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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 SUPPLIERS

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Egis Pharmaceuticals PLC

Hungary

USDMF, CEP/COS, JDMF, EU-WC, NDC, KDMF, VMF, Others

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Virtual BoothEgis is a Hungarian generic pharma company with 110 years history. Our activities incorporate all areas of the pharma value chain.

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Egis Pharmaceuticals

02

Lake Chemicals

India

USDMF, CEP/COS, JDMF, EU-WC, NDC, KDMF, VMF, Others

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03

Symed Labs

India

USDMF, CEP/COS, JDMF, EU-WC, NDC, KDMF, VMF, Others

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Symed Labs

India

USDMF, CEP/COS, JDMF, EU-WC, NDC, KDMF, VMF, Others

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USDMF CEP/COS JDMF EU-WCInactive-api NDC KDMF VMF Others AUDIT
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Virtual BoothEgis is a Hungarian generic pharma company with 110 years history. Our activities incorporate all areas of the pharma value chain.

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Tofisopam

Registration Number : 219MF10297

Registrant's Address : H-1106 BUDAPEST KERESZTURI UT 30-38 HUNGARY

Initial Date of Registration : 2007-09-18

Latest Date of Registration : 2021-09-28

Egis Pharmaceuticals

02

Sanyo Chemical Research Institute C...

Gabon
CPHI Middle east
Not Confirmed
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Sanyo Chemical Research Institute C...

Gabon
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CPHI Middle east
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Japanese Pharmacopoeia Tofisopam (for manufacturing only)

Registration Number : 217MF10163

Registrant's Address : 148-1 Tajii, Mihara-ku, Sakai City, Osaka Prefecture

Initial Date of Registration : 2005-05-31

Latest Date of Registration : 2006-12-18

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EU WC

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Symed Labs

India
CPHI Middle east
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Symed Labs

India
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Tofisopam IH/IP

Date of Issue : 2021-06-22

Valid Till : 2022-08-08

Written Confirmation Number : WC-0382A4

Address of the Firm : Unit -I Sy. No. 353 Domaguda Village Jinnaram Mandal Medak Dist T.S India

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Virtual BoothEgis is a Hungarian generic pharma company with 110 years history. Our activities incorporate all areas of the pharma value chain.

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Topiso Farm

Registrant Name : Hwanin Pharmaceutical Co., Ltd.

Registration Date : 2011-10-14

Registration Number : 20050831-64-C-192-03(1)

Manufacturer Name : Egis Pharmaceuticals PLC (Eg...

Manufacturer Address : H-1106 Budapest Kereszturi ut 30-38, Hungary

Egis Pharmaceuticals

02

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CPHI Middle east
Not Confirmed
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Virtual BoothEgis is a Hungarian generic pharma company with 110 years history. Our activities incorporate all areas of the pharma value chain.

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Topiso Farm

Registrant Name : Masung LS Co., Ltd.

Registration Date : 2005-08-31

Registration Number : 20050831-64-C-192-03

Manufacturer Name : Egis Pharmaceuticals PLC (Eg...

Manufacturer Address : H-1106 Budapest Kereszturi ut 30-38, Hungary

Egis Pharmaceuticals

03

Hanseo Chem

South Korea
CPHI Middle east
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Hanseo Chem

South Korea
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Topiso Farm

Registrant Name : Hanseochem Co., Ltd.

Registration Date : 2010-06-16

Registration Number : 20100616-64-C-272-04

Manufacturer Name : Hanseochem Co., Ltd.

Manufacturer Address : 41 Poseung Industrial Complex-ro, Poseung-eup, Pyeongtaek-si, Gyeonggi-do

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Samhwa Biopharm

South Korea
CPHI Middle east
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Samhwa Biopharm

South Korea
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Topiso Farm

Registrant Name : Samhwa Biopharm Co., Ltd.

Registration Date : 2005-08-31

Registration Number : 20050831-64-C-190-01

Manufacturer Name : Samhwa Biopharm Co., Ltd.

Manufacturer Address : 150 Hyeop-ro, Siheung-si, Gyeonggi-do

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CPHI Middle east
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Topiso Farm

Registrant Name : Hwail Pharmaceutical Co., Ltd.

Registration Date : 2015-09-24

Registration Number : 20050831-64-C-191-02(3)

Manufacturer Name : Sanyo Chemical Laboratories ...

Manufacturer Address : 1-5-1, Yasuuchi, Yatsuo-Machi, Toyama-Shi, Toyama, 939-2366, Japan

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Topiso Farm

Registrant Name : Pampia Co., Ltd.

Registration Date : 2021-12-30

Registration Number : 20211230-64-C-396-06

Manufacturer Name : Symed Labs Ltd(Unit-I)

Manufacturer Address : Sy. No. 353, Domadugu Village Gummadidala (Mandal), Sangreddy District Telangana Stat...

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Virtual BoothEgis is a Hungarian generic pharma company with 110 years history. Our activities incorporate all areas of the pharma value chain.

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Tofisopam

About the Company : Egis is a member of the Servier Group. Egis’ products are manufactured at 3 production sites in Hungary, which are certified by EMA,FDA, ANVISA, PMDA ,KFDA. Egis sells its produc...

Egis is a member of the Servier Group. Egis’ products are manufactured at 3 production sites in Hungary, which are certified by EMA,FDA, ANVISA, PMDA ,KFDA. Egis sells its products under Egis’ brand names in 18 countries. In total, the company’s APIs & finished products reach 100 countries. Egis’ focus lies on treating diseases of cardiovascular & central nervous systems; however, it also provides modern treatment solutions in the fields of diabetology, dermatology & wound care. Our research and development activities focus on high-quality, value-added branded generic products. From 2023, Egis offers its CDMO & CMO services as well.
Egis Pharmaceuticals

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Tofisopam

About the Company : Lake Chemicals is specialized in Benzodiazepine and CNS range of products such as Alprazolam, Bromazepam, Clobazam, Clonazepam, Midazolam Salts, Lorazepam, Olanzapine Form-1 etc. H...

Lake Chemicals is specialized in Benzodiazepine and CNS range of products such as Alprazolam, Bromazepam, Clobazam, Clonazepam, Midazolam Salts, Lorazepam, Olanzapine Form-1 etc. Holding COS for Alprazolam, Clonazepam, Bromazepam, Loperamide & Lorazepam and expecting for CLOBAZAM. Facility is Audited and approved by Cofepris Mexico, MOH Iran and other end customers like Pfizer, Teva, Apotex, J&J, Abbott, Novartis, Actavis etc and also other top generic companies in the world. Holding the EU written confirmation for all the above said products to export to Europe and couple of DMF already registered with few of the MOH in Europe.
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Symed Labs

India
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Symed Labs

India
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Tofisopam

About the Company : Symed Labs Ltd is a leading Hyderabad based manufacturer of Active Pharmaceutical Ingredients (APIs) and an end-to-end solution provider for the pharmaceutical industry for chemist...

Symed Labs Ltd is a leading Hyderabad based manufacturer of Active Pharmaceutical Ingredients (APIs) and an end-to-end solution provider for the pharmaceutical industry for chemistry related services. We are more than 300 employees strong and our core competence is in the application of strong process chemistry to manufacturing in a regulatory environment. For the past 15 years, Symed has been at the forefront of facilitating and accelerating drug development (and GMP manufacturing) of APIs. The company's technical and scientific teams provide reliable solutions and services to the global pharmaceutical industry.
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29-Jan-2021
04-Jul-2024
KGS
overview
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Average Price (USD/KGS)

Number of Transactions

Total Quantity (KGS)

Total Value (USD)

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

API Imports and Exports

Importing Country Total Quantity
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Average Price
(USD/KGS)
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