Identification

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Name
Buspirone
Accession Number
DB00490  (APRD00222)
Type
Small Molecule
Groups
Approved, Investigational
Description

Buspirone is a novel anxiolytic agent with a unique structure and a pharmacological profile. Belonging to the azaspirodecanedione drug class,2 buspirone is a serotonin 5-HT1A receptor agonist that is not chemically or pharmacologically related to benzodiazepines, barbiturates, and other sedative/anxiolytic drugs.13 Unlike many drugs used to treat anxiety, buspirone does not exhibit anticonvulsant, sedative, hypnotic, and muscle-relaxant properties. Due to these characteristics, buspirone been termed 'anxioselective'.1 First synthesized in 1968 then patented in 1975,10 it is commonly marketed under the brand name Buspar®. Buspirone was first approved in 1986 by the FDA 4 and has been used to treat anxiety disorders, such as generalized anxiety disorder (GAD), and relieve symptoms of anxiety. It has also been used as a second-line therapy for unipolar depression when the use of selective serotonin reuptake inhibitors (SSRIs) is deemed clinically inadequate or inappropriate.10 The potential use of buspirone in combination with melatonin in depression and cognitive impairment via promoting neurogenesis has also been investigated.4

Structure
Thumb
Synonyms
  • 8-(4-(4-(2-Pyrimidinyl)-1-piperizinyl)butyl)-8-azaspiro(4,5)decane-7,9-dione
  • Buspiron
  • Buspirona
  • Buspirone
  • Buspironum
External IDs
BCI-024 / MJ 90221-1
Product Ingredients
IngredientUNIICASInChI Key
Buspirone hydrochloride207LT9J9OC33386-08-2RICLFGYGYQXUFH-UHFFFAOYSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
BusparTablet10 mg/1OralBristol Myers Squibb2009-06-012011-03-31Us
BusparTablet15 mg/1OralPhysicians Total Care, Inc.2001-08-312011-05-31Us
BusparTablet10 mg/1OralPhysicians Total Care, Inc.1995-02-142011-05-31Us
BusparTablet5 mg/1OralBristol Myers Squibb2009-06-012012-01-31Us
BusparTablet5 mg/1OralPhysicians Total Care, Inc.1995-07-312011-05-31Us
BusparTablet30 mg/1OralBristol Myers Squibb2009-06-012011-05-31Us
BusparTablet15 mg/1OralBristol Myers Squibb2009-06-012011-05-31Us
Buspar Tab 10mgTabletOralBristol Myers Squibb1989-12-312010-11-12Canada
BuspironeTablet10 mgOralSanis Health Inc2016-02-17Not applicableCanada
Buspirone HydrochlorideTablet10 mg/1OralETHEX2007-04-18Not applicableUs
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-buspirone - Tab 10mgTabletOralApotex Corporation1996-12-31Not applicableCanada
BusparTablet5 mg/1OralDirectrx2016-05-03Not applicableUs
BuspironeTablet10 mg/1OralStat Rx USA2002-03-01Not applicableUs
Buspirone HClTablet5 mg/1OralLake Erie Medical Dba Quality Care Produts Llc2001-03-28Not applicableUs
Buspirone HClTablet10 mg/1OralPd Rx Pharmaceuticals, Inc.2001-03-282017-10-03Us
Buspirone HClTablet10 mg/1OralImpax Generics2016-11-012020-08-31Us
Buspirone HClTablet10 mg/1OralDispensing Solutions, Inc.2001-03-28Not applicableUs
Buspirone HClTablet15 mg/1OralActavis Pharma Company2002-03-132019-03-31Us
busPIRone HClTablet5 mg/1OralAmneal Pharmaceuticals NY LLC2017-05-24Not applicableUs
Buspirone HClTablet5 mg/1Oralbryant ranch prepack2001-03-28Not applicableUs63629 319720180907 15195 16m50xb
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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International/Other Brands
Ansial (Rontag) / Anxiron (Valeant) / Anxut (Eisai) / Bespar / Buscalm (Wockhardt) / Busp (Hexal) / Buspon (Deva) / Dalpas (Biotech) / Epsilat (Coup) / Pasrin (Aspen Pharmacare) / Spamilan (Anpharm)
Categories
UNII
TK65WKS8HL
CAS number
36505-84-7
Weight
Average: 385.5031
Monoisotopic: 385.247775261
Chemical Formula
C21H31N5O2
InChI Key
QWCRAEMEVRGPNT-UHFFFAOYSA-N
InChI
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
IUPAC Name
8-{4-[4-(pyrimidin-2-yl)piperazin-1-yl]butyl}-8-azaspiro[4.5]decane-7,9-dione
SMILES
O=C1CC2(CCCC2)CC(=O)N1CCCCN1CCN(CC1)C1=NC=CC=N1

Pharmacology

Indication

Indicated for the management of anxiety disorders or the short-term relief of the symptoms of anxiety.13

Associated Conditions
Pharmacodynamics

The clinical effect of buspirone in alleviating the symptoms of generalized anxiety disorders typically takes 2 to 4 weeks to achieve.10 The delayed onset of action of buspirone suggests that the therapeutic effectiveness in generalized anxiety may involved more than its molecular mechanism of action at the 5-HT1A receptors,9 or buspirone may induce adaptations of 5-HT1A receptors.10 Buspirone was not shown to alter the psychomotor or cognitive function in healthy volunteers, and the risk of developing sedation is relatively low compared to other anxiolytics, such as benzodiazepines.1 Unlike benzodiazepines and barbiturates used in anxiety disorders, buspirone is not associated with a risk for developing physical dependence or withdrawal, or any significant interaction with central nervous system depressants such as ethanol. This is due to the lack of effects on GABA receptors.1,10 Buspirone also does not exhibit any anticonvulsant or muscle-relaxing properties,5 but may interfere with arousal reactions due to its inhibitory action on the aactivity of noradrenergic locus coerulus neurons.9

Despite its clinical effectiveness in generalized anxiety, buspirone demonstrated limited clinical effectiveness on panic disorders, severe anxiety, phobias, and obsessive compulsive disorders.4,9 The clinical effectiveness of the long-term use of buspirone, for more than 3 to 4 weeks, has not demonstrated in controlled trials but there were no observable significant adverse events in patients receiving buspirone for a year in a study of long-term use.13

Mechanism of action

The therapeutic action of buspirone in generalized anxiety disorders is thought to be mainly derived from its interaction with two major 5-HT1A receptor subtypes that are involved in the brain's anxiety and fear circuitry to enhance the serotonergic activity in these brain areas.10 Buspirone acts as a full agonist at presynaptic 5-HT1A receptors, or 5-HT1A autoreceptors, expressed at dorsal raphe while acting as a partial agonist at the postsynaptic 5-HT1A receptors expressed on hippocampus and cortex.7,8 5-HT1A receptors function as inhibitory autoreceptors by being expressed on the soma or dendrites of serotonergic neurons or mediate postsynaptic actions of 5-HT by being highly expressed on the corticolimbic circuits.9 They are inhibitory G-protein coupled receptors that couple to Gi/Go proteins. When activated, presynaptic 5-HT1A autoreceptors causes neuron hyperpolarization and reduces the firing rate of the serotonergic neuron, thereby decreasing extracellular 5-HT levels in the neuron's projection areas. Activated postsynaptic 5-HT1A receptors promote hyperpolarization to released 5-HT on pyramidal neurons.8

The anxiolytic action of buspirone is mainly thought to arise from the interaction at presynaptic 5-HT1A autoreceptors. Acting as a potent agonist in these receptors, buspirone initially causes activation of these autoreceptors and inhibition of 5-HT release. It is proposed that buspirone induces desensitization of somatodendritic autoreceptors over time, which may explain the delayed onset of action of the drug. Desensitization of the autoreceptors ultimately results in heightened excitation of serotonergic neurons and enhanced 5-HT release.9 Buspirone also displays a weak affinity for serotonin 5HT2 receptors and acts as a weak antagonist on dopamine D2 autoreceptors,10 although there is not much evidence that the action at these receptors contribute to the anxiolytic effect of buspirone.6 It acts as an antagonist at presynaptic dopamine D3 and D4 receptors and may bind to alpha-1 adrenergic receptors as a partial agonist.4

TargetActionsOrganism
A5-hydroxytryptamine receptor 1A
partial agonist
Humans
ADopamine D2 receptor
antagonist
Humans
UDopamine D3 receptor
antagonist
Humans
UDopamine D4 receptor
antagonist
Humans
UAlpha-1 adrenergic receptors
partial agonist
Humans
Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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Absorption

Buspirone is rapidly absorbed following oral administration.13 Bioavailability is low and variable (approximately 5%) due to extensive first pass metabolism. While absorption of buspirone is decreased with concomitant food intake, the first-pass metabolism of the drug is also decreased, resulting in an increased bioavailability 10 as well as increased Cmax and AUC.13 Following oral administration of single oral doses of 20 mg, the Cmax ranged from 1 to 6 ng/mL and the Tmax ranged from 40 to 90 minutes.13

Volume of distribution

In a pharmacokinetic study assessing buspirone over the dose range of 10 to 40 mg, the volume of distribution was 5.3 L/kg.3

Protein binding

Based on the findings of an in vitro protein binding study, approximately 86% of buspirone is bound to plasma proteins.13 It is mainly bound to serum albumin and alpha-1-acid glycoprotein.2

Metabolism

Buspirone is extensively metabolized upon administration, where it primarily undergoes hepatic oxidation mediated by the CYP3A4 enzyme. Hydroxylated derivatives are produced, including a pharmacologically active metabolite 1-pyrimidinylpiperazine (1-PP). In animal studies, 1-PP possessed about one quarter of the pharmacological activity of buspirone.13

Route of elimination

A single-dose pharmacokinetic studies using 14C-labeled buspirone demonstrated that about 29-63% of the dose administered was excreted in the urine within 24 hours, primarily in the form of metabolites. About 18% to 38% of the dose was eliminated via fecal excretion.13

Half life

In a single-dose pharmacokinetic study of 14C-labeled buspirone, the average elimination half-life of unchanged buspirone following administration of single doses ranging from 10 to 40 mg was about 2 to 3 hours.13

Clearance

In a pharmacokinetic study assessing buspirone over the dose range of 10 to 40 mg, the systemic clearance was 1.7 L/h/kg.3

Toxicity

The oral LD50 of buspirone is 196 mg/kg in rat, 655 mg/kg in mouse, 586 mg/kg in dog, and 356 mg/kg in monkey. The intraperitoneal LD50 is 136 mg/kg in rat and 146 mg/kg in mouse.13,11

In clinical pharmacology trials, administration of buspirone at the dose of 375 mg/day resulted in symptoms of nausea, vomiting, dizziness, drowsiness, miosis, and gastric distress. Few cases of overdosage that have been reported usually resulted in complete recovery. In case of overdose, the use of general symptomatic and supportive treatment is recommended along with immediate gastric lavage and monitoring of respiration, pulse, and blood pressure.13

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
(R)-warfarinThe metabolism of Buspirone can be decreased when combined with (R)-warfarin.
(S)-WarfarinThe metabolism of Buspirone can be decreased when combined with (S)-Warfarin.
1-(2-Phenylethyl)-4-phenyl-4-acetoxypiperidineThe metabolism of Buspirone can be decreased when combined with 1-(2-Phenylethyl)-4-phenyl-4-acetoxypiperidine.
1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic AcidThe risk or severity of hypertension can be increased when Buspirone is combined with 1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid.
1-benzylimidazoleThe risk or severity of hypertension can be increased when Buspirone is combined with 1-benzylimidazole.
2,5-Dimethoxy-4-ethylamphetamineThe risk or severity of serotonin syndrome can be increased when Buspirone is combined with 2,5-Dimethoxy-4-ethylamphetamine.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of serotonin syndrome can be increased when Buspirone is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
3,5-diiodothyropropionic acidThe metabolism of Buspirone can be decreased when combined with 3,5-diiodothyropropionic acid.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of serotonin syndrome can be increased when Buspirone is combined with 4-Bromo-2,5-dimethoxyamphetamine.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with Buspirone.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

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  • Evidence Level
    Evidence Level

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  • Action
    Action

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Food Interactions
  • Always take at the same time with respect to meals.
  • Avoid alcohol.
  • Avoid taking grapefruit or grapefruit juice throughout treatment.
  • Take with food.

References

Synthesis Reference
US3717634
General References
  1. Goa KL, Ward A: Buspirone. A preliminary review of its pharmacological properties and therapeutic efficacy as an anxiolytic. Drugs. 1986 Aug;32(2):114-29. doi: 10.2165/00003495-198632020-00002. [PubMed:2874976]
  2. Jann MW: Buspirone: an update on a unique anxiolytic agent. Pharmacotherapy. 1988;8(2):100-16. [PubMed:3041384]
  3. Mahmood I, Sahajwalla C: Clinical pharmacokinetics and pharmacodynamics of buspirone, an anxiolytic drug. Clin Pharmacokinet. 1999 Apr;36(4):277-87. doi: 10.2165/00003088-199936040-00003. [PubMed:10320950]
  4. Howland RH: Buspirone: Back to the Future. J Psychosoc Nurs Ment Health Serv. 2015 Nov;53(11):21-4. doi: 10.3928/02793695-20151022-01. [PubMed:26535760]
  5. Eison AS, Temple DL Jr: Buspirone: review of its pharmacology and current perspectives on its mechanism of action. Am J Med. 1986 Mar 31;80(3B):1-9. doi: 10.1016/0002-9343(86)90325-6. [PubMed:2870639]
  6. Tunnicliff G: Molecular basis of buspirone's anxiolytic action. Pharmacol Toxicol. 1991 Sep;69(3):149-56. [PubMed:1796057]
  7. Yocca FD: Neurochemistry and neurophysiology of buspirone and gepirone: interactions at presynaptic and postsynaptic 5-HT1A receptors. J Clin Psychopharmacol. 1990 Jun;10(3 Suppl):6S-12S. [PubMed:1973941]
  8. Garcia-Garcia AL, Newman-Tancredi A, Leonardo ED: 5-HT(1A) [corrected] receptors in mood and anxiety: recent insights into autoreceptor versus heteroreceptor function. Psychopharmacology (Berl). 2014 Feb;231(4):623-36. doi: 10.1007/s00213-013-3389-x. Epub 2013 Dec 12. [PubMed:24337875]
  9. 43. (2012). In Rang and Dale's Pharmacology (7th ed., pp. 538-539). Edinburgh: Elsevier/Churchill Livingstone. [ISBN:978-0-7020-3471-8]
  10. Buspirone - StatPearls - NCBI Bookshelf [Link]
  11. Buspirone (hydrochloride) Safety Data Sheet - Cayman Chemical [Link]
  12. Buspirone hydrochloride (B7148) - Sigma Aldrich Product Information Sheet [Link]
  13. BuSpar® (buspirone HCl) FDA Label [Link]
External Links
Human Metabolome Database
HMDB0014633
KEGG Drug
D07593
KEGG Compound
C06861
PubChem Compound
2477
PubChem Substance
46508113
ChemSpider
2383
BindingDB
50001859
ChEBI
3223
ChEMBL
CHEMBL49
Therapeutic Targets Database
DAP000031
PharmGKB
PA448689
Guide to Pharmacology
GtP Drug Page
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Buspirone
ATC Codes
N05BE01 — Buspirone
AHFS Codes
  • 28:24.92 — Miscellaneous Anxiolytics Sedatives and Hypnotics

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedTreatmentSclerosis, Progressive Systemic1
0Not Yet RecruitingBasic ScienceSpinal Cord Injuries (SCI)1
1CompletedNot AvailableHealthy Volunteers2
1CompletedNot AvailableTo Determine Bioequivalence Under Fasting Conditions1
1CompletedOtherTo Determine Bioequivalence Under Fed Conditions1
1Not Yet RecruitingTreatmentDrug Effect / Spinal Cord Injuries (SCI)1
1RecruitingTreatmentDependency (Psychology) / Opiate Withdrawal Syndrome / Opioid-Related Disorders / Pain, Chronic1
1RecruitingTreatmentDyskinesias / Movement Disorders / Parkinson's Disease (PD)1
1, 2CompletedBasic ScienceCessation, Smoking / Tobacco Use Cessation1
1, 2CompletedTreatmentAutism, Early Infantile1
1, 2CompletedTreatmentSpinal Cord Injuries (SCI)1
2Active Not RecruitingBasic ScienceSleep Disordered Breathing (SDB) / Spinal Cord Injuries (SCI)1
2CompletedBasic ScienceCannabis Use Disorders1
2CompletedBasic ScienceDependence, Cocaine1
2CompletedTreatmentAnxiety / Parkinson's Disease (PD)1
2CompletedTreatmentAttention Deficit Disorder With Hyperactivity1
2CompletedTreatmentDependence, Cocaine1
2CompletedTreatmentHypoactive Sexual Desire Disorder (HSDD)2
2CompletedTreatmentMajor Depressive Disorder (MDD)2
2CompletedTreatmentMarijuana Abuse1
2CompletedTreatmentMarijuana Abuse / Moods Disorders1
2RecruitingTreatmentAnxiety / Autism Spectrum Conditions/Disorders1
2RecruitingTreatmentGastroparesis1
2TerminatedTreatmentAnxiety Disorders / Depression / Epilepsies / Epilepsy, Localization Related / Seizures1
2WithdrawnTreatmentAutism Spectrum Conditions/Disorders1
2, 3CompletedSupportive CareDyspnea / Pulmonary Complications / Unspecified Adult Solid Tumor, Protocol Specific1
2, 3CompletedTreatmentAutistic Disorder1
3CompletedTreatmentSchizoaffective Disorders / Schizophrenic Disorders1
3RecruitingTreatmentParkinson1
3TerminatedBasic ScienceCentral Apnea / Heart Failure1
3TerminatedTreatmentAcute Ischemic Stroke (AIS)1
3TerminatedTreatmentAnxiety Disorders / Dementias / Depression / Psychosomatic Disorders / Schizophrenic Disorders1
4CompletedTreatmentDepression1
4CompletedTreatmentHeroin Dependence1
4CompletedTreatmentHypothermia1
4CompletedTreatmentIndigestion1
4CompletedTreatmentMarijuana Dependence1
4RecruitingDiagnosticAsthma Bronchial / Asthma: [Nos] or [Attack] / Major Depressive Disorder (MDD)1
4RecruitingOtherAutism Spectrum Conditions/Disorders1
4TerminatedOtherBypass, Gastric1
4Unknown StatusTreatmentMajor Depression Disorder1
4WithdrawnTreatmentAnxiety Disorders1
Not AvailableCompletedBasic ScienceCocaine Use Disorders1
Not AvailableCompletedTreatmentFunctional Dysphagia / Ineffective Esophageal Motility1
Not AvailableEnrolling by InvitationNot AvailableCardiovascular Disease (CVD) / Cardiovascular Risk Factors / High Blood Pressure (Hypertension) / Mental status changes / Sleep Apnea Syndrome / Sleep Bruxism / Sleep disorders and disturbances / Temporomandibular Disorders / Thyroid Dysfunction1
Not AvailableNot Yet RecruitingDiagnosticAnxiety1
Not AvailableRecruitingTreatmentAnxiety / Autism Spectrum Conditions/Disorders1
Not AvailableRecruitingTreatmentTraumatic Brain Injury (TBI)1
Not AvailableUnknown StatusTreatmentAnxiety Disorders1

Pharmacoeconomics

Manufacturers
  • Bristol myers squibb co pharmaceutical research institute
  • Actavis totowa llc
  • Apotex inc
  • Dr reddys laboratories ltd
  • Egis pharmaceuticals
  • Ivax pharmaceuticals inc sub teva pharmaceuticals usa
  • Kv pharmaceutical co
  • Mylan pharmaceuticals inc
  • Sandoz inc
  • Teva pharmaceuticals usa inc
  • Watson laboratories inc
Packagers
  • Advanced Pharmaceutical Services Inc.
  • Amerisource Health Services Corp.
  • Apotex Inc.
  • Apotheca Inc.
  • Apothecon
  • AQ Pharmaceuticals Inc.
  • A-S Medication Solutions LLC
  • Bristol-Myers Squibb Co.
  • Bryant Ranch Prepack
  • BTA Pharmaceuticals
  • Cardinal Health
  • Comprehensive Consultant Services Inc.
  • Corepharma LLC
  • Direct Dispensing Inc.
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • Doctor Reddys Laboratories Ltd.
  • Egis Pharmaceuticals Public Ltd. Co.
  • Ethex Corp.
  • H.E. Butt Grocery Co.
  • Heartland Repack Services LLC
  • Innoviant Pharmacy Inc.
  • Ivax Pharmaceuticals
  • KV Pharmaceutical Co.
  • Lake Erie Medical and Surgical Supply
  • Major Pharmaceuticals
  • Mckesson Corp.
  • Medisca Inc.
  • Murfreesboro Pharmaceutical Nursing Supply
  • Mylan
  • Neuman Distributors Inc.
  • Nucare Pharmaceuticals Inc.
  • Palmetto Pharmaceuticals Inc.
  • Par Pharmaceuticals
  • Patheon Inc.
  • PCA LLC
  • PD-Rx Pharmaceuticals Inc.
  • Pharmaceutical Utilization Management Program VA Inc.
  • Pharmedix
  • Physicians Total Care Inc.
  • Preferred Pharmaceuticals Inc.
  • Prepackage Specialists
  • Prepak Systems Inc.
  • Prx Pharmaceuticals
  • Ranbaxy Laboratories
  • Rebel Distributors Corp.
  • Remedy Repack
  • Resource Optimization and Innovation LLC
  • Sandhills Packaging Inc.
  • Southwood Pharmaceuticals
  • Stat Rx Usa
  • Teva Pharmaceutical Industries Ltd.
  • Torpharm Inc.
  • UDL Laboratories
  • Va Cmop Dallas
  • Vangard Labs Inc.
  • Watson Pharmaceuticals
Dosage forms
FormRouteStrength
TabletOral10 mg/1
TabletOral15 mg/1
TabletOral30 mg/1
TabletOral5 mg/1
TabletOral
TabletOral10 mg
PowderNot applicable1 g/1g
TabletOral10 1/1
TabletOral15 1/1
TabletOral5 1/1
TabletOral7.5 mg/1
Prices
Unit descriptionCostUnit
Wellbutrin xl 300 mg tablet8.68USD tablet
Wellbutrin xl 150 mg tablet6.58USD tablet
Buspar 30 mg tablet5.52USD tablet
Buspirone hcl powder4.74USD g
Buspirone hcl 30 mg tablet3.71USD tablet
Buspar 15 mg tablet3.07USD tablet
Buspirone hcl 15 mg tablet2.16USD tablet
Buspar 10 mg tablet2.05USD tablet
Buspirone hcl 7.5 mg tablet1.62USD tablet
Buspirone hcl 10 mg tablet1.42USD tablet
Buspar 5 mg tablet1.18USD tablet
Vanspar 7.5 mg tablet1.18USD tablet
Buspar 10 mg Tablet1.12USD tablet
Buspirone hcl 5 mg tablet0.79USD tablet
Apo-Buspirone 10 mg Tablet0.62USD tablet
Novo-Buspirone 10 mg Tablet0.62USD tablet
Nu-Buspirone 10 mg Tablet0.62USD tablet
Pms-Buspirone 10 mg Tablet0.62USD tablet
Ratio-Buspirone 10 mg Tablet0.62USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)201.5-202.5Buspirone hydrochloride (B7148) - Sigma Aldrich Product Information Sheet
logP2.63TAKACS-NOVAK,K 1995 (IN PRESS)
Predicted Properties
PropertyValueSource
Water Solubility0.588 mg/mLALOGPS
logP1.95ALOGPS
logP1.78ChemAxon
logS-2.8ALOGPS
pKa (Strongest Basic)7.62ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area69.64 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity108.89 m3·mol-1ChemAxon
Polarizability44.12 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9935
Blood Brain Barrier+0.9839
Caco-2 permeable-0.538
P-glycoprotein substrateSubstrate0.5726
P-glycoprotein inhibitor IInhibitor0.8563
P-glycoprotein inhibitor IINon-inhibitor0.8282
Renal organic cation transporterInhibitor0.598
CYP450 2C9 substrateNon-substrate0.8703
CYP450 2D6 substrateSubstrate0.8918
CYP450 3A4 substrateSubstrate0.6728
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorInhibitor0.8948
CYP450 2D6 inhibitorInhibitor0.7186
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8681
Ames testNon AMES toxic0.6277
CarcinogenicityNon-carcinogens0.8959
BiodegradationNot ready biodegradable0.987
Rat acute toxicity2.8167 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7042
hERG inhibition (predictor II)Inhibitor0.6914
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Mass Spectrum (Electron Ionization)MSsplash10-004i-6940000000-197b8ea9ac79cbda753b
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-000i-0009000000-429c277f63eb2ab52f57
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-000i-0009000000-170a03c9244dada2609b
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00di-0922000000-80c9aa9ae15b661116ad
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00di-1900000000-fafa91d49f01314afdf1
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00dj-4900000000-460409b07d20201af414
MS/MS Spectrum - , positiveLC-MS/MSsplash10-000f-0930000000-081eac0a05abab8fc5fa

Taxonomy

Description
This compound belongs to the class of organic compounds known as n-arylpiperazines. These are organic compounds containing a piperazine ring where the nitrogen ring atom carries an aryl group.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Diazinanes
Sub Class
Piperazines
Direct Parent
N-arylpiperazines
Alternative Parents
Azaspirodecane derivatives / Piperidinediones / Dialkylarylamines / Aminopyrimidines and derivatives / N-alkylpiperazines / Delta lactams / N-substituted carboxylic acid imides / Heteroaromatic compounds / Dicarboximides / Trialkylamines
show 6 more
Substituents
Azaspirodecanedione / N-arylpiperazine / Azaspirodecane / Piperidinedione / Dialkylarylamine / Aminopyrimidine / N-alkylpiperazine / Piperidinone / Delta-lactam / Pyrimidine
show 21 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
N-arylpiperazine, pyrimidines, N-alkylpiperazine, piperidones, azaspiro compound (CHEBI:3223)

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Partial agonist
General Function
Serotonin receptor activity
Specific Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances. Ligand binding causes a conformation change that triggers...
Gene Name
HTR1A
Uniprot ID
P08908
Uniprot Name
5-hydroxytryptamine receptor 1A
Molecular Weight
46106.335 Da
References
  1. de Boer SF, Lesourd M, Mocaer E, Koolhaas JM: Selective antiaggressive effects of alnespirone in resident-intruder test are mediated via 5-hydroxytryptamine1A receptors: A comparative pharmacological study with 8-hydroxy-2-dipropylaminotetralin, ipsapirone, buspirone, eltoprazine, and WAY-100635. J Pharmacol Exp Ther. 1999 Mar;288(3):1125-33. [PubMed:10027850]
  2. Rehman J, Kaynan A, Christ G, Valcic M, Maayani S, Melman A: Modification of sexual behavior of Long-Evans male rats by drugs acting on the 5-HT1A receptor. Brain Res. 1999 Mar 13;821(2):414-25. [PubMed:10064829]
  3. Liang KC: Pre- or post-training injection of buspirone impaired retention in the inhibitory avoidance task: involvement of amygdala 5-HT1A receptors. Eur J Neurosci. 1999 May;11(5):1491-500. [PubMed:10215901]
  4. Becker C, Hamon M, Benoliel JJ: Prevention by 5-HT1A receptor agonists of restraint stress- and yohimbine-induced release of cholecystokinin in the frontal cortex of the freely moving rat. Neuropharmacology. 1999 Apr;38(4):525-32. [PubMed:10221756]
  5. Dupuis DS, Tardif S, Wurch T, Colpaert FC, Pauwels PJ: Modulation of 5-HT1A receptor signalling by point-mutation of cysteine351 in the rat Galpha(o) protein. Neuropharmacology. 1999 Jul;38(7):1035-41. [PubMed:10428422]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  7. Osei-Owusu P, Scrogin KE: Buspirone raises blood pressure through activation of sympathetic nervous system and by direct activation of alpha1-adrenergic receptors after severe hemorrhage. J Pharmacol Exp Ther. 2004 Jun;309(3):1132-40. Epub 2004 Feb 9. [PubMed:14769835]
Details
2. Dopamine D2 receptor
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
Potassium channel regulator activity
Specific Function
Dopamine receptor whose activity is mediated by G proteins which inhibit adenylyl cyclase.
Gene Name
DRD2
Uniprot ID
P14416
Uniprot Name
D(2) dopamine receptor
Molecular Weight
50618.91 Da
References
  1. Malt EA, Olafsson S, Aakvaag A, Lund A, Ursin H: Altered dopamine D2 receptor function in fibromyalgia patients: a neuroendocrine study with buspirone in women with fibromyalgia compared to female population based controls. J Affect Disord. 2003 Jun;75(1):77-82. [PubMed:12781354]
  2. Boido A, Boido CC, Sparatore F: Synthesis and pharmacological evaluation of aryl/heteroaryl piperazinyl alkyl benzotriazoles as ligands for some serotonin and dopamine receptor subtypes. Farmaco. 2001 Apr;56(4):263-75. [PubMed:11421254]
  3. Nader MA, Hannemann M: Interactions of buspirone or gepirone with nicotine on schedule-controlled behavior of pigeons. Behav Pharmacol. 1993 Jun;4(3):263-268. [PubMed:11224194]
  4. Pache DM, Fernandez-Perez S, Sewell RD: Buspirone differentially modifies short-term memory function in a combined delayed matching/non-matching to position task. Eur J Pharmacol. 2003 Sep 23;477(3):205-11. [PubMed:14522358]
  5. Fernandez-Perez S, Pache DM, Sewell RD: Co-administration of fluoxetine and WAY100635 improves short-term memory function. Eur J Pharmacol. 2005 Oct 17;522(1-3):78-83. Epub 2005 Oct 7. [PubMed:16214127]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
G-protein coupled amine receptor activity
Specific Function
Dopamine receptor whose activity is mediated by G proteins which inhibit adenylyl cyclase. Promotes cell proliferation.
Gene Name
DRD3
Uniprot ID
P35462
Uniprot Name
D(3) dopamine receptor
Molecular Weight
44224.335 Da
References
  1. Howland RH: Buspirone: Back to the Future. J Psychosoc Nurs Ment Health Serv. 2015 Nov;53(11):21-4. doi: 10.3928/02793695-20151022-01. [PubMed:26535760]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Sh3 domain binding
Specific Function
Dopamine receptor responsible for neuronal signaling in the mesolimbic system of the brain, an area of the brain that regulates emotion and complex behavior. Its activity is mediated by G proteins ...
Gene Name
DRD4
Uniprot ID
P21917
Uniprot Name
D(4) dopamine receptor
Molecular Weight
48359.86 Da
References
  1. Howland RH: Buspirone: Back to the Future. J Psychosoc Nurs Ment Health Serv. 2015 Nov;53(11):21-4. doi: 10.3928/02793695-20151022-01. [PubMed:26535760]
Kind
Protein group
Organism
Humans
Pharmacological action
Unknown
Actions
Partial agonist
General Function
Protein heterodimerization activity
Specific Function
This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) prot...

Components:
References
  1. Howland RH: Buspirone: Back to the Future. J Psychosoc Nurs Ment Health Serv. 2015 Nov;53(11):21-4. doi: 10.3928/02793695-20151022-01. [PubMed:26535760]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Zhu M, Zhao W, Jimenez H, Zhang D, Yeola S, Dai R, Vachharajani N, Mitroka J: Cytochrome P450 3A-mediated metabolism of buspirone in human liver microsomes. Drug Metab Dispos. 2005 Apr;33(4):500-7. Epub 2005 Jan 7. [PubMed:15640381]
  2. Lamberg TS, Kivisto KT, Neuvonen PJ: Concentrations and effects of buspirone are considerably reduced by rifampicin. Br J Clin Pharmacol. 1998 Apr;45(4):381-5. doi: 10.1046/j.1365-2125.1998.t01-1-00698.x. [PubMed:9578186]
  3. Flockhart Table of Drug Interactions [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxygen binding
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP3A5
Uniprot ID
P20815
Uniprot Name
Cytochrome P450 3A5
Molecular Weight
57108.065 Da
References
  1. Zhu M, Zhao W, Jimenez H, Zhang D, Yeola S, Dai R, Vachharajani N, Mitroka J: Cytochrome P450 3A-mediated metabolism of buspirone in human liver microsomes. Drug Metab Dispos. 2005 Apr;33(4):500-7. Epub 2005 Jan 7. [PubMed:15640381]
  2. Flockhart Table of Drug Interactions [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxygen binding
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP3A7
Uniprot ID
P24462
Uniprot Name
Cytochrome P450 3A7
Molecular Weight
57525.03 Da
References
  1. Flockhart Table of Drug Interactions [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Zhu M, Zhao W, Jimenez H, Zhang D, Yeola S, Dai R, Vachharajani N, Mitroka J: Cytochrome P450 3A-mediated metabolism of buspirone in human liver microsomes. Drug Metab Dispos. 2005 Apr;33(4):500-7. Epub 2005 Jan 7. [PubMed:15640381]
  2. Jagestedt M, von Bahr C: [Combination of serotonergic agents resulted in severe adverse effects]. Lakartidningen. 2004 Apr 29;101(18):1618-9. [PubMed:15185539]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Jann MW: Buspirone: an update on a unique anxiolytic agent. Pharmacotherapy. 1988;8(2):100-16. [PubMed:3041384]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
Not Available
Specific Function
Functions as transport protein in the blood stream. Binds various ligands in the interior of its beta-barrel domain. Also binds synthetic drugs and influences their distribution and availability in...
Gene Name
ORM1
Uniprot ID
P02763
Uniprot Name
Alpha-1-acid glycoprotein 1
Molecular Weight
23511.38 Da
References
  1. Jann MW: Buspirone: an update on a unique anxiolytic agent. Pharmacotherapy. 1988;8(2):100-16. [PubMed:3041384]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Mahar Doan KM, Humphreys JE, Webster LO, Wring SA, Shampine LJ, Serabjit-Singh CJ, Adkison KK, Polli JW: Passive permeability and P-glycoprotein-mediated efflux differentiate central nervous system (CNS) and non-CNS marketed drugs. J Pharmacol Exp Ther. 2002 Dec;303(3):1029-37. [PubMed:12438524]
  2. Feng B, Mills JB, Davidson RE, Mireles RJ, Janiszewski JS, Troutman MD, de Morais SM: In vitro P-glycoprotein assays to predict the in vivo interactions of P-glycoprotein with drugs in the central nervous system. Drug Metab Dispos. 2008 Feb;36(2):268-75. doi: 10.1124/dmd.107.017434. Epub 2007 Oct 25. [PubMed:17962372]

Drug created on June 13, 2005 07:24 / Updated on October 18, 2019 21:36