This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.
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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
Structure for Sulbutiamine (DB13416)
- Weight
- Average: 702.89
Monoisotopic: 702.298173581 - Chemical Formula
- C32H46N8O6S2
- Synonyms
- Sulbutiamina
- Sulbutiamine
Pharmacology
- Indication
Not Available
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Asthenia •••••••••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- 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
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image ARCALION 200 TABLET Tablet 200 mg Oral SERVIER MALAYSIA SDN. BHD. 2020-09-08 Not applicable Malaysia 
ARCALION TABLET 200 MG Tablet, sugar coated 200 mg Oral SERVIER (S) PTE LTD 1991-03-05 Not applicable Singapore 
SULBRIMO Capsule 200mg Capsule Oral Live-Well Nutraceuticals Sdn. Bhd. 2020-09-08 Not applicable Malaysia SULBUMIN 200 CAPSULE Capsule 200 mg Oral PAHANG PHARMACY SDN. BHD. 2020-09-08 Not applicable Malaysia อาร์คาลิออง 200 Tablet, sugar coated 200 mg Oral 2016-06-14 2019-10-21 Thailand 
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
- 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]
- 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]
- Van Reeth O: Pharmacologic and therapeutic features of sulbutiamine. Drugs Today (Barc). 1999 Mar;35(3):187-92. [Article]
- NPRA Product Information: Sulbrimo (sulbutiamine) oral capsules [Link]
- External Links
- KEGG Compound
- C12750
- PubChem Compound
- 3002120
- PubChem Substance
- 347829298
- ChemSpider
- 2273322
- 37317
- ChEBI
- 31290
- ChEMBL
- CHEMBL1874002
- ZINC
- ZINC000072135087
- Wikipedia
- Sulbutiamine
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available Recruiting Treatment Nocturnal Enuresis in Children 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet Oral 200.000 mg Tablet, sugar coated Oral Tablet, coated Oral 200 mg Tablet Oral 200 mg Tablet, film coated Oral 200 mg Capsule Oral Capsule Oral 200 mg Capsule, liquid filled Oral 200 mg Tablet, coated Oral 20000000 mg Tablet Oral 200.00 mg Tablet, sugar coated Oral 200 mg - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Not Available
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.0467 mg/mL ALOGPS logP 3.14 ALOGPS logP 0.82 Chemaxon logS -4.2 ALOGPS pKa (Strongest Basic) 6.56 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 10 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 196.82 Å2 Chemaxon Rotatable Bond Count 19 Chemaxon Refractivity 195.97 m3·mol-1 Chemaxon Polarizability 73.89 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 254.29659 predictedDeepCCS 1.0 (2019) [M+H]+ 256.1215 predictedDeepCCS 1.0 (2019) [M+Na]+ 261.7591 predictedDeepCCS 1.0 (2019)
Drug created at June 23, 2017 20:41 / Updated at June 02, 2021 20:04