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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 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 Formula	C₃₂H₄₆N₈O₆S₂
Molecular Weight	702.9 g/mol
XLogP3	2.7
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	14
Rotatable Bond Count	19
Exact Mass	702.29817356 g/mol
Monoisotopic Mass	702.29817356 g/mol
Topological Polar Surface Area	247 Å²
Heavy Atom Count	48
Formal Charge	0
Complexity	1050
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	2
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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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