Oxythiamine chloride hydrochloride

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Oxythiamine chloride hydrochloride Basic information
Product Name:Oxythiamine chloride hydrochloride
Synonyms:5-(2-HYDROXYETHYL)-3-(4-HYDROXY-2-METHYL-5-PYRIMIDINYLMETHYL)-4-METHYLTHIAZOLIUM CHLORIDE;5-[2-HYDROXYETHYL]-3-[4-HYDROXY-2-METHYL-5-PYRIMIDINYLMETHYL]-4-METHYLTHIAZOLIUM CHLORIDE HYDROCHLORIDE;Oxametholone Hydrochloride;hydroxythiaminechloridehydrochloride;hyl)-4-methyl-,chloride,monohydrochloride;OXYTHIAMINE CHLORIDE HYDROCHLORIDE;OXYTHIAMINE HCL;OXYTHIAMINE CHLORIDE HCL CRYSTALLINE
CAS:614-05-1
MF:C12H17Cl2N3O2S
MW:338.25
EINECS:
Product Categories:Biochemistry;Vitamin Derivatives;Vitamins
Mol File:614-05-1.mol
Oxythiamine chloride hydrochloride Structure
Oxythiamine chloride hydrochloride Chemical Properties
Melting point >190°C (subl.)
storage temp. -20°C
solubility DMSO (Slightly, Heated), Methanol (Slightly), Water (Slightly)
form Solid
color White to Off-White
Stability:Hygroscopic
InChI1S/C12H16N3O2S.2ClH/c1-8-11(3-4-16)18-7-15(8)6-10-5-13-9(2)14-12(10)17;;/h5,7,16H,3-4,6H2,1-2H3,(H,13,14,17);2*1H
InChIKeyQHUYPZVMEJLSEB-UHFFFAOYSA-N
SMILESCC(N1)=NC=C(C[N+]2=CSC(CCO)=C2C)C1=O.Cl.[Cl-]
Safety Information
WGK Germany 3
RTECS XJ7034100
Storage Class11 - Combustible Solids
MSDS Information
ProviderLanguage
SigmaAldrich English
Oxythiamine chloride hydrochloride Usage And Synthesis
Usesthiamine antagonist
UsesOxythiamine chloride hydrochloride is suitable for use:
  • as a reference standard for calibration curve generation in liquid chromatography-tandem mass spectrometry (LC-MS/MS) for oxythiamine pyrophosphate (OTPP) quantification in red blood cells
  • as a thiamine transport inhibitor in human mammary epithelial cells (HMEC) and breast cancer cell lines
  • in the synthesis of oxythiamineH picrolonate salt

DefinitionChEBI: A hydrochloride obtained by combining oxythiamine chloride with one molar equivalent of hydrochloric acid.
General DescriptionOxythiamine is a thiamine antimetabolite and the source through diet is by consuming acidic thiamine rich foods.
Biochem/physiol ActionsOxythiamine (OT) is a thiamine antagonist. It is a transketolase inhibitor and is employed to study anti-metastatic mechanisms, especially those involving metalloproteinases (MMP). It significantly sensitizes human hepatocellular carcinoma cells (HCC) to sorafenib, favoring tumor suppression.
in vivo

Oxythiamine chloride hydrochloride (100-500 mg/kg, i.p. 4 days) inhibits tumor growth in Ehrlich's ascites tumor hosting mice[2].
Oxythiamine chloride hydrochloride (250 or 500 mg/kg, daily for 5 week) inhibits tumor cell metastasis via inhibition of MMPs in mice implanted (s.c.) with LLC cells[4].

Animal Model:Ehrlich's ascites tumor hosting mice[2]
Dosage:100-500 mg/kg
Administration:i.p., 4 days
Result:Inhibited tumor growth by 43% at 300 mg/kg and 84% at 500 mg/kg.
Oxythiamine chloride hydrochloride Preparation Products And Raw materials
Tag:Oxythiamine chloride hydrochloride(614-05-1) Related Product Information
Oxythiamine Oxythiamine diphosphate 5-(2-hydroxyethyl)-3-(4-hydroxy-2-methylpyrimidin-5-ylmethyl)-4-methylthiazolium chloride Thiazolium, 3-[(1,6-dihydro-2-methyl-6-oxo-5-pyrimidinyl)methyl]-4-methyl-5-[2-(phosphonooxy)ethyl]-, inner salt Oxythiamine diphosphate ammonium Oxythiamine chloride hydrochloride