| Identification | Back Directory | [Name]
OXYTHIAMINE HYDROCHLORIDE | [CAS]
136-16-3 | [Synonyms]
azolium
oxythiamin
oxythiamine
Hydroxythiamin
oxythiamine(1+)
OXYTHIAMINE HCL
OXYTHIAMINE HYDROCHLORIDE
Oxythiamine·HCl≥ 99% (assay)
Oxythiamine (Hydroxythiamin)
OXYTHIAMINE CHLORIDE HYDROCHLORIDE
Oxythiamine (Synonyms: Hydroxythiamin)
Oxythiamine
DISCONTINUED. Please see O878508.
5-(2-hydroxyethyl)-3-((4-hydroxy-2-methyl-5-pyrimidinyl)methyl)-4-methyl-thi
thiazolium,5-(2-hydroxyethyl)-3-((4-hydroxy-2-methyl-5-pyrimidinyl)methyl)-4-m
5-(2-Hydroxyethyl)-3-[(4-hydroxy-2-methyl-5-pyrimidinyl)methyl]-4-methylthiazol-3-ium
5-(2-HYDROXYETHYL)-3-(4-HYDROXY-2-METHYL-5-PYRIMIDINYLMETHYL)-4-METHYLTHIAZOLIUM CHLORIDE
3-[(3,4-Dihydro-2-methyl-4-oxopyrimidine-5-yl)methyl]-5-(2-hydroxyethyl)-4-methylthiazolium
Thiazolium,3-[(3,4-dihydro-2-methyl-4-oxo-5-pyrimidinyl)methyl]-5-(2-hydroxyethyl)-4-methyl-
3-[(1,4-Dihydro-2-methyl-4-oxopyrimidin-5-yl)methyl]-5-(2-hydroxyethyl)-4-methylthiazol-3-ium
5-[2-HYDROXYETHYL]-3-[4-HYDROXY-2-METHYL-5-PYRIMIDINYLMETHYL]-4-METHYLTHIAZOLIUM CHLORIDE HYDROCHLORIDE | [Molecular Formula]
C12H17Cl2N3O2S | [MDL Number]
MFCD00050656 | [MOL File]
136-16-3.mol | [Molecular Weight]
338.25 |
| Chemical Properties | Back Directory | [density ]
1.2416 (rough estimate) | [refractive index ]
1.6740 (estimate) | [storage temp. ]
−20°C
| [solubility ]
DMSO : 51.67 mg/mL (194.00 mM) | [form ]
Solid | [color ]
White to off-white |
| Hazard Information | Back Directory | [Chemical Properties]
White solid | [Uses]
Oxythiamine (Hydroxythiamin), an analogue of anti-metabolite, can suppress the non-oxidative synthesis of ribose and induce cell apoptosis. Oxythiamine is a thiamine antagonist and inhibits transketolase (TK). Oxythiamine inhibits cancer cell apoptosis and inhibits cell proliferation[1][2][3]. | [Definition]
ChEBI: A 1,3-thiazolium cation that is 5-(2-hydroxyethyl)-4-methyl-1,3-thiazole alkylated at the N3 position by a (2-methyl-4-oxo-1,4-dihydropyrimidin-5-yl)methyl group. | [Safety Profile]
Moderately toxic by subcutaneous route. Experimental reproductive effects. Whenheated to decomposition it emits toxic fumes of NOx and SOx. | [in vivo]
Oxythiamine (100-500 mg/kg, i.p. 4 days) inhibits tumor growth in Ehrlich's ascites tumor hosting mice[2].
Oxythiamine (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. |
| [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. DOI:10.1186/2162-3619-2-18
[2] Ra?s 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. DOI:10.1016/s0014-5793(99)00924-2
[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. DOI:10.1007/s11571-021-09725-7
[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. DOI:10.1007/s10585-010-9331-2 |
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