Basic information Safety Related Supplier
ChemicalBook >  Product Catalog >  API >  Hormones and the Endocrine System >  Androgen and anabolic hormones >  Danazol

Danazol

Basic information Safety Related Supplier
Danazol Basic information
Danazol Chemical Properties
  • Melting point:224.4-226.80C
  • alpha D25 +7.5° (ethanol); D25 +21.9° (chloroform)
  • Boiling point:473.76°C (rough estimate)
  • Density 1.0909 (rough estimate)
  • refractive index 1.5614 (estimate)
  • storage temp. -20°C Freezer
  • pka13.10±0.60(Predicted)
  • Water Solubility Partly soluble in water. Soluble in chloroform (25 mg/ml), acetone, acetonitrile, and ethanol. 17beta-Hydroxy-2,4,17a-pregnadien-20-yno[2,3-d]isoxazole and 2,4,17a-Pregnadien-20-yno[2,3-d]isoxazol-17-ol are the synonym of this compound.
  • EPA Substance Registry SystemDanazol (17230-88-5)
Safety Information
MSDS
Danazol Usage And Synthesis
  • Chemical PropertiesWhite Solid
  • OriginatorDanol,Winthrop,UK,1974
  • Usesanterior pituitary suppressant
  • UsesDanazol is an anterior pituitary supressant. Danazol is an anabolic steroid derivative of ethisterone, with mild androgenic side effects (an impeded androgen). Antigonadotropin.
  • UsesAnterior pituitary supressant. Anabolic steroid derivative of ethisterone, with mild androgenic side effects (an impeded androgen). Antigonadotropin
  • IndicationsDanazol, a synthetic androgen, has been used to treat the pruritus of primary biliary cirrhosis, urticaria, and also idiopathic pruritus. It has been used for treatment of pruritus associated with polycythemia vera and systemic lupus erythematosus.
  • Manufacturing ProcessDanazol was prepared from 4.32 grams of 17α-ethynyl-2-hydroxymethylene4-androsten-17β-ol-3-one, 1.00 gram of hydroxylamine hydrochloride, 1.12 grams of fused sodium acetate and 135 ml of acetic acid. To a 500 ml, 3- necked flask, equipped with a sealed Hershberg-type stirrer, a reflux condenser and a stopper, was added the above androstenone derivative in 300 ml of 95% ethanol. Stirring was commenced and a slurry of fused sodium acetate and hydroxylamine hydrochloride in glacial acetic acid was added.
    The mixture was refluxed gently on a steam bath for 1? hours. Fifteen minutes after initiating the reaction, the reaction mixture gave a negative ferric chloride test. Most of the ethanol and acetic acid were removed by distillation in vacuo, 300 ml of water and 300 ml of ether were added to the concentrate, and the mixture was shaken. The layers were separated, the aqueous layer extracted with fresh ether, and the combined ether extracts were washed with water, dried over anhydrous sodium sulfate, filtered and evaporated to dryness in vacuo. The residue was crystallized by trituration with ether, and the crystals were collected by filtration, washed with hexane and dried. The mother liquors were concentrated to dryness and dissolved in a minimum amount of acetone, whereupon a second crop was obtained. The two crops were combined, dissolved in ethyl acetate, decolorized with activated charcoal, and recovered by concentration.
    The mixture was refluxed gently on a steam bath for 1? hours. Fifteen minutes after initiating the reaction, the reaction mixture gave a negative ferric chloride test. Most of the ethanol and acetic acid were removed by distillation in vacuo, 300 ml of water and 300 ml of ether were added to the concentrate, and the mixture was shaken. The layers were separated, the aqueous layer extracted with fresh ether, and the combined ether extracts were washed with water, dried over anhydrous sodium sulfate, filtered and evaporated to dryness in vacuo. The residue was crystallized by trituration with ether, and the crystals were collected by filtration, washed with hexane and dried. The mother liquors were concentrated to dryness and dissolved in a minimum amount of acetone, whereupon a second crop was obtained. The two crops were combined, dissolved in ethyl acetate, decolorized with activated charcoal, and recovered by concentration.
  • brand nameDanocrine (Sanofi Aventis).
  • Therapeutic FunctionAnterior pituitary suppressant
  • General DescriptionDanazol, 17α-pregna-2,4-dien-20-yno-[2,3-d]isoxazol-17-ol, is a weak androgen that, in spite ofthe 17α-ethinyl group, has little estrogenic or progestogenicactivity. Danazol has been called a synthetic steroidwith diverse biological effects. Danazol binds to sexhormone–binding globulin (SHBG) and decreases the hepaticsynthesis of this estradiol and testosterone carrier.Free testosterone thus increases. Danazol inhibits FSH andLH production by the hypothalamus and pituitary. It bindsto PRs, GRs, ARs, and ERs. Although the exact mechanismof action is unclear, danazol alters endometrial tissueso that it becomes inactive and atrophic, which allowsdanazol to be an effective treatment for endometriosis.Danazol is also used to treat hereditary angioedema and fibrocysticbreast disease.
  • Side effectsDanazol, a synthetic analogue of 17α-ethynyl testosterone, induces amenorrhea, anovulation and endometrial atrophy via suppression of the hypothalamicpituitary-ovary (HPO) axis. This causes an estrogen-deficient state, but it also causes an increase in androgen production. Danazol generally is not well tolerated because of its androgenic and anabolic side effects, including acne, decreased breast size, facial hair, weight gain, and oily skin. This type of therapy is not a viable option for women with liver disease or hyperlipidemia. Because danazol is teratogenic , it is recommended that effective contraception be utilized during treatment.
  • Veterinary Drugs and TreatmentsBecause of expense and unpredictable efficacy, danazol is not commonly used in veterinary medicine, but has been used as adjunctive therapy (with corticosteroids) in the treatment of canine immunemediated thrombocytopenia and hemolytic anemia, particularly if the patient becomes refractory to glucocorticoids and other immunosuppressive therapy. There is apparently synergism when danazol is combined with corticosteroids for these indications. Once remission is attained, some dogs may have their dosage reduced or other medications may be eliminated and be controlled with danazol alone. In humans, danazol has been used for the treatment of endometriosis, fibrocystic breast disease, idiopathic thrombocytopenic purpura and a variety of other conditions.
Danazol (17230-88-5)Related Product Information
Danazol SupplierMore
  • Company Name:Luyin Pharmaceutical Co., Ltd. in Yantai Gold
  • Tel:0535-6267888
  • Email:
  •  
  • Company Name:LGM Pharma
  • Tel:1-(800)-881-8210
  • Email:inquiries@lgmpharma.com
  •  
  • Company Name:Chemsky(shanghai)International Co.,Ltd.
  • Tel:021-50135380
  • Email:shchemsky@163.com
  •  
  • Company Name:Sinopharm Chemical Reagent Co,Ltd.
  • Tel:86-21-63210123
  • Email:sj_scrc@sinopharm.com
  •  
  • Company Name:Spectrum Chemical Manufacturing Corp.
  • Tel:18616765336
  • Email:marketing_china@spectrumchemical.com;
  •