Sulbutiamine

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

Identification

Summary

Sulbutiamine is a thiamine derivative indicated in the treatment of asthenia.

Generic Name
Sulbutiamine
DrugBank Accession Number
DB13416
Background

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.

Type
Small Molecule
Groups
Experimental
Structure
Thumb
Weight
Average: 702.89
Monoisotopic: 702.298173581
Chemical Formula
C32H46N8O6S2
Synonyms
  • Sulbutiamina
  • Sulbutiamine

Pharmacology

Indication

Not Available

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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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

Adverse Effects
Adverseeffects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Products

Products2
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Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
ARCALION 200 TABLETTabletOralSERVIER MALAYSIA SDN BHD2020-09-08Not applicableMalaysia flag
ARCALION TABLET 200 MGTablet, sugar coated200 mgOralSERVIER (S) PTE LTD1991-05-03Not applicable
SULBRIMO Capsule 200mgCapsuleOralLive-Well Nutraceuticals Sdn. Bhd.2020-09-08Not applicableMalaysia flag
Sulbutiamine 200 CapsuleCapsuleOralPAHANG PHARMACY SDN. BHD.2020-09-08Not applicableMalaysia flag
อาร์คาลิออง 200Tablet, sugar coated200 mgOral2016-06-142019-10-21Thailand flag

Categories

ATC Codes
A11DA02 — Sulbutiamine
Drug Categories
Chemical TaxonomyProvided by Classyfire
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
Amine / Amino acid or derivatives / Aminopyrimidine / Aromatic heteromonocyclic compound / Azacycle / Carbonyl group / Carboxamide group / Carboxylic acid derivative / Carboxylic acid ester / Dicarboxylic acid or derivatives
show 14 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
aminopyrimidine (CHEBI:31290)
Affected organisms
Not Available

Chemical Identifiers

UNII
42NCM1BW43
CAS number
3286-46-2
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

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. [Article]
  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. [Article]
  3. Van Reeth O: Pharmacologic and therapeutic features of sulbutiamine. Drugs Today (Barc). 1999 Mar;35(3):187-92. [Article]
  4. NPRA Product Information: Sulbrimo (sulbutiamine) oral capsules [Link]
KEGG Compound
C12750
PubChem Compound
3002120
PubChem Substance
347829298
ChemSpider
2273322
RxNav
37317
ChEBI
31290
ChEMBL
CHEMBL1874002
ZINC
ZINC000072135087
Wikipedia
Sulbutiamine

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Tablet, sugar coatedOral
Tablet, coatedOral200 mg
TabletOral
Tablet, film coatedOral200 mg
Capsule, liquid filledOral200 mg
CapsuleOral
Tablet, sugar coatedOral200 mg
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

Drug created on June 23, 2017 20:41 / Updated on June 02, 2021 20:04