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T0261

Sigma-Aldrich

Thiamphenicol

Synonym(s):

Raceophenidol, Thiophenicol, D-threo-2,2-Dichloro-N-(β-hydroxy-α-[hydroxymethyl]-4-[methylsulfonyl]phenethyl)acetamide

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About This Item

Empirical Formula (Hill Notation):
C12H15Cl2NO5S
CAS Number:
15318-45-3
Molecular Weight:
356.22
Beilstein:
2819542
EC Number:
239-355-3
MDL number:
MFCD00467983
UNSPSC Code:
51284303
PubChem Substance ID:
24899874
NACRES:
NA.85

form

powder

color

white to off-white

solubility

ethanol: soluble 50 mg/mL

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria

Mode of action

protein synthesis | interferes

SMILES string

CS(=O)(=O)c1ccc(cc1)[C@@H](O)[C@@H](CO)NC(=O)C(Cl)Cl

InChI

1S/C12H15Cl2NO5S/c1-21(19,20)8-4-2-7(3-5-8)10(17)9(6-16)15-12(18)11(13)14/h2-5,9-11,16-17H,6H2,1H3,(H,15,18)/t9-,10-/m1/s1

InChI key

OTVAEFIXJLOWRX-NXEZZACHSA-N

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General description

Chemical structure: phenicole

Application

Thiamphenicol is an antibiotic that has been used to treat chancroid in men and uncomplicated gonorrhea. It is used in studies of bacterial protein synthesis at the level of peptidyl transferase activity associated with the 23S rRNA of the 50S ribosomal subunit. It is used to study chloraniphenicol-thiamphenicol-resistance and the use of fluorinated analogs when resistance is encountered.

Biochem/physiol Actions

Thiamphenicol inhibits mitochondrial protein synthesis of proteins such as cytochrome c oxidase.

Packaging

1G,5G,25G

Other Notes

Keep container tightly closed in a dry and well-ventilated place.

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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D R Rezende et al.
Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment, 29(4), 559-570 (2012-01-14)
A validated method based on European and Brazilian legislation is reported. It is applicable to the simultaneous determination of chloramphenicol (CAP) and florfenicol (FF) by LC-MS/MS in liquid milk, milk powder and bovine muscle. The chromatographic analysis is completed in
Weixin Tao et al.
Applied and environmental microbiology, 78(17), 6295-6301 (2012-07-04)
Chloramphenicol and florfenicol are broad-spectrum antibiotics. Although the bacterial resistance mechanisms to these antibiotics have been well documented, hydrolysis of these antibiotics has not been reported in detail. This study reports the hydrolysis of these two antibiotics by a specific
Sanaz Pilehvar et al.
Analytical chemistry, 84(15), 6753-6758 (2012-06-26)
A novel, label-free folding induced aptamer-based electrochemical biosensor for the detection of chloramphenicol (CAP) in the presence of its analogues has been developed. CAP is a broad-spectrum antibiotic that has lost its favor due to its serious adverse toxic effects
V P Syriopoulou et al.
Antimicrobial agents and chemotherapy, 19(2), 294-297 (1981-02-01)
We evaluated the in vitro antimicrobial activity of Sch 24893, Sch 25298, and Sch 25393, three novel analogs of chloramphenicol and thiamphenicol. All of the analogs had minimal inhibitory concentrations of less than or equal to 10 micrograms/ml for 18
T E Tupasi et al.
The British journal of venereal diseases, 59(3), 172-175 (1983-06-01)
The use of cefuroxime and thiamphenicol in uncomplicated gonococcal infection was studied in 562 women confined to a clinic to preclude reinfection before cultural confirmation of cure. Cefuroxime was as effective as spectinomycin in the treatment of infections due to
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