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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
Structure of TOFISOPAM

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

HIDE SMILES / InChI

Description
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.

Originator

Sources: HU155572

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.9 µM [IC50]
0.68 µM [IC50]
5.9 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Grandaxin

Approved Use

Unknown
Primary
Grandaxin

Approved Use

Unknown
Primary
Grandaxin

Approved Use

Unknown
Primary
Grandaxin

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
[The effect of tofisopam and tinctura leonuri on the color-discrimination function in young humans].
2005 May-Jun
Contribution of human hepatic cytochrome p450 isoforms to the metabolism of psychotropic drugs.
2005 Sep
[Tofisopam and melatonin attenuate the reorganization of circadian locomotor rhythm in rats under injection-induced stress conditions].
2006 Mar-Apr
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
Clinical trial: dextofisopam in the treatment of patients with diarrhoea-predominant or alternating irritable bowel syndrome.
2008 Jan 15
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.
2010 Dec
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Recommended dosage is 50-100mg 1-3 times a day. The maximum daily dose is 300mg.
Route of Administration: Oral
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.
Name Type Language
TOFISOPAM
INN   MART.   MI   WHO-DD  
INN  
Official Name English
EMANDAXIN
Brand Name English
Tofisopam [WHO-DD]
Common Name English
TOFISOPAM [MI]
Common Name English
tofisopam [INN]
Common Name English
1-(3,4-DIMETHOXYPHENYL)-5-ETHYL-7,8-DIMETHOXY-4-METHYL-5H-2,3-BENZODIAZEPINE
Systematic Name English
TOFISOPAM [MART.]
Common Name English
TOFISOPAM [JAN]
Common Name English
(±)-1-(3,4-DIMETHOXYPHENYL)-5-ETHYL-7,8-DIMETHOXY-4-METHYL-5H-2,3-BENZODIAZEPINE
Systematic Name English
Classification Tree Code System Code
WHO-ATC N05BA23
Created by admin on Sat Dec 16 15:54:31 GMT 2023 , Edited by admin on Sat Dec 16 15:54:31 GMT 2023
WHO-VATC QN05BA23
Created by admin on Sat Dec 16 15:54:31 GMT 2023 , Edited by admin on Sat Dec 16 15:54:31 GMT 2023
NCI_THESAURUS C28197
Created by admin on Sat Dec 16 15:54:31 GMT 2023 , Edited by admin on Sat Dec 16 15:54:31 GMT 2023
Code System Code Type Description
EVMPD
SUB11144MIG
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PRIMARY
MESH
C012582
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PRIMARY
ECHA (EC/EINECS)
244-922-3
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PRIMARY
MERCK INDEX
m10932
Created by admin on Sat Dec 16 15:54:31 GMT 2023 , Edited by admin on Sat Dec 16 15:54:31 GMT 2023
PRIMARY Merck Index
WIKIPEDIA
TOFISOPAM
Created by admin on Sat Dec 16 15:54:31 GMT 2023 , Edited by admin on Sat Dec 16 15:54:31 GMT 2023
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ChEMBL
CHEMBL404216
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PRIMARY
CAS
22345-47-7
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SMS_ID
100000077749
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DRUG BANK
DB08811
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RXCUI
38365
Created by admin on Sat Dec 16 15:54:31 GMT 2023 , Edited by admin on Sat Dec 16 15:54:31 GMT 2023
PRIMARY RxNorm
FDA UNII
UZC80HAU42
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PRIMARY
DRUG CENTRAL
2693
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EPA CompTox
DTXSID3023681
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INN
3130
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PRIMARY
NCI_THESAURUS
C90791
Created by admin on Sat Dec 16 15:54:31 GMT 2023 , Edited by admin on Sat Dec 16 15:54:31 GMT 2023
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PUBCHEM
5502
Created by admin on Sat Dec 16 15:54:31 GMT 2023 , Edited by admin on Sat Dec 16 15:54:31 GMT 2023
PRIMARY