Oxandrolone

Base Information

• Chemical Name: Oxandrolone
• CAS No.: 53-39-4
• Molecular Formula: C19H30O3
• Molecular Weight: 306.445
• Hs Code.: 2937290000
• European Community (EC) Number: 200-172-9
• UNII: 7H6TM3CT4L
• DSSTox Substance ID: DTXSID8023399
• Nikkaji Number: J1.367F
• Wikipedia: Oxandrolone
• Wikidata: Q420859
• NCI Thesaurus Code: C29306
• RXCUI: 7779
• Pharos Ligand ID: H7LL2S9VWALU
• Metabolomics Workbench ID: 42948
• ChEMBL ID: CHEMBL1200436
• Mol file: 53-39-4.mol

Synonyms:Anavar;Oxandrin;Oxandrolone;SC 11585;SC-11585;SC11585

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Chemical Property of Oxandrolone

Chemical Property:

• Appearance/Colour: White crystalline powder
• Vapor Pressure: 9.19E-10mmHg at 25°C
• Melting Point: 235-238 °C
• Refractive Index: 1.526
• Boiling Point: 444.4 °C at 760mmHg
• PKA: 15.15±0.60(Predicted)
• Flash Point: 179.1 °C
• PSA: 46.53000
• Density: 1.105 g/cm³
• LogP: 3.54310
• Storage Temp.: Controlled Substance, -20?C Freezer
• Solubility.: DMSO: soluble2mg/mL (clear solution; warmed)
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 306.21949481
• Heavy Atom Count: 22
• Complexity: 503

Purity/Quality:

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 60-63-20/21/22
• Safety Statements: 22-36/37/39-45

MSDS Files:

Useful:

• Canonical SMILES: CC12CCC3C(C1CCC2(C)O)CCC4C3(COC(=O)C4)C
• Isomeric SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C)O)CC[C@@H]4[C@@]3(COC(=O)C4)C
• Recent ClinicalTrials: Oxandrolone Rotator Cuff Trial
• Uses: The use of oxandrolone, an analog of testosterone possessing only 5% of testosterone's virilizing androgenic effects, enhances anabolism of muscle protein by improving the efficiency of protein synthesis in severely burned children. Oxandrolone administration decreases loss of body weight and improves healing of the donor site wound. In a large clinical trial by our group, 0.1 mg/kg oxandrolone administered twice daily reduced length of the acute hospitalization, sustained LBM, and improved liver protein synthesis. Severely burned pediatric patients receiving oxandrolone for 1 year experienced improved growth, decreased cardiac work, and improved muscle strength. Oxandrolone treatment also improved lung function at rest and during exercise in this patient population. These improvements were maintained for up to 4 years after treatment had ended. The benefits of oxandrolone administration after burn injury were further enhanced when the treatment period was increased from 1 to 2 years. androgenic anabolic steroid;reverses catabolic tissue processes; promotes buildup of protein; increases erythropoietin production Oxandrolone is used for the same indications as nandrolone. It is a synthetic, anabolic steroid. Used to promote muscle growth and combat involuntary weight loss. It has also been used to treat cases of osteoporosis.
• Description: Oxandrolone is a synthetic anabolic-androgenic steroid. It is a 17 alpha-methylated version of dihydrotestosterone (DHT). It can be used for the treatment of many kinds of disorders such as idiopathic short stature, body mass loss due to catabolic illness, severe burns, trauma and hereditary angioedema as well as turner syndrome. Oxandrolone is especially effective in the treatment of severe burns without causing obvious side effects. It acts as an agonist of the androgen receptor, which modulates related gene expression to increase protein synthesis, further boosting muscle growth and increasing body mass as well as bone mineral density. However, it should be noted that its androgenic effect is less than its anabolic effect.
• Therapeutic Function: Androgen

Technology Process of Oxandrolone

There total 16 articles about Oxandrolone 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: 94.0%

17-β-hydroxy-17-α-methyl-1-oxo-1,2-seco-A-nor-5-α-androstan-2-oic acid → oxandrolone (53-39-4)

Guidance literature:

17-β-hydroxy-17-α-methyl-1-oxo-1,2-seco-A-nor-5-α-androstan-2-oic acid; With sodium hydroxide; In ethanol; water; at 8 - 9 ℃; Inert atmosphere;

With sodium tetrahydroborate; In ethanol; water; at 5 - 7 ℃; for 1h;

With hydrogenchloride; In ethanol; water; at 1 - 9 ℃; for 8.75h;

DOI:10.1021/op060231b

Reference yield: 91.0%

(4aS,4bS,6aS,7S,9aS,9bR,11aS)-7-(methoxymethoxy)-4a,6a,7-trimethyltetradeca-hydroindeno[4,5-h]isochromen-2(1H)-one (1219000-90-4) → oxandrolone (53-39-4)

Guidance literature:

With 1-thiopropane; zinc dibromide; In dichloromethane; at 20 ℃; for 0.116667h; Inert atmosphere;

DOI:10.1016/j.tet.2010.01.007

Reference yield: 86.0%

→ oxandrolone (53-39-4)

Guidance literature:

upstream raw materials:

mestanolone

17α-methyl-1,3-seco-2-nor-5α-androstane-1,3,17α-triol

17β-hydroxy-17α-methyl-1,3-seco-2-nor-5α-androstane-1,3-diacid 1,3-dimethylester

(3S,3aS,5aS,6S,7S,9aS,9bS)-7-Carboxymethyl-3-hydroxy-3,3a,6-trimethyl-dodecahydro-cyclopenta[a]naphthalene-6-carboxylic acid

Downstream raw materials:

17,17-dimethyl-18-nor-2-oxa-5α-androst-13(14)-en-3-one

Refernces

• 1、 Cabaj, John E.,Kairys, David,Benson, Thomas R.. "Development of a commercial process to produce oxandrolone". . p. 378 - 388. Retrieved 2012/12/31.
• 2、 Ferraboschi, Patrizia,Colombo, Diego,Prestileo, Paolo. "A convenient synthesis of oxandrolone through a regioselective Candida antarctica lipase-catalyzed transformation". . p. 2781 - 2785. Retrieved 2007/10/03.