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T0261

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 Segment

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. 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.

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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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Global Trade Item Number

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