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
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
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 |
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 |
---|---|---|---|---|
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 |
||
minor | ||||
minor |
PubMed
Title | Date | PubMed |
---|---|---|
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 |
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
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Record UNII |
207LT9J9OC
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Validated (UNII)
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NCI_THESAURUS |
C28197
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DBSALT000313
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Related Record | Type | Details | ||
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PARENT -> SALT/SOLVATE |
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Related Record | Type | Details | ||
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IMPURITY -> PARENT |
impurity detected at UV 240 nm
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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||
|
IMPURITY -> PARENT |
Impurity detected at UV 210 nm
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
||
|
IMPURITY -> PARENT |
impurity detected at UV 240 nm
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
||
|
IMPURITY -> PARENT |
impurity detected at UV 240 nm
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
||
|
IMPURITY -> PARENT |
impurity detected at UV 240 nm
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
||
|
IMPURITY -> PARENT |
impurity detected at UV 240 nm
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
||
|
IMPURITY -> PARENT |
impurity detected at UV 210 nm
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
||
|
IMPURITY -> PARENT |
impurity detected at UV 240 nm
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
||
|
IMPURITY -> PARENT |
impurity detected at UV 240 nm
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
||
|
IMPURITY -> PARENT |
Impurity detected at UV 210 nm
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
||
|
IMPURITY -> PARENT |
impurity detected at UV 240 nm
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
||
|
IMPURITY -> PARENT |
impurity detected at UV 240 nm
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
||
|
IMPURITY -> PARENT |
impurity detected at UV 240 nm
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
||
|
IMPURITY -> PARENT |
Impurity detected at UV 210 nm
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
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