Structure via PubChem · Public domain (PubChem)
tofisopam
Sign in to saveAlso known as Emandaxin, Tofizopam
Tofisopam (Emandaxin, Grandaxin, Sériel) is an anxiolytic that is marketed in several European countries. Chemically, it is a 2,3-benzodiazepine. Unlike other anxiolytic benzodiazepines (which are generally 1,4- or 1,5-substituted) however, tofisopam 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) and muscimol, but not sodium valproate, carbamazepine, phenobarbital, or p
Chemical data
- Formula
- C22H26N2O4
- Molecular weight
- 382.5 g/mol
- IUPAC name
- 1-(3,4-dimethoxyphenyl)-5-ethyl-7,8-dimethoxy-4-methyl-5H-2,3-benzodiazepine
- SMILES
- CCC1C(=NN=C(C2=CC(=C(C=C12)OC)OC)C3=CC(=C(C=C3)OC)OC)C
- InChIKey
- RUJBDQSFYCKFAA-UHFFFAOYSA-N
- XLogP
- 3.2
- Polar surface area
- 61.6 Ų
- H-bond donors
- 0
- H-bond acceptors
- 6
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
- Indications
- anxiety
via ChEMBL · EBI
Research
130 papers- Antidepressant-like effect of tofisopam in mice: A behavioural, molecular docking and MD simulation study.Journal of psychopharmacology (Oxford, England) · 2022
- Cardioprotective effect of tofisopam against isoprenaline-induced myocardial infarction in rats via modulation of NLRP3\IL-1β\caspase-1 pathway.Immunopharmacology and immunotoxicology · 2024
- Is tofisopam an atypical anxiolytic?Neuroscience and biobehavioral reviews · 1986
- Antiamnesic effects of tofisopam against scopolamine-induced cognitive impairments in rats.Pharmacology, biochemistry, and behavior · 2020
- Synthesis of Tofisopam by Way of Photoinduced CO(2) Fixation.Chemistry, an Asian journal · 2019
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 382.189
- Has use
- medication
Show 5 more facts
- Commons category
- Tofisopam
- chemical formula
- C₂₂H₂₆N₂O₄
- World Health Organisation international non-proprietary name
- tofisopam
- canonical SMILES
- CCC1C(=NN=C(C2=CC(=C(C=C12)OC)OC)C3=CC(=C(C=C3)OC)OC)C
- subject has role
- antidepressant
via Wikidata · CC0
~2 min read
Encyclopedic overview
2 sectionsContents
- References
- External links
Tofisopam (Emandaxin, Grandaxin, Sériel) is an anxiolytic that is marketed in several European countries. Chemically, it is a 2,3-benzodiazepine. Unlike other anxiolytic benzodiazepines (which are generally 1,4- or 1,5-substituted) however, tofisopam 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) and muscimol, but not sodium valproate, carbamazepine, phenobarbital, or phenytoin. Tofisopam is indicated for the treatment of anxiety and alcohol withdrawal, and is prescribed in a dosage of 50–300 mg per day divided into three doses. Peak plasma levels are attained two hours after an oral dose. Tofisopam is not reported as causing dependence to the same extent as other benzodiazepines, but is still recommended to be prescribed for a maximum of 12 weeks.
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.
Excerpted from Wikipedia’s “tofisopam” article, available under the CC BY-SA 4.0 licence.