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Thiamphenicol

analytical standard

Synonym(s):

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/REAXYS Number:
2819542
EC Number:
239-355-3
MDL number:
MFCD00467983
UNSPSC Code:
41116107
PubChem Substance ID:
329751348
NACRES:
NA.24

grade

analytical standard

Quality Level

100

assay

≥98.0% (HPLC)

shelf life

limited shelf life, expiry date on the label

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

solubility

ethanol: 50 mg/mL, clear, colorless to faintly yellow

application(s)

clinical

format

neat

storage temp.

2-8°C

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: sulfonamide
Thiamphenicol is an analog of a broad spectrum antibiotic, chloramphenicol. It shows therapeutic effects in respiratory infections, venereal diseases and bacterial prostatitis.

Application

Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.
Thiamphenicol may be used as a reference standard in the determination of thiamphenicol in honey using dispersive liquid-liquid microextraction (DLLME) coupled with high-performance liquid chromatography-variable wavelength detector (HPLC-VWD).

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number

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Dispersive liquid--liquid microextraction followed by high-performance liquid chromatography as an efficient and sensitive technique for simultaneous determination of chloramphenicol and thiamphenicol in honey
Chen H, et al.
Analytica Chimica Acta, 632(1), 80-85 (2009)
[Toxicity of chloramphenicol and thiamphenicol (CAP and TAP)].
G Keiser
Haematology and blood transfusion, 21, 179-195 (1978-01-01)
J Raymond et al.
Medecine tropicale : revue du Corps de sante colonial, 64(1), 33-38 (2004-07-01)
Streptococcus pneumoniae and Haemophilus influenzae are the two main pathogens responsible for bacterial respiratory tract infections. Their antimicrobial susceptibility to antibiotics like beta-lactams, macrolides or fluoroquinolones has been largely studied, while it remains less known to other antibiotics like thiamphenicol
D Malvy et al.
Intensive care medicine, 18(8), 485-487 (1992-01-01)
A 27-year-old woman, without compromised immunodefenses, experienced a Listeria meningoencephalitis, with brainstem symptoms. The identified agent exhibited poor susceptibility to usual effective antibiotics, except for penicillins. Knowledge of past history of an allergic reaction to beta-lactam antibiotics lead to appropriate
[Chloramphenicol and thiamphenicol].
L Mariani
La Clinica terapeutica, 86(3), 195-218 (1978-08-15)
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