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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 of LATREPIRDINE

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
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.

Originator

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

Targets

Targets

Primary TargetPharmacologyConditionPotency
42.0 µM [IC50]
7.9 µM [IC50]
57.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
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
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
0.0122 μg/mL
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
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
0.0645 μg × h/mL
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
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
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
6.8 h
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

Doses

DosePopulationAdverse 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:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
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:
AEs

AEs

AESignificanceDosePopulation
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:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
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:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
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:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
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:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
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:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
PubMed

PubMed

TitleDatePubMed
Evaluation of Dimebon in cellular model of Huntington's disease.
2008 Oct 21
The rise and fall of Dimebon.
2010 Oct
Patents

Sample Use Guides

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
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
  • Download
Name Type Language
DIMEBOLIN
MI  
Preferred Name English
LATREPIRDINE
INN   MART.   USAN   WHO-DD  
INN   USAN  
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
Created by admin on Mon Mar 31 18:18:30 GMT 2025 , Edited by admin on Mon Mar 31 18:18:30 GMT 2025
FDA ORPHAN DRUG 282309
Created by admin on Mon Mar 31 18:18:30 GMT 2025 , Edited by admin on Mon Mar 31 18:18:30 GMT 2025
Code System Code Type Description
ChEMBL
CHEMBL589390
Created by admin on Mon Mar 31 18:18:30 GMT 2025 , Edited by admin on Mon Mar 31 18:18:30 GMT 2025
PRIMARY
MERCK INDEX
m4495
Created by admin on Mon Mar 31 18:18:30 GMT 2025 , Edited by admin on Mon Mar 31 18:18:30 GMT 2025
PRIMARY Merck Index
NCI_THESAURUS
C78757
Created by admin on Mon Mar 31 18:18:30 GMT 2025 , Edited by admin on Mon Mar 31 18:18:30 GMT 2025
PRIMARY
SMS_ID
100000124365
Created by admin on Mon Mar 31 18:18:30 GMT 2025 , Edited by admin on Mon Mar 31 18:18:30 GMT 2025
PRIMARY
EPA CompTox
DTXSID20189705
Created by admin on Mon Mar 31 18:18:30 GMT 2025 , Edited by admin on Mon Mar 31 18:18:30 GMT 2025
PRIMARY
INN
9207
Created by admin on Mon Mar 31 18:18:30 GMT 2025 , Edited by admin on Mon Mar 31 18:18:30 GMT 2025
PRIMARY
EVMPD
SUB32096
Created by admin on Mon Mar 31 18:18:30 GMT 2025 , Edited by admin on Mon Mar 31 18:18:30 GMT 2025
PRIMARY
MESH
C010119
Created by admin on Mon Mar 31 18:18:30 GMT 2025 , Edited by admin on Mon Mar 31 18:18:30 GMT 2025
PRIMARY
CAS
3613-73-8
Created by admin on Mon Mar 31 18:18:30 GMT 2025 , Edited by admin on Mon Mar 31 18:18:30 GMT 2025
PRIMARY
DRUG BANK
DB11725
Created by admin on Mon Mar 31 18:18:30 GMT 2025 , Edited by admin on Mon Mar 31 18:18:30 GMT 2025
PRIMARY
FDA UNII
OD9237K1Z6
Created by admin on Mon Mar 31 18:18:30 GMT 2025 , Edited by admin on Mon Mar 31 18:18:30 GMT 2025
PRIMARY
USAN
WW-164
Created by admin on Mon Mar 31 18:18:30 GMT 2025 , Edited by admin on Mon Mar 31 18:18:30 GMT 2025
PRIMARY
PUBCHEM
197033
Created by admin on Mon Mar 31 18:18:30 GMT 2025 , Edited by admin on Mon Mar 31 18:18:30 GMT 2025
PRIMARY
WIKIPEDIA
Latrepirdine
Created by admin on Mon Mar 31 18:18:30 GMT 2025 , Edited by admin on Mon Mar 31 18:18:30 GMT 2025
PRIMARY
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