Basic information
- CAS
136-16-3- Standard SMILES
Cc1ncc(C[n+]2csc(CCO)c2C)c(=O)[nH]1- InChIKey
SRDGSXVLAVRBLU-UHFFFAOYSA-O- Molecular formula
- C12H16N3O2S+
- Average molar mass
- 266.34 g/mol
- Monoisotopic mass
- 266.09632294
Overview
Oxythiamine(1+) is 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. It has a role as an antimetabolite and a vitamin B1 antagonist.
Names & identifiers
- Preferred name
- Oxythiamine
- IUPAC
- 5-[[5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium-3-yl]methyl]-2-methyl-1H-pyrimidin-6-one
- English name
- Oxythiamine
- Molecular formula
- C12H17Cl2N3O2S
- Molecular weight
- 338.25
Names & synonyms
OXYTHIAMINE136-16-31MF36SYZ22DTXSID40929206Thiazolium, 3-((1,4-dihydro-2-methyl-4-oxo-5-pyrimidinyl)methyl)-5-(2-hydroxyethyl)-4-methyl-RefChem:169098DTXCID801772795Oxythiamine (Hydroxythiamin)5-[[5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium-3-yl]methyl]-2-methyl-1H-pyrimidin-6-oneOxythiamin5-(2-hydroxyethyl)-4-methyl-3-[(2-methyl-6-oxo-1,6-dihydropyrimidin-5-yl)methyl]-1,3-thiazol-3-iumUNII-1MF36SYZ22
Show more names
azoliumHydroxythiaminOXYTHIAMINE HCLThiamine Impurity 19OXYTHIAMINE HYDROCHLORIDEOxythiamine·HCl≥ 99% (assay)
oxythiamine(1+)Oxythiamine . HClOXYTHIAMINE IONBRN 41539105-(2-Hydroxyethyl)-3-(4-hydroxy-2-methylpyrimidin-5-ylmethyl)-4-methylthiazolium chlorideA1JWSOXYTHIAMINE CATION5-(2-Hydroxyethyl)-3-((4-hydroxy-2-methyl-5-pyrimidinyl)methyl)-4-methyl-thiazolium
Database identifiers
Properties
Computed structural properties
- XLogP
- 0.1
- Topological polar surface area
- 93.8 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 4
- Heavy atoms
- 18
- Formal charge
- 1
- Complexity
- 395
Experimental & physicochemical properties
Collision Cross Section155.75 Ų [M]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Density
- 1.2416 · 1.2416 (rough estimate)
- refractive index
- 1.674 · 1.6740 (estimate)
- storage temp.
- 20 °C · −20°C
- solubility
- 51.67 mg/mL · DMSO : 51.67 mg/mL (194.00 mM)
- form
- Solid
- color
- White to off-white
- FDA UNII
- 1 MF36SYZ22 · 1MF36SYZ22
- WGK Germany
- 3 · 3
- RTECS
- 7034100 · XJ7034100
- Toxicity
- 50 scu-mus: · LD50 scu-mus: 1430 mg/kg PCJOAU16,848,82
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- 3
- rtecs
- XJ7034100
- Toxicity
- LD50 scu-mus: 1430 mg/kg PCJOAU16,848,82
Chemistry & industry
Pharmacology
MeSH Pharmacological ClassificationDrugs that are chemically similar to naturally occurring metabolites, but differ enough to interfere with normal metabolic pathways. (From AMA Drug Evaluations Annual, 1994, p2033)
Applications
UsesOxythiamine (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].
Suppliers13 total
United Life Science020-82099279 18988968278 · [email protected]
天津普西唐生物医药科技有限公司010-60605840 · [email protected]
上海麦克林生化科技股份有限公司15221275939 15221275939 · [email protected]
青岛海智微元生物科技有限公司18317699790 18317699790 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
开封明仁药业有限公司0371-65741762 · [email protected]
湖北扬信医药科技有限公司15374522761 · [email protected]
江苏艾康生物医药研发有限公司025-58859352 15955137747 · [email protected]
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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