Related CAS #
136-16-3 (free base); 614-05-1 (chloride HCl)
Synonym
Oxythiamine chloride HCl, Oxythiamine chloride hydrochloride
IUPAC/Chemical Name
3-[(1,6-dihydro-2-methyl-6-oxo-5-pyrimidinyl)methyl]-5-(2-hydroxyethyl)-4-methyl-thiazolium, monochloride, monohydrochloride
InChi Key
HGYQKVVWNZFPJS-UHFFFAOYSA-N
InChi Code
InChI=1S/C12H15N3O2S.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;2*1H
SMILES Code
CC(N1)=NC=C(C[N+]2=CSC(CCO)=C2C)C1=O.[Cl-].Cl
Purity
>95% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
Oxythiamine chloride hydrochloride is a thiamine antagonist and inhibits transketolase (TK).
In vitro activity:
In the present study, a quantitative proteomic analysis using the modified SILAC method (mSILAC) was performed to determine the effect of metabolic inhibition on dynamic changes of protein expression in MIA PaCa-2 cancer cells treated with OT at various doses (0 μM, 5 μM, 50 μM and 500 μM) and time points (0 h, 12 h and 48 h). A total of 52 differential proteins in MIA PaCa-2 cells treated with OT were identified, including 14 phosphorylated proteins. Among them, Annexin A1 expression was significantly down-regulated by OT treatment in time-dependent manner, while no change of this protein was observed in OT dose-dependent fashion.
Reference: Exp Hematol Oncol. 2013 Jul 27;2:18. https://pubmed.ncbi.nlm.nih.gov/23890079/
In vivo activity:
This study implanted (s.c.) C57BL/6 mice with LLC cells and supplemented the mice with a low- or a high-dose of OT (oxythiamine) (250 or 500 mg/kg BW) daily for 5 wk. During the 5-wk period, OT supplementation decreased plasma MMP-2 activity in a dose-dependent manner, and this effect was significant after 4 wk of tumor cell implantation. Tumor metastasis was found to confine to the lungs of mice injected with the tumor cells. High-OT supplementation strongly lowered the number and area of tumors and inhibited protein expression of MMP-2 and MMP-9 in the lungs.
Reference: Clin Exp Metastasis. 2010 May;27(5):341-9. https://pubmed.ncbi.nlm.nih.gov/20449639/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMSO |
50.0 |
147.82 |
| PBS (pH 7.2) |
10.0 |
29.56 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
338.25
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Wang J, Zhang X, Ma D, Lee WP, Xiao J, Zhao Y, Go VL, Wang Q, Yen Y, Recker R, Xiao GG. 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. PMID: 23890079; PMCID: PMC3733980.
2. Raïs B, Comin B, Puigjaner J, Brandes JL, Creppy E, Saboureau D, Ennamany R, Lee WN, Boros LG, Cascante M. 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. PMID: 10452541.
3. Lu H, Lan WX, Bo L, Niu C, Zhou JJ, Zhu HL. Metabolic response of LLC xenografted mice to oxythiamine, as measured by [¹H] NMR spectroscopy. Genet Mol Res. 2015 Sep 21;14(3):11043-51. doi: 10.4238/2015.September.21.17. PMID: 26400334.
4. Yang CM, Liu YZ, Liao JW, Hu ML. 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. Epub 2010 May 7. PMID: 20449639.
In vitro protocol:
1. Wang J, Zhang X, Ma D, Lee WP, Xiao J, Zhao Y, Go VL, Wang Q, Yen Y, Recker R, Xiao GG. 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. PMID: 23890079; PMCID: PMC3733980.
2. Raïs B, Comin B, Puigjaner J, Brandes JL, Creppy E, Saboureau D, Ennamany R, Lee WN, Boros LG, Cascante M. 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. PMID: 10452541.
In vivo protocol:
1. Lu H, Lan WX, Bo L, Niu C, Zhou JJ, Zhu HL. Metabolic response of LLC xenografted mice to oxythiamine, as measured by [¹H] NMR spectroscopy. Genet Mol Res. 2015 Sep 21;14(3):11043-51. doi: 10.4238/2015.September.21.17. PMID: 26400334.
2. Yang CM, Liu YZ, Liao JW, Hu ML. 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. Epub 2010 May 7. PMID: 20449639.
1. Tylicki, A., Lotowski, Z., Siemieniuk, M., et al. Thiamine and selected thiamine antivitamines - biological activity and methods of synthesis. Biosci. Rep. 38(1), BSR20171148 (2018).
2. Boros, L.G., Puigjaner, J., Cascante, M., et al. Oxythiamine and dehydroepiandrosterone inhibit the nonoxidative synthesis of ribose and tumor cell proliferation. Cancer Res. 57(19), 4242-4248 (1997).
3. Raïs, B., Comin, B., Puigjaner, J., et al. Oxythiamine and dehydroepiandrosterone induce a G1 phase cycle arrest in Ehrlich’s tumor cells through inhibition of the pentose cycle. FEBS Lett. 456(1), 113-118 (1999).
4. Tseng, C.-W., Kuo, W.-H., Chan, S.-H., et al. Transketolase regulates the metabolic switch to control breast cancer cell metastasis via the α-ketoglutarate signaling pathway. Cancer Res. 78(11), 2799-2812 (2018).
5. Xu, I.M.-J., Lai, R.K.-H., Lin, S.-H., et al. Transketolase counteracts oxidative stress to drive cancer development. Proc. Natl. Acad. Sci. USA 113(6), E725-E734 (2016).
6. Cerecedo, L.R., Soodak, M., and Eusebi, A.J. Studies on thiamine analogues. I. Experiments in vivo. J. Biol. Chem. 189(1), 293-299 (1951).
