Buspirone

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| _other_data=8-{4-[4-(Pyrimidin-2-yl)piperazin-1-yl]butyl}-8-azaspiro[4.5]decane-7,9-dione

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Buspirone, sold under the brand name Buspar among others, is an anxiolytic, a medication primarily used to treat anxiety disorders, particularly generalized anxiety disorder (GAD).<ref name="AHFS2019">{{#invoke:citation/CS1|citation |CitationClass=web }}</ref><ref name=Wil2018/> It is a serotonin 5-HT_1A receptor partial agonist, increasing action at serotonin receptors in the brain.<ref name="pmid22608068" /> It is taken orally and takes two to six weeks to be fully effective.<ref name=AHFS2019/><ref name=Wil2018/>

Common side effects of buspirone include nausea, headaches, dizziness, and difficulty concentrating.<ref name=AHFS2019/><ref name=BNF76>Template:Cite book</ref> Serious side effects may include movement disorders, serotonin syndrome, and seizures.<ref name=BNF76/> Its use in pregnancy appears to be safe but has not been well studied, and use during breastfeeding has not been well studied either.<ref name=BNF76/><ref name=Preg2019>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>

Buspirone was developed in 1968 and approved for medical use in the United States in 1986.<ref name=AHFS2019/><ref name=Wil2018>Template:Cite journal</ref> It is available as a generic medication.<ref name=BNF76/> In 2022, it was the 54th most commonly prescribed medication in the United States, with more than 12Template:Nbspmillion prescriptions.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref><ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> Template:TOC limit

Medical uses

Anxiety

Buspirone is used for the short-term and long-term treatment of anxiety disorders or symptoms of anxiety.<ref name=DM>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref><ref name=TGA>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref><ref name=AMH>Template:Cite book</ref><ref name=EMC>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref><ref name=BNF>Template:Cite book</ref> It is generally preferred over benzodiazepines because it does not activate the receptors that make drugs like alprazolam addictive.<ref name=Wil2018/>

Buspirone has no immediate anxiolytic effects, and hence has a delayed onset of action; its full clinical effectiveness may require 2–4 weeks to manifest itself.<ref name="SadockSadock2014">Template:Cite book</ref> The drug is similarly effective in the treatment of generalized anxiety disorder (GAD) to benzodiazepines including diazepam, alprazolam, lorazepam, and clorazepate.<ref name="pmid22608068" /> Buspirone is not known to be effective in the treatment of other anxiety disorders besides GAD.<ref name="pmid26535760">Template:Cite journal</ref>

Other uses

Sexual dysfunction

There is some evidence that buspirone on its own may be useful in the treatment of hypoactive sexual desire disorder (HSDD) in women.<ref name="pmid27916394">Template:Cite journal</ref> Buspirone may also be effective in treating antidepressant-induced sexual dysfunction.<ref name=Wil2018/><ref name="pmid34247952">Template:Cite journal</ref><ref name="pmid31591339">Template:Cite journal</ref>

Miscellaneous

Buspirone is not effective as a treatment for benzodiazepine withdrawal, barbiturate withdrawal, or alcohol withdrawal.<ref>Template:Cite journal</ref>

SSRI and SNRI antidepressants such as paroxetine and venlafaxine, respectively, may cause jaw pain/jaw spasm reversible syndrome, although it is not common, and buspirone appears to be successful in treating antidepressant-induced bruxism.<ref>Template:Cite journal</ref><ref>Template:Cite journal</ref>

Contraindications

Buspirone has these contraindications:<ref name=mono>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref><ref name="Gelder">Template:Cite book</ref>

• Hypersensitivity to buspirone
• Metabolic acidosis, as in diabetes
• Should not be used with MAO inhibitors
• Severely compromised liver or kidney function

Side effects

{{#invoke:Labelled list hatnote|labelledList|Main article|Main articles|Main page|Main pages}}

Known side effects associated with buspirone include dizziness, headaches, nausea, tinnitus, and paresthesia.<ref name="pmid22608068" /> Buspirone is relatively well tolerated and is not associated with sedation, cognitive and psychomotor impairment, muscle relaxation, physical dependence, or anticonvulsant effects.<ref name="pmid22608068" /> In addition, buspirone does not produce euphoria<ref name="SadockSadock2014" /> and is not a drug of abuse.<ref name=TGA/>

Overdose

Buspirone appears to be relatively benign in cases of single-drug overdose, although no definitive data on this subject appear to be available.<ref name="FultonBrogden1997">Template:Cite journal</ref> In one clinical trial, buspirone was administered to healthy male volunteers at a dosage of 375 mg/day, and produced side effects including nausea, vomiting, dizziness, drowsiness, miosis, and gastric distress.<ref name=DM/><ref name=TGA/><ref name=EMC/> In early clinical trials, buspirone was given at dosages even as high as 2,400 mg/day, with akathisia, tremor, and muscle rigidity observed.<ref name="Dart2004">Template:Cite book</ref> Deliberate overdoses with 250 mg and up to 300 mg buspirone have resulted in drowsiness in about 50% of individuals.<ref name="Dart2004" /> One death has been reported in a co-ingestion of 450 mg buspirone with alprazolam, diltiazem, alcohol, and cocaine.<ref name="Dart2004" />

Interactions

Buspirone has been shown in vitro to be metabolized by the enzyme CYP3A4.<ref name="pmid15640381" /> This finding is consistent with the in vivo interactions observed between buspirone and these inhibitors or inducers of cytochrome P450 3A4 (CYP3A4), among others:<ref name=mono/>

• Itraconazole: Increased plasma level of buspirone
• Rifampicin: Decreased plasma levels of buspirone
• Nefazodone: Increased plasma levels of buspirone
• Haloperidol: Increased plasma levels of buspirone
• Carbamazepine: Decreased plasma levels of buspirone
• Grapefruit: Significantly increases the plasma levels of buspirone.<ref>Template:Cite journal</ref> See grapefruit–drug interactions.
• Fluvoxamine: Moderately increased plasma levels of buspirone.<ref>Template:Cite journal</ref>

Elevated blood pressure has been reported when buspirone has been administered to patients taking monoamine oxidase inhibitors (MAOIs).<ref name=mono/>

Buspirone has been found to markedly reduce the hallucinogenic effects of the serotonergic psychedelic psilocybin in humans.<ref name="HalmanKongSarris2024">Template:Cite journal</ref><ref name="BrandtKavanaghTwamley2018">Template:Cite journal</ref><ref name="PokornyPrellerKraehenmann2016">Template:Cite journal</ref> This parallels findings in which serotonin 5-HT_1A receptor agonists like 8-OH-DPAT attenuate the head-twitch response, a behavioral proxy of psychedelic effects, induced by serotonergic psychedelics in rodents.<ref name="HalberstadtNichols2020">Template:Cite book</ref> Paradoxically however, buspirone enhances the head-twitch response, a behavioral proxy of psychedelic effects, induced by 5-hydroxytryptophan (5-HTP) plus pargyline in rodents.<ref name="HaberzettlBertFink2013">Template:Cite journal</ref><ref name="KitamuraNagataniWatanabe1994">Template:Cite journal</ref>

Pharmacology

Pharmacodynamics

citation

CitationClass=web }}</ref>
Site	Ki (nM)	Action	Species	Ref
5-HT1A	3.98–214 21 (median)	Agonist	Human	<ref name="PDSP" /><ref name="pmid7984267">Template:Cite journal</ref>
5-HT1B	>100,000	Agonist ? <ref name="Sato_2010">Template:Cite journal</ref>	Rat	<ref name="pmid1974152">Template:Cite journal</ref>
5-HT1D	22,000–42,700	Agonist ? <ref name="Sato_2010" />	Human	<ref name="pmid2521959">Template:Cite journal</ref><ref name="pmid2975354">Template:Cite journal</ref>
5-HT2A	138–3,240	Antagonist	Human
5-HT2B	214	?	Human
5-HT2C	490	Antagonist ? <ref name="Sato_2010" />	Human
5-HT7	375–381 840	Antagonist ? <ref name="Sato_2010" />	Rat Human	<ref name="pmid8398139">Template:Cite journal</ref><ref name="pmid8397408">Template:Cite journal</ref> <ref name="pmid31882369">Template:Cite journal</ref>
α1	1,000	Antagonist	Rat	<ref name="pmid1974152" />
α2	6,000	Antagonist	Rat	<ref name="pmid1681447">Template:Cite journal</ref>
α2A	7.3 (Template:Abbrlink)	Antagonist	Human	<ref name="pmid1974152" />
β	8,800	Antagonist	Rat	<ref name="pmid1974152" />
D1	33,000	Antagonist	Rat	<ref name="pmid1974152" />
D2	484 240	Antagonist	Human Rat	<ref name="pmid22827916">Template:Cite journal</ref> <ref name="pmid1974152" />
D3	98	Antagonist	Human	<ref name="pmid22827916" />
D4	29	Antagonist	Human	<ref name="pmid22827916" />
Template:Abbrlink	38,000	?	Rat	<ref name="pmid1974152" />
[[GABAA receptor#Benzodiazepine site|GABAA (Template:Abbr)]]	>100,000	-	Rat	<ref name="pmid1974152" />
Values are Ki (nM). The smaller the value, the more strongly the drug binds to the site.

Buspirone acts as a partial agonist of the serotonin 5-HT_1A receptor with high affinity.<ref name="pmid22608068"/><ref name="pmid1974152" /> It is a partial agonist of both presynaptic 5-HT_1A receptors, which are inhibitory autoreceptors, and postsynaptic 5-HT_1A receptors.<ref name="pmid22608068" /> It is thought that the main effects of buspirone are mediated via its interaction with the presynaptic 5-HT_1A receptor, thus reducing the firing of serotonin-producing neurons.<ref name="pmid22608068" /> Buspirone also seems to have lower affinities for the serotonin 5-HT_2A, 5-HT_2B, 5-HT_2C, 5-HT₆, 5-HT₇ receptors where it probably acts as an antagonist.<ref name="Sato_2010" />

In addition to binding to serotonin receptors, buspirone is an antagonist of the dopamine D₂ receptor with weak affinity.<ref name="pmid22608068"/><ref name="pmid1974152" /> It preferentially blocks inhibitory presynaptic D₂ autoreceptors, and antagonizes postsynaptic D₂ receptors only at higher doses.<ref name="pmid22608068" /> In accordance, buspirone has been found to increase dopaminergic neurotransmission in the nigrostriatal pathway at low doses, whereas at higher doses, postsynaptic D₂ receptors are blocked and antidopaminergic effects such as hypoactivity and reduced stereotypy, though notably not catalepsy, are observed in animals.<ref name="pmid22608068" /> Buspirone has also been found to bind with much higher affinity to the dopamine D₃ and D₄ receptors, where it is similarly an antagonist.<ref name="pmid22827916" />

A major metabolite of buspirone, 1-(2-pyrimidinyl)piperazine (1-PP), occurs at higher circulating levels than buspirone itself and is known to act as a potent α₂-adrenergic receptor antagonist.<ref name="pmid1681447" /><ref name="pmid1796057">Template:Cite journal</ref><ref name="pmid12438536">Template:Cite journal</ref> This metabolite may be responsible for the increased noradrenergic and dopaminergic activity observed with buspirone in animals.<ref name="pmid1796057" /><ref name="pmid17700052">Template:Cite journal</ref> Buspirone also has very weak and probably clinically unimportant affinity for the α₁-adrenergic receptor.<ref name="pmid1974152" /><ref name="SternFava2015">Template:Cite book</ref> However, buspirone has been reported to have shown "significant and selective intrinsic efficacy" at the α₁-adrenergic receptor expressed in a "tissue- and species-dependent manner".<ref name="SternFava2015" />

Unlike benzodiazepines, buspirone does not interact with the GABA_A receptor complex.<ref name="pmid22608068" /><ref name="NuttBallenger2008">Template:Cite book</ref>

Pharmacokinetics

Buspirone has a low oral bioavailability of 3.9% relative to intravenous injection due to extensive first-pass metabolism.<ref name="pmid22608068" /> The time to peak plasma levels following ingestion is 0.9 to 1.5 hours.<ref name="pmid22608068" /> It is reported to have an elimination half-life of 2.8 hours,<ref name="pmid22608068" /> although a review of 14 studies found that the mean terminal half-life ranged between 2 and 11 hours, and one study even reported a terminal half-life of 33 hours.<ref name="pmid3515929">Template:Cite journal</ref> Buspirone is metabolized primarily by CYP3A4, and prominent drug interactions with inhibitors and inducers of this enzyme have been observed.<ref name="pmid10320950" /><ref name="pmid15640381" /> Major metabolites of buspirone include 5-hydroxybuspirone, 6-hydroxybuspirone, 8-hydroxybuspirone, and 1-PP.<ref>Template:Cite journal</ref><ref name="pmid3515929" /><ref name="SchatzbergNemeroff2009" /><ref name="pmid17494642">Template:Cite journal</ref> 6-Hydroxybuspirone has been identified as the predominant hepatic metabolite of buspirone, with plasma levels that are 40-fold greater than those of buspirone after oral administration of buspirone to humans.<ref name="SchatzbergNemeroff2009">Template:Cite book</ref> The metabolite is a high-affinity partial agonist of the 5-HT_1A receptor (K_i=25 nM) similarly to buspirone, and has demonstrated occupancy of the 5-HT_1A receptor in vivo.<ref name="SchatzbergNemeroff2009" /> As such, it is likely to play an important role in the therapeutic effects of buspirone.<ref name="SchatzbergNemeroff2009" /> 1-PP has also been found to circulate at higher levels than those of buspirone itself and may similarly play a significant role in the clinical effects of buspirone.<ref name="pmid1796057" /><ref name="pmid17700052" />

File:Buspirone metabolism.png

Phase I Metabolism of buspirone in humans<ref>Template:Cite journal</ref><ref>Template:Cite journal</ref><ref>Template:Cite journal</ref><ref name="pmid15640381"/>

Chemistry

Buspirone is a member of the azapirone chemical class, and consists of azaspirodecanedione and pyrimidinylpiperazine components linked together by a butyl chain.

Analogues

Structural analogues of buspirone include other azapirones like gepirone, ipsapirone, perospirone, and tandospirone.<ref name="pmid1679210">Template:Cite journal</ref>

A number of analogues are recorded.<ref>Template:Cite journal</ref>

Synthesis

A number of methods of synthesis have also been reported.<ref>Template:Cite journal</ref><ref>Template:Cite journal</ref><ref>Template:Cite journal</ref> One method begins with alkylation of 1-(2-pyrimidyl)piperazine (1) with 3-chloro-1-cyanopropane (4-chlorobutyronitrile) (2) to give (3). Next, reduction of the nitrile group is performed either by catalytic hydrogenation or with lithium aluminium hydride (LAH) giving (4). The primary amine is then reacted with 3,3-tetramethyleneglutaric anhydride (5) in order to yield buspirone (6).<ref name="Psychosedative agents. 2. 8-4-Subs">Template:Cite journal</ref><ref>DE2057845 idem Y Wu, J Rayburn, {{#if:3717634 |[{{#ifeq:|uspto|http://patft.uspto.gov/netacgi/nph-Parser?patentnumber=%7Chttps://patents.google.com/patent/US}}{{#iferror:{{#expr:3717634 }}|3717634}} U.S. patent {{#ifeq:Template:Replace|Template:Digits|Template:Replace|3717634}}] |{{US patent|123456|link text}}}} (1973 to Mead Johnson).</ref><ref>Template:Cite patent</ref><ref>Template:Cite patent</ref><ref>Template:Cite patent</ref>

File:Buspirone-synthesis.svg

Synthesis of buspirone

History

Buspirone was first synthesized by a team at Mead Johnson in 1968<ref name="pmid26535760" /> but was not patented until 1980.<ref>Template:Cite patent</ref><ref name="Psychosedative agents. 2. 8-4-Subs"/><ref>Template:Cite patent</ref> It was initially developed as an antipsychotic acting on the D₂ receptor but was found to be ineffective in the treatment of psychosis; it was then used as an anxiolytic instead.<ref name="pmid22608068" /> In 1986, Bristol-Myers Squibb gained FDA approval for buspirone in the treatment of GAD.<ref name="pmid26535760" /><ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> The patent expired in 2001, and buspirone is now available as a generic drug.

Society and culture

File:Buspar.jpg

Buspar (buspirone) 10-mg tablets

Generic names

Buspirone is the Template:Abbrlink, Template:Abbrlink, Template:Abbrlink, and Template:Abbrlink of buspirone, while buspirone hydrochloride is its Template:Abbrlink, Template:Abbrlink, and Template:Abbrlink.<ref name="Elks2014">Template:Cite book</ref><ref name="IndexNominum2000">Template:Cite book</ref><ref name="MortonHall2012">Template:Cite book</ref><ref name="Drugs.com">{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>

Brand names

Buspirone was primarily sold under the brand name Buspar.<ref name="IndexNominum2000" /><ref name="Drugs.com" /> Buspar is currently listed as discontinued by the U.S. Food and Drug Administration (FDA).<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> In 2010, in response to a citizen petition, the FDA determined that Buspar was not withdrawn from sale for reasons of safety or effectiveness.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>

External links

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