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药品详细

Yohimbine(育亨宾)

化学结构式图
中文名
育亨宾
英文名
Yohimbine
分子式
C21H26N2O3
化学名
methyl (1S,15R,18S,19R,20S)-18-hydroxy-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4,6,8-tetraene-19-carboxylate
分子量
Average: 354.4427
Monoisotopic: 354.194342708
CAS号
146-48-5
ATC分类
G04B 未知
药物类型
small molecule
阶段
approved
商品名
同义名
基本介绍

A plant alkaloid with alpha-2-adrenergic blocking activity. Yohimbine has been used as a mydriatic and in the treatment of impotence. It is also alleged to be an aphrodisiac. [PubChem]

生产厂家
    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
    • Alkaloids and Alkaloid Derivatives
    Substructures
    • Carboxylic Acids and Derivatives
    • Hydroxy Compounds
    • Acetates
    • Indoles and Indole Derivatives
    • Pyrroles
    • Alkaloids and Alkaloid Derivatives
    • Ethers
    • Benzene and Derivatives
    • Aliphatic and Aryl Amines
    • Heterocyclic compounds
    • Aromatic compounds
    • Tryptamines and Derivatives
    • Imines
    • (Iso)quinolines and Derivatives
    • Alcohols and Polyols
    • Piperidines
    适应症
    药理
    Indication Indicated as a sympatholytic and mydriatic. Impotence has been successfully treated with yohimbine in male patients with vascular or diabetic origins and psychogenic origins.
    Pharmacodynamics Yohimbine is an indolalkylamine alkaloid with chemical similarity to reserpine. Yohimbine blocks presynaptic alpha-2 adrenergic receptors. Its action on peripheral blood vessels resembles that of reserpine, though it is weaker and of short duration. Yohimbine's peripheral autonomic nervous system effect is to increase parasympathetic (cholinergic) and decrease sympathetic (adrenergic) activity. It is to be noted that in male sexual performance, erection is linked to cholinergic activity and to alpha-2 adrenergic blockade which may theoretically result in increased penile inflow, decreased penile outflow or both. Yohimbine exerts a stimulating action on the mood and may increase anxiety. Such actions have not been adequately studied or related to dosage although they appear to require high doses of the drug. Yohimbine has a mild anti-diuretic action, probably via stimulation of hypothalmic center and release of posterior pituitary hormone. Reportedly Yohimbine exerts no significant influence on cardiac stimulation and other effects mediated by (beta)-adrenergic receptors. Its effect on blood pressure, if any, would be to lower it; however, no adequate studies are at hand to quantitate this effect in terms of Yohimbine dosage.
    Mechanism of action Yohimbine is a pre-synaptic alpha 2-adrenergic blocking agent. The exact mechanism for its use in impotence has not been fully elucidated. However, yohimbine may exert its beneficial effect on erectile ability through blockade of central alpha 2-adrenergic receptors producing an increase in sympathetic drive secondary to an increase in norepinephrine release and in firing rate of cells in the brain noradrenergic nuclei. Yohimbine-mediated norepinephrine release at the level of the corporeal tissues may also be involved. In addition, beneficial effects may involve other neurotransmitters such as dopamine and serotonin and cholinergic receptors.
    Absorption Rapidly absorbed following oral administration. Bioavailability is highly variable, ranging from 7 to 87% (mean 33%).
    Volume of distribution Not Available
    Protein binding Not Available
    Metabolism
    Yohimbine appears to undergo extensive metabolism in an organ of high flow such as the liver or kidney, however, the precise metabolic fate of yohimbine has not been fully determined.
    Route of elimination Not Available
    Half life Elimination half-life is approximately 36 minutes.
    Clearance Not Available
    Toxicity Not Available
    Affected organisms
    • Humans and other mammals
    Pathways Not Available
    理化性质
    Properties
    State solid
    Experimental Properties
    Property Value Source
    melting point 241 °C PhysProp
    logP 2.73 HANSCH,C ET AL. (1995)
    Predicted Properties
    Property Value Source
    water solubility 3.48e-01 g/l ALOGPS
    logP 2.36 ALOGPS
    logP 2.1 ChemAxon
    logS -3 ALOGPS
    pKa (strongest acidic) 14.68 ChemAxon
    pKa (strongest basic) 7.65 ChemAxon
    physiological charge 1 ChemAxon
    hydrogen acceptor count 3 ChemAxon
    hydrogen donor count 2 ChemAxon
    polar surface area 65.56 ChemAxon
    rotatable bond count 2 ChemAxon
    refractivity 99.63 ChemAxon
    polarizability 40.22 ChemAxon
    药物相互作用
    Drug Interaction
    Asenapine Increased incidence of adverse effects due to pharmacodynamic synergism. Concomitant therapy should be avoided.
    Atomoxetine The CYP2D6 inhibitor could increase the effect and toxicity of atomoxetine
    食物相互作用
    Not Available

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