MedKoo Cat#: 530119 | Name: Lecozotan HCl

Description:

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

Lecozotan, also known as SRA-333, is a potent and selective 5-HT antagonist potentially for the treatment of Alzheimer's disease. Lecozotan (SRA-333) enhances the stimulated release of glutamate and acetylcholine in the hippocampus and possesses cognitive-enhancing properties. Lecozotan significantly potentiated the potassium chloride-stimulated release of glutamate and acetylcholine in the dentate gyrus of the hippocampus. Chronic administration of lecozotan did not induce 5-HT(1A) receptor tolerance or desensitization in a behavioral model indicative of 5-HT(1A) receptor function. Acute lecozotan administration increases learning and memory in rats without affecting anxiety or behavioral depression.

Chemical Structure

Lecozotan HCl
Lecozotan HCl
CAS#433282-68-9 (HCl)

Theoretical Analysis

MedKoo Cat#: 530119

Name: Lecozotan HCl

CAS#: 433282-68-9 (HCl)

Chemical Formula: C28H30ClN5O3

Exact Mass:

Molecular Weight: 520.03

Elemental Analysis: C, 64.67; H, 5.82; Cl, 6.82; N, 13.47; O, 9.23

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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Synonym
SRA-333; SRA333; SRA 333; Lecozotan HCl; Lecozotan hydrochloride.
IUPAC/Chemical Name
Benzamide, 4-cyano-N-((2R)-2-(4-(2,3-dihydro-1,4-benzodioxin-5-yl)-1-piperazinyl)propyl)-N-2-pyridinyl-, monohydrochloride
InChi Key
GXYZREDEYDFJPT-ZMBIFBSDSA-N
InChi Code
InChI=1S/C28H29N5O3.ClH/c1-21(31-13-15-32(16-14-31)24-5-4-6-25-27(24)36-18-17-35-25)20-33(26-7-2-3-12-30-26)28(34)23-10-8-22(19-29)9-11-23;/h2-12,21H,13-18,20H2,1H3;1H/t21-;/m1./s1
SMILES Code
O=C(N(C[C@H](N1CCN(C2=C3OCCOC3=CC=C2)CC1)C)C4=NC=CC=C4)C5=CC=C(C#N)C=C5.[H]Cl
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).
HS Tariff Code
2934.99.9001
More Info
Related CAS# 433282-68-9 (Lecozotan hydrochloride) 434283-16-6 (Lecozotan, free base)

Preparing Stock Solutions

The following data is based on the product molecular weight 520.03 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
1: Parks V, Philipp AW, Raje S, Plotka A, Schechter LE, Connell J, Chalon S. Concomitant blockade of 5-HT(1A) receptor and 5-HT transporter: use of the Hunter Serotonin toxicity criteria in a clinical pharmacology study. Eur Neuropsychopharmacol. 2012 Feb;22(2):92-9. doi: 10.1016/j.euroneuro.2011.06.002. PubMed PMID: 21733663. 2: Skirzewski M, Hernandez L, Schechter LE, Rada P. Acute lecozotan administration increases learning and memory in rats without affecting anxiety or behavioral depression. Pharmacol Biochem Behav. 2010 May;95(3):325-30. doi: 10.1016/j.pbb.2010.02.008. PubMed PMID: 20170670. 3: Sabbagh MN. Drug development for Alzheimer's disease: where are we now and where are we headed? Am J Geriatr Pharmacother. 2009 Jun;7(3):167-85. doi: 10.1016/j.amjopharm.2009.06.003. Review. PubMed PMID: 19616185; PubMed Central PMCID: PMC2948028. 4: Patat A, Parks V, Raje S, Plotka A, Chassard D, Le Coz F. Safety, tolerability, pharmacokinetics and pharmacodynamics of ascending single and multiple doses of lecozotan in healthy young and elderly subjects. Br J Clin Pharmacol. 2009 Mar;67(3):299-308. doi: 10.1111/j.1365-2125.2008.03348.x. PubMed PMID: 19523013; PubMed Central PMCID: PMC2675040. 5: Tomillero A, Moral MA. Gateways to clinical trials. July-August 2008. Methods Find Exp Clin Pharmacol. 2008 Jul-Aug;30(6):459-95. PubMed PMID: 18850047. 6: Raje S, Patat AA, Parks V, Schechter L, Plotka A, Paul J, Langstrom B. A positron emission tomography study to assess binding of lecozotan, a novel 5-hydroxytryptamine-1A silent antagonist, to brain 5-HT1A receptors in healthy young and elderly subjects, and in patients with Alzheimer's disease. Clin Pharmacol Ther. 2008 Jan;83(1):86-96. PubMed PMID: 17507923. 7: Schechter LE, Smith DL, Rosenzweig-Lipson S, Sukoff SJ, Dawson LA, Marquis K, Jones D, Piesla M, Andree T, Nawoschik S, Harder JA, Womack MD, Buccafusco J, Terry AV, Hoebel B, Rada P, Kelly M, Abou-Gharbia M, Barrett JE, Childers W. Lecozotan (SRA-333): a selective serotonin 1A receptor antagonist that enhances the stimulated release of glutamate and acetylcholine in the hippocampus and possesses cognitive-enhancing properties. J Pharmacol Exp Ther. 2005 Sep;314(3):1274-89. PubMed PMID: 15951399. 8: Childers WE Jr, Abou-Gharbia MA, Kelly MG, Andree TH, Harrison BL, Ho DM, Hornby G, Huryn DM, Potestio L, Rosenzweig-Lipson SJ, Schmid J, Smith DL, Sukoff SJ, Zhang G, Schechter LE. Synthesis and biological evaluation of benzodioxanylpiperazine derivatives as potent serotonin 5-HT(1A) antagonists: the discovery of Lecozotan. J Med Chem. 2005 May 19;48(10):3467-70. PubMed PMID: 15887953.