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    Chemistry

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    Also known as: 22345-47-7, Grandaxin, 1-(3,4-dimethoxyphenyl)-5-ethyl-7,8-dimethoxy-4-methyl-5h-2,3-benzodiazepine, Emandaxin, Egyt 341, Tofisopamum
    Molecular Formula
    C22H26N2O4
    Molecular Weight
    382.5  g/mol
    InChI Key
    RUJBDQSFYCKFAA-UHFFFAOYSA-N
    FDA UNII
    UZC80HAU42
    Tofisopam
    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.
    1 2D Structure

    Tofisopam

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    1-(3,4-dimethoxyphenyl)-5-ethyl-7,8-dimethoxy-4-methyl-5H-2,3-benzodiazepine
    2.1.2 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
    2.1.3 InChI Key
    RUJBDQSFYCKFAA-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CCC1C(=NN=C(C2=CC(=C(C=C12)OC)OC)C3=CC(=C(C=C3)OC)OC)C
    2.2 Other Identifiers
    2.2.1 UNII
    UZC80HAU42
    2.3 Synonyms
    2.3.1 MeSH Synonyms

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

    2. Dextofisopam

    3. Egyt-341

    4. Grandaxin

    5. Levotofisopam

    6. Tofizopam

    2.3.2 Depositor-Supplied Synonyms

    1. 22345-47-7

    2. Grandaxin

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

    4. Emandaxin

    5. Egyt 341

    6. Tofisopamum

    7. Uzc80hau42

    8. Seriel

    9. 5h-2,3-benzodiazepine, 1-(3,4-dimethoxyphenyl)-5-ethyl-7,8-dimethoxy-4-methyl-

    10. 1-(3,4-dimethoxyphenyl)-5-ethyl-7,8-dimethoxy-4-methyl-5h-benzo[d][1,2]diazepine

    11. Tofizopam

    12. Ncgc00165912-02

    13. Benzodiazepine; Egyt 341; Grandaxin; Nodeprine; Seriel

    14. Tofisopamum [inn-latin]

    15. Tofisopam [inn:dcf:jan]

    16. 82059-50-5

    17. Einecs 244-922-3

    18. Unii-uzc80hau42

    19. Ccris 8738

    20. Emandaxin (tn)

    21. 7,8-dimethoxy-1-(3,4-dimethoxyphenyl)-5-ethyl-4-methyl-5h-2,3-benzodiazepine

    22. Tofisopam [inn]

    23. Tofisopam [jan]

    24. Tofisopam [mi]

    25. Dsstox_cid_3681

    26. Tofisopam (jp17/inn)

    27. Tofisopam [mart.]

    28. Tofisopam [who-dd]

    29. Dsstox_rid_77145

    30. Dsstox_gsid_23681

    31. Schembl43522

    32. Tofisopam (patented In Japan)

    33. Chembl404216

    34. Schembl8086894

    35. Dtxsid3023681

    36. Chebi:32241

    37. Bcp09600

    38. Hy-a0165

    39. Tox21_112269

    40. Tofisopam, >=98% (hplc), Solid

    41. Akos025401672

    42. Db08811

    43. Sb17495

    44. Sb17496

    45. Ncgc00165912-01

    46. Ncgc00165912-03

    47. Ac-24288

    48. Ls-14948

    49. Cas-22345-47-7

    50. Db-045872

    51. Ft-0638212

    52. T3509

    53. D01254

    54. 345t477

    55. A878592

    56. Q945537

    57. Q-201839

    58. Brd-a69095630-001-01-1

    59. 1-(3,4-dimethoxyphenyl)-4-methyl-5-ethyl-7,8-dimethoxy-5h-2,3-benzodiazepine

    60. 1-[3,4-bis(methyloxy)phenyl]-5-ethyl-4-methyl-7,8-bis(methyloxy)-5h-2,3-benzodiazepine

    61. (+/-)-1-(3,4-dimethoxyphenyl)-5-ethyl-7,8-dimethoxy-4-methyl-5h-2,3-benzodiazepine

    62. (1z,3z)-1-(3,4-dimethoxyphenyl)-5-ethyl-7,8-dimethoxy-4-methyl-5h-benzo[d][1,2]diazepine

    2.4 Create Date
    2005-03-25
    3 Chemical and Physical Properties
    Molecular Weight 382.5 g/mol
    Molecular Formula C22H26N2O4
    XLogP33.2
    Hydrogen Bond Donor Count0
    Hydrogen Bond Acceptor Count6
    Rotatable Bond Count6
    Exact Mass382.18925731 g/mol
    Monoisotopic Mass382.18925731 g/mol
    Topological Polar Surface Area61.6 Ų
    Heavy Atom Count28
    Formal Charge0
    Complexity579
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count1
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    For the treatment of anxiety and alcohol withdrawal.

    5 Pharmacology and Biochemistry
    5.1 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. It enhances the anticonvulsant activity of 1,4-benzodiazepines like diazepam but not sodium valproate, carbamazepine, phenobarbital, or phenytoin.

    5.2 MeSH Pharmacological Classification

    Antidepressive Agents

    Mood-stimulating drugs used primarily in the treatment of affective disorders and related conditions. Several MONOAMINE OXIDASE INHIBITORS are useful as antidepressants apparently as a long-term consequence of their modulation of catecholamine levels. The tricyclic compounds useful as antidepressive agents (ANTIDEPRESSIVE AGENTS, TRICYCLIC) also appear to act through brain catecholamine systems. A third group (ANTIDEPRESSIVE AGENTS, SECOND-GENERATION) is a diverse group of drugs including some that act specifically on serotonergic systems. (See all compounds classified as Antidepressive Agents.)

    5.3 ATC Code

    N - Nervous system

    N05 - Psycholeptics

    N05B - Anxiolytics

    N05BA - Benzodiazepine derivatives

    N05BA23 - Tofisopam

    5.4 Metabolism/Metabolites

    Hepatic.

    5.5 Biological Half-Life

    6-8 hours

    5.6 Mechanism of Action

    Tofisopam does not bind to the benzodiazepine binding site of the gamma-aminobutyric acid receptor. One study (Rundfeldt C. et al.) has shown that tofisopam acts as an isoenzyme-selective inhibitor of phosphodiesterases (PDEs) with highest affinity to PDE-4A1 (0.42 M) followed by PDE-10A1 (0.92 M), PDE-3 (1.98 M) and PDE-2A3 (2.11 M).

    API Reference Price

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    07-Apr-2021
    18-May-2024
    KGS
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    Average Price (USD/KGS)

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    Quantity (KGS) & Unit rate (USD/KGS) over time

    API Imports and Exports

    Importing Country Total Quantity
    (KGS)    		 Average Price
    (USD/KGS)    		 Number of Transactions

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    DSSTox_CID_3681 Manufacturers | Traders | Suppliers

    DSSTox_CID_3681 Manufacturers, Traders, Suppliers 1
    63

    We have 3 companies offering DSSTox_CID_3681

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    1. Egis Pharmaceuticals PLC
    2. Lake Chemicals
    3. Symed Labs
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