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药品详细

Testosterone(睾酮)

化学结构式图
中文名
睾酮
英文名
Testosterone
分子式
C19H28O2
化学名
(1S,2R,10R,11S,14S,15S)-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one
分子量
Average: 288.4244
Monoisotopic: 288.20893014
CAS号
58-22-0
ATC分类
G03B 未知;G03B 未知;G03E 未知
药物类型
small molecule
阶段
approved
商品名
同义名
基本介绍

Testosterone is a steroid sex hormone found in both men and women. In men, testosterone is produced primarily by the Leydig (interstitial) cells of the testes when stimulated by luteinizing hormone (LH). It functions to stimulate spermatogenesis, promote physical and functional maturation of spermatozoa, maintain accessory organs of the male reproductive tract, support development of secondary sexual characteristics, stimulate growth and metabolism throughout the body and influence brain development by stimulating sexual behaviors and sexual drive. In women, testosterone is produced by the ovaries (25%), adrenals (25%) and via peripheral conversion from androstenedione (50%). Testerone in women functions to maintain libido and general wellbeing. Testosterone exerts a negative feedback mechanism on pituitary release of LH and follicle-stimulating hormone (FSH). Testosterone may be further converted to dihydrotestosterone or estradiol depending on the tissue.

生产厂家
  • Alza corp
  • Auxilium pharmaceuticals
  • Bedford laboratories div ben venue laboratories inc
  • Columbia laboratories inc
  • Eli lilly and co
  • Endo pharmaceutical solutions inc
  • Heather drug co inc
  • Impax laboratories inc
  • Inwood laboratories inc sub forest laboratories inc
  • Kv pharmaceutical co
  • Lannett co inc
  • Novartis pharmaceuticals corp
  • Paddock laboratories inc
  • Par pharmaceutical
  • Parke davis div warner lambert co
  • Pharmacia and upjohn co
  • Private formulations inc
  • Purepac pharmaceutical co
  • Sandoz canada inc
  • Schering corp sub schering plough corp
  • Slate pharmaceuticals inc
  • Solvay Pharmaceuticals, Inc.
  • Synerx pharma llc
  • Tablicaps inc
  • Unimed pharmaceuticals inc
  • Usl pharma inc
  • Valeant pharmaceuticals international
  • Watson laboratories
  • Watson laboratories inc
  • West ward pharmaceutical corp
封装厂家
参考
Synthesis Reference Not Available
General Reference
  1. Freeman ER, Bloom DA, McGuire EJ: A brief history of testosterone. J Urol. 2001 Feb;165(2):371-3. Pubmed
  2. Hoberman JM, Yesalis CE: The history of synthetic testosterone. Sci Am. 1995 Feb;272(2):76-81. Pubmed
  3. Contraceptive efficacy of testosterone-induced azoospermia in normal men. World Health Organization Task Force on methods for the regulation of male fertility. Lancet. 1990 Oct 20;336(8721):955-9. Pubmed
剂型
规格
化合物类型
Type small molecule
Classes
  • Steroids and Steroid Derivatives
Substructures
  • Steroids and Steroid Derivatives
  • Hydroxy Compounds
  • Alkanes and Alkenes
  • Alcohols and Polyols
  • Cyclohexenes and Derivatives
  • Ketones
适应症
药理
Indication To be used as hormone replacement or substitution of diminished or absent endogenous testosterone. Use in males: For management of congenital or acquired hypogonadism, hypogonadism associated with HIV infection, and male climacteric (andopause). Use in females: For palliative treatment of androgen-responsive, advanced, inoperable, metastatis (skeletal) carcinoma of the breast in women who are 1-5 years postmenopausal; testosterone esters may be used in combination with estrogens in the management of moderate to severe vasomotor symptoms associated with menopause in women who do not respond to adequately to estrogen therapy alone.
Pharmacodynamics Testosterone is a steroid hormone from the androgen group. Testosterone is primarily secreted from the testes of males. In females, it is produced in the ovaries, adrenal glands and by conversion of adrostenedione in the periphery. It is the principal male sex hormone and an anabolic steroid. In both males and females, it plays key roles in health and well-being. Examples include enhanced libido, energy, immune function, and protection against osteoporosis. On average, the adult male body produces about twenty times the amount of testosterone than an adult female's body does.
Mechanism of action The effects of testosterone in humans and other vertebrates occur by way of two main mechanisms: by activation of the androgen receptor (directly or as DHT), and by conversion to estradiol and activation of certain estrogen receptors. Free testosterone (T) is transported into the cytoplasm of target tissue cells, where it can bind to the androgen receptor, or can be reduced to 5α-dihydrotestosterone (DHT) by the cytoplasmic enzyme 5α-reductase. DHT binds to the same androgen receptor even more strongly than T, so that its androgenic potency is about 2.5 times that of T. The T-receptor or DHT-receptor complex undergoes a structural change that allows it to move into the cell nucleus and bind directly to specific nucleotide sequences of the chromosomal DNA. The areas of binding are called hormone response elements (HREs), and influence transcriptional activity of certain genes, producing the androgen effects.
Absorption Approximately 10% of the testosterone dose applied on the skin surface is absorbed into systemic circulation
Volume of distribution Not Available
Protein binding 40% of testosterone in plasma is bound to sex hormone-binding globulin and 2% remains unbound and the rest is bound to albumin and other proteins.
Metabolism
Testosterone is metabolized to 17-keto steroids through two different pathways. The major active metabolites are estradiol and dihydrotestosterone (DHT).

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

Substrate Enzymes Product
Testosterone
6-beta-hydroxytestosterone Details
Testosterone
    		Estradiol Details
    Testosterone
      		Testosterone sulfate Details
      Testosterone
        		Dihydrotestosterone Details
        Testosterone
          		Testosterone glucuronide Details
          Testosterone
            		5-alpha-Dihydrotestosterone glucuronide Details
            Testosterone
              		5a-Dihydrotestosterone sulfate Details
              Testosterone
                		17-Hydroxyandrostane-3-glucuronide Details
                Route of elimination About 90% of a dose of testosterone given intramuscularly is excreted in the urine as glucuronic and sulfuric acid conjugates of testosterone and its metabolites; about 6% of a dose is excreted in the feces, mostly in the unconjugated form.
                Half life 10-100 minutes
                Clearance Not Available
                Toxicity Side effects include amnesia, anxiety, discolored hair, dizziness, dry skin, hirsutism, hostility, impaired urination, paresthesia, penis disorder, peripheral edema, sweating, and vasodilation.
                Affected organisms
                • Humans and other mammals
                Pathways Not Available
                理化性质
                Properties
                State solid
                Experimental Properties
                Property Value Source
                melting point 155 °C PhysProp
                water solubility 23.4 mg/L (at 25 °C) YALKOWSKY,SH & HE,Y (2003)
                logP 3.32 HANSCH,C ET AL. (1995)
                Caco2 permeability -4.34 ADME Research, USCD
                Predicted Properties
                Property Value Source
                water solubility 3.33e-02 g/l ALOGPS
                logP 2.99 ALOGPS
                logP 3.37 ChemAxon
                logS -3.9 ALOGPS
                pKa (strongest acidic) 19.09 ChemAxon
                pKa (strongest basic) -0.88 ChemAxon
                physiological charge 0 ChemAxon
                hydrogen acceptor count 2 ChemAxon
                hydrogen donor count 1 ChemAxon
                polar surface area 37.3 ChemAxon
                rotatable bond count 0 ChemAxon
                refractivity 84.43 ChemAxon
                polarizability 34.02 ChemAxon
                药物相互作用
                Drug Interaction
                Acenocoumarol The androgen, Testosterone, may incrase the anticoagulant effect of the Vitamin K antagonist, Acenocoumarol. Monitor for changes in the therapeutic effect of Acenocoumarol if Testosterone is initiated, discontinued or dose changed.
                Anisindione The androgen may increase the anticoagulant effect of anisindione.
                Cyclosporine The androgen, Testosterone, may increase the hepatotoxicity of Cyclosporine. Testosterone may also elevate serum concentrations of Cyclosporine. Consider alternate therapy or monitor for signs of renal and hepatic toxicity.
                Dicumarol The androgen may increase the anticoagulant effect of dicumarol.
                Docetaxel Testosterone may increase the serum levels and toxicity of docetaxel.
                Warfarin Testosterone may increase the serum concentration and anticoagulant effect of warfarin. Monitor for changes in prothrombin time and therapeutic effects of warfarin if testosterone is initiated, discontinued or dose changed.
                食物相互作用
                Not Available

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