Oxythiamine chloride HCl
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MedKoo CAT#: 574315

CAS#: 614-05-1 (chloride HCl)

Description: Oxythiamine chloride HCl is a thiamine antimetabolite that has anticancer activities. It is converted by thiamine pyrophosphokinase to oxythiamine pyrophosphate, a transketolase inhibitor. Oxythiamine decreases transketolase activity in breast cancer. It inhibits the nonoxidative synthesis of ribose and decreases RNA and DNA synthesis in pancreatic cancer. In vivo, oxythiamine induces cell cycle arrest at the G1 phase and apoptosis in an adenocarcinoma model. Oxythiamine, in combination with sorafenib, reduces tumor growth in an SMMC mouse xenograft model and has also been used to induce thiamine deficiency in mice.


Chemical Structure

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Oxythiamine chloride HCl
CAS# 614-05-1 (chloride HCl)

Theoretical Analysis

MedKoo Cat#: 574315
Name: Oxythiamine chloride HCl
CAS#: 614-05-1 (chloride HCl)
Chemical Formula: C12H17Cl2N3O2S
Exact Mass: 337.0419
Molecular Weight: 338.25
Elemental Analysis: C, 42.61; H, 5.07; Cl, 20.96; N, 12.42; O, 9.46; S, 9.48

Price and Availability

Size Price Availability Quantity
1.0g USD 215.0 2 Weeks
5.0g USD 405.0 2 Weeks
10.0g USD 660.0 2 Weeks
25.0g USD 995.0 2 Weeks
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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

Appearance: Solid powder

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

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.

Recalculate based on batch purity %
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

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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).