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
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
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 |
DescriptionSources: http://adisinsight.springer.com/drugs/800021875Curator'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
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.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL231 |
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Target ID: CHEMBL220 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11462798 |
42.0 µM [IC50] | ||
Target ID: CHEMBL1914 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11462798 |
7.9 µM [IC50] | ||
Target ID: CHEMBL2095229 |
57.0 µM [IC50] | ||
Target ID: CHEMBL2095203 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18939977 |
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Target ID: CHEMBL3371 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18939977 |
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Target ID: CHEMBL225 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18939977 |
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Target ID: CHEMBL3426 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18939977 |
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Target ID: CHEMBL1941 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18939977 |
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Target ID: GO:0005757 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21031168 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Dimebon Approved UseDimebon was initially developed and launched in Russia (USSR at the time) in 1983 as an over-the-counter oral antihistamine for allergy treatment. Launch Date1982 |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
Cmax
Value | Dose | Co-administered | 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 | Co-administered | 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 |
T1/2
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: |
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%) Sources: Rash (2.2%) Headache (2.2%) Renal and urinary disorders (2.2%) Supraventricular tachycardia (2.2%) |
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: |
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: |
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18939977
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
Edited
Mon Mar 31 18:18:30 GMT 2025
by
admin
on
Mon Mar 31 18:18:30 GMT 2025
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Record UNII |
OD9237K1Z6
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Record Status |
Validated (UNII)
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Record Version |
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-
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C29578
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FDA ORPHAN DRUG |
282309
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Code System | Code | Type | Description | ||
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CHEMBL589390
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PRIMARY | |||
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m4495
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PRIMARY | Merck Index | ||
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C78757
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PRIMARY | |||
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100000124365
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PRIMARY | |||
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DTXSID20189705
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PRIMARY | |||
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9207
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PRIMARY | |||
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SUB32096
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PRIMARY | |||
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C010119
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PRIMARY | |||
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3613-73-8
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PRIMARY | |||
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DB11725
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PRIMARY | |||
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OD9237K1Z6
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PRIMARY | |||
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WW-164
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197033
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PRIMARY | |||
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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
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PRIMARY |
Related Record | Type | Details | ||
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TARGET -> INHIBITOR |
Ki
|
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TARGET -> INHIBITOR |
Ki
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TARGET -> INHIBITOR |
IC50
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TARGET->WEAK INHIBITOR |
IC50
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OFF-TARGET->INHIBITOR |
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
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