Tofisopam
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Hodoodo CAT#: H318882

CAS#: 22345-47-7

Description: Tofisopam 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 (but not sodium valproate, carbamazepine, phenobarbital, or phenytoin). Tofisopam is indicated for the treatment of anxiety and alcohol withdrawal.


Chemical Structure

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Tofisopam
CAS# 22345-47-7

Theoretical Analysis

Hodoodo Cat#: H318882
Name: Tofisopam
CAS#: 22345-47-7
Chemical Formula: C22H26N2O4
Exact Mass: 382.19
Molecular Weight: 382.453
Elemental Analysis: C, 69.09; H, 6.85; N, 7.32; O, 16.73

Price and Availability

Size Price Availability Quantity
50mg USD 275
250mg USD 750
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Synonym: Tofisopam, Emandaxin, Grandaxin, Sériel, EGYT-341

IUPAC/Chemical Name: 1-(3,4-dimethoxyphenyl)-5-ethyl-7,8-dimethoxy-4-methyl-5H-2,3-benzodiazepine

InChi Key: RUJBDQSFYCKFAA-UHFFFAOYSA-N

InChi Code: 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

SMILES Code: CC1=NN=C(C2=CC=C(OC)C(OC)=C2)C3=CC(OC)=C(OC)C=C3C1CC

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 382.45 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Hatayama M, Sumida C, Kurajoh M, Shiraishi J, Okazaki H, Shoji T, Koyama H, Tsutsumi Z, Moriwaki Y, Namba M, Yamamoto T. Acute Effects of Oral Tofisopam on Plasma Concentration and Urinary Excretion of Uric Acid and Oxypurinol. Curr Clin Pharmacol. 2015 Jan 26. [Epub ahead of print] PubMed PMID: 25619490.

2: Ramadan NK, Mohamed AO, Fouad RM, Moustafa AA. Different techniques for the determination of tofisopam. J AOAC Int. 2014 Jan-Feb;97(1):105-13. PubMed PMID: 24672866.

3: Abrushanian ÉB, Popov AV. [Pineal hormone melatonin in low doses potentiates psychotropic and chronotropic activity of tofisopam in rats]. Eksp Klin Farmakol. 2013;76(4):15-7. Russian. PubMed PMID: 23762983.

4: Bihel FJ, Justiniano H, Schmitt M, Hellal M, Ibrahim MA, Lugnier C, Bourguignon JJ. New PDE4 inhibitors based on pharmacophoric similarity between papaverine and tofisopam. Bioorg Med Chem Lett. 2011 Nov 1;21(21):6567-72. doi: 10.1016/j.bmcl.2011.08.036. Epub 2011 Aug 12. PubMed PMID: 21920746.

5: Rundfeldt C, Socała K, Wlaź 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 (Vienna). 2010 Nov;117(11):1319-25. doi: 10.1007/s00702-010-0507-3. Epub 2010 Oct 22. PubMed PMID: 20967473; PubMed Central PMCID: PMC2993883.

6: Tóth M, Drabant S, Varga B, Végso G, Cseh A, Szentpéteri I, Klebovich I. Tofisopam inhibits the pharmacokinetics of CYP3A4 substrate midazolam. Eur J Clin Pharmacol. 2008 Jan;64(1):93-4. Epub 2007 Nov 8. PubMed PMID: 17989974.

7: Arushunian EB, Popov AV. [Tofisopam and melatonin attenuate the reorganization of circadian locomotor rhythm in rats under injection-induced stress conditions]. Eksp Klin Farmakol. 2006 Mar-Apr;69(2):14-7. Russian. PubMed PMID: 16845933.

8: Drabant S, Tóth M, Bereczki A, Bajnógel J, Tömlö J, Klebovich I. Effect of tofisopam on the single-oral-dose pharmacokinetics and pharmacodynamics of the cyp3a4 probe drug alprazolam. Eur J Clin Pharmacol. 2006 Jul;62(7):587-8. Epub 2006 Jun 22. PubMed PMID: 16791582.

9: Tóth M, Bajnógel J, Egyed A, Drabant S, Tömlo J, Klebovich I. [Effect of tofisopam on CYP3A4 enzyme activity on human recombinant 3A4 supersome]. Acta Pharm Hung. 2005;75(4):195-8. Hungarian. PubMed PMID: 16711396.

10: Ovanesov KB. [The effect of tofisopam and tinctura leonuri on the color-discrimination function in young humans]. Eksp Klin Farmakol. 2005 May-Jun;68(3):56-9. Russian. PubMed PMID: 16047683.

11: Eros E, Czeizel AE, Rockenbauer M, Sorensen HT, Olsen J. A population-based case-control teratologic study of nitrazepam, medazepam, tofisopam, alprazolum and clonazepam treatment during pregnancy. Eur J Obstet Gynecol Reprod Biol. 2002 Mar 10;101(2):147-54. PubMed PMID: 11858890.

12: Miklya I, Knoll J. A new sensitive method which unlike the Vogel test detects the anxiolytic effect of tofisopam. Pol J Pharmacol Pharm. 1988 Nov-Dec;40(6):561-72. PubMed PMID: 2908362.

13: Pellow S, File SE. Is tofisopam an atypical anxiolytic? Neurosci Biobehav Rev. 1986 Summer;10(2):221-7. PubMed PMID: 2874535.

14: Oelschläger H, Volke J, Bresch C. [Drug analysis by polarographic methods. 24. The polarographic behavior of tofisopam]. Arch Pharm (Weinheim). 1985 Mar;318(3):271-6. German. PubMed PMID: 4015339.

15: Yamaguchi K, Suzuki K, Niho T, Shimora M, Ito C, Ohnishi H. Tofisopam, a new 2,3-benzodiazepine. Inhibition of changes induced by stress loading and hypothalamic stimulation. Can J Physiol Pharmacol. 1983 Jun;61(6):619-25. PubMed PMID: 6136319.

16: Szórády I, Borsodi A. Observations with tofisopam (grandaxin) treatment in children's diseases. Ther Hung. 1983;31(4):172-5. PubMed PMID: 6152818.

17: Sato M, Kitagawa H, Fujiwara M. [Effects of tofisopam on gastric functions in rats (author's transl)]. Nihon Yakurigaku Zasshi. 1982 Apr;79(4):307-15. Japanese. PubMed PMID: 7095653.

18: Bond A, Lader M. A comparison of the psychotropic profiles of tofisopam and diazepam. Eur J Clin Pharmacol. 1982;22(2):137-42. PubMed PMID: 6124424.

19: Ohnishi H, Ito C, Suzuki K, Niho T, Shimora M, Yamaguchi K. [Effects of tofisopam on the physiological changes induced by stress loading and hypothalamic stimulation (author's transl)]. Nihon Yakurigaku Zasshi. 1981 Sep;78(3):139-44. Japanese. PubMed PMID: 7327446.

20: Libusová E, Libus J. Our experience with tofisopam (grandaxin egypt). Act Nerv Super (Praha). 1979 Oct;21(3):154. PubMed PMID: 42265.