Buspirone - Wikipedia, The Free Encyclopedia

6/16/2014 Buspirone - Wikipedia, the free encyclopedia
http://en.wikipedia.org/wiki/Buspirone 1/11
Buspirone
Systematic (IUPAC) name
8-[4-(4-pyrimidin-2-ylpiperazin-1-yl)but yl]-8-
azaspiro[4.5]decane-7,9-dione
Clinical data
Trade names Buspar
AHFS/Drugs.com monograph
MedlinePlus a688005
Pregnancy cat. B1 (AU) B (US)
Legal status Prescription Only (S4) (AU) -
only (CA) POM (UK) -only (US)
Routes Oral
Pharmacokinetic data
Bioavailability ~4%[1]
Protein binding 86-95%[1]
Metabolism
Hepatic
mostly via
CYP3A4
[1]
Half-life 2-3 hours[1]
Excretion Urine (29-63%), Faeces (18-
38%)[1]
Identifiers
Buspirone
From Wikipedia, the free encyclopedia
Buspirone (pronounced /bjuspron/ BEW-spi-rohn), trade name Buspar
(pronounced BYOO-spar), is an anxiolytic psychoactive drug of the azapirone
chemical class. It is primarily used to treat generalized anxiety disorder (GAD).
Unlike most drugs predominately used to treat anxiety, buspirone's
pharmacology is not related to benzodiazepines or barbiturates, and so does
not carry the risk of withdrawal symptoms those drug classes are known for
when discontinued.
Buspirone was first identified by a team at Mead Johnson
[2]
in 1972, but
wasn't patented until 1975.
[3]
In 1986, Bristol-Myers Squibb (BMS) gained Food and Drug Administration
(FDA) approval for buspirone in the treatment of GAD. The BMS patent
placed on buspirone expired in 2001 and buspirone is now available as a
generic drug.
Contents
1 Medical uses
2 Adverse effects
2.1 Contraindications
2.2 Interactions
2.3 Overdose
3 Pharmacology and Mechanism
4 Research
5 Comparison to benzodiazepines
6 Chemistry
7 See also
8 References
Medical uses
Buspirone is approved, in the US, by the FDA for the treatment of anxiety
disorders and the short-term relief of the symptoms of anxiety.
[4]
Likewise in
Australia buspirone is licensed for the treatment of anxiety disorders.
[5][6]
In
the UK buspirone is indicated only for the short-term treatment of anxiety.
[7][8]
Although not approved for this indication, studies have shown buspirone to be
an effective augmentation agent alongside treatment with SSRIs (selective
serotonin reuptake inhibitors) for clinical depression and is also used to counter
the sexual side-effects (HSDD, anorgasmy, impotence...) of the
SSRI.
[9][10][11]
CAS number
36505-84-7

ATC code N05BE01
PubChem CID 2477
IUPHAR ligand 36
DrugBank DB00490
ChemSpider
2383

UNII
TK65WKS8HL

KEGG
D07593

ChEBI
CHEBI:3223

ChEMBL
CHEMBL49

Chemical data
Formula
C
21
H
31
N
5
O
2

Mol. mass 385.50314 g/mol
(what is this?) (verify)
Buspar (buspirone) 10 mg tablets
Several clinical trials, most randomised double-blind trials (and in one
buspirone was used as an adjunct to atomoxetine) and one open-label, have
been conducted to evaluate the utility of buspirone in the treatment of attention
deficit hyperactivity disorder with mostly positive results.
[12][13][14][15]
Adverse effects
Adverse effects by incidence
[1][4][5][7]
Very common (>10% incidence) adverse effects include:
Dizziness/light-headedness
Headache
Somnolence
Premature Ejaculation
Common (1-10% incidence) adverse effects include:
Nervousness
Insomnia
Disturbance in attention
Depression
Confusional state
Sleep disorder
Anger
Tachycardia
Chest pain
Nasal congestion
Pharyngolaryngeal pain
Paraesthesia
Blurred vision
Coordination abnormal
Tremor
SMILES
InChI
Uncommon (0.1-1%) adverse effects include:
Cold sweat
Rash
Nausea
Abdominal pain
Dry mouth
Diarrhoea
Constipation
Vomiting
Fatigue
Musculoskeletal pain
Syncope
Hypotension
Hypertension
Redness and itching of the eyes
Altered taste
Conjunctivitis
Flatulence
Anorexia
Increased appetite
Salivation
Rectal bleeding
Urinary frequency
Urinary hesitancy
Menstrual irregularity or spotting
Dysuria
Muscle cramps
Muscle spasms
Muscle rigidity/stiffness
Involuntary movements
Shortness of breath
Chest congestion
Changes in libido
Oedema
Rare (<0.1% incidence) adverse effects include:
Pruritus
Flushing
Easy bruising
Dry skin
Facial oedema
Mild increases in hepatic aminotransferases (AST, ALT)
Weight gain
Fever
Roaring sensation in the head
Weight loss
Malaise
Depersonalisation
Noise intolerance
Euphoria
Akathisia
Fearfulness
Loss of interest
Dissociative reaction
Cerebrovascular accident (stroke)
Myocardial infarction (heart attack)
Cardiomyopathy
Congestive heart failure
Bradycardia
Dysphoria
Hallucinations
Feelings of claustrophobia
Cold intolerance
Stupor
Seizures
Slurred speech
Extrapyramidal symptoms including dyskinesias (acute & delayed)
Dystonic reactions
Cogwheel rigidity
Emotional lability
Psychosis
Suicidal ideation
Ataxias
Transient difficulty with recall
Serotonin syndrome
Parkinsonism
Restless leg syndrome
Restlessness
Eye pain
Altered sense of smell
Photophobia
Pressure on eyes
Inner ear abnormality
Tunnel vision
Galactorrhoea
Irritable colon
Burning of the tongue
Arthralgias
Amenorrhoea (cessation of menstrual cycles)
Enuresis
Nocturia
Pelvic inflammatory disease
Urinary retention
Hyperventilation
Epistaxis
Delayed ejaculation
Impotence
Acne
Hair loss
Blisters
Thinning of nails
Allergic reactions including urticaria, ecchymosis, angioedema
Eosinophilia
Leucopenia
Thrombocytopaenia
Alcohol abuse
Bleeding disturbance
Loss of voice
Hiccoughs
Thyroid abnormality
Contraindications
Buspirone has the following contraindications:
[16][17]
Hypersensitivity to buspirone
Metabolic acidosis, as in diabetes
Should not be used with MAO inhibitors
Severely compromised liver and/or renal function
Interactions
Buspirone has been shown in vitro to be metabolized by CYP3A4.
This finding is consistent with the in vivo interactions observed between buspirone and the following inhibitors / inducers of
Cytochrome P450 3A4 (CYP3A4), among others:
[16]
Itraconazole: Increased plasma level of buspirone
Rifampicin: Decreased plasma levels of buspirone
Nefazodone: Increased plasma levels of buspirone
Haloperidol: Increased plasma levels of haloperidol
Carbamazepine: Decreased plasma levels of buspirone
Grapefruit or grapefruit juice: Significantly increases the plasma levels of buspirone
The likely mechanism of the interaction caused by grapefruit juice is delayed gastric emptying / inhibition of cytochrome P450 3A4-
mediated first-pass metabolism of buspirone.
[18]
There have been reports of the occurrence of elevated blood pressure when Buspirone hydrochloride has been added to a regimen
including an monoamine oxidase inhibitor (MAOI).
[16]
Overdose
Activated charcoal is believed to be an effective treatment for overdose, provided the patient is treated sufficiently promptly.
[5][4][7]
Expected symptoms (based on symptoms in male healthy volunteers treated with 375 mg/day compared to the maximum daily
licensed dosage in Australia, the UK and the US):
[5][4][7]
Nausea
Vomiting
Dizziness
Drowsiness
Miosis
Gastric distress
It is likely (although no definitive data on this subject appears to be available) that buspirone is relatively benign in cases of single-drug
overdose.
[19]
Pharmacology and Mechanism
Buspirone functions as a serotonin 5-HT
1A
receptor partial agonist
[16][20]
(IA = 0.465).
[21]
It is this action that is thought to mediate
its anxiolytic and antidepressant effects. Additionally, it functions as a presynaptic dopamine antagonist at the D
2
, D
3
and D
4

[16][22]
receptors. Buspirone is also a partial
1
receptor agonist. The ability of buspirone to selectively block presynaptic mesolimbic D
2
autoreceptors in lower doses appears to result in increased dopamine synthesis and release.
[23][24]
Positive results for the treatment of depression when buspirone was combined with melatonin has been shown. It is suspected that the
method of action differs from SSRI medications. Preliminary research suggests that the combination of buspirone and melatonin
stimulates the growth of new neurons in the brain, also known as neurogenesis.
[25][26][27]
Although never commercially produced,
Bristol-Myers Squibb applied for a patent on Oct 28, 1993 and received the patent on Jul 11, 1995 for an extended release
formulation of buspirone.
[28]
It also appears to produce some oxytocin stimulation via 5-HT1A receptor-induced action.
[29][30]
Binding Profile of Buspirone (towards cloned human receptors)
[31]
Receptor K
i
(nM)
5-HT
1A
28.62
5-HT
2A
138.03
5-HT
2B
213.79
5-HT
2C
489.77
D
4
107
Research
In September 2012 a five-year $2,137,500 grant was given to the Indiana University School of Medicine and Rehabilitation
Hospital of Indiana by the United States Federal Government. One of the major focuses of research will be to study the
effectiveness of Buspirone as a treatment for symptoms resulting from traumatic brain injuries.
[32]
A study of acute morphine withdrawal found that co-administration of Buspirone and morphine reduced synaptic ultrastructural
changes in hippocampus leading to a reduction of anxiety and withdrawal symptoms.
[33]
In a 1996 study, buspirone was shown to be effective as an augmentative agent for the treatment of alcohol dependence.
[34]
Several studies have shown that administration of buspirone can improve spatial learning and memory function following a
traumatic brain injury (TBI).
[35][36]
New research is being conducted to test the antagonist properties of buspirone at both D3 and D4 receptors as a
pharmacological treatment for cocaine dependence.
[22][37][38]
In a 2007 study conducted on rats, buspirone showed a complete remission of haloperidol-induced tardive vacuous chewing
symptoms when co-administered for five weeks.
[39]
Comparison to benzodiazepines
Buspirone's efficacy is comparable to that of members of the benzodiazepine family in treating GAD, although it tends to have a
delayed onset of action.
[40][41]
Abrupt discontinuation of diazepam after 6 weeks of continuous administration resulted in withdrawal symptoms. This was not the
case when administration of buspirone was ceased after six weeks.
[42]
It may take several weeks before buspirone's anxiolytic effects
become noticeable, and many patients may also need a higher dosage to adequately respond to treatment.
[16]
Buspirone's chemical structure and mechanism of action are completely unrelated to those of benzodiazepines and is not effective as a
treatment for benzodiazepine withdrawal.
[43]
Unlike benzodiazepines buspirone is not a drug of abuse.
[5]
Chemistry
Synthesis begins with N-alkylation 1-(2-pyrimidyl)piperazine w/ 4-chlorobutyronitrile followed by hydrogenation nitrile over Raney
nickel catalyst.
The primary amine product of the previous step is reacted with the graphically represented spirocyclic acid anhydride in order to yield
buspirone.
[44]
See also
Gepirone
Tandospirone
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Retrieved from "http://en.wikipedia.org/w/index.php?title=Buspirone&oldid=612853065"
Categories: 5-HT1A agonists Imides Pyrimidines Azapirones
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