Related CAS #
136-16-3 (free base); 614-05-1 (chloride HCl)
Synonym
Oxythiamine Free Base; BRN4153910; BRN-4153910; BRN 4153910
IUPAC/Chemical Name
Thiazolium, 3-((1,4-dihydro-2-methyl-4-oxo-5-pyrimidinyl)methyl)-5-(2-hydroxyethyl)-4-methyl-
InChi Key
SRDGSXVLAVRBLU-UHFFFAOYSA-O
InChi Code
InChI=1S/C12H15N3O2S/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/p+1
SMILES Code
CC1=C(CCO)SC=[N+]1CC2=CNC(C)=NC2=O
Purity
>98% (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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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
266.34
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 |
1: Golan O, Dyer R, Sinclair G, Blydt-Hansen T. Investigating oxythiamine levels in children undergoing kidney transplantation and the risk of immediate post- operative metabolic and hemodynamic decompensation. Pediatr Nephrol. 2021 Apr;36(4):987-993. doi: 10.1007/s00467-020-04797-9. Epub 2020 Oct 16. PMID: 33067673.
2: Thiamine and oxythiamine metabolism. Nutr Rev. 1969 Mar;27(3):88-90. doi: 10.1111/j.1753-4887.1969.tb04972.x. PMID: 4891096.
3: Siemieniuk M, Sosnowska K, Czerniecki J, Czyzewska U, Winnicka K, Tylicki A. Oxythiamine improves antifungal activity of ketoconazole evaluated in canine Malassezia pachydermatis strains. Vet Dermatol. 2018 Dec;29(6):476-e160. doi: 10.1111/vde.12688. Epub 2018 Sep 24. PMID: 30251451.
4: Zhang F, Masania J, Anwar A, Xue M, Zehnder D, Kanji H, Rabbani N, Thornalley PJ. The uremic toxin oxythiamine causes functional thiamine deficiency in end- stage renal disease by inhibiting transketolase activity. Kidney Int. 2016 Aug;90(2):396-403. doi: 10.1016/j.kint.2016.03.010. Epub 2016 May 16. PMID: 27198804.
5: Vinogradov VV, Vodoevich VP, Rozhko AV. Iavliaetsia li oksitiamin antivitaminom? [Is oxythiamine an antivitamin?]. Biokhimiia. 1995 Oct;60(10):1564-74. Russian. PMID: 8555356.
6: Tylicki A, Czerniecki J, Dobrzyn P, Matanowska A, Olechno A, Strumilo S. Modification of thiamine pyrophosphate dependent enzyme activity by oxythiamine in Saccharomyces cerevisiae cells. Can J Microbiol. 2005 Oct;51(10):833-9. doi: 10.1139/w05-072. PMID: 16333342.
7: Szoka L, Karna E, Palka J. The mechanism of oxythiamine-induced collagen biosynthesis in cultured fibroblasts. Mol Cell Biochem. 2015 May;403(1-2):51-60. doi: 10.1007/s11010-015-2336-z. Epub 2015 Jan 28. PMID: 25626895; PMCID: PMC4383821.
8: Grabowska E, Czerniecka M, Czyżewska U, Zambrzycka A, Łotowski Z, Tylicki A. Differences in the efficiency of 3-deazathiamine and oxythiamine pyrophosphates as inhibitors of pyruvate dehydrogenase complex and growth of HeLa cells in vitro. J Enzyme Inhib Med Chem. 2021 Dec;36(1):122-129. doi: 10.1080/14756366.2020.1844681. PMID: 33187452; PMCID: PMC7671598.
9: Tseng CW, Kuo WH, Chan SH, Chan HL, Chang KJ, Wang LH. Transketolase Regulates the Metabolic Switch to Control Breast Cancer Cell Metastasis via the α-Ketoglutarate Signaling Pathway. Cancer Res. 2018 Jun 1;78(11):2799-2812. doi: 10.1158/0008-5472.CAN-17-2906. Epub 2018 Mar 29. PMID: 29599405.
10: 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.
