MedKoo Cat#: 529184 | Name: Tezampanel hydrate

Description:

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

Tezampanel, also known as LY 293558 and NGX-424, is a competitive antagonist of the AMPA and kainate subtypes of the ionotropic glutamate receptor family, with selectivity for the GluR5 subtype of the kainate receptor. It has neuroprotective and anticonvulsant properties, the former of which may, at least in part, occur via blockade of calcium uptake into neurons. Tezampanel has a range of effects which may be useful for medicinal purposes, as well as its applications in scientific research. It suppresses both the withdrawal symptoms from morphine and other opioids, and the development of tolerance, as well as having antihyperalgesic and analgesic effects in its own right..

Chemical Structure

Tezampanel hydrate
Tezampanel hydrate
CAS#317819-68-4 (hydrate)

Theoretical Analysis

MedKoo Cat#: 529184

Name: Tezampanel hydrate

CAS#: 317819-68-4 (hydrate)

Chemical Formula: C13H23N5O3

Exact Mass: 297.1801

Molecular Weight: 297.36

Elemental Analysis: C, 52.51; H, 7.80; N, 23.55; O, 16.14

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
317819-68-4 (hydrate) 154652-83-2 (anhydrous) 150131-79-6 (isomer LY293559) 150010-68-7 (rel-isomer LY215490) 150131-78-5 (deleted)
Synonym
Tezampanel hydrate; LY 293558 hydrate; LY-293558; LY293558; NGX-424; NGX 424; NGX424;
IUPAC/Chemical Name
3-Isoquinolinecarboxylic acid, decahydro-6-(2-(1H-tetrazol-5-yl)ethyl)-, monohydrate, (3S,4aR,6R,8aR)-
InChi Key
LNDYQNTTYXLTNH-RTBBDAMFSA-N
InChi Code
InChI=1S/C13H21N5O2.H2O/c19-13(20)11-6-10-5-8(1-3-9(10)7-14-11)2-4-12-15-17-18-16-12;/h8-11,14H,1-7H2,(H,19,20)(H,15,16,17,18);1H2/t8-,9+,10-,11+;/m1./s1
SMILES Code
O=C([C@H]1NC[C@]2([H])CC[C@H](CCC3=NN=NN3)C[C@]2([H])C1)O.[H]O[H]
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
>3 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

Preparing Stock Solutions

The following data is based on the product molecular weight 297.36 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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Epub 2015 Feb 15. PubMed PMID: 25689173; PubMed Central PMCID: PMC4545593. 4: Prager EM, Figueiredo TH, Long RP 2nd, Aroniadou-Anderjaska V, Apland JP, Braga MF. LY293558 prevents soman-induced pathophysiological alterations in the basolateral amygdala and the development of anxiety. Neuropharmacology. 2015 Feb;89:11-8. doi: 10.1016/j.neuropharm.2014.08.014. Epub 2014 Sep 6. PubMed PMID: 25204221; PubMed Central PMCID: PMC4250288. 5: Chan K, MaassenVanDenBrink A. Glutamate receptor antagonists in the management of migraine. Drugs. 2014 Jul;74(11):1165-76. doi: 10.1007/s40265-014-0262-0. Review. PubMed PMID: 25030431. 6: Moshiri M, Darchini-Maragheh E, Balali-Mood M. Advances in toxicology and medical treatment of chemical warfare nerve agents. Daru. 2012 Nov 28;20(1):81. doi: 10.1186/2008-2231-20-81. PubMed PMID: 23351280; PubMed Central PMCID: PMC3556041. 7: Wallace MS, Lam V, Schettler J. NGX426, an oral AMPA-kainate antagonist, is effective in human capsaicin-induced pain and hyperalgesia. Pain Med. 2012 Dec;13(12):1601-10. doi: 10.1111/j.1526-4637.2012.01509.x. Epub 2012 Oct 30. PubMed PMID: 23110368. 8: Apland JP, Aroniadou-Anderjaska V, Figueiredo TH, Green CE, Swezey R, Yang C, Qashu F, Braga MF. Efficacy of the GluK1/AMPA receptor antagonist LY293558 against seizures and neuropathology in a soman-exposure model without pretreatment and its pharmacokinetics after intramuscular administration. J Pharmacol Exp Ther. 2013 Jan;344(1):133-40. doi: 10.1124/jpet.112.198689. Epub 2012 Oct 5. PubMed PMID: 23042954; PubMed Central PMCID: PMC3533413. 9: Lionetto L, Negro A, Palmisani S, Gentile G, Del Fiore MR, Mercieri M, Simmaco M, Smith T, Al-Kaisy A, Arcioni R, Martelletti P. Emerging treatment for chronic migraine and refractory chronic migraine. Expert Opin Emerg Drugs. 2012 Sep;17(3):393-406. doi: 10.1517/14728214.2012.709846. Epub 2012 Aug 3. Review. PubMed PMID: 22862686. 10: Moon MJ, Kim HY, Park S, Kim DK, Cho EB, Hwang JI, Seong JY. Insulin contributes to fine-tuning of the pancreatic beta-cell response to glucagon-like peptide-1. Mol Cells. 2011 Oct;32(4):389-95. doi: 10.1007/s10059-011-0157-9. Epub 2011 Sep 7. PubMed PMID: 21904878; PubMed Central PMCID: PMC3887647. 11: Oshiro M, Hefferan MP, Kakinohana O, Lukacova N, Sugahara K, Yaksh TL, Marsala M. Suppression of stretch reflex activity after spinal or systemic treatment with AMPA receptor antagonist NGX424 in rats with developed baclofen tolerance. Br J Pharmacol. 2010 Nov;161(5):976-85. doi: 10.1111/j.1476-5381.2010.00954.x. PubMed PMID: 20977450; PubMed Central PMCID: PMC2998680. 12: Figueiredo TH, Qashu F, Apland JP, Aroniadou-Anderjaska V, Souza AP, Braga MF. The GluK1 (GluR5) Kainate/{alpha}-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid receptor antagonist LY293558 reduces soman-induced seizures and neuropathology. J Pharmacol Exp Ther. 2011 Feb;336(2):303-12. doi: 10.1124/jpet.110.171835. Epub 2010 Oct 20. PubMed PMID: 20962029; PubMed Central PMCID: PMC3033714. 13: Gómez-Soriano J, Goiriena E, Taylor J. Spasticity therapy reacts to astrocyte GluA1 receptor upregulation following spinal cord injury. Br J Pharmacol. 2010 Nov;161(5):972-5. doi: 10.1111/j.1476-5381.2010.00964.x. PubMed PMID: 20662840; PubMed Central PMCID: PMC2998679. 14: Bannerman DM. Fractionating spatial memory with glutamate receptor subunit-knockout mice. Biochem Soc Trans. 2009 Dec;37(Pt 6):1323-7. doi: 10.1042/BST0371323. PubMed PMID: 19909269. 15: Tomillero A, Moral MA. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2008 Oct;30(8):643-72. PubMed PMID: 19088949. 16: Hefferan MP, Kucharova K, Kinjo K, Kakinohana O, Sekerkova G, Nakamura S, Fuchigami T, Tomori Z, Yaksh TL, Kurtz N, Marsala M. Spinal astrocyte glutamate receptor 1 overexpression after ischemic insult facilitates behavioral signs of spasticity and rigidity. J Neurosci. 2007 Oct 17;27(42):11179-91. PubMed PMID: 17942713. 17: Jin HC, Keller AJ, Jung JK, Subieta A, Brennan TJ. Epidural tezampanel, an AMPA/kainate receptor antagonist, produces postoperative analgesia in rats. Anesth Analg. 2007 Oct;105(4):1152-9, table of contents. PubMed PMID: 17898404. 18: Lee HJ, Pogatzki-Zahn EM, Brennan TJ. The effect of the AMPA/kainate receptor antagonist LY293558 in a rat model of postoperative pain. J Pain. 2006 Oct;7(10):768-77. PubMed PMID: 17018337. 19: Alt A, Weiss B, Ogden AM, Li X, Gleason SD, Calligaro DO, Bleakman D, Witkin JM. In vitro and in vivo studies in rats with LY293558 suggest AMPA/kainate receptor blockade as a novel potential mechanism for the therapeutic treatment of anxiety disorders. Psychopharmacology (Berl). 2006 Apr;185(2):240-7. Epub 2006 Feb 10. PubMed PMID: 16470401. 20: Chang HY, Cheng CL, Chen JJ, Peng CW, de Groat WC. Reflexes evoked by electrical stimulation of afferent axons in the pudendal nerve under empty and distended bladder conditions in urethane-anesthetized rats. J Neurosci Methods. 2006 Jan 15;150(1):80-9. Epub 2005 Jul 21. PubMed PMID: 16039722; PubMed Central PMCID: PMC3119341.