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3 API Suppliers, 1 JDMF, 1 EU WC, 6 KDMF, 3 Listed Suppliers, $ API Reference Price

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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 (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 Formula	C₂₂H₂₆N₂O₄
Molecular Weight	382.5 g/mol
XLogP3	3.2
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	6
Exact Mass	382.18925731 g/mol
Monoisotopic Mass	382.18925731 g/mol
Topological Polar Surface Area	61.6 Å²
Heavy Atom Count	28
Formal Charge	0
Complexity	579
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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).

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API Reference Price

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