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Details

Stereochemistry ACHIRAL
Molecular Formula C21H31N5O2
Molecular Weight 385.5031
Optical Activity UNSPECIFIED
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
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

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
24.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
BUSPIRONE HYDROCHLORIDE
PubMed

PubMed

TitleDatePubMed
[Efficacy and withdrawal of clobazam, lorazepam and buspirone in the treatment of anxiety disorders].
1996 Nov-Dec
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
Possible serotonin syndrome associated with buspirone added to fluoxetine.
2000 Jul-Aug
Cerebellar Ataxia.
2000 May
Effects of serotoninergic drugs on tremor induced by physostigmine in rats.
2000 May
Involvement of 5-hydroxytryptamine(1A) receptors in nicotine-induced tail tremor in rats.
2000 Nov 10
Controversies in dyspepsia.
2001
Separation anxiety disorder in children and adolescents: epidemiology, diagnosis and management.
2001
Contemporary management of comorbid anxiety and depression in geriatric patients.
2001
New developments in the pharmacotherapy of alcohol dependence.
2001
Synthesis and pharmacological evaluation of aryl/heteroaryl piperazinyl alkyl benzotriazoles as ligands for some serotonin and dopamine receptor subtypes.
2001 Apr
Molecular dynamics of buspirone analogues interacting with the 5-HT1A and 5-HT2A serotonin receptors.
2001 Apr
Review of pharmacokinetic and pharmacodynamic interaction studies with citalopram.
2001 Aug
Ataxia from lithium toxicity successfully treated with high-dose buspirone: a single-case experimental design.
2001 Aug
Effect of nonnicotine pharmacotherapy on smoking behavior.
2001 Dec
Extracellular serotonin is enhanced in the striatum, but not in the dorsal hippocampus or prefrontal cortex, in rats subjected to an operant conflict procedure.
2001 Feb
Acute hypokalemic paralysis associated with long-term lithium therapy.
2001 Feb
Citalopram-induced bruxism.
2001 Feb
Treatment of the agitation of late-life psychosis and Alzheimer's disease.
2001 Jan
Recovery from chronic fatigue syndrome associated with changes in neuroendocrine function.
2001 Jan
Pharmacokinetics of buspirone extended-release tablets: a single-dose study.
2001 Jul
Serotonin-based pharmacotherapy for acute neuroleptic-induced akathisia: a new approach to an old problem.
2001 Jul
An investigation of the mechanisms responsible for acute fluoxetine-induced anxiogenic-like effects in mice.
2001 Jun
Discriminative stimulus properties of indorenate in a conditioned taste aversion paradigm.
2001 Mar
Generalized anxiety disorder in children and adolescents.
2001 Mar
Pharmacologic treatment of generalized anxiety disorder.
2001 Mar
S 14506: novel receptor coupling at 5-HT(1A) receptors.
2001 Mar
Conformational analysis and pharmacophore design for selected 1-(2-pyrimidinyl)piperazine derivatives with sedative-hypnotic activity.
2001 Mar-Apr
Compounds with affinity for serotonergic receptors in the treatment of premenstrual dysphoria: a comparison of buspirone, nefazodone and placebo.
2001 May
5-HT1A receptor activation and antidepressant-like effects: F 13714 has high efficacy and marked antidepressant potential.
2001 May 25
Neuropharmacological analysis of the role of the serotoninergic system in forming hyperalgesia in neurotic rats.
2001 May-Jun
Acoustic startle, conditioned startle potentiation and the effects of 8-OH-DPAT and buspirone in rats selectively bred for differences in 8-OH-DPAT-induced hypothermia.
2001 Nov
Quantifying the 5-HT1A agonist action of buspirone in man.
2001 Nov
Astrocyte-mediated trophic support of developing serotonin neurons: effects of ethanol, buspirone, and S100B.
2001 Nov 26
The effect of glucocorticoids on the anxiolytic efficacy of buspirone.
2001 Oct
Effectiveness of pharmacotherapy for body dysmorphic disorder: a chart-review study.
2001 Sep
Tandospirone potentiates the fluoxetine-induced increases in extracellular dopamine via 5-HT(1A) receptors in the rat medial frontal cortex.
2002 Apr
Olfactory-mediated fear-potentiated startle.
2002 Feb
Bupropion-induced acute dystonia.
2002 Feb
Light-enhanced startle: further pharmacological and behavioral characterization.
2002 Jan
Effect of drug proportion and mixing time on the content uniformity of a low dose drug in a high shear mixer.
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
Contact leukoderma caused by buspirone patches.
2002 Mar
Patents

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
Created
by admin
on Tue Oct 22 00:21:21 UTC 2019
Edited
by admin
on Tue Oct 22 00:21:21 UTC 2019
Record UNII
TK65WKS8HL
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
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
GEN-BUSPIRONE
Brand Name English
Classification Tree Code System Code
WHO-VATC QN05BE01
Created by admin on Tue Oct 22 00:21:21 UTC 2019 , Edited by admin on Tue Oct 22 00:21:21 UTC 2019
LIVERTOX 129
Created by admin on Tue Oct 22 00:21:21 UTC 2019 , Edited by admin on Tue Oct 22 00:21:21 UTC 2019
WHO-ATC N05BE01
Created by admin on Tue Oct 22 00:21:21 UTC 2019 , Edited by admin on Tue Oct 22 00:21:21 UTC 2019
NCI_THESAURUS C28197
Created by admin on Tue Oct 22 00:21:21 UTC 2019 , Edited by admin on Tue Oct 22 00:21:21 UTC 2019
Code System Code Type Description
CAS
36505-84-7
Created by admin on Tue Oct 22 00:21:21 UTC 2019 , Edited by admin on Tue Oct 22 00:21:21 UTC 2019
PRIMARY
MERCK INDEX
M2777
Created by admin on Tue Oct 22 00:21:21 UTC 2019 , Edited by admin on Tue Oct 22 00:21:21 UTC 2019
PRIMARY Merck Index
ChEMBL
CHEMBL49
Created by admin on Tue Oct 22 00:21:21 UTC 2019 , Edited by admin on Tue Oct 22 00:21:21 UTC 2019
PRIMARY
PUBCHEM
2477
Created by admin on Tue Oct 22 00:21:21 UTC 2019 , Edited by admin on Tue Oct 22 00:21:21 UTC 2019
PRIMARY
EVMPD
SUB05992MIG
Created by admin on Tue Oct 22 00:21:21 UTC 2019 , Edited by admin on Tue Oct 22 00:21:21 UTC 2019
PRIMARY
IUPHAR
36
Created by admin on Tue Oct 22 00:21:21 UTC 2019 , Edited by admin on Tue Oct 22 00:21:21 UTC 2019
PRIMARY
RXCUI
1827
Created by admin on Tue Oct 22 00:21:21 UTC 2019 , Edited by admin on Tue Oct 22 00:21:21 UTC 2019
PRIMARY RxNorm
MESH
D002065
Created by admin on Tue Oct 22 00:21:21 UTC 2019 , Edited by admin on Tue Oct 22 00:21:21 UTC 2019
PRIMARY
ECHA (EC/EINECS)
253-072-2
Created by admin on Tue Oct 22 00:21:21 UTC 2019 , Edited by admin on Tue Oct 22 00:21:21 UTC 2019
PRIMARY
WIKIPEDIA
BUSPIRONE
Created by admin on Tue Oct 22 00:21:21 UTC 2019 , Edited by admin on Tue Oct 22 00:21:21 UTC 2019
PRIMARY
NCI_THESAURUS
C62013
Created by admin on Tue Oct 22 00:21:21 UTC 2019 , Edited by admin on Tue Oct 22 00:21:21 UTC 2019
PRIMARY
INN
3456
Created by admin on Tue Oct 22 00:21:21 UTC 2019 , Edited by admin on Tue Oct 22 00:21:21 UTC 2019
PRIMARY
DRUG BANK
DB00490
Created by admin on Tue Oct 22 00:21:21 UTC 2019 , Edited by admin on Tue Oct 22 00:21:21 UTC 2019
PRIMARY
LactMed
36505-84-7
Created by admin on Tue Oct 22 00:21:21 UTC 2019 , Edited by admin on Tue Oct 22 00:21:21 UTC 2019
PRIMARY
EPA CompTox
36505-84-7
Created by admin on Tue Oct 22 00:21:21 UTC 2019 , Edited by admin on Tue Oct 22 00:21:21 UTC 2019
PRIMARY
Related Record Type Details
TARGET->PARTIAL AGONIST
METABOLIC ENZYME -> SUBSTRATE
BINDER->LIGAND
BINDING
TARGET -> INHIBITOR
METABOLIC ENZYME -> SUBSTRATE
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC