Zanapezil fumarate

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 326959

CAS#: 263248-42-6 (fumarate)

Description: Zanapezil, also known as TAK-147, is an acetylcholinesterase (AChE) inhibitor potentially for the treatment of Alzheimer's disease (AD). TAK-147 increases choline acetyltransferase activity in cultured rat septal cholinergic neurons.


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Zanapezil fumarate is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 326959
Name: Zanapezil fumarate
CAS#: 263248-42-6 (fumarate)
Chemical Formula: C29H36N2O5
Exact Mass:
Molecular Weight: 492.616
Elemental Analysis: C, 70.71; H, 7.37; N, 5.69; O, 16.24


Related CAS #: 142852-50-4 (free base)   142852-51-5   263248-42-6 (fumarate)    

Synonym: Zanapezil fumarate; TAK-147; TAK 147; TAK147.

IUPAC/Chemical Name: 3-(1-benzylpiperidin-4-yl)-1-(2,3,4,5-tetrahydro-1H-benzo[b]azepin-8-yl)propan-1-one fumarate

InChi Key: CWEHWZPCDBRUNO-WLHGVMLRSA-N

InChi Code: InChI=1S/C25H32N2O.C4H4O4/c28-25(23-11-10-22-8-4-5-15-26-24(22)18-23)12-9-20-13-16-27(17-14-20)19-21-6-2-1-3-7-21;5-3(6)1-2-4(7)8/h1-3,6-7,10-11,18,20,26H,4-5,8-9,12-17,19H2;1-2H,(H,5,6)(H,7,8)/b;2-1+

SMILES Code: O=C(C1=CC=C2CCCCNC2=C1)CCC3CCN(CC4=CC=CC=C4)CC3.O=C(O)/C=C/C(O)=O


Technical Data

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

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).

Harmonized System Code:
293490


Additional Information

Related CAS#
142852-50-4 (Zanapezil)
142852-51-5 (TAK 147)
263248-42-6 (Zanapezil fumarate)


References

1: Hatip-Al-Khatib I, Iwasaki K, Yoshimitsu Y, Arai T, Egashira N, Mishima K, Ikeda T, Fujiwara M. Effect of oral administration of zanapezil (TAK-147) for 21 days on acetylcholine and monoamines levels in the ventral hippocampus of freely moving rats. Br J Pharmacol. 2005 Aug;145(8):1035-44. PubMed PMID: 15951830; PubMed Central PMCID: PMC1576235.

2: Zhang LS, Jin CL, Li Q, Sun YC, Chen Z. [Influence of chronic epilepsy on spatial memory retrieval in rats]. Zhejiang Da Xue Xue Bao Yi Xue Ban. 2004 May;33(3):205-8. Chinese. PubMed PMID: 15179678.

3: Hatip-Al-Khatib I, Takashi A, Egashira N, Iwasaki K, Fujiwara M. Comparison of the effect of TAK-147 (zanapezil) and E-2020 (donepezil) on extracellular acetylcholine level and blood flow in the ventral hippocampus of freely moving rats. Brain Res. 2004 Jun 25;1012(1-2):169-76. PubMed PMID: 15158174.

4: Rakonczay Z. Potencies and selectivities of inhibitors of acetylcholinesterase and its molecular forms in normal and Alzheimer's disease brain. Acta Biol Hung. 2003;54(2):183-9. PubMed PMID: 14535624.

5: Xu AJ, Chen Z, Li R, Zhu CY, Wei EQ. [Effects of TAK-147, a novel acetylcholinesterase inhibitor, on spatial memory deficit as evaluated by Morris water maze of rats]. Zhejiang Da Xue Xue Bao Yi Xue Ban. 2002 Apr;31(2):98-102. Chinese. PubMed PMID: 12539269.

6: Xu AJ, Chen Z, Yanai K, Huang YW, Wei EQ. Effect of 3-[1-(phenylmethyl)-4-piperidinyl]-1-(2,3,4,5-tetrahydro-1H-1-benzazepin-8-yl)-1- propanone fumarate, a novel acetylcholinesterase inhibitor, on spatial cognitive impairment induced by chronic cerebral hypoperfusion in rats. Neurosci Lett. 2002 Oct 4;331(1):33-6. PubMed PMID: 12359317.

7: Chen Z, Xu AJ, Li R, Wei EQ. Reversal of scopolamine-induced spatial memory deficits in rats by TAK-147. Acta Pharmacol Sin. 2002 Apr;23(4):355-60. PubMed PMID: 11931694.

8: Mucke H. TAK-147 (Takeda). Curr Opin Investig Drugs. 2001 Nov;2(11):1595-9. Review. PubMed PMID: 11763163.

9: Ogura H, Kosasa T, Kuriya Y, Yamanishi Y. Central and peripheral activity of cholinesterase inhibitors as revealed by yawning and fasciculation in rats. Eur J Pharmacol. 2001 Mar;415(2-3):157-64. PubMed PMID: 11274994.

10: Ogura H, Kosasa T, Kuriya Y, Yamanishi Y. Comparison of inhibitory activities of donepezil and other cholinesterase inhibitors on acetylcholinesterase and butyrylcholinesterase in vitro. Methods Find Exp Clin Pharmacol. 2000 Oct;22(8):609-13. PubMed PMID: 11256231.

11: Takeda M, Shinosaki K, Nishikawa T, Tanaka T, Kudo T, Nakamura Y, Kashiwagi Y. [Treatment of the elderly dementia patients]. Nihon Ronen Igakkai Zasshi. 2000 Nov;37(11):879-81. Japanese. PubMed PMID: 11193359.

12: Rakonczay Z, Török L, Kása P. Preferential inhibition of acetylcholinesterase molecular forms in normal human brain. Neurobiology (Bp). 1999;7(1):75-7. PubMed PMID: 10746253.

13: Kosasa T, Kuriya Y, Matsui K, Yamanishi Y. Inhibitory effect of orally administered donepezil hydrochloride (E2020), a novel treatment for Alzheimer's disease, on cholinesterase activity in rats. Eur J Pharmacol. 2000 Feb 18;389(2-3):173-9. PubMed PMID: 10688981.

14: Ishihara Y, Goto G, Miyamoto M. Central selective acetylcholinesterase inhibitor with neurotrophic activity: structure-activity relationships of TAK-147 and related compounds. Curr Med Chem. 2000 Mar;7(3):341-54. Review. PubMed PMID: 10637368.

15: Kosasa T, Kuriya Y, Yamanishi Y. Effect of donepezil hydrochloride (E2020) on extracellular acetylcholine concentration in the cerebral cortex of rats. Jpn J Pharmacol. 1999 Oct;81(2):216-22. PubMed PMID: 10591480.

16: Kato K, Hayako H, Ishihara Y, Marui S, Iwane M, Miyamoto M. TAK-147, an acetylcholinesterase inhibitor, increases choline acetyltransferase activity in cultured rat septal cholinergic neurons. Neurosci Lett. 1999 Jan 22;260(1):5-8. PubMed PMID: 10027686.

17: Hirai K, Kato K, Nakayama T, Hayako H, Ishihara Y, Goto G, Miyamoto M. Neurochemical effects of 3-[1-(phenylmethyl)-4-piperidinyl]-1-(2,3,4,5-tetrahydro-1H-1-b enzazepin-8-yl)-1-propanone fumarate (TAK-147), a novel acetylcholinesterase inhibitor, in rats. J Pharmacol Exp Ther. 1997 Mar;280(3):1261-9. PubMed PMID: 9067312.

18: Nakayama T, Takahashi H, Miyamoto M, Goto G, Nagai Y. Effect of TAK-147, a novel AChE inhibitor, on cerebral energy metabolism. Neurobiol Aging. 1996 Nov-Dec;17(6):849-57. PubMed PMID: 9363795.

19: Miyamoto M, Takahashi H, Kato K, Hirai K, Ishihara Y, Goto G. Effects of 3-[1-(phenylmethyl)-4-piperidinyl]-1-(2,3,4,5-tetrahydro-1 -H-1-benzazepin-8-yl)-1-propanone fumarate (TAK-147), a novel acetylcholinesterase inhibitor, on impaired learning and memory in animal models. J Pharmacol Exp Ther. 1996 Jun;277(3):1292-304. PubMed PMID: 8667190.

20: Ishihara Y, Hirai K, Miyamoto M, Goto G. Central cholinergic agents. 6. Synthesis and evaluation of 3-[1-(phenylmethyl)-4-piperidinyl]-1-(2,3,4,5-tetrahydro-1H-1-benzazepi n-8-yl)-1-propanones and their analogs as central selective acetylcholinesterase inhibitors. J Med Chem. 1994 Jul 22;37(15):2292-9. PubMed PMID: 8057278.