WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 317579
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.
MedKoo Cat#: 317579
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
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
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.
|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|
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.