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    Also known as: 3286-46-2, Bisibuthiamine, Sulbutiamine [inn], Vitaberin, Thiamine disulfide o,o-diisobutyrate, 42ncm1bw43
    Molecular Formula
    C32H46N8O6S2
    Molecular Weight
    702.9  g/mol
    InChI Key
    CKHJPWQVLKHBIH-GPAWKIAZSA-N
    FDA UNII
    42NCM1BW43
    Sulbutiamine
    Sulbutiamine is a synthetic derivative of thiamine (vitamin B1) under the market name Arcalion that is composed of two modified thiamine molecules to form a dimer. It is highly lipophilic, allowing it to cross the blood-brain barrier more easily than other thiamine derivatives. Although its clinical efficacy is not yet defined, sulbutiamine is used to treat asthenia. While its other uses include improvement of erectile dysfunction and reduction of psycho-behavioural inhibition, sulbutiamine showed evidence of modulatory effect on dopaminergic and glutamatergic cortical transmissions. The chronic administration of the drug has demonstrated to improve long term memory formation in mice.
    1 2D Structure

    Sulbutiamine

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    [(E)-4-[(4-amino-2-methylpyrimidin-5-yl)methyl-formylamino]-3-[[(E)-2-[(4-amino-2-methylpyrimidin-5-yl)methyl-formylamino]-5-(2-methylpropanoyloxy)pent-2-en-3-yl]disulfanyl]pent-3-enyl] 2-methylpropanoate
    2.1.2 InChI
    InChI=1S/C32H46N8O6S2/c1-19(2)31(43)45-11-9-27(21(5)39(17-41)15-25-13-35-23(7)37-29(25)33)47-48-28(10-12-46-32(44)20(3)4)22(6)40(18-42)16-26-14-36-24(8)38-30(26)34/h13-14,17-20H,9-12,15-16H2,1-8H3,(H2,33,35,37)(H2,34,36,38)/b27-21+,28-22+
    2.1.3 InChI Key
    CKHJPWQVLKHBIH-GPAWKIAZSA-N
    2.1.4 Canonical SMILES
    CC1=NC=C(C(=N1)N)CN(C=O)C(=C(CCOC(=O)C(C)C)SSC(=C(C)N(CC2=CN=C(N=C2N)C)C=O)CCOC(=O)C(C)C)C
    2.1.5 Isomeric SMILES
    CC1=NC=C(C(=N1)N)CN(/C(=C(/SS/C(=C(/N(C=O)CC2=CN=C(N=C2N)C)\C)/CCOC(=O)C(C)C)\CCOC(=O)C(C)C)/C)C=O
    2.2 Other Identifiers
    2.2.1 UNII
    42NCM1BW43
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 2-isobutyrylthiamine Disulfide

    2. Arcalion

    3. Bis(2-(isobutyryloxy)ethyl-1-n-((4-amino-2-methylpyrimidin-5-yl)methyl)formamido-2-propene-1-yl)disulfide

    4. Enerion

    5. S 5007

    6. Sulbuthiamine

    7. Sulbutiamin

    8. Surmenalit

    2.3.2 Depositor-Supplied Synonyms

    1. 3286-46-2

    2. Bisibuthiamine

    3. Sulbutiamine [inn]

    4. Vitaberin

    5. Thiamine Disulfide O,o-diisobutyrate

    6. 42ncm1bw43

    7. Chebi:31290

    8. O-isobutyroylthiamine Disulfide

    9. Propanoic Acid, 2-methyl-,dithiobis[3-[1-[[(4-amino-2-methyl-5-pyrimidinyl)methyl]formylamino]ethylidene]-3,1-propanediyl] Ester

    10. Bisibutiamin

    11. Arcalion

    12. Youvitan

    13. N,n'-(dithiobis(2-(2-hydroxyethyl)-1-methylvinylene))bis(n-((4-amino-2-methyl-5-pyrimidinyl)methyl)formamide) Diisobutyrate (ester)

    14. Sulbutiamina

    15. Sulbutiaminum

    16. Sulbutiaminum [inn-latin]

    17. Sulbutiamina [inn-spanish]

    18. (3e,3'e)-disulfanediylbis(4-(n-((4-amino-2-methylpyrimidin-5-yl)methyl)formamido)pent-3-ene-3,1-diyl) Bis(2-methylpropanoate)

    19. Propanoic Acid, 2-methyl-, Dithiobis(3-(1-(((4-amino-2-methyl-5-pyrimidinyl)methyl)formylamino)ethylidene)-3,1-propanediyl) Ester

    20. Bisibuthiamine [jan]

    21. O,o'-diisobutyrylthiamine Disulfide

    22. Einecs 221-937-3

    23. Brn 0741531

    24. Unii-42ncm1bw43

    25. Propanoic Acid, 2-methyl-, Dithiobis[3-[1-[[(4-amino-2-methyl-5-pyrimidinyl)methyl]formylamino]ethylidene]-3,1-propanediyl] Ester

    26. Sulbutiamine [vandf]

    27. Sulbutiamine [mart.]

    28. 5-25-12-00169 (beilstein Handbook Reference)

    29. Bis(1-(2-isobutyryloxyethyl)-2-(n-((4-amino-2-methyl-5-pyrimidinyl)methyl)formamido)-1-propenyl)disulfid

    30. Bis(1-(4-amino-2-methyl-5-pyrimidinyl)-2-formyl-3,9-dimethyl-8-oxo-2-aza-7-oxa-3-decen-4-yl)disulfid

    31. Sulbutiamine [who-dd]

    32. Schembl1651347

    33. Chembl1874002

    34. Schembl20561698

    35. Zinc72135087

    36. Akos015994746

    37. Db13416

    38. Ks-1287

    39. [(e)-4-[(4-amino-2-methyl-pyrimidin-5-yl)methyl-formyl-amino]-3-[[(e)-2-[(4-amino-2-methyl-pyrimidin-5-yl)methyl-formyl-amino]-1-[2-(2-methylpropanoyloxy)ethyl]prop-1-enyl]disulfanyl]pent-3-enyl] 2-methylpropanoate

    40. Formamide, N,n'-(dithiobis(2-(2-hydroxyethyl)-1-methylvinylene))bis(n-((4-amino-2-methyl-5-pyrimidinyl)methyl)-, Diisobutyrate (ester)

    41. 286s462

    42. Sr-01000945276

    43. Thiamine Disulfide O,o-diisobutyrate [mi]

    44. Q2581447

    45. Sr-01000945276-1

    46. F0001-2410

    2.4 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 702.9 g/mol
    Molecular Formula C32H46N8O6S2
    XLogP32.7
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count14
    Rotatable Bond Count19
    Exact Mass702.29817356 g/mol
    Monoisotopic Mass702.29817356 g/mol
    Topological Polar Surface Area247 Ų
    Heavy Atom Count48
    Formal Charge0
    Complexity1050
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count2
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Pharmacology and Biochemistry
    4.1 ATC Code

    A - Alimentary tract and metabolism

    A11 - Vitamins

    A11D - Vitamin b1, plain and in combination with vitamin b6 and b12

    A11DA - Vitamin b1, plain

    A11DA02 - Sulbutiamine

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