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Thiamphenicol

Product Name:
Thiamphenicol
CAS No.
15318-45-3
Chemical Name:
Thiamphenicol
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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N-Bromosuccinimide Price More Price(14)

Sigma-Aldrich Gold
Product number:
T0261
Product name :
Thiamphenicol
Packaging:
1g
Price:
$53.6
Updated:
2019/12/02
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Buy
Sigma-Aldrich Gold
Product number:
T0261
Product name :
Thiamphenicol
Packaging:
5g
Price:
$154
Updated:
2019/12/02
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TCI Chemical Gold
Product number:
T2802
Product name :
Thiamphenicol
Purity:
>98.0%(HPLC)(N)
Packaging:
5g
Price:
$52
Updated:
2020/06/24
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TCI Chemical Gold
Product number:
T2802
Product name :
Thiamphenicol
Purity:
>98.0%(HPLC)(N)
Packaging:
25g
Price:
$155
Updated:
2020/06/24
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Alfa Aesar Gold
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

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.

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

Raw materials

Preparation Products

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Thiamphenicol Suppliers

Global(291)Suppliers
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15318-45-3, ThiamphenicolRelated Search:

Acetamide Thiamphenicol Amine,Thiamphenicol Sulfone Amine racefenicol ThiamphenicolBp98 Thiamphenicol amino-compound Thiamphenicol ester-compound THIAMPHENICOLGLYCLINATEHCL Thiamphenicol Aminoacetate Ester Hydrochloride thiamphenicol glycinate acetylcysteinate thiamphenicol acetyltransferase Thiamphenicol glycinate THIAMPHENICOL PALMITATE,THIAMPHENICOL PALMITATE HCL thiamphenicol glycine hydrochloride,THIAMPHENICOL GLYCINATE HCL,THIAMPHENICOL GLYCINATE HYDROCHLORIDE,Thiamphenicol Glycinatd,thiamphenicol aminoacetate hydrochloride [R-(R*,R*)]-2-[(dichloroacetyl)amino]-3-hydroxy-3-[4-(methylsulphonyl)phenyl]propyl palmitate Thiamphenicol Chloramphenicol Florfenicol demethylvancomycin
  • THIAMPHENICOL
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  • D-THREO-2,2-DICHLORO-N-[BETA-HYDROXY-ALPHA-(HYDROXYMETHYL)-P-(METHYL-SULFONYL)PHENETHYL]ACETAMIDE
  • Acetamide, 2,2-dichloro-N-(1R,2R)-2-hydroxy-1-(hydroxymethyl)-2-4-(methylsulfonyl)phenylethyl-
  • d-threo-2,2-dichloro-n-(β-hydroxy-α-[hydroxymethyl]-4-[methylsulfonyl]phenethyl)acetamide
  • Acetamide, 2,2-dichloro-N-[(1R,2R)-2-hydroxy-1-(hydroxymethyl)-2-[4-(methylsulfonyl)phenyl]ethyl]- (9CI)
  • Acetamide, 2,2-dichloro-N-[2-hydroxy-1-(hydroxymethyl)-2-[4-(methylsulfonyl)phenyl]ethyl]-, [R-(R*,R*)]-
  • Acetamide, 2,2-dichloro-N-[b-hydroxy-a-(hydroxymethyl)-p-(methylsulfonyl)phenethyl]-, D-threo-(+)- (8CI)
  • D-d-threo-2-Dichloroacetamido-1-(4-methylsulfonylphenyl)-1,3-propanediol
  • D-Thiocymetin
  • D-Thiophenicol
  • D-threo-(1R,2R)-1-(p-Methylsulfonylphenyl)-2-dichloroacetamido-1,3-propanediol
  • NSC 522822
  • 2,2-Dichloro-N[(1R,2R)-2-hydroxy-1-hydroxymethyl-2-(4-methylsulphonylphenyl)-acetamide
  • 2,2-Dichloro-N-[(1R,2R)-1,3-dihydroxy-1-(4-methylsulfonylphenyl)propan-2-yl]acetamide
  • D-threo-2,2-Dichloro-N-(b-hydroxy-a-[hydroxymethyl]-4-[methylsulfonyl]phenethyl)acetamide
  • (+)-2,2-Dichloro-N-[(αR,βR)-β-hydroxy-α-(hydroxymethyl)-4-(methylsulfonyl)phenethyl]acetamide
  • Neomyson
  • Thiamphenicol,D-threo-2,2-Dichloro-N-(β-hydroxy-α-[hydroxymethyl]-4-[methylsulfonyl]phenethyl)acetamide
  • THIAMPHENICHOL
  • 2,2-Dichloro-N-[(1R,2R)-2-hydroxy-1-hydroxymethyl-2-(4-methylsulfonylphenyl)ethyl]acetamide
  • Thiamphenicol BP2007
  • methanesulfonic acid [2-[(2,2-dichloro-1-oxoethyl)amino]-3-hydroxy-3-(4-nitrophenyl)propyl] ester
  • Thiamphenicol, 99.5%
  • 8065c.b.
  • acetamide,2,2-dichloro-n-(beta-hydroxy-alpha-(hydroxymethyl)-p-(methylsulfonyl
  • dextrosulphenidol
  • thiocymetin
  • thiophenicol
  • win-5063-2
  • ThiaMphenicol / Methylsulfonyl chloraMphenicol
  • 2,2-dichloro-N-[(1R,2R)-1,3-dihydroxy-1-(4-Methanesulfonylphenyl)propan-2-yl]acetaMide
  • ThiaMphenicol API
  • 2,2-Dichloro-N-[(1R,2R)-1,3-dihydroxy-1-[4-(methylsulfonyl)phenyl]-2-propyl]acetamide
  • ThiocyMetin, Thiophenicol, Win 5062-2, NSC 522822
  • ThiamphenicolBP, 98.0-100.5% (Assay)
  • Thiamphenicol, 98%, an antimicrobial antibiotic
  • Thiamphenicol 15318-45-3
  • Thinmphcnicol
  • Thiamphenical
  • 15318-45-3
  • 156-2-16
  • 15218-45-3
  • C12H14Cl2N2O7S
  • C12H15Cl2NO5S
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Description Chemical Properties Uses