Talampanel
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MedKoo CAT#: 202740

CAS#: 161832-65-1

Description: Talampanel, also known as LY300164 and GYKI-53773, is a glutamate receptor inhibitor with anti-seizure activity. Talampanel is also an orally active, potent and selective AMPA-receptor antagonist, and can noncompetitively bind to the AMPA subtype of glutamate excitatory amino acid receptors and may inhibit the growth of gliomas by interfering with neurotransmitters involved in brain tumor growth. This agent may also protect against traumatic brain injury. Talampanel (GYKI 53405) is being investigated for the treatment of epilepsy, malignant gliomas and amyotrophic lateral sclerosis (ALS). As of May 2010, results from the trial for ALS have been found negative.


Chemical Structure

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Talampanel
CAS# 161832-65-1

Theoretical Analysis

MedKoo Cat#: 202740
Name: Talampanel
CAS#: 161832-65-1
Chemical Formula: C19H19N3O3
Exact Mass: 337.14264
Molecular Weight: 337.37
Elemental Analysis: C, 67.64; H, 5.68; N, 12.46; O, 14.23

Price and Availability

Size Price Availability Quantity
10.0mg USD 110.0 Same day
25.0mg USD 190.0 Same day
50.0mg USD 350.0 Same day
100.0mg USD 650.0 Same day
200.0mg USD 1150.0 Same day
500.0mg USD 2450.0 Same day
1.0g USD 3950.0 Same day
2.0g USD 5650.0 Same day
5.0g USD 9650.0 Same day
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Synonym: LY300164, LY 300164, LY-300164, GYKI53773, Gyki 53405, Gyki-53405, LY293606, LY-293606, LY 293606, Talampanel

IUPAC/Chemical Name: (8R)-7-Acetyl-5-(4-aminophenyl)-8,9-dihydro-8-methyl-7H-1,3-dioxolo[4,5-h][2,3]benzodiazepine

InChi Key: JACAAXNEHGBPOQ-LLVKDONJSA-N

InChi Code: InChI=1S/C19H19N3O3/c1-11-7-14-8-17-18(25-10-24-17)9-16(14)19(21-22(11)12(2)23)13-3-5-15(20)6-4-13/h3-6,8-9,11H,7,10,20H2,1-2H3/t11-/m1/s1

SMILES Code: C[C@H]1N(C(C)=O)N=C(C2=CC=C(N)C=C2)C3=CC(OCO4)=C4C=C3C1

Appearance: White 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

Preparing Stock Solutions

The following data is based on the product molecular weight 337.37 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

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1: Wang C, Niu L. Mechanism of Inhibition of the GluA2 AMPA Receptor Channel Opening by Talampanel and Its Enantiomer: The Stereochemistry of the 4-Methyl Group on the Diazepine Ring of 2,3-Benzodiazepine Derivatives. ACS Chem Neurosci. 2013 Feb 12. [Epub ahead of print] PubMed PMID: 23402301.

2: Paizs M, Tortarolo M, Bendotti C, Engelhardt JI, Siklós L. Talampanel reduces the level of motoneuronal calcium in transgenic mutant SOD1 mice only if applied presymptomatically. Amyotroph Lateral Scler. 2011 Sep;12(5):340-4. doi: 10.3109/17482968.2011.584627. Epub 2011 May 30. PubMed PMID: 21623665; PubMed Central PMCID: PMC3231880.

3: Iwamoto FM, Kreisl TN, Kim L, Duic JP, Butman JA, Albert PS, Fine HA. Phase 2 trial of talampanel, a glutamate receptor inhibitor, for adults with recurrent malignant gliomas. Cancer. 2010 Apr 1;116(7):1776-82. doi: 10.1002/cncr.24957. PubMed PMID: 20143438; PubMed Central PMCID: PMC2846997.

4: Pascuzzi RM, Shefner J, Chappell AS, Bjerke JS, Tamura R, Chaudhry V, Clawson L, Haas L, Rothstein JD. A phase II trial of talampanel in subjects with amyotrophic lateral sclerosis. Amyotroph Lateral Scler. 2010 May 3;11(3):266-71. doi: 10.3109/17482960903307805. PubMed PMID: 19961264.

5: Grossman SA, Ye X, Chamberlain M, Mikkelsen T, Batchelor T, Desideri S, Piantadosi S, Fisher J, Fine HA. Talampanel with standard radiation and temozolomide in patients with newly diagnosed glioblastoma: a multicenter phase II trial. J Clin Oncol. 2009 Sep 1;27(25):4155-61. doi: 10.1200/JCO.2008.21.6895. Epub 2009 Jul 27. PubMed PMID: 19636006; PubMed Central PMCID: PMC2734427.

6: Aujla PK, Fetell MR, Jensen FE. Talampanel suppresses the acute and chronic effects of seizures in a rodent neonatal seizure model. Epilepsia. 2009 Apr;50(4):694-701. doi: 10.1111/j.1528-1167.2008.01947.x. Epub 2009 Feb 12. PubMed PMID: 19220413; PubMed Central PMCID: PMC2672962.

7: Howes JF, Bell C. Talampanel. Neurotherapeutics. 2007 Jan;4(1):126-9. Review. PubMed PMID: 17199027.

8: Denes L, Szilágyi G, Gál A, Nagy Z. Talampanel a non-competitive AMPA-antagonist attenuates caspase-3 dependent apoptosis in mouse brain after transient focal cerebral ischemia. Brain Res Bull. 2006 Jul 31;70(3):260-2. Epub 2006 Mar 31. PubMed PMID: 16861112.

9: Sólyom S, Pallagi I, Abrahám G, Kertész M, Horváth G, Berzsenyi P. New features in synthesis of talampanel related 2,3-benzodiazepines. Med Chem. 2005 Sep;1(5):481-5. PubMed PMID: 16787333.

10: Buchwald P, Juhász A, Bell C, Pátfalusi M, Kovács P, Hochhaus G, Howes J, Bodor N. Influence of the N-acetylation polymorphism on the metabolism of talampanel: an investigation in fasted and fed subjects genotyped for NAT2 variants. Pharmazie. 2006 Feb;61(2):125-34. PubMed PMID: 16526560.

11: Erdo F, Berzsenyi P, Német L, Andrási F. Talampanel improves the functional deficit after transient focal cerebral ischemia in rats. A 30-day follow up study. Brain Res Bull. 2006 Jan 15;68(4):269-76. Epub 2005 Sep 19. PubMed PMID: 16377432.

12: Buchwald P, Juhász A, Bell C, Pátfalusi M, Howes J, Bodor N. Unified pharmacogenetics-based parent-metabolite pharmacokinetic model incorporating acetylation polymorphism for talampanel in humans. J Pharmacokinet Pharmacodyn. 2005 Aug;32(3-4):377-400. PubMed PMID: 16320099.

13: Erdo F, Berzsenyi P, Andrási F. The AMPA-antagonist talampanel is neuroprotective in rodent models of focal cerebral ischemia. Brain Res Bull. 2005 Jul 15;66(1):43-9. Epub 2005 Apr 21. PubMed PMID: 15925143.

14: Andrási F, Berzsenyi P, Farkas L, Körösi J, Hámori T, Botka P, Ling I, Láng T. Omeprazole and talampanel as two examples of retrometabolic drug design. Pharmazie. 2004 May;59(5):365-6. PubMed PMID: 15212302.

15: Langan YM, Lucas R, Jewell H, Toublanc N, Schaefer H, Sander JW, Patsalos PN. Talampanel, a new antiepileptic drug: single- and multiple-dose pharmacokinetics and initial 1-week experience in patients with chronic intractable epilepsy. Epilepsia. 2003 Jan;44(1):46-53. PubMed PMID: 12581229.

16: Világi I, Takács J, Gulyás-Kovács A, Banczerowski-Pelyhe I, Tarnawa I. Protective effect of the antiepileptic drug candidate talampanel against AMPA-induced striatal neurotoxicity in neonatal rats. Brain Res Bull. 2002 Oct 15;59(1):35-40. PubMed PMID: 12372546.

17: Chappell AS, Sander JW, Brodie MJ, Chadwick D, Lledo A, Zhang D, Bjerke J, Kiesler GM, Arroyo S. A crossover, add-on trial of talampanel in patients with refractory partial seizures. Neurology. 2002 Jun 11;58(11):1680-2. PubMed PMID: 12058100.

18: Belayev L, Alonso OF, Liu Y, Chappell AS, Zhao W, Ginsberg MD, Busto R. Talampanel, a novel noncompetitive AMPA antagonist, is neuroprotective after traumatic brain injury in rats. J Neurotrauma. 2001 Oct;18(10):1031-8. PubMed PMID: 11686490.



Additional Information

Talampanel  is  currently being investigated for the treatment of epilepsy, malignant gliomas and amyotrophic lateral sclerosis (ALS). It is a noncompetitive antagonist of the AMPA receptor, a type of glutamate receptor in the central nervous system. (source: http://en.wikipedia.org/wiki/Talampanel).
 
Teva has exclusive worldwide rights to develop and market talampanel for the treatment of neurological disorders. Based on talampanel',s anti-glutamate excitatory activity, Teva believes that talampanel can significantly delay the functional deterioration of ALS patients. Based on the scientific, mechanistic rationale and a positive signal from a small Phase II study in ALS, Teva is proceeding with the development of talampanel for the latter indication, and a Phase II study has been initiated in centers in the U.S., Canada, Europe, and Israel. to evaluate the efficacy, tolerability and safety of an oral administration of 75mg and 150mg daily doses of talampanel for 52 weeks.The recruitment of 559 ALS patients has been completed and the study is scheduled to end by the second quarter of 2010. (source: http://www.tevapharm.com/research/products_ni.asp#Talampanel).
 
On May 17, 2010,  Teva announced the results of the recently completed trial of Talampanel for people with ALS. The results were conclusively negative. The ALS Functional Rating scale, a tool instrument used to assess changes in physical functioning in people with ALS over time, was the primary outcome measure; both this measure and the other measures investigated showed no difference in the rate of progression in participants with ALS treated with placebo or either of 2 doses of the study medication. While there were more side effects seen in participants treated with the Talampanel, the dropout rates were very similar in all groups, making the negative results more convincing. While this is a very disappointing result for patients, caregivers, and physicians, the convincing nature of the results provides a clear answer to the effectiveness of this treatment for people with ALS. Fortunately, there are many other promising drugs now being tested; it is important for all to remain hopeful and committed to finding improved therapies for ALS.  (sourcing: http://www.alsa.org/patient/drug.cfm?id=1370).