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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

Quality Level

100

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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A S Latif
The British journal of venereal diseases, 58(1), 54-55 (1982-02-01)
Thiamphenicol was used to treat 547 men with chancroid. An oral dose of 2.5g was given on the first day and a further dose of 1.25g a week later if the lesions had not healed. Eighty-seven (15.9%) patients defaulted from
Yang Liu et al.
Antimicrobial agents and chemotherapy, 56(3), 1650-1654 (2011-12-29)
The multiresistance gene cfr was identified for the first time in an Enterococcus faecalis isolate of animal origin. The 32,388-bp plasmid pEF-01, which carried the cfr gene, was sequenced completely. Three copies of the insertion sequence IS1216 were identified in
Kevin S Lang et al.
Applied and environmental microbiology, 78(9), 3379-3386 (2012-02-22)
The multidrug resistance-encoding plasmids belonging to the IncA/C incompatibility group have recently emerged among Escherichia coli and Salmonella enterica strains in the United States. These plasmids have a unique genetic structure compared to other enterobacterial plasmid types, a broad host
Yang Wang et al.
The Journal of antimicrobial chemotherapy, 67(8), 1824-1827 (2012-05-12)
To investigate the presence and the genetic environment of the multiresistance gene cfr in Jeotgalicoccus pinnipedialis and Macrococcus caseolyticus from pigs. A total of 391 bacterial isolates with florfenicol MICs ≥16 mg/L were obtained from nasal swabs of 557 individual
E Soto et al.
Journal of fish diseases, 36(4), 411-418 (2012-11-09)
Francisella noatunensis subsp. orientalis (Fno) (syn. F. asiatica) is an emergent Gram-negative facultative intracellular bacterium. Although it is considered one of the most pathogenic bacteria in fish, there are no commercially available treatments or vaccines. The objective of this project was
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