Thiamphenicol

Base Information

• Chemical Name: Thiamphenicol
• CAS No.: 15318-45-3
• Deprecated CAS: 14786-51-7,32430-04-9,3785-14-6,90-91-5
• Molecular Formula: C12H15Cl2NO5S
• Molecular Weight: 356.227
• Hs Code.: 29414000
• European Community (EC) Number: 239-355-3
• NSC Number: 758396
• UNII: FLQ7571NPM,283383NO13
• DSSTox Substance ID: DTXSID5021338
• Nikkaji Number: J9.286J
• Wikipedia: Thiamphenicol
• Wikidata: Q425015
• NCI Thesaurus Code: C61920,C61969
• Metabolomics Workbench ID: 54518
• ChEMBL ID: CHEMBL1236282
• Mol file: 15318-45-3.mol

Synonyms:Dextrosulfenidol;Raceophenidol;Thiamcol;Thiamphenicol;Thiomycetin;Thiophenicol;Urfamycin;Vicemycetin

Chemical Property of Thiamphenicol

Chemical Property:

• Appearance/Colour: off-white solid
• Melting Point: 163-166 °C
• Refractive Index: 1.589
• Boiling Point: 695.9 °C at 760 mmHg
• PKA: 11.05±0.46(Predicted)
• Flash Point: 374.7 °C
• PSA: 112.08000
• Density: 1.491 g/cm³
• LogP: 1.87600
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• Solubility.: ethanol: 50 mg/mL, clear, colorless
• Water Solubility.: Soluble in acetonitrile or DMF. Slightly soluble in water
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 355.0047991
• Heavy Atom Count: 21
• Complexity: 443

Purity/Quality:

99% ^*data from raw suppliers

Thiamphenicol ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Uses -> Pharmaceuticals
• Canonical SMILES: CS(=O)(=O)C1=CC=C(C=C1)C(C(CO)NC(=O)C(Cl)Cl)O
• Isomeric SMILES: CS(=O)(=O)C1=CC=C(C=C1)[C@H]([C@@H](CO)NC(=O)C(Cl)Cl)O
• Recent ClinicalTrials: Effect of Thiamphenicol on EAAT2 and Other Biomarkers From Nasal Biopsied Tissue
• Recent EU Clinical Trials: Efficacy and tollerability of thiamphenicol glycinate acetylcysteinate, given in sequential therapy sistematic and aerosol or by aerosol in the treatment of hight respiratory tract acute infection and/or subacute/recurring clinical study, multicentre, randomized, controlled vs standard therapy
• Description: Thiamphenicol is a broad-spectrum antibiotic chloramphenicol, which is more effective to the gram-negative bacteria than the gram-positive bacteria. At room temperature, it is a white to off-white crystalline powder or crystal, which can be quickly and completely absorped by oral adminstration, as well as it is excreted mainly in the prototype from the urine for metabolism. It is clinically applied for the treatment of respiratory, urinary tract, liver and gallbladder, typhoid and other intestinal surgery, gynecology and ENT infections. Especially in the mild infections it is more effective. It has the similar chemical structure with the chloramphenicol. Its methyl sulfone substituted the nitro of chloramphenicol, which reduced its toxicity, and in vivo its antibacterial activity is 2.5-5 times stronger than chloramphenicol. For gram-positive bacteria, such as streptococcus pneumoniae and hemolytic streptococcus, it has very strong antibacterial effect, while for gram-negative bacteria, such as Neisseria gonorrhoeae, meningococcus, lung Bacteroides, E. coli, Vibrio cholerae, Shigella and influenza bacillus, it also has strong antibacterial effect. For anaerobic bacteria, Rickettsia and amoeba, it has antibacterial effect in some extent. It has the same antimicrobial mechanism with chloramphenicol, which mainly inhibits the synthesis of bacterial protein. This drug is absorped quickly by oral administration, which reaches peak blood concentration within two hours. Its half-life is 5 hours, that is more longer than chloramphenicol. The bacteria have complete cross resistance to it and chloramphenicol, while the bacteria have some cross-resistance phenomenon to it and tetracycline. Thiamphenicol also has strong immunosuppressive effects, which is an excellent immunosuppressant. Its mechanism of action have significantly different with other immunosuppressive agents. The immunosuppressive effect is several times higher than the chloramphenicol. It can be as the effective extender for transplantation reaction and surgically allogeneic transplantation.
• Uses: It is applied for the treatment of respiratory, urinary tract, liver and gallbladder, typhoid and other intestinal surgery, gynecology and ENT infections. Especially in the mild infections it is more effective. Antimicrobial chelating agent, antiseborrheic Thiamphenicol is an antibiotic. Thiamphenicol is the methyl-sulfonyl analogue of chloramphenicol and has a similar spectrum of activity, but is 2.5 to 5 times as potent. Thiamphenicol is used particul arly for the treatment of sexually transmitted infections and pelvic inflammatory disease. Thiamphenicol is a semi-synthetic chloramphenicol prepared by total synthesis from thiophenol in which the nitro moiety of chloramphenicol is replaced by a methylsulphone, first synthesised at Sterling Winthrop in 1952. Thiamphenicol is a broad spectrum antibiotic with good activity against Gram negative and anaerobic bacteria. Thiamphenicol acts by binding to the 23S sub-unit of the 50S ribosome inhibiting protein synthesis. Thiamphenicol has been extensively studied with over 800 literature citations.
• Therapeutic Function: Antibacterial
• Clinical Use: Similar to that of chloramphenicol.

Technology Process of Thiamphenicol

There total 77 articles about Thiamphenicol 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: 99.0%

dichloroacetic acid methyl ester (116-54-1) + (1R,2R)-2-amino-1-<4-(methylsulphonyl)phenyl>-1,3-propanediol (51458-28-7) → thiamphenicol (15318-45-3,90-91-5)

Guidance literature:

With triethylamine; In methanol; at 30 ℃; for 0.166667h; Temperature;

Reference yield: 96.0%

(2R,3R)-2-benzylamino-3-(4-methylsulfonylphenyl)-propane-1,3-diol (895570-99-7) + ethyl 1,1-dichloroacetate (535-15-9) → thiamphenicol (15318-45-3,90-91-5)

Guidance literature:

(2R,3R)-2-benzylamino-3-(4-methylsulfonylphenyl)-propane-1,3-diol; With hydrogenchloride; hydrogen; palladium on activated charcoal; In ethanol; at 20 ℃; for 2h;

ethyl 1,1-dichloroacetate; With triethylamine; In methanol; at 30 ℃; for 6h; Further stages.;

DOI:10.1016/j.tet.2008.05.113

Reference yield: 91.0%

methyl 2-(2,2-dichloroacetamido)-3-hydroxy-3-(4-(methylsulfonyl)phenyl)propanoate → thiamphenicol (15318-45-3,90-91-5)

Guidance literature:

With methanol; sodium tetrahydroborate; at 0 - 20 ℃; for 5h;

DOI:10.1002/ejoc.201800658

upstream raw materials:

dichloroacetic acid methyl ester

(1R,2R)-2-amino-1-<4-(methylsulphonyl)phenyl>-1,3-propanediol

pentachloroacetone

dichloroacetyl-phosphorous acid diethyl ester

Downstream raw materials:

(1R,2R)-2-amino-1-<4-(methylsulphonyl)phenyl>-1,3-propanediol

(1S,2S)-2-amino-1-(4-(methylsulfonyl)phenyl)propane-1,3-diol

D,L-threo-1-(p-methylsulphonylphenyl)-2-aminopropane-1, 3-diol hydrochloride

threo-(1R,2R)-1-<(4-methylsulfonyl)phenyl>-2-(dichloroacetamido)-1,3-propanediol 3-palmitate

Refernces

• 1、 Perez, Marc,Echeverria, Pierre-Georges,Martinez-Arripe, Elsa,Ez Zoubir, Mehdi,Touati, Ridha,Zhang, Zhaoguo,Genet, Jean-Pierre,Phansavath, Phannarath,Ayad, Tahar,Ratovelomanana-Vidal, Virginie. "An Efficient Stereoselective Total Synthesis of All Stereoisomers of the Antibiotic Thiamphenicol through Ruthenium-Catalyzed Asymmetric Reduction by Dynamic Kinetic Resolution". . p. 5949 - 5958. Retrieved 2015.
• 2、 Chen, Fener,Cheng, Dang,Huang, Huashan,Jiang, Meifen,Liu, Minjie,Qu, Hongmin,Xia, Yingqi,Xiong, Tong,Zhang, Yan. "Catalytic Syn-Selective Nitroaldol Approach to Amphenicol Antibiotics: Evolution of a Unified Asymmetric Synthesis of (-)-Chloramphenicol, (-)-Azidamphenicol, (+)-Thiamphenicol, and (+)-Florfenicol". . p. 11557 - 11570. Retrieved 2021/09/02.
• 3、 -. "Thiamphenicol synthesis method". Paragraph 0008. . Retrieved 2020/01/25.