Sulbutiamine

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Name
Sulbutiamine
Accession Number
DB13416
Type
Small Molecule
Groups
Experimental
Description

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. Due to its highly lipophilic property, sulbutiamine crosses the blood-brain barrier more readily than thiamine and increases the levels of thiamine and thiamine phosphate esters in the brain [Wikipedia]. 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.

Structure
Thumb
Synonyms
  • Sulbutiamina
Categories
UNII
42NCM1BW43
CAS number
3286-46-2
Weight
Average: 702.89
Monoisotopic: 702.298173581
Chemical Formula
C32H46N8O6S2
InChI Key
CKHJPWQVLKHBIH-GPAWKIAZSA-N
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+
IUPAC Name
(3E)-4-{N-[(4-amino-2-methylpyrimidin-5-yl)methyl]formamido}-3-{[(2E)-2-{N-[(4-amino-2-methylpyrimidin-5-yl)methyl]formamido}-5-[(2-methylpropanoyl)oxy]pent-2-en-3-yl]disulfanyl}pent-3-en-1-yl 2-methylpropanoate
SMILES
CC(C)C(=O)OCC\C(SS\C(CCOC(=O)C(C)C)=C(/C)N(CC1=C(N)N=C(C)N=C1)C=O)=C(\C)N(CC1=C(N)N=C(C)N=C1)C=O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
Not Available
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
  1. Trovero F, Gobbi M, Weil-Fuggaza J, Besson MJ, Brochet D, Pirot S: Evidence for a modulatory effect of sulbutiamine on glutamatergic and dopaminergic cortical transmissions in the rat brain. Neurosci Lett. 2000 Sep 29;292(1):49-53. [PubMed:10996447]
  2. Micheau J, Durkin TP, Destrade C, Rolland Y, Jaffard R: Chronic administration of sulbutiamine improves long term memory formation in mice: possible cholinergic mediation. Pharmacol Biochem Behav. 1985 Aug;23(2):195-8. [PubMed:4059305]
  3. Van Reeth O: Pharmacologic and therapeutic features of sulbutiamine. Drugs Today (Barc). 1999 Mar;35(3):187-92. [PubMed:12973384]
External Links
KEGG Compound
C12750
PubChem Compound
3002120
PubChem Substance
347829298
ChemSpider
2273322
ChEBI
31290
ChEMBL
CHEMBL1874002
Wikipedia
Sulbutiamine
ATC Codes
A11DA02 — Sulbutiamine

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0467 mg/mLALOGPS
logP3.14ALOGPS
logP0.82ChemAxon
logS-4.2ALOGPS
pKa (Strongest Basic)6.56ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area196.82 Å2ChemAxon
Rotatable Bond Count19ChemAxon
Refractivity195.97 m3·mol-1ChemAxon
Polarizability73.89 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as aminopyrimidines and derivatives. These are organic compounds containing an amino group attached to a pyrimidine ring. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Diazines
Sub Class
Pyrimidines and pyrimidine derivatives
Direct Parent
Aminopyrimidines and derivatives
Alternative Parents
Imidolactams / Dicarboxylic acids and derivatives / Tertiary carboxylic acid amides / Heteroaromatic compounds / Organic disulfides / Carboxylic acid esters / Amino acids and derivatives / Sulfenyl compounds / Azacyclic compounds / Primary amines
show 4 more
Substituents
Aminopyrimidine / Dicarboxylic acid or derivatives / Imidolactam / Heteroaromatic compound / Tertiary carboxylic acid amide / Amino acid or derivatives / Carboxamide group / Carboxylic acid ester / Organic disulfide / Carboxylic acid derivative
show 14 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
aminopyrimidine (CHEBI:31290)

Drug created on June 23, 2017 14:41 / Updated on November 05, 2018 17:50