Lubeluzole

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Lubeluzole
	File:Lubeluzole.png
Clinical data
ATC code	none;
Identifiers
	IUPAC name (2S)-1-[4-(1,3-benzothiazol-2-yl-methylamino)piperidin-1-yl]-3-(3,4-difluorophenoxy)propan-2-ol;
CAS Number	144665-07-6 ;
PubChem CID	65998;
UNII	V2SIB71583;
KEGG	D04789 ;
ChEMBL	ChEMBL281724 ;
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C22H25F2N3O2S
Molar mass	433.515 g/mol
3D model (JSmol)	Interactive image;
	SMILES CN(C1CCN(CC1)C[C@@H](COC2=CC(=C(C=C2)F)F)O)C3=NC4=CC=CC=C4S3;
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Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

Lubeluzole (Prosynap) is a drug which acts as an indirect NMDA antagonist. It inhibits the release of glutamate, inhibits nitric oxide synthesis, and blocks calcium and sodium gated ion channels.^[1] It has neuroprotective effects particularly in hypoxic conditions,^[2]^[3] and was developed for the treatment of stroke.^[4] Trials showed it to be safe, effective and well tolerated at low doses, but unfortunately higher doses produced the dangerous cardiac side effect of lengthening the QTc interval,^[5]^[6] which could potentially lead to heart failure, and so this meant that subsequent trials were limited to using only the low dose range.^[7] Animal studies had shown lubeluzole to produce neuroprotective effects when administered for prolonged periods, but the aim of its developers was to produce a drug that would be effective for preventing damage from acute stroke, and so ultimately it failed to show sufficient efficacy in trials and development for medical use was halted.^[8]

References

↑ Culmsee C, Junker V, Wolz P, Semkova I, Krieglstein J. Lubeluzole protects hippocampal neurons from excitotoxicity in vitro and reduces brain damage caused by ischemia. European Journal of Pharmacology. 1998 Jan 26;342(2-3):193-201. PMID 9548385
↑ Ashton D, Willems R, Wynants J, Van Reempts J, Marrannes R, Clincke G. Altered Na(+)-channel function as an in vitro model of the ischemic penumbra: action of lubeluzole and other neuroprotective drugs. Brain Research. 1997 Jan 16;745(1-2):210-21. PMID 9037412
↑ Maiese K, TenBroeke M, Kue I. Neuroprotection of lubeluzole is mediated through the signal transduction pathways of nitric oxide. Journal of Neurochemistry. 1997 Feb;68(2):710-4. PMID 9003060
↑ Grotta J. Lubeluzole treatment of acute ischemic stroke. The US and Canadian Lubeluzole Ischemic Stroke Study Group. Stroke. 1997 Dec;28(12):2338-46. PMID 9412611
↑ 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. International Journal of Clinical Pharmacology and Therapeutics. 1997 Nov;35(11):491-5. PMID 9401829
↑ Wood PL, Hawkinson JE. N-methyl-D-aspartate antagonists for stroke and head trauma. Expert Opinion on Investigational Drugs. 1997 Apr;6(4):389-97. PMID 15989606
↑ 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. Cerebrovascular Diseases. 1998 Sep-Oct;8(5):247-54. PMID 9712921
↑ Gandolfo C, Sandercock P, Conti M. Lubeluzole for acute ischaemic stroke. Cochrane Database of Systematic Reviews. 2002;(1):CD001924. PMID 11869612

Template:Glutamate receptor ligands

Template:Nervous-system-drug-stub

[1] Culmsee C, Junker V, Wolz P, Semkova I, Krieglstein J. Lubeluzole protects hippocampal neurons from excitotoxicity in vitro and reduces brain damage caused by ischemia. European Journal of Pharmacology. 1998 Jan 26;342(2-3):193-201. PMID 9548385

[2] Ashton D, Willems R, Wynants J, Van Reempts J, Marrannes R, Clincke G. Altered Na(+)-channel function as an in vitro model of the ischemic penumbra: action of lubeluzole and other neuroprotective drugs. Brain Research. 1997 Jan 16;745(1-2):210-21. PMID 9037412

[3] Maiese K, TenBroeke M, Kue I. Neuroprotection of lubeluzole is mediated through the signal transduction pathways of nitric oxide. Journal of Neurochemistry. 1997 Feb;68(2):710-4. PMID 9003060

[4] Grotta J. Lubeluzole treatment of acute ischemic stroke. The US and Canadian Lubeluzole Ischemic Stroke Study Group. Stroke. 1997 Dec;28(12):2338-46. PMID 9412611

[5] 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. International Journal of Clinical Pharmacology and Therapeutics. 1997 Nov;35(11):491-5. PMID 9401829

[6] Wood PL, Hawkinson JE. N-methyl-D-aspartate antagonists for stroke and head trauma. Expert Opinion on Investigational Drugs. 1997 Apr;6(4):389-97. PMID 15989606

[7] 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. Cerebrovascular Diseases. 1998 Sep-Oct;8(5):247-54. PMID 9712921

[8] Gandolfo C, Sandercock P, Conti M. Lubeluzole for acute ischaemic stroke. Cochrane Database of Systematic Reviews. 2002;(1):CD001924. PMID 11869612

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Clinical data
File:Lubeluzole.png
ATC code	none
Identifiers
IUPAC name (2S)-1-[4-(1,3-benzothiazol-2-yl-methylamino)piperidin-1-yl]-3-(3,4-difluorophenoxy)propan-2-ol
CAS Number	144665-07-6^Y
PubChem CID	65998
UNII	V2SIB71583
KEGG	D04789^Y
ChEMBL	ChEMBL281724^N
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C₂₂H₂₅F₂N₃O₂S
Molar mass	433.515 g/mol
3D model (JSmol)	Interactive image
SMILES CN(C1CCN(CC1)C[C@@H](COC2=CC(=C(C=C2)F)F)O)C3=NC4=CC=CC=C4S3
^NY (what is this?) (verify)

Lubeluzole

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