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Details

Stereochemistry ACHIRAL
Molecular Formula C21H31N5O2
Molecular Weight 385.5031
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BUSPIRONE

SMILES

O=C1CC2(CCCC2)CC(=O)N1CCCCN3CCN(CC3)C4=NC=CC=N4

InChI

InChIKey=QWCRAEMEVRGPNT-UHFFFAOYSA-N
InChI=1S/C21H31N5O2/c27-18-16-21(6-1-2-7-21)17-19(28)26(18)11-4-3-10-24-12-14-25(15-13-24)20-22-8-5-9-23-20/h5,8-9H,1-4,6-7,10-17H2

HIDE SMILES / InChI

Molecular Formula C21H31N5O2
Molecular Weight 385.5031
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Buspirone is the first of a new class of anxioselective agents, the azaspirodecanediones. Animal studies have suggested antianxiety activity and the absence of abuse potential. Behavioural, electrophysiological and receptor binding experiments gradually led to the idea that buspirone owes much of its anxiolytic activity to its ability to attenuate central 5-hydroxytryptamine neurotransmission. In vitro preclinical studies have shown that buspirone has a high affinity for serotonin (5-HT1A) receptors. Some studies do suggest that buspirone may have indirect effects on other neurotransmitter systems. Buspirone differs from typical benzodiazepine anxiolytics in that it does not exert anticonvulsant or muscle relaxant effects. It also lacks the prominent sedative effect that is associated with more typical anxiolytics. The drug was approved by FDA for the treatment of anxiety.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
24.0 nM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
BUSPIRONE HYDROCHLORIDE

Cmax

ValueDoseCo-administeredAnalytePopulation
1.613 ng/mL
15 mg 2 times / day steady-state, oral
BUSPIRONE plasma
Homo sapiens
1.711 ng/mL
15 mg single, oral
BUSPIRONE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
6.837 ng × h/mL
15 mg 2 times / day steady-state, oral
BUSPIRONE plasma
Homo sapiens
9.402 ng × h/mL
15 mg single, oral
BUSPIRONE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
3.062 h
15 mg single, oral
BUSPIRONE plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
14%
BUSPIRONE plasma
Homo sapiens

Doses

AEs

Overview

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as victim

PubMed

Sample Use Guides

In Vivo Use Guide
The recommended initial dose is 15 mg daily (7.5 mg b.i.d.). To achieve an optimal therapeutic response, at intervals of 2 to 3 days the dosage may be increased 5 mg per day, as needed. The maximum daily dosage should not exceed 60 mg per day. In clinical trials allowing dose titration, divided doses of 20 mg to 30 mg per day were commonly employed.
Route of Administration: Oral
In Vitro Use Guide
Buspiron was incubated with hippocampal pyramidal cells at concentration of 50 uM. Buspirone was shown to attenuate the synaptic activation of cells.
Substance Class Chemical
Record UNII
TK65WKS8HL
Record Status Validated (UNII)
Record Version