Oxythiamine chloride hydrochloride

Names

[ CAS No. ]:
614-05-1

[ Name ]:
Oxythiamine chloride hydrochloride

[Synonym ]:
Thiazolium,3-((1,4-dihydro-2-methyl-4-oxo-5-pyrimidinyl)methyl)-5-(2-hydroxyethyl)-4-methyl-,chloride,monohydrochloride
5-(2-Hydroxy-aethyl)-4-methyl-3-(2-methyl-6-oxo-1,6-dihydro-pyrimidin-5-ylmethyl)-thiazolium,Chlorid-hydrochlorid
OXYTHIAMINE CHLORIDE HCL
5-(2-hydroxy-ethyl)-4-methyl-3-(2-methyl-6-oxo-1,6-dihydro-pyrimidin-5-ylmethyl)-thiazolium,chloride-hydrochloride
5-(2-Hydroxyethyl)-3-(4-hydroxy-2-methyl-5-pyrimidinylmethyl)-4-methylthiazolium chloride
5-[[5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium-3-yl]methyl]-2-methyl-1H-pyrimidin-6-one,chloride,hydrochloride
thiazolium,5-(2-hydroxyethyl)-3-[(4-hydroxy-2-methyl-5-pyrimidinyl)methyl]-4-methyl-,chloride,hydrochloride(1:1:1)
MFCD00050656

Biological Activity

[Description]:

Oxythiamine (Hydroxythiamine) chloride hydrochloride, an analogue of anti-metabolite, can suppress the non-oxidative synthesis of ribose and induce cell apoptosis. Oxythiamine chloride hydrochloride is a thiamine antagonist and inhibits transketolase (TK). Oxythiamine chloride hydrochloride inhibits cancer cell apoptosis and inhibits cell proliferation[1][2][3].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis

Research Areas >> Cancer

[Target]

Vitamin B1, Thiamine, Transketolase[1].

[In Vitro]

Oxythiamine chloride hydrochloride (0-40 μM，2 天) 抑制 MIA PaCa-2 细胞的细胞活力(IC50: 14.95 μM)[1]。 Oxythiamine chloride hydrochloride (0-500 μM，48 小时) 抑制 MIA PaCa-2 细胞中 14-3-3 蛋白 beta/alpha 的表达[1]。 Oxythiamine chloride hydrochloride (0.1-100 μM, 6-48 h) 抑制 A549 细胞增殖[3]. Oxythiamine chloride hydrochloride (0.1-100 μM, 24 h) 诱导A549细胞凋亡[3]. [3]. Oxythiamine chloride hydrochloride (0-20 μM) 抑制 Lewis 肺癌 (LLC) 细胞的侵袭和迁移 (IC50: 8.75 μM)[4]。 Cell Viability Assay[1] Cell Line: MIA PaCa-2 cells Concentration: 0-40 μM Incubation Time: 2 days Result: Inhibited cell viability with an IC50 of 14.95 μM. Western Blot Analysis[1] Cell Line: MIA PaCa-2 cells Concentration: 0, 5, 50, 500 μM Incubation Time: 48 h Result: Inhibited 14-3-3 protein beta/alpha expression, and increased alpha-enolase.

[In Vivo]

Oxythiamine chloride hydrochloride (100-500 mg/kg，i.p. 4 天) 抑制艾氏腹水瘤宿主小鼠的肿瘤生长[2]。 Oxythiamine chloride hydrochloride (250 或 500 mg/kg，每日一次，持续 5 周) 通过抑制植入 (s.c.) LLC 细胞的小鼠体内的 MMPs 来抑制肿瘤细胞转移[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.

[References]

[1]. Wang J, et al. Inhibition of transketolase by oxythiamine altered dynamics of protein signals in pancreatic cancer cells. Exp Hematol Oncol. 2013 Jul 27;2:18.

[2]. Raïs B, et al. Oxythiamine and dehydroepiandrosterone induce a G1 phase cycle arrest in Ehrlich's tumor cells through inhibition of the pentose cycle. FEBS Lett. 1999 Jul 30;456(1):113-8.

[3]. Bai L, et al. A dose- and time-dependent effect of oxythiamine on cell growth inhibition in non-small cell lung cancer. Cogn Neurodyn. 2022 Jun;16(3):633-641.

[4]. Yang CM, et al. The in vitro and in vivo anti-metastatic efficacy of oxythiamine and the possible mechanisms of action. Clin Exp Metastasis. 2010 May;27(5):341-9.

Chemical & Physical Properties

[ Molecular Formula ]:
C₁₂H₁₆Cl₂N₄O₂S

[ Molecular Weight ]:
351.25200

[ Exact Mass ]:
350.03700

[ PSA ]:
107.56000

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: XJ7034100

CHEMICAL NAME :: Thiazolium, 3-((1,4-dihydro-2-methyl-4-oxo-5-pyrimidinyl)methyl)- 5-(2-hydroxyethyl)-4- methyl-, chloride, monohydrochloride

CAS REGISTRY NUMBER :: 614-05-1

LAST UPDATED :: 199707

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C12-H16-N3-O2-S.Cl.Cl-H

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Mammal - species unspecified

DOSE/DURATION :: 1835 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: VMDKAM Voprosy Meditsinskoi Khimii. Problems of Medical Chemistry. (V/O Me zhdunarodnaya Kniga, 113095 Moscow, USSR) V.1- 1955- Volume(issue)/page/year: 33,70,1987

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ RIDADR ]:
NONH for all modes of transport

[ RTECS ]:
XJ7034100

[ HS Code ]:
2934100090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2934100090

[ Summary ]:
2934100090 other compounds containing an unfused thiazole ring (whether or not hydrogenated) in the structure VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:6.5% General tariff:20.0%

Articles

Inhibition of protein phosphorylation in MIA pancreatic cancer cells: confluence of metabolic and signaling pathways.

J. Proteome Res. 9 , 980-989, (2010)

Oxythiamine (OT), a transketolase inhibitor, is known to inhibit pancreatic cancer cell proliferation. In this study, we investigated the effect of inhibition of the transketolase pathway on signaling...

The in vitro and in vivo anti-metastatic efficacy of oxythiamine and the possible mechanisms of action.

Clin. Exp. Metastasis 27 , 341-349, (2010)

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 migra...