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CasNo: 15318-45-3
MF: C12H15Cl2NO5S
Appearance: off-white solid
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Thiamphenicol is off-white solid, while it's Molecular Formula is C12H15Cl2NO5S. 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.
The CAS number of Thiamphenicol is 15318-45-3.
More information of Thiamphenicol 15318-45-3 are:
Synonyms |
Acetamide,2,2-dichloro-N-[2-hydroxy-1-(hydroxymethyl)-2-[4-(methylsulfonyl)phenyl]ethyl]-,[R-(R*,R*)]-;(Methylsulfonyl)chloramphenicol;8065CB;D-Thiocymetin;D-Thiophenicol;D-d-threo-2-Dichloroacetamido-1-(4-methylsulfonylphenyl)-1,3-propanediol;Dextrosulphenidol;NSC 522822;Thiocymetin;Thiophenicol;Win 5063-2; |
CAS Number |
15318-45-3 |
Molecular Formula |
C12H15Cl2NO5S |
Molecular Weight |
356.227 |
Density |
1.491 g/cm3 |
Melting Point |
163-166 °C |
Boiling Point |
695.9 °C at 760 mmHg |
Flash Point |
374.7 °C |
HS CODE |
29414000 |
PSA |
112.08000 |
LogP |
1.87600 |
Pka |
11.05±0.46(Predicted) |
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.
InChI:InChI=1/C12H14Cl2N2O7S/c1-24(21,22)23-6-9(15-12(18)11(13)14)10(17)7-2-4-8(5-3-7)16(19)20/h2-5,9-11,17H,6H2,1H3,(H,15,18)/t9-,10-/m1/s1
Articles related to Thiamphenicol:
Article |
Source |
Regioselective preparation of thiamphenicol esters through lipase-catalyzed processes |
Da Silva, Marcos R.,Montenegro, Tasso G.C.,De Mattos, Marcos C.,De Oliveira, Maria Da Conceic?a?o F.,De Lemos, Telma L.G.,De Gonzalo, Gonzalo,Lavandera, Iva?n,Gotor-Ferna?ndez, Vicente,Gotor, Vicente , p. 987 - 994 (2014) |
Method for continuously preparing thiamphenicol by using micro-reaction system |
- Paragraph 0021-0043, (2021/08/14) |
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