Lubeluzole | CAS#144665-07-6 | neuroprotective agent

MedKoo Cat#: 461099 | Name: Lubeluzole

Description:

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

Lubeluzole is a a well-known neuroprotective agent recently proved useful to potentiate the activity of anti-cancer drugs.

Chemical Structure

Lubeluzole

CAS#144665-07-6

Theoretical Analysis

MedKoo Cat#: 461099

Name: Lubeluzole

CAS#: 144665-07-6

Chemical Formula: C22H25F2N3O2S

Exact Mass: 433.1636

Molecular Weight: 433.51

Elemental Analysis: C, 60.95; H, 5.81; F, 8.76; N, 9.69; O, 7.38; S, 7.40

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.

Bulk Inquiry

Related CAS #

No Data

Synonym

Lubeluzole; Prosynap; R 87926; R-87926; R87926;

IUPAC/Chemical Name

(S)-1-(4-(benzo[d]thiazol-2-yl(methyl)amino)piperidin-1-yl)-3-(3,4-difluorophenoxy)propan-2-ol

InChi Key

OZFSWVOEXHGDES-INIZCTEOSA-N

InChi Code

InChI=1S/C22H25F2N3O2S/c1-26(22-25-20-4-2-3-5-21(20)30-22)15-8-10-27(11-9-15)13-16(28)14-29-17-6-7-18(23)19(24)12-17/h2-7,12,15-16,28H,8-11,13-14H2,1H3/t16-/m0/s1

SMILES Code

Fc1ccc(OC[C@@H](O)CN(CC2)CCC2N(C)c3sc(cccc4)c4n3)cc1F

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

2934.99.03.00

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 433.51 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.

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: Desaphy JF, Carbonara R, Costanza T, Lentini G, Cavalluzzi MM, Bruno C, Franchini C, Camerino DC. Molecular dissection of lubeluzole use-dependent block of voltage-gated sodium channels discloses new therapeutic potentials. Mol Pharmacol. 2013 Feb;83(2):406-15. doi: 10.1124/mol.112.080804. Epub 2012 Nov 21. PubMed PMID: 23175529. 2: Bruno C, Cavalluzzi MM, Rusciano MR, Lovece A, Carrieri A, Pracella R, Giannuzzi G, Polimeno L, Viale M, Illario M, Franchini C, Lentini G. The chemosensitizing agent lubeluzole binds calmodulin and inhibits Ca(2+)/calmodulin-dependent kinase II. Eur J Med Chem. 2016 Jun 30;116:36-45. doi: 10.1016/j.ejmech.2016.03.045. Epub 2016 Mar 19. PubMed PMID: 27043269. 3: Kommi DN, Kumar D, Seth K, Chakraborti AK. Protecting group-free concise synthesis of (RS)/(S)-lubeluzole. Org Lett. 2013 Mar 15;15(6):1158-61. doi: 10.1021/ol302601b. Epub 2013 Feb 22. PubMed PMID: 23432765. 4: Cavalluzzi MM, Viale M, Bruno C, Carocci A, Catalano A, Carrieri A, Franchini C, Lentini G. A convenient synthesis of lubeluzole and its enantiomer: evaluation as chemosensitizing agents on human ovarian adenocarcinoma and lung carcinoma cells. Bioorg Med Chem Lett. 2013 Sep 1;23(17):4820-3. doi: 10.1016/j.bmcl.2013.06.077. Epub 2013 Jul 4. PubMed PMID: 23886686. 5: Grotta J. Lubeluzole treatment of acute ischemic stroke. The US and Canadian Lubeluzole Ischemic Stroke Study Group. Stroke. 1997 Dec;28(12):2338-46. PubMed PMID: 9412611. 6: Hantson L, Tritsmans L, Crabbé R, Gheuens J, Van Rooy P. The safety and tolerability of single intravenous doses of lubeluzole (Prosynap) in healthy volunteers. Int J Clin Pharmacol Ther. 1997 Nov;35(11):491-5. PubMed PMID: 9401829. 7: Le Grand B, Talmant JM, Rieu JP, Patoiseau JF, John GW. Study of the interaction of lubeluzole with cardiac sodium channels. J Cardiovasc Pharmacol. 2003 Nov;42(5):581-7. PubMed PMID: 14576504. 8: Hacke W, Lees KR, Timmerhuis T, Haan J, Hantson L, Hennerici M, Diener HC. Cardiovascular safety of lubeluzole (Prosynap(R)) in patients with ischemic stroke. Cerebrovasc Dis. 1998 Sep-Oct;8(5):247-54. PubMed PMID: 9712921. 9: Diener HC, Hacke W, Hennerici M, Rådberg J, Hantson L, De Keyser J. Lubeluzole in acute ischemic stroke. A double-blind, placebo-controlled phase II trial. Lubeluzole International Study Group. Stroke. 1996 Jan;27(1):76-81. PubMed PMID: 8553408. 10: Grotta J; Combination Therapy Stroke Trial Investigators. Combination Therapy Stroke Trial: recombinant tissue-type plasminogen activator with/without lubeluzole. Cerebrovasc Dis. 2001;12(3):258-63. PubMed PMID: 11641593. 11: Mueller RN, Deyo DJ, Brantley DR, Disterhoft JF, Zornow MH. Lubeluzole and conditioned learning after cerebral ischemia. Exp Brain Res. 2003 Oct;152(3):329-34. Epub 2003 Aug 1. PubMed PMID: 12904938. 12: Koinig H, Vornik V, Rueda C, Zornow MH. Lubeluzole inhibits accumulation of extracellular glutamate in the hippocampus during transient global cerebral ischemia. Brain Res. 2001 Apr 20;898(2):297-302. PubMed PMID: 11306016. 13: Aronowski J, Strong R, Grotta JC. Combined neuroprotection and reperfusion therapy for stroke. Effect of lubeluzole and diaspirin cross-linked hemoglobin in experimental focal ischemia. Stroke. 1996 Sep;27(9):1571-6; discussion 1576-7. PubMed PMID: 8784132. 14: Hernández-Guijo JM, Gandía L, de Pascual R, García AG. Differential effects of the neuroprotectant lubeluzole on bovine and mouse chromaffin cell calcium channel subtypes. Br J Pharmacol. 1997 Sep;122(2):275-85. PubMed PMID: 9313936; PubMed Central PMCID: PMC1564921. 15: Que M, Witte OW, Zilles K. Transient up-regulation of gamma-aminobutyric acid(A) receptor binding by lubeluzole after neocortical specify lesion in rats. Neurosci Lett. 2000 Dec 22;296(2-3):125-8. PubMed PMID: 11108997. 16: Diener HC, Cortens M, Ford G, Grotta J, Hacke W, Kaste M, Koudstaal PJ, Wessel T. Lubeluzole in acute ischemic stroke treatment: A double-blind study with an 8-hour inclusion window comparing a 10-mg daily dose of lubeluzole with placebo. Stroke. 2000 Nov;31(11):2543-51. PubMed PMID: 11062273. 17: Marrannes R, De Prins E. Site of action of lubeluzole on voltage-sensitive Ca(2+) channels in isolated dorsal root ganglion cells of the rat: influence of pH. J Pharmacol Exp Ther. 2000 Nov;295(2):531-45. PubMed PMID: 11046086. 18: Kroppenstedt SN, Stroop R, Kern M, Thomale UW, Schneider GH, Unterberg AW. Lubeluzole following traumatic brain injury in the rat. J Neurotrauma. 1999 Jul;16(7):629-37. PubMed PMID: 10447074. 19: Maiese K, TenBroeke M, Kue I. Neuroprotection of lubeluzole is mediated through the signal transduction pathways of nitric oxide. J Neurochem. 1997 Feb;68(2):710-4. PubMed PMID: 9003060. 20: Haseldonckx M, Van Reempts J, Van de Ven M, Wouters L, Borgers M. Protection with lubeluzole against delayed ischemic brain damage in rats. A quantitative histopathologic study. Stroke. 1997 Feb;28(2):428-32. PubMed PMID: 9040701.