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Danazol

CAS No.
17230-88-5
Chemical Name:
Danazol
Synonyms
danazole;danocrine;Danazol Usp;17α-Pregna-2,4-dien-20-yne-[2,3-d]isoxazole-17b-ol;4-ANDROSTEN-[2,3-D]ISOXAZOLE-17-ALPHA-ETHYNYL-17-BETA-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);Dano;danol;Bonzol;DANZOL
CBNumber:
CB9463336
Molecular Formula:
C22H27NO2
Molecular Weight:
337.46
MDL Number:
MFCD00056838
MOL File:
17230-88-5.mol
Last updated:2023-06-08 09:02:17

Danazol 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
solubility Acetonitrile (Slightly), Chloroform (Slightly), Ethanol (Slightly), Methanol (Slightly)
pka 13.10±0.60(Predicted)
form Solid
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.
NCI Dictionary of Cancer Terms danazol
FDA UNII N29QWW3BUO
NCI Drug Dictionary danazol
ATC code G03XA01
Proposition 65 List Danazol
EPA Substance Registry System Danazol (17230-88-5)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictograms
GHS07,GHS08
Signal word  Warning
Hazard statements  H312+H332-H361
Precautionary statements  P201-P280-P302+P352+P312-P304+P340+P312-P308+P313
Hazard Codes  Xn,Xi
Risk Statements  20/21/22-63-36/37/38
Safety Statements  22-36-37/39-26
WGK Germany  3
RTECS  TU4157070
HS Code  29372900
Toxicity dog,LD50,oral,> 5gm/kg (5000mg/kg),Journal of International Medical Research. Vol. 5(Suppl,
NFPA 704
0
3 0

Danazol price More Price(24)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich D8399 Danazol ≥98% 17230-88-5 1g $669 2024-03-01 Buy
Sigma-Aldrich 1162501 Danazol United States Pharmacopeia (USP) Reference Standard 17230-88-5 200mg $436 2024-03-01 Buy
Alfa Aesar J62200 Danazol 17230-88-5 100mg $58.1 2024-03-01 Buy
Alfa Aesar J62200 Danazol 17230-88-5 500mg $226 2024-03-01 Buy
Cayman Chemical 16471 Danazol ≥98% 17230-88-5 50mg $44 2024-03-01 Buy
Product number Packaging Price Buy
D8399 1g $669 Buy
1162501 200mg $436 Buy
J62200 100mg $58.1 Buy
J62200 500mg $226 Buy
16471 50mg $44 Buy

Danazol Chemical Properties,Uses,Production

Chemical Properties

White Solid

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.

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.

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.

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.

Danazol Preparation Products And Raw materials

Raw materials

Preparation Products

Global( 234)Suppliers
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View Lastest Price from Danazol manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Danazol pictures 2022-02-24 Danazol
17230-88-5
US $99.99-77.77 / g 10g 99.99%HPLC.USP42 1000kgs Shanghai Biolang Biotechnology Co., Ltd.
Danazol pictures 2021-07-13 Danazol
17230-88-5
US $15.00-10.00 / KG 1KG 99%+ HPLC Monthly supply of 1 ton Zhuozhou Wenxi import and Export Co., Ltd
Danazol pictures 2021-07-10 Danazol
17230-88-5
US $15.00-10.00 / KG 1KG 99%+ HPLC Monthly supply of 1 ton Zhuozhou Wenxi import and Export Co., Ltd
  • Danazol pictures
  • Danazol
    17230-88-5
  • US $99.99-77.77 / g
  • 99.99%HPLC.USP42
  • Shanghai Biolang Biotechnology Co., Ltd.
  • Danazol pictures
  • Danazol
    17230-88-5
  • US $15.00-10.00 / KG
  • 99%+ HPLC
  • Zhuozhou Wenxi import and Export Co., Ltd
  • Danazol pictures
  • Danazol
    17230-88-5
  • US $15.00-10.00 / KG
  • 99%+ HPLC
  • Zhuozhou Wenxi import and Export Co., Ltd

Danazol Spectrum

DANZOL DANAZOL 17alpha-pregna-2,4-dien-20-yno[2,3-d]isoxazol-17-ol (17A)-PREGNA-2,4-DIEN-20-YNO[2,3-D]ISOXAZOL-17-OL 17BETA-HYDROXY-2,4,17ALPHA-PREGNADIEN-20-YNO[2,3-D]ISOXAZOLE 17a-Ethynyl-17b- hydroxy-4-androsteno[2,3-d]isoxazole Bonzol Cyclomen Danatrol Dano DANAZOL((17ALPHA)-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 (8CI) 1H-Cyclopenta[7,8]phenanthro[3,2-d]isoxazole, pregna-2,4-dien-20-yno[2,3-d]isoxazol-17-ol deriv. DANAZOL >98% ANTERIOR PITUITARY SU DanazolUspC22H27No2 2,4,17-ALPHA-PREGNADIEN-20-YNO[2,3-D]ISOXAZOL-17-OL 17-alpha-2,4-pregnadien-20-yno(2,3-d)isoxazol-17-ol 17-alpha-pregn-4-en-20-yno(2,3-d)isoxazol-17-ol 3-d)isoxazol-17-ol,(17-alpha)-pregna-4-dien-20-yno(2 danol win17757 Chronogyn Danazolum Danovaol Ladogal NSC 270916 Pregna-2,4-dien-20-yno[2,3-d]isoxazol-17-ol, (17α)- Winobanin 17a-Ethynyl-17- hydroxy-4-androsteno[2,3-d]isoxazole 2,4,17α-Pregnadien-20-yno[2,3-d]isoxazol-17-ol, 17β-Hydroxy-2,4,17α-pregnadien-20-yno[2,3-d]isoxazole 17b-Hydroxy-2,4,17a-pregnadien-20-yno[2,3-d]isoxazole Danazol Solution, 100ppm 17β-Hydroxy-2,4,17α-pregnadien-20-yno[2,3-d]isoxazole 2,4,17α-Pregnadien-20-yno[2,3-d]isoxazol-17-ol (17R)-Pregn-2-eno[2,3-d]isoxazol-4-en-20-yn-17-ol 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 Danazol (200 mg) (17α)-Pregna-2,4-dien-20-yno[2,3-d]isoxazol-17-ol 17α-Ethynyl-17β hydroxy-4-androsteno[2,3-d]isoxazole Danazol RS 2,3-Isoxazolethisterone Danazol standard solution, 100ppm anazol Danazol USP/EP/BP Danazol (1.0 mg/mL in acetonitrile) 4-ANDROSTEN-[2,3-D]ISOXAZOLE-17-ALPHA-ETHYNYL-17-BETA-OL 17α-Pregna-2,4-dien-20-yne-[2,3-d]isoxazole-17b-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) Danazol Usp danazole danocrine danazol([1,2]oxazolo[4',5':2,3]pregna-4-en-20-yn-17α-ol) Cefotetan Impurity 14 4-ANDROSTEN-[2, 3-d]Isoxazole-17α-ETHYNYL-17β-OL 17230-88-5 C22H27NO2 Cell Signaling and Neuroscience Cell Biology