Key Documents

Thiamphenicol

Name: Thiamphenicol
Brand: SIGMA

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

UNSPSC Code:

51284303

NACRES:

NA.85

PubChem Substance ID:

24899874

EC Number:

239-355-3

Beilstein/REAXYS Number:

2819542

MDL number:

MFCD00467983

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Properties

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

Description

General description

Chemical structure: phenicole

Application

Thiamphenicol is an antibiotic that has been used to treat chancroid in men and uncomplicated gonorrhea[1][2]. 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[3].

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.

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1 of 1

This Item	16715	T1100000	C0378
Sigma-Aldrich T0261 Thiamphenicol	Supelco 16715 Thiamphenicol	T1100000 Thiamphenicol	Sigma-Aldrich C0378 Chloramphenicol
antibiotic activity spectrum Gram-negative bacteria, Gram-positive bacteria	antibiotic activity spectrum -	antibiotic activity spectrum -	antibiotic activity spectrum Gram-negative bacteria, Gram-positive bacteria, mycobacteria, mycoplasma
Quality Level 100	Quality Level 100	Quality Level -	Quality Level 200
form powder	form -	form -	form powder or crystals
solubility ethanol: soluble 50 mg/mL	solubility ethanol: 50 mg/mL, clear, colorless to faintly yellow	solubility -	solubility -
color white to off-white	color -	color -	color -
mode of action protein synthesis \| interferes	mode of action -	mode of action -	mode of action protein synthesis \| interferes

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Storage Class

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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First report of the multidrug resistance gene cfr in Enterococcus faecalis of animal origin.

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

Thiamphenicol in the treatment of chancroid in men.

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

Detection of the staphylococcal multiresistance gene cfr in Macrococcus caseolyticus and Jeotgalicoccus pinnipedialis.

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

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Global Trade Item Number

SKU	GTIN
T0261-5G	04061837334672
T0261-25G	04061832992389
T0261-1G	04061837334665

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