Danazol
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MedKoo CAT#: 317579

CAS#: 17230-88-5

Description: Danazol is a derivative of the synthetic steroid ethisterone that suppresses the production of gonadotropins and has some weak androgenic effects. Before becoming available as a generic drug, danazol was marketed as Danocrine in the United States. It was approved by the US Food and Drug Administration (FDA) as the first drug to specifically treat endometriosis in the early 1970s. Although effective for endometriosis, its use is limited by its masculinizing side-effects. Its role as a treatment for endometriosis has been largely replaced by the GnRH agonists.


Chemical Structure

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Danazol
CAS# 17230-88-5

Theoretical Analysis

MedKoo Cat#: 317579
Name: Danazol
CAS#: 17230-88-5
Chemical Formula: C22H27NO2
Exact Mass: 337.20418
Molecular Weight: 337.46
Elemental Analysis: C, 78.30; H, 8.06; N, 4.15; O, 9.48

Price and Availability

Size Price Availability Quantity
200.0mg USD 250.0 2 Weeks
500.0mg USD 450.0 2 Weeks
1.0g USD 850.0 2 Weeks
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Synonym: Danazol; Danocrine; Danol; Cyclomen; Chronogyn; Ladogal

IUPAC/Chemical Name: (1R,3aS,3bR,10aR,10bS,12aS)-1-ethynyl-10a,12a-dimethyl-2,3,3a,3b,4,5,10,10a,10b,11,12,12a-dodecahydro-1H-cyclopenta[7,8]phenanthro[3,2-d]isoxazol-1-ol

InChi Key: POZRVZJJTULAOH-LHZXLZLDSA-N

InChi Code: 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

SMILES Code: C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C#C)O)CCC4=CC5=C(C[C@]34C)C=NO5

Appearance: White to light yellow crystalline powder.

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Product Data:

Biological target: Danazol is a derivative of the synthetic steroid ethisterone, that suppresses the production of gonadotrophins and has some weak androgenic effects.
In vitro activity: In the present study, a clinically used synthetic steroid hormone, danazol, was investigated for its CS properties and cytotoxic mechanisms. Danazol exhibited strong and moderate selectivity toward HepG2/VIN (SI 211.83) and NCI-H460/MX20 (SI 4.45), demonstrating CS effects across multiple kinds of MDR cancer cell lines (Table 1). In the cell cycle distribution analysis, 40x higher concentration of danazol for 24 h was first treated to evaluate the acute selective-effect of danazol in MDR cell lines. The results showed that KB/VIN cells represented an increase in the subG1-phase after high-dose and short-term danazol treatment. Danazol significantly activated caspase-8 in the KB/VIN, but not the HeLaS33, cell line (Fig. 5a). Moreover, danazol elicited high ROS levels in HeLaS3 as well as KB/VIN cells (Fig. 5c). These results demonstrated the compound’s selective property and apoptosis regulation in MDR cancer cells. The effects of danazol were further investigated on STAT3-related pathways. The data showed that danazol significantly reduced the phosphorylation of STAT3 as well as downstream MYC expression in MDR KB/VIN cells but not the parental HeLaS3 cells (Fig. 6a,b). In addition, the ELISA results demonstrated that danazol treatment inhibited CDC25 and CDK1 activation in KB/VIN cells (Fig. 6c,d). Furthermore, danazol treatment also resulted in increased levels of p21 in KB/VIN cells (Fig. 6e). Taken together, the results suggest that danazol exerts a CS effect by inhibiting the STAT3 pathway in MDR cancer cells and thus provides a possible solution for MDR cancers. Reference: Sci Rep. 2019 Aug 12;9(1):11628. https://pubmed.ncbi.nlm.nih.gov/31406162/
In vivo activity: The aim of this study was to investigate the effect of danazol on alloimmune responses in murine heart transplantation. CBA male mice (H2(k) ) underwent transplantation of C57BL/6 male (H2(b) ) hearts and received a single dose of danazol (0.4, 1.2 or 4mg/kg/day) by intraperitoneal injection on the day of transplantation and for 6 days thereafter. The median survival time (MST) of allografts in danazol-treated (1.2 and 4mg/kg/day) mice was 28 and 63 days, respectively, compared with 7days in untreated mice. Moreover, secondary CBA recipients given whole splenocytes or CD4(+) cells from primary danazol-treated (4mg/kg/day) CBA recipients 30 days after transplantation had prolonged allograft survival (MSTs, 29 and 60days, respectively). Cell proliferation, interleukin (IL)-2 and interferon-γ were suppressed in danazol-treated mice, whereas IL-4 and IL-10 were up-regulated. Moreover, danazol directly suppressed allo-proliferation in a mixed leukocyte culture. Flow cytometry showed an increased CD4(+) CD25(+) Foxp3(+) cell population in splenocytes from danazol-treated mice. In conclusion, danazol prolongs cardiac allograft survival and generates regulatory CD4(+) cells. Reference: Transpl Int. 2012 Mar;25(3):357-65. https://pubmed.ncbi.nlm.nih.gov/22239184/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 35.0 103.72
Ethanol 20.0 56.27

Preparing Stock Solutions

The following data is based on the product molecular weight 337.46 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Kusakabe K, Morishima S, Nakamuta N, Li ZL, Otsuki Y. Effect of danazol on NK cells and cytokines in the mouse uterus. J Reprod Dev. 2007 Feb;53(1):87-94. doi: 10.1262/jrd.18074. Epub 2006 Nov 1. PMID: 17077583. 2. Chang YT, Teng YN, Lin KI, Wang CCN, Morris-Natschke SL, Lee KH, Hung CC. Danazol mediates collateral sensitivity via STAT3/Myc related pathway in multidrug-resistant cancer cells. Sci Rep. 2019 Aug 12;9(1):11628. doi: 10.1038/s41598-019-481692. PMID: 31406162; PMCID: PMC6690972. 3. Uchiyama M, Jin X, Zhang Q, Hirai T, Bashuda H, Watanabe T, Amano A, Niimi M. Danazol induces prolonged survival of fully allogeneic cardiac grafts and maintains the generation of regulatory CD4(+) cells in mice. Transpl Int. 2012 Mar;25(3):357-65. doi: 10.1111/j.1432-2277.2011.01427.x. Epub 2012 Jan 13. PMID: 22239184.
In vitro protocol: 1. Kusakabe K, Morishima S, Nakamuta N, Li ZL, Otsuki Y. Effect of danazol on NK cells and cytokines in the mouse uterus. J Reprod Dev. 2007 Feb;53(1):87-94. doi: 10.1262/jrd.18074. Epub 2006 Nov 1. PMID: 17077583. 2. Chang YT, Teng YN, Lin KI, Wang CCN, Morris-Natschke SL, Lee KH, Hung CC. Danazol mediates collateral sensitivity via STAT3/Myc related pathway in multidrug-resistant cancer cells. Sci Rep. 2019 Aug 12;9(1):11628. doi: 10.1038/s41598-019-481692. PMID: 31406162; PMCID: PMC6690972.
In vivo protocol: 1. Kusakabe K, Morishima S, Nakamuta N, Li ZL, Otsuki Y. Effect of danazol on NK cells and cytokines in the mouse uterus. J Reprod Dev. 2007 Feb;53(1):87-94. doi: 10.1262/jrd.18074. Epub 2006 Nov 1. PMID: 17077583. 2. Uchiyama M, Jin X, Zhang Q, Hirai T, Bashuda H, Watanabe T, Amano A, Niimi M. Danazol induces prolonged survival of fully allogeneic cardiac grafts and maintains the generation of regulatory CD4(+) cells in mice. Transpl Int. 2012 Mar;25(3):357-65. doi: 10.1111/j.1432-2277.2011.01427.x. Epub 2012 Jan 13. PMID: 22239184.

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1: Podhorecka M, Macheta A, Chocholska S, Bojarska-Junak A, Szymczyk A, Goracy A, Dmoszynska A, Hus M. Danazol induces apoptosis and cytotoxicity of leukemic cells alone and in combination with purine nucleoside analogs in chronic lymphocytic leukemia. Ann Hematol. 2015 Dec 22. [Epub ahead of print] PubMed PMID: 26692089.

2: Liu W, Gu X, Fu R, Li Y, Lv M, Sun T, Lv C, Liu X, Xue F, Zhang L, Yang R. The Effect of Danazol in Primary Immune Thrombocytopenia: An Analysis of a Large Cohort From a Single Center in China. Clin Appl Thromb Hemost. 2015 Dec 16. pii: 1076029615622002. [Epub ahead of print] PubMed PMID: 26681745.

3: Sayyah-Melli M, Bidadi S, Taghavi S, Ouladsahebmadarek E, Jafari-Shobeiri M, Ghojazadeh M, Rahmani V. Comparative study of vaginal danazol vs diphereline (a synthetic GnRH agonist) in the control of bleeding during hysteroscopic myomectomy in women with abnormal uterine bleeding: a randomized controlled clinical trial. Eur J Obstet Gynecol Reprod Biol. 2015 Nov 26;196:48-51. doi: 10.1016/j.ejogrb.2015.10.021. [Epub ahead of print] PubMed PMID: 26675055.

4: Baydoun E, Atia-Tul-Wahab, Mehmood H, Ahmad MS, Malik R, Smith C, Choudhary MI. Microbial transformation of danazol with Cunninghamella blakesleeana and anti-cancer activity of danazol and its transformed products. Steroids. 2015 Dec 5;105:121-127. doi: 10.1016/j.steroids.2015.11.010. [Epub ahead of print] PubMed PMID: 26666360.

5: Godin R, Marcoux V. Vaginally Administered Danazol: An Overlooked Option in the Treatment of Rectovaginal Endometriosis? J Obstet Gynaecol Can. 2015 Dec;37(12):1098-103. PubMed PMID: 26637082.

6: Jackson MJ, Kestur US, Hussain MA, Taylor LS. Dissolution of Danazol Amorphous Solid Dispersions: Supersaturation and Phase Behavior as a Function of Drug Loading and Polymer Type. Mol Pharm. 2015 Dec 9. [Epub ahead of print] PubMed PMID: 26618718.

7: Mancano MA. High-Dose Loperamide Abuse Inducing Life-Threatening Cardiac Arrhythmias; Topiramate-Induced Diarrhea in a Breastfed Infant; Danazol-Induced Stevens-Johnson Syndrome; Asenapine-Induced Myasthenic Syndrome; Black Hairy Tongue Due to Linezolid; Adalimumab-Induced Priapism. Hosp Pharm. 2015 May;50(5):351-5. doi: 10.1310/hpj5005-351. PubMed PMID: 26405319; PubMed Central PMCID: PMC4567199.

8: Suwatanapongched T, Boonsarngsuk V, Amornputtisathaporn N, Leelachaikul P. Thoracic endometriosis with catamenial haemoptysis and pneumothorax: computed tomography findings and long-term follow-up after danazol treatment. Singapore Med J. 2015 Jul;56(7):e120-3. doi: 10.11622/smedj.2015115. PubMed PMID: 26243981; PubMed Central PMCID: PMC4520924.

9: Cervantes F, Isola IM, Alvarez-Larrán A, Hernández-Boluda JC, Correa JG, Pereira A. Danazol therapy for the anemia of myelofibrosis: assessment of efficacy with current criteria of response and long-term results. Ann Hematol. 2015 Nov;94(11):1791-6. doi: 10.1007/s00277-015-2435-7. Epub 2015 Jun 28. PubMed PMID: 26122869.

10: Zlateska B, Ciccolini A, Dror Y. Treatment of dyskeratosis congenita-associated pulmonary fibrosis with danazol. Pediatr Pulmonol. 2015 Jun 17. doi: 10.1002/ppul.23235. [Epub ahead of print] PubMed PMID: 26083318.

Danazol

200.0mg / USD 250.0