1-(3,4-dimethoxyphenyl)-5-ethyl-7,8-dimethoxy-4-methyl-5H-2,3-benzodiazepine

• ChemBase ID: 6411
• Molecular Formular: C22H26N2O4
• Molecular Mass: 382.45284
• Monoisotopic Mass: 382.18925732
• SMILES: O(c1cc2C(CC)C(=NN=C(c2cc1OC)c1cc(OC)c(OC)cc1)C)C
• Canonical SMILES: CCC1C(=NN=C(c2c1cc(OC)c(c2)OC)c1ccc(c(c1)OC)OC)C
• InChI: 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
• InChIKey: RUJBDQSFYCKFAA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(3,4-dimethoxyphenyl)-5-ethyl-7,8-dimethoxy-4-methyl-5H-2,3-benzodiazepine
• IUPAC Traditional name: tofisopam
• Brand Name: Emandaxin; Grandaxin; Seriel
• Synonyms: Tofizopam; Tofisopam

Database IDs

• CAS Number: 22345-47-7
• PubChem SID: 160969718
• PubChem CID: 5502

CALCULATED PROPERTIES

JChem

• H Acceptors: 6
• H Donor: 0
• LogD (pH = 5.5): 3.8256044
• LogD (pH = 7.4): 3.8256044
• Log P: 3.8256044
• Molar Refractivity: 109.0347 cm^3
• Polarizability: 41.73672 Å^3
• Polar Surface Area: 61.64 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 4.29
• LOG S: -5.21
• Solubility (Water): 2.39e-03 g/l

DETAILS

DrugBank - DB08811

• Drug Groups: approved
• Description: Tofisopam (marketed under brand names Emandaxin and Grandaxin) is a 2,3-benzodiazepine drug which is a benzodiazepine derivative. In contrast to classical 1,4-benzodiazepines, the compound does not bind to the benzodiazepine binding site of the gamma-aminobutyric acid receptor and its psychopharmacological profile differs from such compounds. Although Tofisopam is not approved for sale in North America, it is approved for use in various countries worldwide, including parts of Europe. The D-enantiomer (dextofisopam) is currently in phase II trials in the U.S. for the treatment of irritable bowel syndrome.
• Indication: For the treatment of anxiety and alcohol withdrawal.
• Pharmacology: 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).
• Toxicity: The onset of impairment of consciousness is relatively rapid in benzodiazepine poisoning. Onset is more rapid following larger doses and with agents of shorter duration of action. The most common and initial symptom is somnolence. This may progress to coma (Grade I or Grade II) following very large ingestions. Oral, rat LD50 is 825 mg/kg.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic.
• Half Life: 6-8 hours
• References: Rundfeldt C, Socala K, Wlaz P: The atypical anxiolytic drug, tofisopam, selectively blocks phosphodiesterase isoenzymes and is active in the mouse model of negative symptoms of psychosis. J Neural Transm. 2010 Nov;117(11):1319-25. Epub 2010 Oct 22. [Pubmed]
• External Links: Wikipedia

REFERENCES

• Rundfeldt C, Socala K, Wlaz P: The atypical anxiolytic drug, tofisopam, selectively blocks phosphodiesterase isoenzymes and is active in the mouse model of negative symptoms of psychosis. J Neural Transm. 2010 Nov;117(11):1319-25. Epub 2010 Oct 22. Pubmed