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Details

Stereochemistry ACHIRAL
Molecular Formula C16H17N3.ClH
Molecular Weight 287.787
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BESIPIRDINE HYDROCHLORIDE

SMILES

Cl.CCCN(N1C=CC2=C1C=CC=C2)C3=CC=NC=C3

InChI

InChIKey=ZDFVWDHZXAGROF-UHFFFAOYSA-N
InChI=1S/C16H17N3.ClH/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;1H

HIDE SMILES / InChI
Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
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

Description
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

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2849
 5.66 µM [Ki]
Antagonist
2849
 0.38 µM [Ki]
Binding Agent
1076
 17.0 µM [IC50]
Voltage-dependent sodium channel (rat)
2
Target ID: Voltage-dependent sodium channel (rat)
Inhibitor
8504
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase III
665
Unknown

Approved Use

Unknown
Primary
Phase II
1147
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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

Doses

DosePopulationAdverse 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:
https://pubmed.ncbi.nlm.nih.gov/7674813/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/7674813/
Disc. AE: Angina, Coronary vasospasm...
AEs leading to
discontinuation/dose reduction:
Angina (grade 3, 11.1%)
Coronary vasospasm (grade 3, 11.1%)
Sinus arrhythmia (grade 3, 11.1%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/7674813/
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:
https://pubmed.ncbi.nlm.nih.gov/7674813/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/7674813/
Disc. AE: Postural hypotension, Nausea...
AEs leading to
discontinuation/dose reduction:
Postural hypotension (grade 2, 11.1%)
Nausea (grade 3, 11.1%)
Vomiting (grade 3, 11.1%)
Lightheadedness (11.1%)
Dizziness (11.1%)
Weakness (11.1%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/7674813/
AEs

AEs

AESignificanceDosePopulation
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:
https://pubmed.ncbi.nlm.nih.gov/7674813/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/7674813/
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:
https://pubmed.ncbi.nlm.nih.gov/7674813/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/7674813/
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:
https://pubmed.ncbi.nlm.nih.gov/7674813/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/7674813/
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:
https://pubmed.ncbi.nlm.nih.gov/7674813/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/7674813/
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:
https://pubmed.ncbi.nlm.nih.gov/7674813/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/7674813/
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:
https://pubmed.ncbi.nlm.nih.gov/7674813/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/7674813/
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:
https://pubmed.ncbi.nlm.nih.gov/7674813/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/7674813/
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:
https://pubmed.ncbi.nlm.nih.gov/7674813/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/7674813/
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:
https://pubmed.ncbi.nlm.nih.gov/7674813/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/7674813/
PubMed

PubMed

TitleDatePubMed
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
Patents

Patents

CA2642687A1
2
EP0287982
2
US20090048304
2
US4970218
2
WO2007096777A
2

Sample Use Guides

In Vivo Use Guide
5 and 20 mg b.i.d.
Route of Administration: Oral
In Vitro Use Guide
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 Mon Mar 31 21:25:49 GMT 2025
Edited
by admin
on Mon Mar 31 21:25:49 GMT 2025
Record UNII
2541WG0P2F
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BESIPIRDINE HYDROCHLORIDE
MI   USAN   WHO-DD  
USAN  
Official Name English
HP 749
Preferred Name English
1H-INDOL-1-AMINE, N-PROPYL-N-4-PYRIDINYL-, MONOHYDROCHLORIDE
Common Name English
1-(Propyl-4-pyridylamino)indole monohydrochloride
Systematic Name English
Besipirdine hydrochloride [WHO-DD]
Common Name English
HP-749
Code English
BESIPIRDINE HCL
Common Name English
BESIPIRDINE HYDROCHLORIDE [USAN]
Common Name English
BESIPIRDINE HYDROCHLORIDE [MI]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C87053
Created by admin on Mon Mar 31 21:25:49 GMT 2025 , Edited by admin on Mon Mar 31 21:25:49 GMT 2025
Code System Code Type Description
EVMPD
SUB00766MIG
Created by admin on Mon Mar 31 21:25:49 GMT 2025 , Edited by admin on Mon Mar 31 21:25:49 GMT 2025
PRIMARY
USAN
DD-43
Created by admin on Mon Mar 31 21:25:49 GMT 2025 , Edited by admin on Mon Mar 31 21:25:49 GMT 2025
PRIMARY
ChEMBL
CHEMBL29835
Created by admin on Mon Mar 31 21:25:49 GMT 2025 , Edited by admin on Mon Mar 31 21:25:49 GMT 2025
PRIMARY
SMS_ID
100000085003
Created by admin on Mon Mar 31 21:25:49 GMT 2025 , Edited by admin on Mon Mar 31 21:25:49 GMT 2025
PRIMARY
EPA CompTox
DTXSID20156811
Created by admin on Mon Mar 31 21:25:49 GMT 2025 , Edited by admin on Mon Mar 31 21:25:49 GMT 2025
PRIMARY
MERCK INDEX
m1024
Created by admin on Mon Mar 31 21:25:49 GMT 2025 , Edited by admin on Mon Mar 31 21:25:49 GMT 2025
PRIMARY Merck Index
NCI_THESAURUS
C90630
Created by admin on Mon Mar 31 21:25:49 GMT 2025 , Edited by admin on Mon Mar 31 21:25:49 GMT 2025
PRIMARY
PUBCHEM
68742
Created by admin on Mon Mar 31 21:25:49 GMT 2025 , Edited by admin on Mon Mar 31 21:25:49 GMT 2025
PRIMARY
FDA UNII
2541WG0P2F
Created by admin on Mon Mar 31 21:25:49 GMT 2025 , Edited by admin on Mon Mar 31 21:25:49 GMT 2025
PRIMARY
CAS
130953-69-4
Created by admin on Mon Mar 31 21:25:49 GMT 2025 , Edited by admin on Mon Mar 31 21:25:49 GMT 2025
PRIMARY
Related Record Type Details
Structure of BESIPIRDINE
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of BESIPIRDINE
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