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药品详细

Buspirone(丁螺环酮)

化学结构式图
中文名
丁螺环酮
英文名
Buspirone
分子式
C21H31N5O2
化学名
8-{4-[4-(pyrimidin-2-yl)piperazin-1-yl]butyl}-8-azaspiro[4.5]decane-7,9-dione
分子量
Average: 385.5031
Monoisotopic: 385.247775261
CAS号
36505-84-7
ATC分类
N05B 未知
药物类型
small molecule
阶段
approved
商品名
同义名
基本介绍

An anxiolytic agent and a serotonin receptor agonist belonging to the azaspirodecanedione class of compounds. Its structure is unrelated to those of the benzodiazepines, but it has an efficacy comparable to diazepam. [PubChem]

生产厂家
  • Actavis totowa llc
  • Apotex inc
  • Bristol myers squibb co pharmaceutical research institute
  • 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
封装厂家
参考
Synthesis Reference Not Available
General Reference Not Available
剂型
规格
化合物类型
Type small molecule
Classes
  • Delta Lactams
  • Azaspirodecanes
Substructures
  • Delta Lactams
  • Amino Ketones
  • Aliphatic and Aryl Amines
  • Piperazines
  • Pyrimidines and Derivatives
  • Piperidines
  • Heterocyclic compounds
  • Aromatic compounds
  • Carboxamides and Derivatives
  • Carboxylic Acids and Derivatives
  • Azaspirodecanes
  • Cyanamides
适应症
药理
Indication For the management of anxiety disorders or the short-term relief of the symptoms of anxiety, and also as an augmention of SSRI-treatment against depression.
Pharmacodynamics Buspirone is used in the treatment of generalized anxiety where it has advantages over other antianxiety drugs because it does not cause sedation (drowsiness) and does not cause tolerance or physical dependence. 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. in vitro preclinical studies have shown that buspirone has a high affinity for serotonin (5-HT1A) receptors. Buspirone has no significant affinity for benzodiazepine receptors and does not affect GABA binding in vitro or in vivo when tested in preclinical models. Buspirone has moderate affinity for brain D2-dopamine receptors. Some studies do suggest that buspirone may have indirect effects on other neurotransmitter systems.
Mechanism of action Buspirone binds to 5-HT type 1A serotonin receptors on presynaptic neurons in the dorsal raphe and on postsynaptic neurons in the hippocampus, thus inhibiting the firing rate of 5-HT-containing neurons in the dorsal raphe. Buspirone also binds at dopamine type 2 (DA2) receptors, blocking presynaptic dopamine receptors. Buspirone increases firing in the locus ceruleus, an area of brain where norepinephrine cell bodies are found in high concentration. The net result of buspirone actions is that serotonergic activity is suppressed while noradrenergic and dopaminergic cell firing is enhanced.
Absorption Rapidly absorbed in man. Bioavailability is low and variable (approximately 5%) due to extensive first pass metabolism.
Volume of distribution Not Available
Protein binding 95% (approximately 70% bound to albumin, 30% bound to alpha 1 -acid glycoprotein)
Metabolism
Metabolized hepatically, primarily by oxidation by cytochrome P450 3A4 producing several hydroxylated derivatives and a pharmacologically active metabolite, 1-pyrimidinylpiperazine (1-PP)

Important The metabolism module of DrugBank is currently in beta. Questions or suggestions? Please contact us.

Substrate Enzymes Product
Buspirone
1-Pyrimidinylpiperazine Details
Buspirone
Buspirone N-oxide Details
Buspirone
3′-Hydroxybuspirone Details
Buspirone
5-Hydroxybuspirone Details
Buspirone
6'-Hydroxybuspirone Details
Route of elimination In a single-dose study using 14C-labeled buspirone, 29% to 63% of the dose was excreted in the urine within 24 hours, primarily as metabolites; fecal excretion accounted for 18% to 38% of the dose.
Half life 2-3 hours (although the action of a single dose is much longer than the short halflife indicates).
Clearance Not Available
Toxicity Oral, rat LD50 = 136 mg/kg. Symptoms of overdose include dizziness, drowsiness, nausea or vomiting, severe stomach upset, and unusually small pupils.
Affected organisms
  • Humans and other mammals
Pathways Not Available
理化性质
Properties
State solid
Experimental Properties
Property Value Source
melting point 201.5-202.5 °C Not Available
water solubility 21.4 mg/L Not Available
logP 2.63 TAKACS-NOVAK,K 1995 (IN PRESS)
Predicted Properties
Property Value Source
water solubility 5.88e-01 g/l ALOGPS
logP 1.95 ALOGPS
logP 1.78 ChemAxon
logS -2.8 ALOGPS
pKa (strongest basic) 7.62 ChemAxon
physiological charge 1 ChemAxon
hydrogen acceptor count 6 ChemAxon
hydrogen donor count 0 ChemAxon
polar surface area 69.64 ChemAxon
rotatable bond count 6 ChemAxon
refractivity 108.89 ChemAxon
polarizability 44.12 ChemAxon
药物相互作用
Drug Interaction
Clarithromycin Clarithromycin may increase the effect and toxicity of buspirone.
Desvenlafaxine Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Diltiazem The calcium channel blocker, diltiazem, increases the effect and toxicity of buspirone.
Erythromycin The macrolide, erythromycin, may increase the effect and toxicity of buspirone.
Isocarboxazid Possible blood pressure elevation
Josamycin The macrolide, josamycin, may increase the effect and toxicity of buspirone.
Nefazodone Nefazodone increases the effect of buspirone
Phenelzine Possible blood pressure elevation
Rasagiline Possible blood pressure elevation
Rifabutin Rifabutin decreases the effect of buspirone
Rifampin Rifampin decreases the effect of buspirone
Ritonavir Ritonavir increases the effect and toxicity of buspirone
Telithromycin Telithromycin may reduce clearance of Buspirone. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Buspirone if Telithromycin is initiated, discontinued or dose changed.
Tranylcypromine Buspirone may increase the adverse effects of Tranylcypromine. Elevation of blood pressure may occur. Concomitant therapy also may increase the risk of serotonin syndrome. Concomitant therapy should be avoided.
Trazodone Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Trimipramine Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Venlafaxine Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Verapamil Verapamil may increase the serum concentration of Buspirone. The likely occurs via Verapamil-mediated CYP3A4 inhibition resulting in decreased Buspirone metabolism. Monitor for changes in the therapeutic/adverse effects of Buspirone if Verpamil is initiated, discontinued or dose changed.
Voriconazole Voriconazole may increase the serum concentration of buspirone likely by decreasing its metabolism via CYP3A4. Monitor for changes in the therapeutic and adverse effects of buspirone if voriconazole is initiated, discontinued or dose changed.
Zolmitriptan Use of two serotonin modulators, such as zolmitriptan and buspirone, increases the risk of serotonin syndrome. Consider alternate therapy or monitor for serotonin syndrome during concomitant therapy.
食物相互作用
  • Always take at the same time with respect to meals.
  • Avoid alcohol.
  • Avoid taking grapefruit or grapefruit juice throughout treatment.
  • Take with food.

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