LATREPIRDINE

Possibly Marketed Outside US

Details

Stereochemistry	ACHIRAL
Molecular Formula	C21H25N3
Molecular Weight	319.4433
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN1CCC2=C(C1)C3=C(C=CC(C)=C3)N2CCC4=CC=C(C)N=C4

InChI

InChIKey=JNODQFNWMXFMEV-UHFFFAOYSA-N

InChI=1S/C21H25N3/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

HIDE SMILES / InChI

Molecular Formula	C21H25N3
Molecular Weight	319.4433
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://adisinsight.springer.com/drugs/800021875
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

Approval Year

Targets

Primary Target	Pharmacology	Potency
Histamine H1 receptor 316 Target ID: CHEMBL231 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6225678 \| https://www.ncbi.nlm.nih.gov/pubmed/18939977	Antagonist 2849
Glutamate [NMDA] receptor 125 Target ID: CHEMBL2094124 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11462798 \| https://www.ncbi.nlm.nih.gov/pubmed/14968164 \| https://www.ncbi.nlm.nih.gov/pubmed/21031168	Antagonist 2849
Acetylcholinesterase 209 Target ID: CHEMBL220 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11462798	Inhibitor 8504	42.0 µM [IC50]
Butyrylcholinesterase 45 Target ID: CHEMBL1914 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11462798	Inhibitor 8504	7.9 µM [IC50]
Voltage-gated L-type calcium channel 95 Target ID: CHEMBL2095229 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11865327 \| https://www.ncbi.nlm.nih.gov/pubmed/21031168	Blocker 555	57.0 µM [IC50]
Adrenergic receptor alpha 65 Target ID: CHEMBL2095203 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18939977	Inhibitor 8504
Serotonin 6 (5-HT6) receptor 44 Target ID: CHEMBL3371 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18939977	Inhibitor 8504
Serotonin 2c (5-HT2c) receptor 131 Target ID: CHEMBL225 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18939977	Inhibitor 8504
Serotonin 5a (5-HT5a) receptor 11 Target ID: CHEMBL3426 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18939977	Inhibitor 8504
Histamine H2 receptor 46 Target ID: CHEMBL1941 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18939977	Inhibitor 8504
mitochondrial permeability transition pore complex 3 Target ID: GO:0005757 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21031168	Inhibitor 8504

Conditions

Condition	Modality	Highest Phase	Product
Allergy 44 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21031168 http://adisinsight.springer.com/drugs/800021875	Primary	Approved 8583	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
Alzheimer’s disease 278 Sources: http://adisinsight.springer.com/drugs/800021875 https://www.ncbi.nlm.nih.gov/pubmed/21031168	Primary	Phase III 665	Unknown Approved Use Unknown
Huntington's disease 28 Sources: http://adisinsight.springer.com/drugs/800021875 https://www.ncbi.nlm.nih.gov/pubmed/21031168	Primary	Phase III 665	Unknown Approved Use Unknown

C_max

Value	Dose	Analyte	Population
0.0122 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/33898159/	20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered:	LATREPIRDINE unknown	Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN
0.03 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/33898159/	40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered:	LATREPIRDINE unknown	Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN
1.3 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27072954/	8.14 mg single, oral dose: 8.14 mg route of administration: Oral experiment type: SINGLE co-administered:	LATREPIRDINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
0.0645 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/33898159/	20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered:	LATREPIRDINE unknown	Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN
0.149 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/33898159/	40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered:	LATREPIRDINE unknown	Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN
10.4 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27072954/	8.14 mg single, oral dose: 8.14 mg route of administration: Oral experiment type: SINGLE co-administered:	LATREPIRDINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
6.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27072954/	8.14 mg single, oral dose: 8.14 mg route of administration: Oral experiment type: SINGLE co-administered:		LATREPIRDINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
20 mg 3 times / day multiple, oral Studied dose Dose: 20 mg, 3 times / day Route: oral Route: multiple Dose: 20 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/20142523/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/20142523/	Disc. AE: Loss of consciousness, Rash... AEs leading to discontinuation/dose reduction: Loss of consciousness (grade 3, 2.2%) Rash (2.2%) Headache (2.2%) Renal and urinary disorders (2.2%) Supraventricular tachycardia (2.2%) Sources: https://pubmed.ncbi.nlm.nih.gov/20142523/

AEs

AE	Significance	Dose	Population
Headache	2.2% Disc. AE	20 mg 3 times / day multiple, oral Studied dose Dose: 20 mg, 3 times / day Route: oral Route: multiple Dose: 20 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/20142523/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/20142523/
Rash	2.2% Disc. AE	20 mg 3 times / day multiple, oral Studied dose Dose: 20 mg, 3 times / day Route: oral Route: multiple Dose: 20 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/20142523/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/20142523/
Renal and urinary disorders	2.2% Disc. AE	20 mg 3 times / day multiple, oral Studied dose Dose: 20 mg, 3 times / day Route: oral Route: multiple Dose: 20 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/20142523/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/20142523/
Supraventricular tachycardia	2.2% Disc. AE	20 mg 3 times / day multiple, oral Studied dose Dose: 20 mg, 3 times / day Route: oral Route: multiple Dose: 20 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/20142523/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/20142523/
Loss of consciousness	grade 3, 2.2% Disc. AE	20 mg 3 times / day multiple, oral Studied dose Dose: 20 mg, 3 times / day Route: oral Route: multiple Dose: 20 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/20142523/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/20142523/

PubMed

Title	Date	PubMed
Evaluation of Dimebon in cellular model of Huntington's disease.	2008 Oct 21	18939977
The rise and fall of Dimebon.	2010 Oct	21031168

Patents

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.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:18:30 GMT 2025` Edited by `admin` on `Mon Mar 31 18:18:30 GMT 2025`
Record UNII	OD9237K1Z6
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DIMEBOLIN

Preferred Name

English

LATREPIRDINE

Official Name

English

Latrepirdine [WHO-DD]

Common Name

English

PF-01913539

Common Name

English

LATREPIRDINE [MART.]

Common Name

English

DIMEBOLIN [MI]

Common Name

English

2,8-Dimethyl-5-[2-(6-methylpyridin-3-yl)ethyl]-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

Systematic Name

English

latrepirdine [INN]

Common Name

English

1H-PYRIDO(4,3-B)INDOLE, 2,3,4,5-TETRAHYDRO-2,8-DIMETHYL-5-(2-(6-METHYL-3-PYRIDINYL)ETHYL)-

Systematic Name

English

DIMEBON

Common Name

English

LATREPIRDINE [USAN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29578