U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C32H46N8O6S2
Molecular Weight 702.891
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of SULBUTIAMINE

SMILES

CC(C)C(=O)OCC/C(=C(/C)\N(Cc1cnc(C)[nH]c1=N)C=O)/SS/C(=C(\C)/N(Cc2cnc(C)[nH]c2=N)C=O)/CCOC(=O)C(C)C

InChI

InChIKey=CKHJPWQVLKHBIH-GPAWKIAZSA-N
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+

HIDE SMILES / InChI

Molecular Formula C32H46N8O6S2
Molecular Weight 702.891
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 2
Optical Activity NONE

Description
Curator's Comment:: description was created based on several sources, including https://www.unitedpharmacies.com/Arcalion-Sulbutiamine.html https://www.ncbi.nlm.nih.gov/pubmed/12973384 http://www.smartnootropics.co.uk/sulbutiamine/

Sulbutiamine (isobutyryl thiamine disulfide) is a lipophilic derivative of thiamine. It is available over-the-counter in several countries either as a component of nutritional supplements or as a pharmaceutical preparation. Arcalion (Sulbutiamine) is prescribed as a treatment to help patients with a range of conditions such as asthenia, chronic fatigue, diabetes, hypothyroidism, renal disease, fibromyalgia, and depression (post partum). It remedies the symptoms of weakness by increasing focus, strength (both physical and mental), and energy, making you more alert, less lethargic, and more upbeat whilst also helping to stabilize sleeping patterns. In addition, this medication can also help a patient`s memory, and strengthen thinking processes. Some patient`s have even reported slight eyesight improvements. This product is also popular with athletes as a nutritional supplement as it is a vitamin compound which will not show up in competitive sports blood testing. It can help to achieve your maximum potential and replenish energy after strenuous activities, making it possible to maintain your edge. The presence of sulbutiamine in urinary doping control samples was monitored to evaluate the relevance of its use in sports. The motivating, confidence enhancing effects of sulbutiamine are thought to be related to its ability to enhance dopamine sensitivity. In animal models sulbutiamine has been shown to increase the number of dopamine binding sites (specifically D1) in the prefrontal cortex, this effect is achieved through reduction of dopamine release. Sulbutiamine could be best thought of as a dopamine modulator rather than a compound that directly inhibits or enhances the release of dopamine. Additionally sulbutiamine has been found to enhance memory, possibly by cholinergic transmission. Research indicates that high affinity choline uptake (HACU) was moderately increased in rodent brains following sulbutiamine consumption. However it should be noted the doses used were high (300 mg/kg).

CNS Activity

Curator's Comment:: can cross the blood-brain barrier easily

Originator

Sources: Bitamin (1965), 32, (2), 265-77.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Arcalion

Approved Use

Unknown
Primary
Arcalion

Approved Use

Unknown
Palliative
Arcalion

Approved Use

Unknown
Palliative
Arcalion

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Pharmacologic and therapeutic features of sulbutiamine.
1999 Mar
Patents

Patents

Sample Use Guides

2 tablets per day, taken for 2 weeks
Route of Administration: Oral
Sulbutiamine dose-dependently attenuated apoptotic cell death induced by serum deprivation and stimulated GSH and GST activity. Moreover, sulbutiamine decreased the expression of cleaved caspase-3 and AIF
Substance Class Chemical
Created
by admin
on Sat Jun 26 14:58:48 UTC 2021
Edited
by admin
on Sat Jun 26 14:58:48 UTC 2021
Record UNII
42NCM1BW43
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SULBUTIAMINE
INN   MART.   VANDF   WHO-DD  
INN  
Official Name English
SULBUTIAMINE [WHO-DD]
Common Name English
SULBUTIAMINE [MART.]
Common Name English
BISIBUTHIAMINE [JAN]
Common Name English
THIAMINE DISULFIDE O,O-DIISOBUTYRATE
MI  
Common Name English
SULBUTIAMINE [VANDF]
Common Name English
SULBUTIAMINE [INN]
Common Name English
THIAMINE DISULFIDE O,O-DIISOBUTYRATE [MI]
Common Name English
BISIBUTHIAMINE
JAN  
Common Name English
N,N'-(DITHIOBIS(2-(2-HYDROXYETHYL)-1-METHYLVINYLENE))BIS(N-((4-AMINO-2-METHYL-5-PYRIMIDINYL)METHYL)FORMAMIDE) DIISOBUTYRATE (ESTER)
Common Name English
YOUVITAN
Brand Name English
Classification Tree Code System Code
NCI_THESAURUS C45812
Created by admin on Sat Jun 26 14:58:48 UTC 2021 , Edited by admin on Sat Jun 26 14:58:48 UTC 2021
WHO-VATC QA11DA02
Created by admin on Sat Jun 26 14:58:48 UTC 2021 , Edited by admin on Sat Jun 26 14:58:48 UTC 2021
DSLD 3147 (Number of products:20)
Created by admin on Sat Jun 26 14:58:48 UTC 2021 , Edited by admin on Sat Jun 26 14:58:48 UTC 2021
WHO-ATC A11DA02
Created by admin on Sat Jun 26 14:58:48 UTC 2021 , Edited by admin on Sat Jun 26 14:58:48 UTC 2021
Code System Code Type Description
EVMPD
SUB10679MIG
Created by admin on Sat Jun 26 14:58:48 UTC 2021 , Edited by admin on Sat Jun 26 14:58:48 UTC 2021
PRIMARY
CAS
3286-46-2
Created by admin on Sat Jun 26 14:58:48 UTC 2021 , Edited by admin on Sat Jun 26 14:58:48 UTC 2021
PRIMARY
INN
4827
Created by admin on Sat Jun 26 14:58:48 UTC 2021 , Edited by admin on Sat Jun 26 14:58:48 UTC 2021
PRIMARY
RXCUI
37317
Created by admin on Sat Jun 26 14:58:48 UTC 2021 , Edited by admin on Sat Jun 26 14:58:48 UTC 2021
PRIMARY RxNorm
EPA CompTox
3286-46-2
Created by admin on Sat Jun 26 14:58:48 UTC 2021 , Edited by admin on Sat Jun 26 14:58:48 UTC 2021
PRIMARY
NCI_THESAURUS
C152450
Created by admin on Sat Jun 26 14:58:48 UTC 2021 , Edited by admin on Sat Jun 26 14:58:48 UTC 2021
PRIMARY
PUBCHEM
3002120
Created by admin on Sat Jun 26 14:58:48 UTC 2021 , Edited by admin on Sat Jun 26 14:58:48 UTC 2021
PRIMARY
DRUG CENTRAL
2494
Created by admin on Sat Jun 26 14:58:48 UTC 2021 , Edited by admin on Sat Jun 26 14:58:48 UTC 2021
PRIMARY
ECHA (EC/EINECS)
221-937-3
Created by admin on Sat Jun 26 14:58:48 UTC 2021 , Edited by admin on Sat Jun 26 14:58:48 UTC 2021
PRIMARY
WIKIPEDIA
SULBUTIAMINE
Created by admin on Sat Jun 26 14:58:48 UTC 2021 , Edited by admin on Sat Jun 26 14:58:48 UTC 2021
PRIMARY
MERCK INDEX
M10719
Created by admin on Sat Jun 26 14:58:48 UTC 2021 , Edited by admin on Sat Jun 26 14:58:48 UTC 2021
PRIMARY Merck Index
FDA UNII
42NCM1BW43
Created by admin on Sat Jun 26 14:58:48 UTC 2021 , Edited by admin on Sat Jun 26 14:58:48 UTC 2021
PRIMARY
ChEMBL
CHEMBL2105813
Created by admin on Sat Jun 26 14:58:48 UTC 2021 , Edited by admin on Sat Jun 26 14:58:48 UTC 2021
PRIMARY
DRUG BANK
DB13416
Created by admin on Sat Jun 26 14:58:48 UTC 2021 , Edited by admin on Sat Jun 26 14:58:48 UTC 2021
PRIMARY
MESH
C031331
Created by admin on Sat Jun 26 14:58:48 UTC 2021 , Edited by admin on Sat Jun 26 14:58:48 UTC 2021
PRIMARY
Related Record Type Details
ACTIVE MOIETY