Danatrol

Base Information

• Chemical Name: Danatrol
• CAS No.: 17230-88-5
• Molecular Formula: C22H27NO2
• Molecular Weight: 337.462
• Hs Code.: 29372900
• NSC Number: 270916
• DSSTox Substance ID: DTXSID80860200
• Wikidata: Q27163410
• ChEMBL ID: CHEMBL4296981
• Mol file: 17230-88-5.mol

Synonyms:Azol;Cyclomen;Danatrol;Danazant;Danazol;Danazol Ratiopharm;Danazol-ratiopharm;Danocrine;Danol;Danoval;Ladogal;Norciden;Panacrine

Chemical Property of Danatrol

Chemical Property:

• Appearance/Colour: White solid
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 224.4-226.8 °C
• Refractive Index: 1.604
• Boiling Point: 478.2 °C at 760 mmHg
• PKA: 13.10±0.60(Predicted)
• Flash Point: 243 °C
• PSA: 46.26000
• Density: 1.21 g/cm³
• LogP: 4.22100
• Storage Temp.: -20°C Freezer
• Solubility.: Acetonitrile (Slightly), Chloroform (Slightly), Ethanol (Slightly), Methanol (Sl
• Water Solubility.: Partly soluble in water. Soluble in chloroform (25 mg/ml), acetone, acetonitrile, and ethanol. 17beta-Hydroxy-2,4,17a-pregnadien
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 337.204179104
• Heavy Atom Count: 25
• Complexity: 677

Purity/Quality:

99.0% ^*data from raw suppliers

Danazol ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi
• Statements: 20/21/22-63-36/37/38
• Safety Statements: 22-36-37/39-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC12CCC3C(C1CCC2(C#C)O)CCC4=CC5=C(CC34C)C=NO5
• Recent ClinicalTrials: Study to Determine Intraperitoneal,Tissue, Serum Concentrations of VML-0501 Following Five Days of Daily Vaginal Single Dose of VML-0501 (100 mg Danazol), in Comparison to Oral Danazol Capsules Daily 600 mg), in Women With Signs and Symptoms of Endometriosis Undergoing Laparoscopy
• Recent EU Clinical Trials: Study of the effects of telomerase reactivation with Danazol on ovarian function. A Pilot Study.
• Uses: anterior pituitary suppressant Danazol is an anterior pituitary supressant. Danazol is an anabolic steroid derivative of ethisterone, with mild androgenic side effects (an impeded androgen). Antigonadotropin. Anterior pituitary supressant. 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.
• Therapeutic Function: Anterior pituitary suppressant

Technology Process of Danatrol

There total 7 articles about Danatrol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

17α-ethenyl-17β-hydroxy-2-hydroxymethylene-4-androsten-3-one (2787-02-2) → danazol (17230-88-5)

Guidance literature:

With hydroxylamine hydrochloride; sodium acetate; In water; acetic acid; Heating;

DOI:10.1021/jm00337a001

Reference yield:

3-ethoxy-17α-ethynylandrosta-3,5-dien-17β-ol-3-one (24594-68-1) → danazol (17230-88-5)

Guidance literature:

Multi-step reaction with 3 steps

1: sulfuric acid / tetrahydrofuran / 6 h / pH 2 - 3

2: pyridine; sodium ethanolate / 72 h / 20 °C / Inert atmosphere

3: hydroxylamine hydrochloride; sodium acetate; acetic acid / 3.5 h / 75 °C

With pyridine; sulfuric acid; hydroxylamine hydrochloride; sodium ethanolate; sodium acetate; acetic acid; In tetrahydrofuran;

Reference yield:

Androstenedione (63-05-8) → danazol (17230-88-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: toluene-4-sulfonic acid / ethanol / 6.5 h / 40 °C

1.2: 0.5 h / 5 °C

2.1: potassium hydroxide / 1.5 h / 8 °C

2.2: 3 h / 20 - 25 °C

3.1: sulfuric acid / tetrahydrofuran / 6 h / pH 2 - 3

4.1: pyridine; sodium ethanolate / 72 h / 20 °C / Inert atmosphere

5.1: hydroxylamine hydrochloride; sodium acetate; acetic acid / 3.5 h / 75 °C

With pyridine; sulfuric acid; hydroxylamine hydrochloride; sodium ethanolate; sodium acetate; toluene-4-sulfonic acid; acetic acid; potassium hydroxide; In tetrahydrofuran; ethanol;

upstream raw materials:

17α-ethenyl-17β-hydroxy-2-hydroxymethylene-4-androsten-3-one

3-ethoxy-17α-ethynylandrosta-3,5-dien-17β-ol-3-one

Androstenedione

3-ethoxyandrosta-3,5-dien-17-one

Downstream raw materials:

17α-ethynyl-17β-hydroxy-2α-hydroxymethyl-4-androsten-3-one

17β-hydroxy-2-(hydroxymethyl)-17α-pregna-1,4-dien-20-yn-3-one

Refernces

• 1、 -. "Methods for predicting the response to statins". . . Retrieved 2011/10/13.
• 2、 MANSON,STONNER,NEUMANN,CHRISTIANSEN,CLARKE,ACKERMAN,PAGE,DEAN,PHILLIPS,POTTS,ARNOLD,BEYLER,CLINTON. "STEROIDAL HETEROCYCLES. VII. ANDROSTANO(2,3-D)ISOXAZOLES AND RELATED". . p. 1 - 9. Retrieved 2007/10/09.