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O4000

Sigma-Aldrich

Oxythiamine chloride hydrochloride

≥95% (HPLC)

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Synonym(s):
5-(2-Hydroxyethyl)-3-(4-hydroxy-2-methyl-5-pyrimidinylmethyl)-4-methylthiazolium chloride
Empirical Formula (Hill Notation):
C12H16ClN3O2S · HCl
CAS Number:
Molecular Weight:
338.25
MDL number:
PubChem Substance ID:
NACRES:
NA.79

Quality Level

assay

≥95% (HPLC)

form

powder

technique(s)

HPLC: suitable

color

white to off-white

storage temp.

−20°C

SMILES string

CC(N1)=NC=C(C[N+]2=CSC(CCO)=C2C)C1=O.Cl.[Cl-]

InChI

1S/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

InChI key

QHUYPZVMEJLSEB-UHFFFAOYSA-N

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This Item
P9130271748P9255
Oxythiamine chloride hydrochloride ≥95% (HPLC)

O4000

Oxythiamine chloride hydrochloride

Pyridoxal hydrochloride ≥99% (HPLC)

P9130

Pyridoxal hydrochloride

Pyridoxal hydrochloride 99%

271748

Pyridoxal hydrochloride

Pyridoxal 5′-phosphate hydrate ≥98%

P9255

Pyridoxal 5′-phosphate hydrate

assay

≥95% (HPLC)

assay

≥99% (HPLC)

assay

99%

assay

≥98%

form

powder

form

powder

form

powder

form

powder

storage temp.

−20°C

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

−20°C

color

white to off-white

color

white to off-white

color

white to off-white

color

beige, off-white to yellow

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

General description

Oxythiamine is a thiamine antimetabolite and the source through diet is by consuming acidic thiamine rich foods.

Application

Oxythiamine 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

Biochem/physiol Actions

Oxythiamine (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.
Oxythiamine inhibits Transketolase, the enzyme that controls the nonoxidative branch of the pentose phosphate pathway.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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Chih-Min Yang et al.
Clinical & experimental metastasis, 27(5), 341-349 (2010-05-08)
This study examined the anti-metastatic effects of oxythiamine (OT) both in cell culture and in vivo. Cell culture results revealed that OT (0-20 microM) significantly inhibited the invasion and migration (IC(50) = 8.75 microM) of Lewis lung carcinoma (LLC) cells.
Functional thiamine deficiency in end-stage renal disease: malnutrition despite ample nutrients
Moradi H and Said HM
Kidney International, 90(2), 252-254 (2016)
Thiamine antimetabolite causes functional thiamine deficiency in patients with end stage renal disease
Zhang F, et al.
Kidney International, 90(2), 396-403 (2016)
Novel structural aspects of oxythiamine, an antagonist of thiamine. Crystal structures of three salts,(oxythiamineH)(picrolonate) 2textperiodcentered
Hu NH, et al.
Inorgorganica Chimica Acta, 295(1), 71-83 (1999)
Emerging role of the pentose phosphate pathway in hepatocellular carcinoma
Kowalik MA, et al.
Frontiers in Oncology, 7, 87-87 (2017)

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