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Details

Stereochemistry ACHIRAL
Molecular Formula C21H25N3.2ClH
Molecular Weight 392.365
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LATREPIRDINE DIHYDROCHLORIDE

SMILES

Cl.Cl.CN1CCC2=C(C1)C3=C(C=CC(C)=C3)N2CCC4=CN=C(C)C=C4

InChI

InChIKey=GTWLIQOLGOZTLF-UHFFFAOYSA-N
InChI=1S/C21H25N3.2ClH/c1-15-4-7-20-18(12-15)19-14-23(3)10-9-21(19)24(20)11-8-17-6-5-16(2)22-13-17;;/h4-7,12-13H,8-11,14H2,1-3H3;2*1H

HIDE SMILES / InChI

Description
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/21031168 | https://www.ncbi.nlm.nih.gov/pubmed/18939977

Dimebon (latrepirdine) is an orally available, small molecule, gamma carboline derivative that was developed and used in Russia as an over-the-counter oral antihistamine for allergy treatment since 1980s. In 1990s it was shown that Dimebon has promising potential in treating neurodegenerative diseases. In 2003, Medivation Inc acquired the rights to Dimebon. Medivation went public in December 2004, with Dimebon as the only drug in its pipeline. The product was being developed by Medivation and Pfizer as a treatment for early-stage Alzheimer's disease and Huntington's disease. However, development was discontinued by Medivation and Pfizer in early 2012. Dimebon inhibits alpha-Adrenergic receptors (alpha1A, alpha1B, alpha1D, and alpha2A), Histamine H1 and H2 receptors and Serotonin 5-HT2c, 5-HT5A, 5-HT6 receptors with high affinity. Dimebon may act by blocking NMDA receptors or voltage-gated Ca2+ channels and by preventing mitochondrial permeability pore transition.

CNS Activity

Originator

Shadurski, K.S. et al.
2
Sources: Shadurski KS, Danusevich IK, Kost AN, Vinogradova EV. 1138164 US Patent No. Chem Abstr. 1985;102:190810.
Curator's Comment: Reference retrieved from https://www.ncbi.nlm.nih.gov/pubmed/21517088

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2778
Antagonist
2778
Inhibitor
8297
 42.0 µM [IC50]
Inhibitor
8297
 7.9 µM [IC50]
Blocker
537
 57.0 µM [IC50]
Inhibitor
8297
Inhibitor
8297
Inhibitor
8297
Inhibitor
8297
Inhibitor
8297
Inhibitor
8297
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
Dimebon

Approved Use

Dimebon was initially developed and launched in Russia (USSR at the time) in 1983 as an over-the-counter oral antihistamine for allergy treatment.

Launch Date

1982
Primary
Phase III
656
Unknown

Approved Use

Unknown
Primary
Phase III
656
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Antihistamine agent Dimebon as a novel neuroprotector and a cognition enhancer.
2001 Jun
Effect of dimebon on cognition, activities of daily living, behaviour, and global function in patients with mild-to-moderate Alzheimer's disease: a randomised, double-blind, placebo-controlled study.
2008 Jul 19
Evaluation of Dimebon in cellular model of Huntington's disease.
2008 Oct 21
The rise and fall of Dimebon.
2010 Oct
Latrepirdine improves cognition and arrests progression of neuropathology in an Alzheimer's mouse model.
2013 Aug
Patents

Patents

08338408
2
WO2008036400A3
2
WO2008051599A3
2
WO2008112238A1
2

Sample Use Guides

In Vivo Use Guide
As anti-allergic medicine Dimebon was used in doses 10–20 mg 2–3 times per day. Oral dimebon, 20 mg three times a day was tested in Alzheimer's disease patients.
Route of Administration: Oral
In Vitro Use Guide
50 uM Dimebon stabilized glutamate-induced Ca2+ signals in primary striatal neuronal cultures (MSN) from YAC128 HD transgenic mice (YAC128 MSN) and protected cultured YAC128 MSN from glutamate-induced apoptosis. Lower concentrations of Dimebon (5 uM and 10 uM) did not stabilize glutamate-induced Ca2+ signals and did not exert neuroprotective effects in experiments with YAC128 MSN.
Name Type Language
LATREPIRDINE DIHYDROCHLORIDE
USAN   WHO-DD  
USAN  
Official Name English
DIMEBON DIHYDROCHLORIDE
Common Name English
Latrepirdine dihydrochloride [WHO-DD]
Common Name English
2,8-Dimethyl-5-[2-(6-methylpyridin-3-yl)ethyl]-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole dihydrochloride
Systematic Name English
DIMEBOLIN HYDROCHLORIDE
Common Name English
1H-PYRIDO(4,3-B)INDOLE, 2,3,4,5-TETRAHYDRO-2,8-DIMETHYL-5-(2-(6-METHYL-3-PYRIDINYL)ETHYL)-, DIHYDROCHLORIDE
Common Name English
LATREPIRDINE DIHYDROCHLORIDE [USAN]
Common Name English
9-(2-(2-METHYLPYRIDYL-5)ETHYL)-3,6-DIMETHYL-1,2,3,4-TETRAHYDRO-.GAMMA.-CARBOLINE 2HCL
Common Name English
1H-PYRIDO(4,3-B)INDOLE, 2,3,4,5-TETRAHYDRO-2,8-DIMETHYL-5-(2-(6-METHYL-3- PYRIDINYL)ETHYL)-, HYDROCHLORIDE (1:2)
Systematic Name English
DIMEBOLIN DIHYDROCHLORIDE
MI  
Common Name English
DIMEBOLIN DIHYDROCHLORIDE [MI]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29578
Created by admin on Fri Dec 15 16:04:51 GMT 2023 , Edited by admin on Fri Dec 15 16:04:51 GMT 2023
Code System Code Type Description
EU-Orphan Drug
EU/3/08/597(WITHDRAWN)
Created by admin on Fri Dec 15 16:04:51 GMT 2023 , Edited by admin on Fri Dec 15 16:04:51 GMT 2023
PRIMARY Please note that this product was withdrawn from the Community Register of designated Orphan Medicinal Products in February 2015 on request of the Sponsor. On 20 January 2009, orphan designation (EU/3/08/597) was granted by the European Commission to Innovative Drug European Associates Limited, United Kingdom, for 2,3,4,5 tetrahydro-2,8-dimethyl-5-[2-(6-methyl-3-pyridinyl)ethyl]-1H-pyrido[4,3-b]indole dihydrochloride for the treatment of Huntington’s disease. In December 2012, Innovative Drug European Associates Limited changed name to IDEA Innovative Drug European Associates Limited.
PUBCHEM
23729232
Created by admin on Fri Dec 15 16:04:51 GMT 2023 , Edited by admin on Fri Dec 15 16:04:51 GMT 2023
PRIMARY
SMS_ID
100000183860
Created by admin on Fri Dec 15 16:04:51 GMT 2023 , Edited by admin on Fri Dec 15 16:04:51 GMT 2023
PRIMARY
EVMPD
SUB32956
Created by admin on Fri Dec 15 16:04:51 GMT 2023 , Edited by admin on Fri Dec 15 16:04:51 GMT 2023
PRIMARY
FDA UNII
8B9414QQ5M
Created by admin on Fri Dec 15 16:04:51 GMT 2023 , Edited by admin on Fri Dec 15 16:04:51 GMT 2023
PRIMARY
EPA CompTox
DTXSID10243103
Created by admin on Fri Dec 15 16:04:51 GMT 2023 , Edited by admin on Fri Dec 15 16:04:51 GMT 2023
PRIMARY
USAN
WW-165
Created by admin on Fri Dec 15 16:04:51 GMT 2023 , Edited by admin on Fri Dec 15 16:04:51 GMT 2023
PRIMARY
NCI_THESAURUS
C78758
Created by admin on Fri Dec 15 16:04:51 GMT 2023 , Edited by admin on Fri Dec 15 16:04:51 GMT 2023
PRIMARY
CAS
97657-92-6
Created by admin on Fri Dec 15 16:04:51 GMT 2023 , Edited by admin on Fri Dec 15 16:04:51 GMT 2023
PRIMARY
MERCK INDEX
m4495
Created by admin on Fri Dec 15 16:04:51 GMT 2023 , Edited by admin on Fri Dec 15 16:04:51 GMT 2023
PRIMARY Merck Index
ChEMBL
CHEMBL589390
Created by admin on Fri Dec 15 16:04:51 GMT 2023 , Edited by admin on Fri Dec 15 16:04:51 GMT 2023
PRIMARY
ACTIVE MOIETY
Structure of LATREPIRDINE
NIH
NCATS
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