:

With potassium carbonate; In acetone; at 50 ℃; for 12h;

Reference yield: 80.0%

(1R,3S,5S)-8-methyl-8-azabicyclo[3.2.1]octane-3-thiol (848130-83-6) + {(3aS,4R,5S,6S,8R,9R,9aR,10R)-6-ethenyldeca hydro-5-hydroxy-4,6,9,10-tetramethyl-1-oxo-3a,9-propano-3aH-cyclopentacyclo-octen-8-yl methanesulfonyloxyacetate} (60924-38-1) → retapamulin (224452-66-8)

Guidance literature:

With triethylamine; In 4-methyl-2-pentanone; at 20 - 40 ℃; for 2 - 24h; Product distribution / selectivity;

upstream raw materials:

(1R,3S,5S)-8-methyl-8-azabicyclo[3.2.1]octane-3-thiol

{(3aS,4R,5S,6S,8R,9R,9aR,10R)-6-ethenyldeca hydro-5-hydroxy-4,6,9,10-tetramethyl-1-oxo-3a,9-propano-3aH-cyclopentacyclo-octen-8-yl methanesulfonyloxyacetate}

pleuromutilin tosylate

3-tropanol

Refernces

• 1、 -. "A Swedish he Moline synthesis method". . . Retrieved 2017/07/11.
• 2、 -. "Process for the preparation of Retapamulin and its intermediates". Page/Page column 3; 5; 6. . Retrieved 2009/06/27.