Description Chemical Properties Uses
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Thiamphenicol

Description Chemical Properties Uses
Product Name
Thiamphenicol
CAS No.
15318-45-3
Chemical Name
Thiamphenicol
Synonyms
Neomyson;8065c.b.;NSC 522822;win-5063-2;thiocymetin;thiophenicol;D-Thiocymetin;THIAMPHENICOL;Thinmphcnicol;Thiamphenical
CBNumber
CB0102588
Molecular Formula
C12H15Cl2NO5S
Formula Weight
356.22
MOL File
15318-45-3.mol
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Thiamphenicol Property

Melting point:
163-166 °C
alpha 
D25 +12.9° (ethanol)
Density 
1.3281 (rough estimate)
refractive index 
1.6000 (estimate)
storage temp. 
-20°C Freezer, Under Inert Atmosphere
solubility 
ethanol: 50 mg/mL, clear, colorless
pka
11.05±0.46(Predicted)
form 
powder
Boiling point:
695.9±55.0 °C(Predicted)
color 
white to off-white
Water Solubility 
Soluble in acetonitrile or DMF. Slightly soluble in water
Merck 
14,9301
BRN 
2819542
InChIKey
OTVAEFIXJLOWRX-NXEZZACHSA-N
CAS DataBase Reference
15318-45-3
EPA Substance Registry System
Thiamphenicol (15318-45-3)
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Safety

Safety Statements 
22-24/25
WGK Germany 
2
RTECS 
AB6680000
HS Code 
29414000
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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
T0261
Product name
Thiamphenicol
Packaging
1g
Price
$55.7
Updated
2020/08/18
Sigma-Aldrich
Product number
T0261
Product name
Thiamphenicol
Packaging
5g
Price
$161
Updated
2020/08/18
TCI Chemical
Product number
T2802
Product name
Thiamphenicol
Purity
>98.0%(HPLC)(N)
Packaging
5g
Price
$52
Updated
2020/06/24
TCI Chemical
Product number
T2802
Product name
Thiamphenicol
Purity
>98.0%(HPLC)(N)
Packaging
25g
Price
$155
Updated
2020/06/24
Alfa Aesar
Product number
J63575
Product name
Thiamphenicol
Packaging
5g
Price
$51.9
Updated
2020/06/24
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Thiamphenicol Chemical Properties,Usage,Production

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.

Chemical Properties

White to off-white crystalline powder or crystal. Melting point (℃) 178-180 (swirled), 164-166 (right-handed).

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.

Chemical Properties

Off-White Solid

Originator

Thiophenicol,Clin Midy,France,1967

Uses

Antimicrobial

Uses

chelating agent, antiseborrheic

Uses

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.

Uses

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.

Manufacturing Process

A mixture of 50 parts by weight of racemic 2-acetylamino-1-(4- methylmercaptophenyl)-1,3-propanediol, 100 parts by weight of concentrated hydrochloric acid, and 500 parts by weight of water was warmed on a steam bath for thirty minutes. The resulting solution was cooled to about 40°C and was then made strongly alkaline by addition of 35% aqueous sodium hydroxide solution. The alkaline solution was then refrigerated. The white solid which separated from the cooled solution was collected on a filter. There was thus obtained 27 parts by weight of 2-amino-1-(4-methylmercaptophenyl)- 1,3-propanediol. This product melted at 130.7°C to 131.9°C after recrystallization from methanol.
This compound was converted to the tartrate and the optical isomers were resolved.
A mixture of 1.1 g of 2-amino-1-(4-methylmercaptophenyl)-1,3-propanediol, obtained as described above and 1.6 ml of ethyl dichloroacetate was heated on a steam bath for three hours. The resulting viscous yellow oil was dissolved in 25 ml of ethylene chloride and filtered hot with charcoal, and the filtrate was allowed to cool to about 25°C. From the filtrate there separated 0.92 g of tiny white leaflets which were collected on a filter. Recrystallization of this product, which was a dextro-rotary form of 2-dichloroacetylamino-1-(4- methylmercaptophenyl)-1,3-propanediol from nitroethane yielded the pure product, which melted at 111.6°C to 112.6°C.
7 g of the 2-dichloroacetylamino-1-(4-methylmercaptophenyl)-1,3-propanediol obtained as described above was dissolved in 30 ml of acetone. To this solution there was added dropwise with stirring 10 ml of 40% peracetic acid. The temperature during the reaction was maintained at 39°C to 45°C by cooling the reaction vessel. After stirring the mixture for two hours, it was diluted with 100 ml of water and the solution allowed to stand over the weekend in the refrigerator. The solid which separated from solution was collected on a filter, washed several times with ice water, and dried overnight at 70°C.

Therapeutic Function

Antibacterial

Antimicrobial activity

It is generally less active than chloramphenicol, but is equally active against Str. pyogenes, Str. pneumoniae, H. influenzae and N. meningitidis, including some strains resistant to chloramphenicol. It is more actively bactericidal against Haemophilus and Neisseria spp.

Acquired resistance

There is complete cross-resistance with chloramphenicol in those bacteria which elaborate acetyltransferase, although the affinity of the enzyme for thiamphenicol is lower. Organisms that owe their resistance to other mechanisms may be susceptible.

Pharmacokinetics

An oral dose of 500 mg produces a peak plasma level of 3–6 mg/L after about 2 h. The plasma half-life is 2.6–3.5 h. It is said to reach the bronchial lumen in concentrations sufficient to exert a bactericidal effect on H. influenzae. Unlike chloramphenicol it is not a substrate for hepatic glucuronyl transferase; it is not eliminated by conjugation, and its half-life is not affected by phenobarbital induction.
About 50% of the dose can be recovered in an active form in the urine within 8 h and 70% over 24 h. The drug is correspondingly retained in the presence of renal failure, and in anuric patients the plasma half-life has been reported to be 9 h, a value not significantly affected by peritoneal dialysis. Biliary excretion is believed to account for removal of the antibiotic in anuric patients. The plasma concentration is elevated and half-life prolonged in patients with hepatitis or cirrhosis.

Clinical Use

Similar to that of chloramphenicol.

Side effects

There are no reports of irreversible bone-marrow toxicity. This has been related to the absence of the nitro group, and hence its reduction products, and differences in the biochemical effects of thiamphenicol and chloramphenicol on mammalian cells. It exerts a greater dose-dependent reversible depression of hemopoiesis and immunogenesis than chloramphenicol, and has been used for its immunosuppressive effect. Therapeutic doses (1–1.5 g) are likely to depress erythropoiesis in the elderly or others with impaired renal function.

Purification Methods

Recrystallise thiamphenicol from H2O or CHCl3. The UV has max at 224, 266 and 274nm ( 13,700, 800 and 700) in 95% EtOH. The 1S,2S-isomer [1478651-7] has m 164.3-166.3o (from H2O/EtOAc/pet ether) and [] D 25 -12.6o (c 1, EtOH); and the racemate 1RS,2RS-Racefenical [847-25-6] has m 181-183o (dec) from CHCl3/EtOAc/pet ether. [Cutler et al. J Am Chem Soc 74 5475, 5482 1952, UV: Nachod & Cutler J Am Chem Soc 74 1291 1952, Suter et al. J Am Chem Soc 75 4330 1953, Cutler et al. J Am Pharm Assoc 43 687 1954, Beilstein 13 IV 2957.]

Thiamphenicol Preparation Products And Raw materials

Raw materials

Preparation Products

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Thiamphenicol Suppliers

Banff Green Technologies, Inc.
Tel
(+86)21 54795870
Fax
(+86)21 54795870
Email
support@banffgt.com
Country
China
ProdList
32
Advantage
55
Wuhan hongde yuexin pharmaceutical technology co. LTD
Tel
027-83855391-
Fax
027-83855391
Email
hbzlkschem2009@163.com;
Country
China
ProdList
1919
Advantage
58
J & K SCIENTIFIC LTD.
Tel
010-82848833- ;010-82848833-
Fax
86-10-82849933
Email
jkinfo@jkchemical.com;market6@jkchemical.com
Country
China
ProdList
96815
Advantage
76
Meryer (Shanghai) Chemical Technology Co., Ltd.
Tel
21-61259100-
Fax
86-21-61259102
Email
sh@meryer.com
Country
China
ProdList
40268
Advantage
62
future industrial shanghai co., ltd
Tel
400-0066-400;021-60496031
Fax
021-55660885
Email
sales@jonln.com;sales@jonln.com
Country
China
ProdList
2000
Advantage
65
TCI (Shanghai) Development Co., Ltd.
Tel
021-67121386 / 800-988-0390
Fax
021-67121385
Email
Sales-CN@TCIchemicals.com
Country
China
ProdList
24555
Advantage
81
BeiJing Hwrk Chemicals Limted
Tel
010-57411839-
Fax
021-55236763
Email
bjsales@hwrkchemical.com
Country
China
ProdList
18708
Advantage
55
Shanghai Longsheng chemical Co.,Ltd.
Tel
021-58099652-8005;021-58099637-8009
Fax
021-58099609
Email
bin.wu@shlschem.com;sales@shlschem.com
Country
China
ProdList
9830
Advantage
59
Nanjing Chemlin Chemical Co., Ltd
Tel
025-83697070
Fax
+86-25-83453306
Email
info@chemlin.com.cn
Country
China
ProdList
19993
Advantage
64
Shanghai Hanhong Scientific Co.,Ltd.
Tel
021-54306202- ;021-54308259-
Fax
+86-21-64545202
Email
info@hanhonggroup.com;info@hanhonggroup.com
Country
China
ProdList
43258
Advantage
64
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View Lastest Price from Thiamphenicol manufacturers

Shaanxi Dideu Medichem Co. Ltd
Product
Thiamphenicol 15318-45-3
Price
US $0.00-0.00/公斤
Min. Order
1公斤
Purity
99.0%
Supply Ability
500 MT
Release date
2020-05-25
Hebei shuoxi biotechnology co. LTD
Product
thiamphenicol 15318-45-3
Price
US $0.00/KG
Min. Order
1g
Purity
99.9%
Supply Ability
1 ton
Release date
2019-10-30
career henan chemical co
Product
Thiamphenicol 15318-45-3
Price
US $7.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
100KG
Release date
2018-12-22

15318-45-3, ThiamphenicolRelated Search:


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