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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
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/1796057 https://www.ncbi.nlm.nih.gov/pubmed/6151170

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.

Originator

Sources: ISBN-13: 978-1285845227

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
24.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
BUSPIRONE HYDROCHLORIDE

Approved Use

Buspirone hydrochloride tablets are indicated for the management of anxiety disorders or the short-term relief of the symptoms of anxiety. Anxiety or tension associated with the stress of everyday life usually does not require treatment with an anxiolytic.

Launch Date

2001
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1.711 ng/mL
15 mg single, oral
dose: 15 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BUSPIRONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
1.613 ng/mL
15 mg 2 times / day steady-state, oral
dose: 15 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
BUSPIRONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
9.402 ng × h/mL
15 mg single, oral
dose: 15 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BUSPIRONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
6.837 ng × h/mL
15 mg 2 times / day steady-state, oral
dose: 15 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
BUSPIRONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
3.062 h
15 mg single, oral
dose: 15 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BUSPIRONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
14%
BUSPIRONE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
major
yes (co-administration study)
Comment: coadministration of buspirone (10 mg as a single dose) with verapamil (80 mg t.i.d.) or diltiazem (60 mg t.i.d.) increased plasma buspirone concentrations; coadministration of buspirone (10 mg as a single dose) with erythromycin (1.5 g/day for 4 days) increased plasma buspirone concentrations (5-fold increase in Cmax and 6-fold increase in AUC); coadministration of buspirone (10 mg as a single dose) with itraconazole (200 mg/day for 4 days) increased plasma buspirone concentrations (13-fold increase in Cmax and 19-fold increase in AUC); coadministration of buspirone (2.5 or 5 mg b.i.d.) with nefazodone (250 mg b.i.d.) resulted in marked increases in plasma buspirone concentrations (increases up to 20-fold in Cmax and up to 50-fold in AUC); coadministration of buspirone (30 mg as a single dose) with rifampin (600 mg/day for 5 days) decreased the plasma concentrations (83.7% decrease in Cmax; 89.6% decrease in AUC);
Page: 3.0
minor
minor
PubMed

PubMed

TitleDatePubMed
Effect of buspirone on sexual dysfunction in depressed patients treated with selective serotonin reuptake inhibitors.
1999 Jun
5-HT1A receptor agonists buspirone and gepirone attenuate apomorphine-induced aggressive behaviour in adult male Wistar rats.
2000 Dec
Synthesis and pharmacological evaluation of aryl/heteroaryl piperazinyl alkyl benzotriazoles as ligands for some serotonin and dopamine receptor subtypes.
2001 Apr
Switching from benzodiazepines to buspirone using a tapered overlap method in generalized anxiety disorder.
2001 Aug
An open study of buspirone augmentation of neuroleptics in patients with schizophrenia.
2001 Aug
Serotonergic regulation of inhibitory avoidance and one-way escape in the rat elevated T-maze.
2001 Dec
The impact of impulsivity on cocaine use and retention in treatment.
2001 Dec
Effect of nonnicotine pharmacotherapy on smoking behavior.
2001 Dec
Pharmacokinetics and tolerability of buspirone during oral administration to children and adolescents with anxiety disorder and normal healthy adults.
2001 Dec
Comparison of antidepressant activity in 4- and 40-week-old male mice in the forced swimming test: involvement of 5-HT1A and 5-HT1B receptors in old mice.
2001 Feb
Prenatal stress and postnatal development of neonatal rats--sex-dependent effects on emotional behavior and learning ability of neonatal rats.
2001 Feb
Treatment of the agitation of late-life psychosis and Alzheimer's disease.
2001 Jan
Use of negatively reinforcing electrical brain stimulation to detect conventional and nonconventional anxiolytics as well as an anxiogenic drug.
2001 Jan
Drug-induced potentiation of prepulse inhibition of acoustic startle reflex in mice: a model for detecting antipsychotic activity?
2001 Jul
Late-onset bipolar disorder due to hyperthyroidism.
2001 Jul
Serotonin-based pharmacotherapy for acute neuroleptic-induced akathisia: a new approach to an old problem.
2001 Jul
Is imipramine or buspirone treatment effective in patients wishing to discontinue long-term benzodiazepine use?
2001 Mar
Pattern of symptom improvement following treatment with venlafaxine XR in patients with generalized anxiety disorder.
2001 Nov
A double-blind placebo-controlled study of buspirone-stimulated prolactin release in non-ulcer dyspepsia--are central serotoninergic responses enhanced?
2001 Oct
Bupropion-induced acute dystonia.
2002 Feb
Benzodiazepine discontinuation in generalized anxiety disorder.
2002 Feb
Short term aerobic exercise training in young males does not alter sensitivity to a central serotonin agonist.
2002 Jan
The stimulus effect of 5,6,7,8-tetrahydro-1,3-dioxolo[4,5-g]isoquinoline is similar to that of cocaine but different from that of amphetamine.
2002 Jan-Feb
Patents

Sample Use Guides

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
Created
by admin
on Mon Mar 31 18:12:28 GMT 2025
Edited
by admin
on Mon Mar 31 18:12:28 GMT 2025
Record UNII
TK65WKS8HL
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
GEN-BUSPIRONE
Preferred Name English
BUSPIRONE
INN   MI   VANDF   WHO-DD  
INN  
Official Name English
BUSPIRONE [VANDF]
Common Name English
buspirone [INN]
Common Name English
8-(4-(4-(2-PYRIMIDINYL)-1-PIPERIZINYL)BUTYL)-8-AZASPIRO(4,5)DECANE-7,9-DIONE
Systematic Name English
BUSPIRONE [MI]
Common Name English
BCI-024
Code English
Buspirone [WHO-DD]
Common Name English
Classification Tree Code System Code
WHO-VATC QN05BE01
Created by admin on Mon Mar 31 18:12:28 GMT 2025 , Edited by admin on Mon Mar 31 18:12:28 GMT 2025
LIVERTOX NBK547966
Created by admin on Mon Mar 31 18:12:28 GMT 2025 , Edited by admin on Mon Mar 31 18:12:28 GMT 2025
WHO-ATC N05BE01
Created by admin on Mon Mar 31 18:12:28 GMT 2025 , Edited by admin on Mon Mar 31 18:12:28 GMT 2025
NCI_THESAURUS C28197
Created by admin on Mon Mar 31 18:12:28 GMT 2025 , Edited by admin on Mon Mar 31 18:12:28 GMT 2025
Code System Code Type Description
SMS_ID
100000088473
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PRIMARY
CAS
36505-84-7
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PRIMARY
CHEBI
3223
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PRIMARY
DAILYMED
TK65WKS8HL
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PRIMARY
MERCK INDEX
m2777
Created by admin on Mon Mar 31 18:12:28 GMT 2025 , Edited by admin on Mon Mar 31 18:12:28 GMT 2025
PRIMARY Merck Index
ChEMBL
CHEMBL49
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PRIMARY
PUBCHEM
2477
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PRIMARY
EVMPD
SUB05992MIG
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PRIMARY
IUPHAR
36
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PRIMARY
RXCUI
1827
Created by admin on Mon Mar 31 18:12:28 GMT 2025 , Edited by admin on Mon Mar 31 18:12:28 GMT 2025
PRIMARY RxNorm
DRUG CENTRAL
437
Created by admin on Mon Mar 31 18:12:28 GMT 2025 , Edited by admin on Mon Mar 31 18:12:28 GMT 2025
PRIMARY
MESH
D002065
Created by admin on Mon Mar 31 18:12:28 GMT 2025 , Edited by admin on Mon Mar 31 18:12:28 GMT 2025
PRIMARY
ECHA (EC/EINECS)
253-072-2
Created by admin on Mon Mar 31 18:12:28 GMT 2025 , Edited by admin on Mon Mar 31 18:12:28 GMT 2025
PRIMARY
WIKIPEDIA
BUSPIRONE
Created by admin on Mon Mar 31 18:12:28 GMT 2025 , Edited by admin on Mon Mar 31 18:12:28 GMT 2025
PRIMARY
NCI_THESAURUS
C62013
Created by admin on Mon Mar 31 18:12:28 GMT 2025 , Edited by admin on Mon Mar 31 18:12:28 GMT 2025
PRIMARY
INN
3456
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PRIMARY
FDA UNII
TK65WKS8HL
Created by admin on Mon Mar 31 18:12:28 GMT 2025 , Edited by admin on Mon Mar 31 18:12:28 GMT 2025
PRIMARY
DRUG BANK
DB00490
Created by admin on Mon Mar 31 18:12:28 GMT 2025 , Edited by admin on Mon Mar 31 18:12:28 GMT 2025
PRIMARY
EPA CompTox
DTXSID2022707
Created by admin on Mon Mar 31 18:12:28 GMT 2025 , Edited by admin on Mon Mar 31 18:12:28 GMT 2025
PRIMARY
LACTMED
Buspirone
Created by admin on Mon Mar 31 18:12:28 GMT 2025 , Edited by admin on Mon Mar 31 18:12:28 GMT 2025
PRIMARY
Related Record Type Details
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
TARGET->PARTIAL AGONIST
BINDER->LIGAND
BINDING
TARGET -> INHIBITOR
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
Related Record Type Details
METABOLITE -> PARENT
METABOLITE -> PARENT
METABOLITE -> PARENT
METABOLITE ACTIVE -> PARENT
METABOLITE ACTIVE -> PARENT
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ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC