Details
Stereochemistry | RACEMIC |
Molecular Formula | C22H26N2O4 |
Molecular Weight | 382.4528 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCC1C2=C(C=C(OC)C(OC)=C2)C(=NN=C1C)C3=CC(OC)=C(OC)C=C3
InChI
InChIKey=RUJBDQSFYCKFAA-UHFFFAOYSA-N
InChI=1S/C22H26N2O4/c1-7-15-13(2)23-24-22(14-8-9-18(25-3)19(10-14)26-4)17-12-21(28-6)20(27-5)11-16(15)17/h8-12,15H,7H2,1-6H3
DescriptionSources: https://www.drugbank.ca/drugs/DB08811Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/21920746 | https://www.ncbi.nlm.nih.gov/pubmed/18027916 | https://topbrainboosters.com/grandaxin/ | https://www.ncbi.nlm.nih.gov/pubmed/10670703
Sources: https://www.drugbank.ca/drugs/DB08811
Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/21920746 | https://www.ncbi.nlm.nih.gov/pubmed/18027916 | https://topbrainboosters.com/grandaxin/ | https://www.ncbi.nlm.nih.gov/pubmed/10670703
Tofisopam (marketed under brand names Emandaxin and Grandaxin) is a 2,3-benzodiazepine derivative that is marketed in several European countries as the anxiolytic drug. Tofisopam does not bind to the benzodiazepine binding site of the gamma-aminobutyric acid receptor. One study has shown that tofisopam acts as an isoenzyme-selective inhibitor of phosphodiesterases (PDEs) with the highest affinity to PDE-4A1 followed by PDE-10A1, PDE-3, and PDE-2A3. Like other benzodiazepines, tofisopam possesses anxiolytic properties but unlike other benzodiazepines, it does not have anticonvulsant, sedative, skeletal muscle relaxant, motor skill-impairing or amnestic properties. While it may not be an anticonvulsant in and of itself, it has been shown to enhance the anticonvulsant action of classical 1,4-benzodiazepines such as diazepam (but not sodium valproate, carbamazepine, phenobarbital, or phenytoin). Tofisopam is not approved for sale in the United States or Canada. However, Vela Pharmaceuticals of New Jersey is developing the D-enantiomer (dextofisopam) as a treatment for irritable bowel syndrome, with moderate efficacy demonstrated in clinical trials so far.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2760 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18027916 |
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Target ID: CHEMBL2169736 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21920746 |
0.9 µM [IC50] | ||
Target ID: CHEMBL2093863 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21920746 |
0.68 µM [IC50] | ||
Target ID: CHEMBL2094125 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21920746 |
5.9 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Grandaxin Approved UseUnknown |
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Sources: https://topbrainboosters.com/grandaxin/ |
Primary | Grandaxin Approved UseUnknown |
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Primary | Grandaxin Approved UseUnknown |
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Primary | Grandaxin Approved UseUnknown |
PubMed
Title | Date | PubMed |
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[The effect of tofisopam and tinctura leonuri on the color-discrimination function in young humans]. | 2005 May-Jun |
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Contribution of human hepatic cytochrome p450 isoforms to the metabolism of psychotropic drugs. | 2005 Sep |
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[Tofisopam and melatonin attenuate the reorganization of circadian locomotor rhythm in rats under injection-induced stress conditions]. | 2006 Mar-Apr |
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Method validation and determination of enantiomers and conformers in tofisopam drug substances and drug products by chiral high-performance liquid chromatography and kinetic and thermodynamic study of the interconversion of the conformers. | 2006 Sep 29 |
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Clinical trial: dextofisopam in the treatment of patients with diarrhoea-predominant or alternating irritable bowel syndrome. | 2008 Jan 15 |
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Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method. | 2010 Dec |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://topbrainboosters.com/grandaxin/
Recommended dosage is 50-100mg 1-3 times a day. The maximum daily dose is 300mg.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17646282
All microsomal incubations were conducted in 100 mM phosphate buffer, pH 7.4, initiated by the addition of NADPH (1 mM final concentration), and stopped by the addition of 0.5 ml of ethyl acetate and vortexing after a predetermined incubation time period. Pilot microsomal incubations were conducted to determine appropriate concentrations of tofisopam and human liver microsomal protein, as well as incubation time. On the basis of these pilot incubations, the following incubation conditions were used for the remainder of the microsomal work: 500 ng/ml tofisopam, 0.2 mg/ml human liver microsomes, and a 10-min incubation time.
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WHO-ATC |
N05BA23
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WHO-VATC |
QN05BA23
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NCI_THESAURUS |
C28197
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SUB11144MIG
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C012582
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244-922-3
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m10932
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TOFISOPAM
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CHEMBL404216
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22345-47-7
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100000077749
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DB08811
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38365
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UZC80HAU42
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2693
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DTXSID3023681
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3130
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C90791
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5502
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ACTIVE MOIETY