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Danazol (Synonyms: Danocrine,Ladogal,NSC 270916,WIN 17,757)

Catalog No.GC10785 Copy One-Click Copy Product Info

Danazol is a synthetic anabolic steroid with properties of inhibition of interleukin-1 and TNF-α production.

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Danazol Chemical Structure

Cas No.: 17230-88-5

Size Price Stock Qty
10mM (in 1mL DMSO)
$44.00
In stock
100mg
$40.00
In stock
250mg
$76.00
In stock

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Sample solution is provided at 25 µL, 10mM.



Description of Danazol

Danazol is a synthetic anabolic steroid with properties of inhibition of interleukin-1 and TNF-α production[1]. Danazol has antigonadotrophic effects, suppressing follicle-stimulating hormone and luteinizing hormone at the hypothalamic-pituitary level, and Danazol is an impeded androgen with anabolic and attenuated masculinizing properties[2]. Danazol has been widely used to alter red cell membranes directly to increase the surface area, enhancing the resistance to osmotic lysi[3].

In vitro, Danazol treatment for 48 hours significantly inhibited the viability of MDAMB-231 and MCF-7 cells, with IC50 values of 65μM and 31μM, respectively[4]. Treatment with 100μM Danazol for 24 hours reduced the proliferation of human umbilical vein endothelial cells (HUVECs) and decreased the formation of tubular structures[5]. 30μM Danazol treatment for 72 hours induced a cell cycle arrest in Mcf10A cells, decreased mitochondrial membrane potential, and promoted the downregulation of energy metabolism transcripts[6].

In vivo, Danazol, administered at an oral dose of 100mg/kg (5 times a week) significantly prolonged survival of female lupus MRL/MpJ mice and decreased serum amyloid protein (SAP) levels during the 200-day experiment[7]. Consecutively administered intraperitoneal injection of Danazol (4mg/kg/day) for 6 days, extended the survival of mice undergoing allogeneic cardiac grafts and maintained the generation of regulatory CD4+ cells in mice[8]. Subcutaneous injection of Danazol (25mg/kg), three times a week for 4 weeks, inhibited the progression of endometriosis in the female nude mouse model of endometriosis and led to the formation of fibrotic and avascular lesions[9].

References:
[1] Jaime-Pérez J C, Colunga-Pedraza P R, Gómez-Ramírez C D, et al. Danazol as first-line therapy for aplastic anemia[J]. Annals of hematology, 2011, 90(5): 523-527.
[2] Letchumanan P, Thumboo J. Danazol in the treatment of systemic lupus erythematosus: a qualitative systematic review[C]//Seminars in arthritis and rheumatism. WB Saunders, 2011, 40(4): 298-306. 
[3] Ahn Y S, Fernandez L F, Kim C I, et al. Danazol therapy renders red cells resistant to osmotic lysis 1[J]. The FASEB journal, 1989, 3(2): 157-162.
[4] Deka S J, Roy A, Ramakrishnan V, et al. Danazol has potential to cause PKC translocation, cell cycle dysregulation, and apoptosis in breast cancer cells[J]. Chemical biology & drug design, 2017, 89(6): 953-963.
[5] Thomas G W, Rael L T, Shimonkevitz R, et al. Effects of danazol on endothelial cell function and angiogenesis[J]. Fertility and sterility, 2007, 88(4): 1065-1070.
[6] Irgebay Z, Yeszhan B, Sen B, et al. Danazol alters mitochondria metabolism of fibrocystic breast Mcf10A cells[J]. The Breast, 2017, 35: 55-62.
[7] Connolly K M, Stecher V J, Snyder B W, et al. The effect of danazol in the MRL/lpr mouse model of autoimmune disease[J]. Agents and Actions, 1988, 25(1): 164-170.
[8] Uchiyama M, Jin X, Zhang Q, et al. Danazol induces prolonged survival of fully allogeneic cardiac grafts and maintains the generation of regulatory CD4+ cells in mice[J]. Transplant International, 2012, 25(3): 357-365.
[9] Ngô C, Chéreau C, Nicco C, et al. Reactive oxygen species controls endometriosis progression[J]. The American journal of pathology, 2009, 175(1): 225-234.

Protocol of Danazol

Cell experiment [1]:

Cell lines

Human umbilical vein endothelial cells (HUVECs)

Preparation Method

Human umbilical vein endothelial cells (HUVECs) were cultivated in endothelial cell medium-2 (EGM-2) supplemented with 5% fetal bovine serum, 100U/ml penicillin, and 100μg/ml streptomycin at 37°C in an incubator with 5% CO2. HUVECs were thawed and plated in 96-well tissue culture plates at 5000 cells/cm2 for 24h. The cells were treated with complete EGM-2 medium containing final concentrations of Danazol (0.1, 1, 10, and 100μM) in triplicates for 48h. Cell proliferation was measured.

Reaction Conditions

0.1, 1, 10, and 100μM; 48h

Applications

Danazol treatment reduced the cell viability of HUVECs in a dose-dependent manner.
Animal experiment [2]:

Animal models

Female nude mice

Preparation Method

Female nude mice (8 weeks of age) were housed in a specific pathogen-free (SPF) barrier environment and were continuously provided with sterilized food, water, and bedding. Mice were anesthetized with intraperitoneal injections of 500μl of 0.04M 2,2-tribromoethanol and 2.5% methyl-2-butanol. An incision was made on the ventral midline and one 5-mm2 fragment of human endometrioma was sutured to the parietal peritoneum with 7/0 Proline. The cuti was sutured with a 6/0 nylon thread. On day 14 after implantation, mice were operated to confirm the viability of the implant. Treatments started on day 14: the first group received subcutaneous injections of RU-486 (50mg/kg in 200μl of sesame oil; three times a week); the second group received subcutaneous injections of danazol (25mg/kg in 200μl of sesame oil; three times a week). The control group received intraperitoneal injections of 300μl of PBS or subcutaneous injections of 200μl of sesame oil three times a week. After 4 weeks of treatment, mice were sacrificed by cervical dislocation. Implants were extracted for histological analysis.

Dosage form

25mg/kg; three times a week; 4 weeks; s.c.

Applications

Danazol treatment caused fibrotic and avascular lesions in mice with endometriosis.

References:
[1] Thomas G W, Rael L T, Shimonkevitz R, et al. Effects of danazol on endothelial cell function and angiogenesis[J]. Fertility and sterility, 2007, 88(4): 1065-1070.
[2] Ngô C, Chéreau C, Nicco C, et al. Reactive oxygen species controls endometriosis progression[J]. The American journal of pathology, 2009, 175(1): 225-234.

Chemical Properties of Danazol

Cas No. 17230-88-5 SDF
Synonyms Danocrine,Ladogal,NSC 270916,WIN 17,757
Chemical Name pregna-2,4-dien-20-yno[2,3-d]isoxazol-17α-ol
Canonical SMILES O[C@@]1(C#C)CC[C@@]2([H])[C@]3([H])CCC4=CC5=C(C=NO5)C[C@]4(C)[C@@]3([H])CC[C@@]21C
Formula C22H27NO2 M.Wt 337.5
Solubility ≥ 11.05 mg/mL in DMSO, ≥ 14.84 mg/mL in EtOH with ultrasonic Storage Store at -20°C
Shipping Condition Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request.

Complete Stock Solution Preparation Table of Danazol

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1 mg 5 mg 10 mg
1 mM 2.963 mL 14.8148 mL 29.6296 mL
5 mM 592.6 μL 2.963 mL 5.9259 mL
10 mM 296.3 μL 1.4815 mL 2.963 mL
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3. All of the above co-solvents are available for purchase on the GlpBio website.

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Average Rating: 5 ★★★★★ (Based on Reviews and 20 reference(s) in Google Scholar.)

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