LUBELUZOLE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C22H25F2N3O2S
Molecular Weight	433.515
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN(C1CCN(C[C@H](O)COC2=CC(F)=C(F)C=C2)CC1)C3=NC4=C(S3)C=CC=C4

InChI

InChIKey=OZFSWVOEXHGDES-INIZCTEOSA-N

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

HIDE SMILES / InChI

Molecular Formula	C22H25F2N3O2S
Molecular Weight	433.515
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.cell.com/biophysj/pdf/S0006-3495(11)03121-3.pdf | https://www.ncbi.nlm.nih.gov/pubmed/8553408

Lubeluzole is a medication, developed by Janssen Research Foundation for the treatment of acute ischemic stroke. The drug action is discussed to involve the inhibition of NMDA receptor and sodium channels.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Glutamate [NMDA] receptor 125 Target ID: CHEMBL2094124 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12038658	Antagonist 2849
Sodium channel alpha subunit 72 Target ID: CHEMBL2331043 Sources: http://www.cell.com/biophysj/pdf/S0006-3495(11)03121-3.pdf	Blocker 555		9.5 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Acute ischemic stroke 19 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8553408	Primary		Phase III 665	Unknown Approved Use Unknown

AUC

Value	Dose	Analyte	Population
2191 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9444444	15 mg single, intravenous dose: 15 mg route of administration: Intravenous experiment type: SINGLE co-administered:	LUBELUZOLE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
1422 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9444444	10 mg single, intravenous dose: 10 mg route of administration: Intravenous experiment type: SINGLE co-administered:	LUBELUZOLE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
904 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9444444	5 mg single, intravenous dose: 5 mg route of administration: Intravenous experiment type: SINGLE co-administered:	LUBELUZOLE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Analyte	Population
101 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9444444	15 mg single, intravenous dose: 15 mg route of administration: Intravenous experiment type: SINGLE co-administered:	LUBELUZOLE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
58.8 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9444444	10 mg single, intravenous dose: 10 mg route of administration: Intravenous experiment type: SINGLE co-administered:	LUBELUZOLE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
46.3 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9444444	5 mg single, intravenous dose: 5 mg route of administration: Intravenous experiment type: SINGLE co-administered:	LUBELUZOLE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Sourcing

Vendor/Aggregator	ID	URL
Alfa Chemistry	67769	http://www.alfa-chemistry.com/search.aspx?q=67769
Alfa Chemistry	ACM144665076	http://www.alfa-chemistry.com/search.aspx?q=ACM144665076
Compound Cloud	65998
MuseChem	M098152	https://www.musechem.com/product/M098152.html

PubMed

Title	Date	PubMed
Mammalian target of rapamycin: hitting the bull's-eye for neurological disorders.	2011-02-11	21307646
New strategies for Alzheimer's disease and cognitive impairment.	2010-08-19	20716915
Therapeutic promise and principles: metabotropic glutamate receptors.	2009-09-15	19750024
Anemia and red blood cell transfusion in neurocritical care.	2009	19519893
Stroke management.	2008-09-16	19445805
The fraction of activated N-methyl-D-aspartate receptors during synaptic transmission remains constant in the presence of the glutamate release inhibitor riluzole.	2008-08	18493706
Measuring disability in stroke: relationship between the modified Rankin scale and the Barthel index.	2007-08	17668259
Moderate hyperglycaemia is associated with favourable outcome in acute lacunar stroke.	2007-06	17525141
Neuroprotection and thrombolysis: combination therapy in acute ischaemic stroke.	2006-08	16872260
Facile, alternative route to lubeluzole, its enantiomer, and the racemate.	2006-05-05	16521088
Combined effects of mechanical and ischemic injury to cortical cells: secondary ischemia increases damage and decreases effects of neuroprotective agents.	2005-12	16046227
Methodological quality of animal studies on neuroprotection in focal cerebral ischaemia.	2005-09	16170651
Study of the interaction of lubeluzole with cardiac sodium channels.	2003-11	14576504
Lubeluzole and conditioned learning after cerebral ischemia.	2003-10	12904938
Detection of proarrhythmia in the female rabbit heart: blinded validation.	2003-03	12716112
Excitatory amino acid antagonists for acute stroke.	2003	12917902
Gateways to clinical trials.	2002-10	12500432
A comparison of the anti-nociceptive effects of voltage-activated Na+ channel blockers in the formalin test.	2002-06-12	12079688
Lubeluzole pretreatment does not provide neuroprotection against transient global cerebral ischemia in fetal sheep near term.	2002-04	11919339
Neuroprotective agents in acute ischemic stroke.	2002-02	12038658
Nitrous oxide modulator: lubeluzole.	2002	12365825
Lubeluzole for acute ischaemic stroke.	2002	11869612
Lubeluzole attenuates K(+)-evoked extracellular accumulation of taurine in the striatum of healthy rats and rats with hepatic failure.	2001-06-15	11516427
Circulatory responses to acute asphyxia are not affected by the glutamate antagonist lubeluzole in fetal sheep near term.	2001-06-08	11390248
Combination therapy stroke trial. rt-PA +/- lubeluzole.	2001-06	11462784
Effects of lubeluzole on the methamphetamine-induced increase in extracellular glutamate and the long-term depletion of striatal dopamine.	2001-05	11252020
Lubeluzole inhibits accumulation of extracellular glutamate in the hippocampus during transient global cerebral ischemia.	2001-04-20	11306016
Combination Therapy Stroke Trial: recombinant tissue-type plasminogen activator with/without lubeluzole.	2001	11641593
Synthesis of the antistroke drug lubeluzole and its enantiomer. Lipase-catalyzed resolution of chiral building block.	2001	11270322
Thrombolysis in ischaemic stroke -- present and future: role of combined therapy.	2001	11244201

Patents

Sample Use Guides

In Vivo Use Guide

One cohort of patients received 7.5 mg of lubeluzole over 1 hour followed by 10 mg/d for 5 days, and another cohort received lubeluzole 15 mg over 1 hour followed by 20 mg/d for 5 days.

Route of Administration: Intravenous

In Vitro Use Guide

Hippocampal cultures were exposed to 500 nM glutamate for 1 h and lubeluzole (0.1-100 nM). The drug reduced the percentage of damaged neurons from 42% to 18%.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:01:14 GMT 2025` Edited by `admin` on `Mon Mar 31 18:01:14 GMT 2025`
Record UNII	V2SIB71583
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PROSYNAP

Preferred Name

English

LUBELUZOLE

Official Name

English

(+)-(S)-4-(2-BENZOTHIAZOLYLMETHYLAMINO)-.ALPHA.-((3,4-DIFLUOROPHENOXY)METHYL)-1-PIPERIDINEETHANOL

Systematic Name

English

R-87926

Code

English

R-86926

Code

English

1-PIPERIDINEETHANOL, 4-(2-BENZOTHIAZOLYLMETHYLAMINO)-.ALPHA.-((3,4-DIFLUOROPHENOXY)METHYL)-, (S)-

Systematic Name

English

R86926

Code

English

LUBELUZOLE [MART.]

Common Name

English

LUBELUZOLE [MI]

Common Name

English

LUBELUZOLE [USAN]

Common Name

English

R87926

Code

English

Lubeluzole [WHO-DD]

Common Name

English

lubeluzole [INN]

Common Name

English

Code System Code Type Description

NCI_THESAURUS

C170134