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=C(F)C(F)=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 2778
Sodium channel alpha subunit 76 Target ID: CHEMBL2331043 Sources: http://www.cell.com/biophysj/pdf/S0006-3495(11)03121-3.pdf	Blocker 537		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 656	Unknown Approved Use Unknown

AUC

Value	Dose	Analyte	Population
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
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
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
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
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
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
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
Lubeluzole inhibits accumulation of extracellular glutamate in the hippocampus during transient global cerebral ischemia.	2001 Apr 20	11306016
Effects of lubeluzole on the methamphetamine-induced increase in extracellular glutamate and the long-term depletion of striatal dopamine.	2001 May	11252020
A comparison of the anti-nociceptive effects of voltage-activated Na+ channel blockers in the formalin test.	2002 Jun 12	12079688
Gateways to clinical trials.	2002 Oct	12500432
Excitatory amino acid antagonists for acute stroke.	2003	12917902
Detection of proarrhythmia in the female rabbit heart: blinded validation.	2003 Mar	12716112
Study of the interaction of lubeluzole with cardiac sodium channels.	2003 Nov	14576504
Lubeluzole and conditioned learning after cerebral ischemia.	2003 Oct	12904938
Facile, alternative route to lubeluzole, its enantiomer, and the racemate.	2006 May 5	16521088
Moderate hyperglycaemia is associated with favourable outcome in acute lacunar stroke.	2007 Jun	17525141
Anemia and red blood cell transfusion in neurocritical care.	2009	19519893

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 `Fri Dec 15 15:33:42 GMT 2023` Edited by `admin` on `Fri Dec 15 15:33:42 GMT 2023`
Record UNII	V2SIB71583
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

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

PROSYNAP

Brand 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