Metabolism / Metabolites
Metabolized in the liver, the main metabolites are norethindrone and 17-hydroxymethylnorethindrone.

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Biological half-life
Approximately 24 hours.

Danazol may cause developmental toxicity depending on state or federal labeling requirements. Danazol is a 17β-hydroxysteroid and a terminal alkyne compound. It has anti-estrogenic, estrogen antagonist, and anti-aging effects. It is derived from the hydrogenation of pregnane. It is a synthetic steroid with anti-gonadotropic and anti-estrogenic activity, acting as an anterior pituitary inhibitor by inhibiting the output of pituitary gonadotropins. It has some androgenic properties. Danazol has been used to treat endometriosis and some benign breast diseases. Danazol is an androgen. The mechanism of action of danazol is as an androgen receptor agonist. Danazol is a synthetic androgen derived from ethinyltestosterone. Danazol indirectly reduces estrogen production by decreasing the secretion of follicle-stimulating hormone and luteinizing hormone from the pituitary gland, and exerts anti-estrogenic, anabolic, and weak androgenic effects by binding to sex hormone receptors in target tissues. (NCI04)
A synthetic steroid with anti-gonadotropic and anti-estrogen activity, acting as an anterior pituitary inhibitor by suppressing the output of pituitary gonadotropins. It has some androgenic properties. Danazol has been used to treat endometriosis and some benign breast diseases.

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Drug Indications
Used to treat endometriosis and fibrocystic breast disease (in patients unresponsive to simple treatments). Also used to prevent various types of hereditary angioedema in men and women.

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Mechanism of Action
As a gonadotropin inhibitor, danazol may suppress the pituitary-ovarian axis by inhibiting the secretion of pituitary gonadotropins. Danazol can also suppress the pre-ovulatory surge of follicle-stimulating hormone (FSH) and luteinizing hormone (LH), thereby reducing ovarian estrogen production. Danazol may also directly inhibit ovarian steroid production; bind to androgen, progesterone, and glucocorticoid receptors; bind to sex hormone-binding globulin and corticosteroid-binding globulin; and increase the metabolic clearance of progesterone. Another mechanism by which danazol promotes the regression of endometriosis may be by reducing the concentrations of IgG, IgM, and IgA, as well as the levels of phospholipids and IgG isotope autoantibodies. In the treatment of endometriosis, due to the suppression of ovarian function, danazol causes both normal and ectopic endometrial tissue to lose activity and atrophy, leading to anovulation and amenorrhea. In fibrocystic breast disease, the exact mechanism of action of danazol is unclear, but it may be related to the suppression of estrogen stimulation caused by decreased ovarian estrogen secretion. Danazol may also act directly on steroid receptor sites in breast tissue, leading to nodule disappearance, relief of pain and tenderness, and possible alteration of the menstrual cycle. In the case of hereditary angioedema, danazol corrects the underlying biochemical deficiency by increasing the serum concentration of the deficient C1 esterase inhibitor, thereby increasing the serum concentration of the C4 component of the complement system. (Source: PharmGKB) Danazol is a derivative of the synthetic steroid norethindrone (a modified testosterone). It was initially approved by the U.S. Food and Drug Administration (FDA) as the first drug specifically for the treatment of endometriosis, but its role in endometriosis treatment has been superseded by gonadotropin-releasing hormone (GnRH) agonists. Danazol possesses anti-gonadotropic and anti-estrogenic activities. Danazol acts as an anterior pituitary inhibitor by inhibiting the output of pituitary gonadotropins. It also exhibits some androgenic properties.

C22H27NO2

337.46

337.204

C, 78.30; H, 8.06; N, 4.15; O, 9.48

17230-88-5

17230-88-5

28417

White to light yellow crystalline powder

1.2±0.1 g/cm3

478.2±45.0 °C at 760 mmHg

224.4-226.8ºC

243.0±28.7 °C

0.0±1.3 mmHg at 25°C

1.604

4.7

1

3

1

25

677

6

C#C[C@]1(O)CC[C@@]2([H])[C@]3([H])CCC4=CC5=C(C=NO5)C[C@]4(C)[C@@]3([H])CC[C@@]21C

POZRVZJJTULAOH-LHZXLZLDSA-N

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+/m1/s1

(1S,2R,13R,14S,17R,18S)-17-ethynyl-2,18-dimethyl-7-oxa-6-azapentacyclo[11.7.0.02,10.04,8.014,18]icosa-4(8),5,9-trien-17-ol

Danazol; Danol; Danocrine; Chronogyn; Ladogal; Cyclomen

2934.99.9001

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

DMSO: ~25 mg/mL (~74.1 mM;)
Ethanol: ~20 mg/mL (~59.3 mM)

Solubility in Formulation 1: 2.5 mg/mL (7.41 mM) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), suspension solution; with sonication.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 2: ≥ 2.5 mg/mL (7.41 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.

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Solubility in Formulation 3: ≥ 2 mg/mL (5.93 mM) (saturation unknown) in 10% EtOH + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.0 mg/mL clear EtOH stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 4: ≥ 2 mg/mL (5.93 mM) (saturation unknown) in 10% EtOH + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.0 mg/mL clear EtOH stock solution to 900 μL of corn oil and mix well.

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 (Please use freshly prepared in vivo formulations for optimal results.)