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3286-46-2

Basic Information
CAS No.: 3286-46-2
Name: Sulbutiamine
Article Data: 8
Cas Database
Molecular Structure:
Molecular Structure of 3286-46-2 (Sulbutiamine)
Formula: C32H46N8O6S2
Molecular Weight: 702.899
Synonyms: Arcalion;Bisibutiamine;[4-[(4-Amino-2-methylpyrimidin-5-yl)methylformylamino]-3-[2-[(4-amino-2-methylpyrimidin-5-yl)methylformylamino]-5-(2-methylpropanoyloxy)pent-2-en-3-yl]disulfanylpent-3-enyl] 2-methylpropanoate;
EINECS: 221-937-3
Density: 1.268 g/cm3
Melting Point: 140.5-141.5 °C
Boiling Point: 892.5 °C at 760 mmHg
Flash Point: 493.5 °C
Solubility: N/A
Appearance: White to off-white crystalline powder
Hazard Symbols: N/A
Risk Codes: N/A
Safety:
Transport Information: N/A
PSA: 247.42000
LogP: 7.12200
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History

The history of sulbutiamine is closely tied to the study of thiamine in Japan. A deficiency of thiamine causes a nervous system disorder called beriberi. Until the twentieth century, beriberi was prevalent in Japan and other Asian countries due to the widespread dependence on white rice as a staple food. The relationship between beriberi and diet was first noted by a navy surgeon named Takaki Kanehiro.Additional work resulted in the discovery of thiamine, which was isolated in 1926 and synthesized in 1936. The establishment of a Vitamin B Research Committee in Japan led to additional scientific investigation into the properties of thiamine and its derivatives.
The first lipophilic thiamine derivative to be discovered was allithiamine, which was isolated from garlic (Allium sativum) in 1951. Allithiamine is an allyl disulfide derivative. After the discovery of allithiamine, several additional derivatives were synthesized with the hope that they would have better pharmacokinetic properties than thiamine. Thiamine is unable to diffuse across plasma membranes because it has a positively charged thiazole moiety. Instead, it must be transported across plasma membranes by high affinity carriers, and the rate of transport is low. Sulbutiamine overcomes the poor oral bioavailability of thiamine because it is highly lipophilic. It is not clear when sulbutiamine was first synthesized, but the earliest reference to it in the literature is from 1973.

Specification

The Sulbutiamine, with the CAS registry number 3286-46-2, is also known as O-Isobutyroylthiamine disulfide. It belongs to the product category of Vitamins and derivatives.Its IUPAC name is called [(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. This chemical's classification code is Drug / Therapeutic Agent. Sulbutiamine (brand name: Arcalion) is a synthetic derivative of thiamine. It is the only compound used to treat asthenia that is known to selectively target the areas that are involved in the condition.

Physical properties of Sulbutiamine are: (1)ACD/LogP: 6.154; (2)# of Rule of 5 Violations: 3; (3)ACD/LogD (pH 5.5): 5.39; (4)ACD/LogD (pH 7.4): 6.14; (5)ACD/BCF (pH 5.5): 4849.95; (6)ACD/BCF (pH 7.4): 26983.07; (7)ACD/KOC (pH 5.5): 9191.60; (8)ACD/KOC (pH 7.4): 51138.15; (9)#H bond acceptors: 14; (10)#H bond donors: 4; (11)#Freely Rotating Bonds: 19; (12)Index of Refraction: 1.602; (13)Molar Refractivity: 190.198 cm3; (14)Molar Volume: 554.327 cm3; (15)Polarizability: 75.4 10-24cm3; (16)Surface Tension: 57.898998260498 dyne/cm; (17)Density: 1.268 g/cm3; (18)Flash Point: 493.539 °C; (19)Enthalpy of Vaporization: 129.752 kJ/mol; (20)Boiling Point: 892.455 °C at 760 mmHg

You can still convert the following datas into molecular structure:
(1)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)InChIKey=CKHJPWQVLKHBIH-GPAWKIAZSA-N;
(3)SmilesCc1ncc(CN(C=O)C(\C)=C(/SSC(\CCOC(C(C)C)=O)=C(\C)N(C=O)Cc2cnc(C)nc2N)CCOC(C(C)C)=O)c(N)n1;

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal > 2500mg/kg (2500mg/kg)   Drugs in Japan Vol. 6, Pg. 606, 1982.
mouse LD50 oral > 5gm/kg (5000mg/kg)   Drugs in Japan Vol. 6, Pg. 606, 1982.
mouse LD50 subcutaneous > 3gm/kg (3000mg/kg)   Drugs in Japan Vol. 6, Pg. 606, 1982.
rat LD50 intraperitoneal 660mg/kg (660mg/kg)   Drugs in Japan Vol. 6, Pg. 606, 1982.
rat LD50 intravenous 110mg/kg (110mg/kg)   Drugs in Japan Vol. 6, Pg. 606, 1982.
rat LD50 oral > 5gm/kg (5000mg/kg)   Drugs in Japan Vol. 6, Pg. 606, 1982.
rat LD50 subcutaneous 850mg/kg (850mg/kg)   Drugs in Japan Vol. 6, Pg. 606, 1982.

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