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Thiamine Disulfide Hydrate

Names

[ CAS No. ]:
67-16-3

[ Name ]:
Thiamine Disulfide Hydrate

[Synonym ]:
Formamide, N,N'-[dithiobis[(Z)-2-(2-hydroxyethyl)-1-methyl-2,1-ethenediyl]]bis[N-[(4-amino-2-methyl-5-pyrimidinyl)methyl]-
MFCD00010427
Thiamine Disulfide
Vitamin B1 Disulfide
EINECS 200-644-4
Aneurine Disulfide
AKTIVIN
N,N'-{Disulfanediylbis[(2Z)-5-hydroxypent-2-ene-3,2-diyl]}bis{N-[(4-amino-2-methylpyrimidin-5-yl)methyl]formamide}
N,N'-{Disulfanediylbis[(2Z)-5-hydroxy-2-pentene-3,2-diyl]}bis{N-[(4-amino-2-methyl-5-pyrimidinyl)methyl]formamide}

Biological Activity

[Description]:

Thiamine disulfide, a vitamin B1 derivative, is an oxidized dimer of Thiamine. Thiamine disulfide is a potent HIV-1 inhibitor. Thiamine disulfide significantly depresses HIV-1 transactivator (Tat) activity[1][2].

[Related Catalog]:

Signaling Pathways >> Anti-infection >> HIV
Research Areas >> Infection
Research Areas >> Metabolic Disease

[In Vitro]

Thiamine disulfide markedly inhibits production of progeny HIV-1 in acute and chronic HIV-1-infected CEM at nontoxic concentrations of 500-1000 μM. Thiamine disulfide (500 μM) blocks 99.7% of HIV-1 production after 96 hours culture in acute HIV-1 (LAV-1) infection, whereas it inhibits 90-98% of HIV-1 production in chronic-infected cells (CEM/LAV-1, H9/MN, and Molt-4/IIIB)[1].

[References]

[1]. S Shoji, et al. Thiamine disulfide as a potent inhibitor of human immunodeficiency virus (type-1) production. Biochem Biophys Res Commun. 1994 Nov 30;205(1):967-75.

[2]. Y Komata, et al. In vitro percutaneous absorption of thiamine disulfide from a mixture of propylene glycol and fatty acid. J Pharm Sci. 1992 Aug;81(8):744-6.

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
886.1±65.0 °C at 760 mmHg

[ Melting Point ]:
177ºC

[ Molecular Formula ]:
C24H34N8O4S2

[ Molecular Weight ]:
562.708

[ Flash Point ]:
489.7±34.3 °C

[ Exact Mass ]:
562.214417

[ PSA ]:
235.28000

[ LogP ]:
2.79

[ Vapour Pressure ]:
0.0±0.3 mmHg at 25°C

[ Index of Refraction ]:
1.669

MSDS

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Safety Information

[ RTECS ]:
LQ2715000

Synthetic Route

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Precursor & DownStream

Precursor

DownStream

Related Compounds