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
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
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 |
DescriptionCurator'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
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.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL214 |
24.0 nM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | BUSPIRONE HYDROCHLORIDE Approved UseBuspirone 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 Date2001 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
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1.711 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11504277 |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11504277 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
9.402 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11504277 |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11504277 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
3.062 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11504277 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
14% |
BUSPIRONE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 3.0 |
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 |
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minor | ||||
minor |
PubMed
Title | Date | PubMed |
---|---|---|
Effect of buspirone on sexual dysfunction in depressed patients treated with selective serotonin reuptake inhibitors. | 1999 Jun |
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5-HT1A receptor agonists buspirone and gepirone attenuate apomorphine-induced aggressive behaviour in adult male Wistar rats. | 2000 Dec |
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Synthesis and pharmacological evaluation of aryl/heteroaryl piperazinyl alkyl benzotriazoles as ligands for some serotonin and dopamine receptor subtypes. | 2001 Apr |
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Switching from benzodiazepines to buspirone using a tapered overlap method in generalized anxiety disorder. | 2001 Aug |
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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 |
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Effect of nonnicotine pharmacotherapy on smoking behavior. | 2001 Dec |
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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 |
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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 |
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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 |
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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 |
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3339401
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
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on
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Record UNII |
TK65WKS8HL
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Validated (UNII)
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WHO-VATC |
QN05BE01
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LIVERTOX |
NBK547966
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WHO-ATC |
N05BE01
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NCI_THESAURUS |
C28197
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36505-84-7
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m2777
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CHEMBL49
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BUSPIRONE
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DB00490
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Buspirone
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Related Record | Type | Details | ||
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METABOLIC ENZYME -> SUBSTRATE | |||
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METABOLIC ENZYME -> SUBSTRATE | |||
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TARGET->PARTIAL AGONIST |
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BINDER->LIGAND |
BINDING
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TARGET -> INHIBITOR | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT |
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METABOLITE -> PARENT |
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METABOLITE -> PARENT |
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METABOLITE -> PARENT | |||
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METABOLITE ACTIVE -> PARENT |
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METABOLITE ACTIVE -> PARENT |
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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Volume of Distribution | PHARMACOKINETIC |
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