| Identification | Back Directory | [Name]
Danazol | [CAS]
17230-88-5 | [Synonyms]
Dano
danol
DANZOL
Bonzol
Ladogal
DANAZOL
win17757
danazole
Danovaol
Cyclomen
Danatrol
Winobanin
Chronogyn
Danazolum
danocrine
NSC 270916
Danazol Usp
Danazol (200 mg)
DanazolUspC22H27No2
Danazol Solution, 100ppm
DANAZOL >98% ANTERIOR PITUITARY SU
2,4,17α-Pregnadien-20-yno[2,3-d]isoxazol-17-ol
17-alpha-pregn-4-en-20-yno(2,3-d)isoxazol-17-ol
(17A)-PREGNA-2,4-DIEN-20-YNO[2,3-D]ISOXAZOL-17-OL
(17α)-Pregna-2,4-dien-20-yno[2,3-d]isoxazol-17-ol
(17R)-Pregn-2-eno[2,3-d]isoxazol-4-en-20-yn-17-ol
17α-Pregna-2,4-dien-20-yne-[2,3-d]isoxazole-17b-ol
Pregna-2,4-dien-20-yno[2,3-d]isoxazol-17-ol, (17α)-
17-alpha-2,4-pregnadien-20-yno(2,3-d)isoxazol-17-ol
17alpha-pregna-2,4-dien-20-yno[2,3-d]isoxazol-17-ol
2,4,17-ALPHA-PREGNADIEN-20-YNO[2,3-D]ISOXAZOL-17-OL
3-d)isoxazol-17-ol,(17-alpha)-pregna-4-dien-20-yno(2
17a-Ethynyl-17-hydroxy-4-androsteno[2,3-d]isoxazole
17α-Ethynyl-17β hydroxy-4-androsteno[2,3-d]isoxazole
17β-Hydroxy-2,4,17α-pregnadien-20-yno[2,3-d]isoxazole
17b-Hydroxy-2,4,17a-pregnadien-20-yno[2,3-d]isoxazole
17α-Pregna-2,4-dien-20-yno[2,3-d]isoxazol-17-ol (8CI)
17a-Ethynyl-17b-hydroxy-4-androsteno[2,3-d]isoxazole
4-ANDROSTEN-[2,3-D]ISOXAZOLE-17-ALPHA-ETHYNYL-17-BETA-OL
17BETA-HYDROXY-2,4,17ALPHA-PREGNADIEN-20-YNO[2,3-D]ISOXAZOLE
DANAZOL((17ALPHA)-PREGNA-2,4-DIEN-20-YNO[2,3-D]ISOXAZOL-17-OL)
1H-Cyclopenta[7,8]phenanthro[3,2-d]isoxazole, pregna-2,4-dien-20-yno[2,3-d]isoxazol-17-ol deriv.
2,4,17α-Pregnadien-20-yno[2,3-d]isoxazol-17-ol, 17β-Hydroxy-2,4,17α-pregnadien-20-yno[2,3-d]isoxazole
Danazol,17β-Hydroxy-2,4,17α-pregnadien-20-yno[2,3-d]isoxazole, 2,4,17α-Pregnadien-20-yno[2,3-d]-isoxa-zol-17-ol
1H-Cyclopenta[7,8]phenanthro[3,2-d]isoxazol-1-ol, 1-ethynyl-2,3,3a,3b,4,5,10,10a,10b,11,12,12a-dodecahydro-10a,12a-dimethyl-(7CI) | [EINECS(EC#)]
241-270-1 | [Molecular Formula]
C22H27NO2 | [MDL Number]
MFCD00056838 | [MOL File]
17230-88-5.mol | [Molecular Weight]
337.46 |
| Chemical Properties | Back Directory | [Appearance]
White Solid | [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 | [solubility ]
Acetonitrile (Slightly), Chloroform (Slightly), Ethanol (Slightly), Methanol (Slightly) | [form ]
Solid | [pka]
13.10±0.60(Predicted) | [color ]
White to Pale Yellow | [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. | [InChI]
1S/C22H27NO2/c1-4-22(24)10-8-18-16-6-5-15-11-19-14(13-23-25-19)12-20(15,2)17(16)7-9-21(18,22)3/h1,11,13,16-18,24H,5-10,12H2,2-3H3/t16?,17?,18?,20?,21?,22-/m0/s1 | [InChIKey]
POZRVZJJTULAOH-QLPJIZEUNA-N | [SMILES]
[C@]12([H])CC[C@]3(C)[C@](CC[C@@]3([H])[C@]1([H])CCC1=CC3ON=CC=3C[C@]21C)(O)C#C |&1:0,4,6,9,11,23,r| | [EPA Substance Registry System]
Pregna-2,4-dien-20-yno[2,3-d]isoxazol-17-ol, (17.alpha.)-(17230-88-5) |
| Hazard Information | Back Directory | [Chemical Properties]
White Solid | [Usage]
anterior pituitary suppressant | [Usage]
Anterior pituitary supressant. Anabolic steroid derivative of ethisterone, with mild androgenic side effects (an impeded androgen). Antigonadotropin | [Usage]
Danazol is an anterior pituitary supressant. Danazol is an anabolic steroid derivative of ethisterone, with mild androgenic side effects (an impeded androgen). Antigonadotropin. | [Originator]
Danol,Winthrop,UK,1974 | [Uses]
anterior pituitary suppressant | [Uses]
Anterior pituitary supressant. Anabolic steroid derivative of ethisterone, with mild androgenic side effects (an impeded androgen). Antigonadotropin | [Uses]
Danazol is an anterior pituitary supressant. Danazol is an anabolic steroid derivative of ethisterone, with mild androgenic side effects (an impeded androgen). Antigonadotropin. | [Definition]
ChEBI: Danazol is a 17beta-hydroxy steroid and a terminal acetylenic compound. It has a role as an anti-estrogen, an estrogen antagonist and a geroprotector. It derives from a hydride of a pregnane. | [Indications]
Danazol, 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 Process]
Danazol 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 name]
Danocrine (Sanofi Aventis). | [Therapeutic Function]
Anterior pituitary suppressant | [General Description]
Danazol, 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. | [Biological Activity]
danazol showed weak androgenic effects.danazol is a derivative of testosterone and ethisterone. an androgen is any natural or synthetic agent stimulating or controling the development and maintenance of male characteristics by binding to androgen receptors. this includes the activity of the primary male sex organs and development of male secondary sex characteristics. | [Biochem/physiol Actions]
Danazol is a weak androgen; anterior pituitary suppressant. | [Side effects]
Danazol, 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 Treatments]
Because 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. | [in vitro]
previous study found that danazol as low as 1 micrometer could suppress lh-stimulated testosterone and androstenedione production in cultured leydig cells. the addition of danazol to a preparation of testicular microsomes elicited a type i cytochrome p-450 binding spectrum. danazol could inhibit progesterone and 17alpha-hydroxy-progesterone binding to microsomal p-450 [1]. | [in vivo]
the purpose of a previous study was to examine the role of androgen and estrogen receptors in danazol suppression of luteinizing hormone (lh) in the rat. the estrogen receptor antagonist, ly 156758, partially antagonized the suppressed levels of lh after administration of danazol to ovariectomized rats. in contrast, the androgen receptor antagonist, flutamide, had no effect on suppressed lh levels after danazol treatment, but did partially reverse the inhibition of lh 24 hr after danazol administration to ovariectomized rats [2]. | [References]
[1] barbieri rl, canick ja, ryan kj. danazol inhibits steroidogenesis in the rat testis in vitro. endocrinology. 1977 dec;101(6):1676-82.
[2] snyder bw, beecham gd, winneker rc. danazol suppression of luteinizing hormone in the rat: evidence for mediation by both androgen and estrogen receptors. proc soc exp biol med. 1990 may;194(1):54-7.
[3] cole rm, raghavan d, caterson i, teriana n, pearson b, boulas j, rosen m. danazol treatment of advanced prostate cancer: clinical and hormonal effects. prostate. 1986;9(1):15-20. |
|
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Sigma-Aldrich
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