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Details

Stereochemistry ACHIRAL
Molecular Formula C21H31N5O2.ClH
Molecular Weight 421.964
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Buspirone hydrochloride

SMILES

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

InChI

InChIKey=RICLFGYGYQXUFH-UHFFFAOYSA-N
InChI=1S/C21H31N5O2.ClH/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;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 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
Pharmacotherapy of generalized anxiety disorder.
2001
A comparative multidose pharmacokinetic study of buspirone extended-release tablets with a reference immediate-release product.
2001 Aug
The impact of impulsivity on cocaine use and retention in treatment.
2001 Dec
Behavioral effects of buspirone in the marmoset employing a predator confrontation test of fear and anxiety.
2001 Feb
Effect of citalopram and buspirone on the antinociceptive action of analgesic drugs.
2001 Jul-Aug
Behavioral and biochemical effects of L-tryptophan and buspirone in a model of cerebellar atrophy.
2001 Jul-Aug
Generalized anxiety disorder in children and adolescents.
2001 Mar
Neuropharmacological analysis of the role of the serotoninergic system in forming hyperalgesia in neurotic rats.
2001 May-Jun
Buspirone and meperidine synergistically reduce the shivering threshold.
2001 Nov
Small platform stress increases exploratory activity of mice in staircase test.
2001 Oct
Hypomania induced by herbal and pharmaceutical psychotropic medicines following mild traumatic brain injury.
2002 Apr
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 18:09:11 GMT 2025
Edited
by admin
on Mon Mar 31 18:09:11 GMT 2025
Record UNII
207LT9J9OC
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
Buspirone hydrochloride
EP   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN  
Official Name English
BUSPAR
Preferred Name English
8-Azaspiro[4.5]decane-7,9-dione, 8-[4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl]-, monohydrochloride
Systematic Name English
Buspirone hydrochloride [MART.]
Common Name English
MJ 9022-1
Code English
Buspirone hydrochloride [VANDF]
Common Name English
Buspirone hydrochloride [WHO-DD]
Common Name English
Buspirone hydrochloride [USP-RS]
Common Name English
Buspirone hydrochloride [ORANGE BOOK]
Common Name English
Buspirone hydrochloride [EP MONOGRAPH]
Common Name English
N-[4-[4-(2-Pyrimidinyl)-1-piperazinyl]butyl]-1,1-cyclopentanediacetamide monohydrochloride
Systematic Name English
1,1-Cyclopentanediacetimide, N-[4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl]-, monohydrochloride
Systematic Name English
APD-405
Code English
Buspirone HCL
Common Name English
APD405
Code English
Buspirone hydrochloride [USAN]
Common Name English
NSC-759571
Code English
Buspirone hydrochloride [MI]
Common Name English
Buspirone hydrochloride [USP MONOGRAPH]
Common Name English
NSC-751138
Code English
MJ-9022-1
Code English
Buspirone hydrochloride[JAN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C28197
Created by admin on Mon Mar 31 18:09:11 GMT 2025 , Edited by admin on Mon Mar 31 18:09:11 GMT 2025
Code System Code Type Description
RS_ITEM_NUM
1078802
Created by admin on Mon Mar 31 18:09:11 GMT 2025 , Edited by admin on Mon Mar 31 18:09:11 GMT 2025
PRIMARY
NSC
759571
Created by admin on Mon Mar 31 18:09:11 GMT 2025 , Edited by admin on Mon Mar 31 18:09:11 GMT 2025
PRIMARY
MERCK INDEX
m2777
Created by admin on Mon Mar 31 18:09:11 GMT 2025 , Edited by admin on Mon Mar 31 18:09:11 GMT 2025
PRIMARY Merck Index
ECHA (EC/EINECS)
251-489-4
Created by admin on Mon Mar 31 18:09:11 GMT 2025 , Edited by admin on Mon Mar 31 18:09:11 GMT 2025
PRIMARY
NSC
751138
Created by admin on Mon Mar 31 18:09:11 GMT 2025 , Edited by admin on Mon Mar 31 18:09:11 GMT 2025
PRIMARY
FDA UNII
207LT9J9OC
Created by admin on Mon Mar 31 18:09:11 GMT 2025 , Edited by admin on Mon Mar 31 18:09:11 GMT 2025
PRIMARY
RXCUI
203116
Created by admin on Mon Mar 31 18:09:11 GMT 2025 , Edited by admin on Mon Mar 31 18:09:11 GMT 2025
PRIMARY RxNorm
EPA CompTox
DTXSID1037193
Created by admin on Mon Mar 31 18:09:11 GMT 2025 , Edited by admin on Mon Mar 31 18:09:11 GMT 2025
PRIMARY
EVMPD
SUB00906MIG
Created by admin on Mon Mar 31 18:09:11 GMT 2025 , Edited by admin on Mon Mar 31 18:09:11 GMT 2025
PRIMARY
ChEMBL
CHEMBL49
Created by admin on Mon Mar 31 18:09:11 GMT 2025 , Edited by admin on Mon Mar 31 18:09:11 GMT 2025
PRIMARY
CAS
33386-08-2
Created by admin on Mon Mar 31 18:09:11 GMT 2025 , Edited by admin on Mon Mar 31 18:09:11 GMT 2025
PRIMARY
SMS_ID
100000091051
Created by admin on Mon Mar 31 18:09:11 GMT 2025 , Edited by admin on Mon Mar 31 18:09:11 GMT 2025
PRIMARY
DAILYMED
207LT9J9OC
Created by admin on Mon Mar 31 18:09:11 GMT 2025 , Edited by admin on Mon Mar 31 18:09:11 GMT 2025
PRIMARY
PUBCHEM
36431
Created by admin on Mon Mar 31 18:09:11 GMT 2025 , Edited by admin on Mon Mar 31 18:09:11 GMT 2025
PRIMARY
CHEBI
3224
Created by admin on Mon Mar 31 18:09:11 GMT 2025 , Edited by admin on Mon Mar 31 18:09:11 GMT 2025
PRIMARY
NCI_THESAURUS
C26641
Created by admin on Mon Mar 31 18:09:11 GMT 2025 , Edited by admin on Mon Mar 31 18:09:11 GMT 2025
PRIMARY
DRUG BANK
DBSALT000313
Created by admin on Mon Mar 31 18:09:11 GMT 2025 , Edited by admin on Mon Mar 31 18:09:11 GMT 2025
PRIMARY
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IMPURITY -> PARENT
impurity detected at UV 240 nm
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IMPURITY -> PARENT
impurity detected at UV 240 nm
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IMPURITY -> PARENT
impurity detected at UV 240 nm
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT
Impurity detected at UV 210 nm
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ACTIVE MOIETY