Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C16H17N3 |
| Molecular Weight | 251.3263 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCN(N1C=CC2=C1C=CC=C2)C3=CC=NC=C3
InChI
InChIKey=OTPPJICEBWOCKD-UHFFFAOYSA-N
InChI=1S/C16H17N3/c1-2-12-18(15-7-10-17-11-8-15)19-13-9-14-5-3-4-6-16(14)19/h3-11,13H,2,12H2,1H3
| Molecular Formula | C16H17N3 |
| Molecular Weight | 251.3263 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionCurator's Comment: description was created based on several sources, including:
http://www.evaluategroup.com/Universal/View.aspx?type=Story&id=269038 | http://adisinsight.springer.com/drugs/800001339 | https://www.ncbi.nlm.nih.gov/pubmed/9103515 | https://www.ncbi.nlm.nih.gov/pubmed/7674813
Curator's Comment: description was created based on several sources, including:
http://www.evaluategroup.com/Universal/View.aspx?type=Story&id=269038 | http://adisinsight.springer.com/drugs/800001339 | https://www.ncbi.nlm.nih.gov/pubmed/9103515 | https://www.ncbi.nlm.nih.gov/pubmed/7674813
Besipirdine is a potential novel first-in-class oral treatment for over active bladder currently in Phase II development, with a mechanism of action clearly different from that of antimuscarinics. It was under evaluation by Aventis up to phase III for Alzheimer’s disease, involving the administration of the compound to over 1500 patients. However, this research has been discontinued. Besipirdine antagonizes alpha-2 and alpha-1 adrenoceptors and inhibits both norepinephrine and serotonin uptake. The most common adverse events were asymptomatic postural hypotension and asymptomatic bradycardia.
CNS Activity
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL1907610 |
5.66 µM [Ki] | ||
Target ID: CHEMBL2093864 |
0.38 µM [Ki] | ||
Target ID: CHEMBL273 |
17.0 µM [IC50] | ||
Target ID: Voltage-dependent sodium channel (rat) |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
72.2 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7674813/ |
50 mg 2 times / day multiple, oral dose: 50 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
BESIPIRDINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
|
165 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7674813/ |
60 mg 2 times / day multiple, oral dose: 60 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
BESIPIRDINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
Doses
| Dose | Population | Adverse events |
|---|---|---|
60 mg 2 times / day multiple, oral Highest studied dose Dose: 60 mg, 2 times / day Route: oral Route: multiple Dose: 60 mg, 2 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Disc. AE: Angina, Coronary vasospasm... AEs leading to discontinuation/dose reduction: Angina (grade 3, 11.1%) Sources: Coronary vasospasm (grade 3, 11.1%) Sinus arrhythmia (grade 3, 11.1%) |
50 mg 2 times / day multiple, oral MTD Dose: 50 mg, 2 times / day Route: oral Route: multiple Dose: 50 mg, 2 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Disc. AE: Postural hypotension, Nausea... AEs leading to discontinuation/dose reduction: Postural hypotension (grade 2, 11.1%) Sources: Nausea (grade 3, 11.1%) Vomiting (grade 3, 11.1%) Lightheadedness (11.1%) Dizziness (11.1%) Weakness (11.1%) |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Angina | grade 3, 11.1% Disc. AE |
60 mg 2 times / day multiple, oral Highest studied dose Dose: 60 mg, 2 times / day Route: oral Route: multiple Dose: 60 mg, 2 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| Coronary vasospasm | grade 3, 11.1% Disc. AE |
60 mg 2 times / day multiple, oral Highest studied dose Dose: 60 mg, 2 times / day Route: oral Route: multiple Dose: 60 mg, 2 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| Sinus arrhythmia | grade 3, 11.1% Disc. AE |
60 mg 2 times / day multiple, oral Highest studied dose Dose: 60 mg, 2 times / day Route: oral Route: multiple Dose: 60 mg, 2 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| Dizziness | 11.1% Disc. AE |
50 mg 2 times / day multiple, oral MTD Dose: 50 mg, 2 times / day Route: oral Route: multiple Dose: 50 mg, 2 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| Lightheadedness | 11.1% Disc. AE |
50 mg 2 times / day multiple, oral MTD Dose: 50 mg, 2 times / day Route: oral Route: multiple Dose: 50 mg, 2 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| Weakness | 11.1% Disc. AE |
50 mg 2 times / day multiple, oral MTD Dose: 50 mg, 2 times / day Route: oral Route: multiple Dose: 50 mg, 2 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| Postural hypotension | grade 2, 11.1% Disc. AE |
50 mg 2 times / day multiple, oral MTD Dose: 50 mg, 2 times / day Route: oral Route: multiple Dose: 50 mg, 2 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| Nausea | grade 3, 11.1% Disc. AE |
50 mg 2 times / day multiple, oral MTD Dose: 50 mg, 2 times / day Route: oral Route: multiple Dose: 50 mg, 2 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| Vomiting | grade 3, 11.1% Disc. AE |
50 mg 2 times / day multiple, oral MTD Dose: 50 mg, 2 times / day Route: oral Route: multiple Dose: 50 mg, 2 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| The pharmacokinetics and cardiovascular pharmacodynamics of HP 749 (besipirdine HCl) and metabolite P86-7480 in the conscious monkey. | 1995-07 |
|
| HP 749 enhances calcium-independent release of [3H]norepinephrine from rat cortical slices and synaptosomes. | 1994-10 |
|
| Determination of HP 749, a potential therapeutic agent for Alzheimer's disease, in plasma by high-performance liquid chromatography. | 1991-12-06 |
Sample Use Guides
Besipirdine inhibited [3H]-batrachotoxin binding (IC50 = 5.5 uM) in a rat brain vesicular preparation and concentration-dependently inhibited veratridine (25 uM)-stimulated increases in intracellular free sodium ([Na+]i) and calcium ([Ca2+]i) in primary cultured cortical neurones of rat. Besipirdine (30-100 uM) concentration-dependently inhibited (up to 100%) veratridine-stimulated release of [3H]-noradrenaline (NA) from rat cortical slices.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 19:26:57 GMT 2025
by
admin
on
Mon Mar 31 19:26:57 GMT 2025
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| Record UNII |
95PY16J933
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| Record Status |
Validated (UNII)
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| Record Version |
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C171657
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CHEMBL29835
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BESIPIRDINE
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95PY16J933
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119257-34-0
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SUB05788MIG
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100000086073
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7116
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C074872
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60691
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m1024
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DTXSID50152361
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