Fluoxymesterone

CAS No:
76-43-7 Category:
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Product Details:

  • CAS No: 76-43-7
  • AHFC code:
  • Synonyms: Androfluorene Androfluorone Fluossimesterone [DCIT] Fluoximesterona [INN-Spanish] Fluoximesterone Fluoximesteronum Fluoxymesteronum [INN-Latin] Fluoxymestrone
  • ATC Code: G03BA01
  • Chemical Formula: C19H24N2O4
  • Molecular Weight: 336.4409
  • Assay/Purity: Typically NLT 98%
  • DrugBank: DB01185 (APRD00981)
  • SMILES: C[C,]1(O)CC[C,H]2[C,,H]3CCC4=CC(=O)CC[C,]4(C)[C,,]3(F)[C,,H](O)C[C,]12C
  • InChl: YLRFCQOZQXIBAB-RBZZARIASA-N
  • PubChem: 6446
  • IUPAC: (1R,2S,10S,11S,14S,15S,17S)-1-fluoro-14,17-dihydroxy-2,14,15-trimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one

Additional Details

Indication:
In males, used as replacement therapy in conditions associated with symptoms of deficiency or absence of endogenous testosterone. In females, for palliation of androgenresponsive recurrent mammary cancer in women who are more than one year but less than five years postmenopausal.
Pharmacodynamics:
Fluoxymesterone is a synthetic androgen, or male hormone, similar to testosterone. Fluoxymesterone works by attaching itself to androgen receptors; this causes it to interact with the parts of the cell involved in the making of proteins. It may cause an increase in the synthesis of some proteins or a decrease in the synthesis of others. These proteins have a variety of effects, including blocking the growth of some types of breast cancer cells, stimulating cells that cause male sexual characteristics, and stimulating the production of red blood cells.
Mode of Action:
Fluoxymesterone is a synthetic androgenic anabolic steroid and is approximately 5 times as potent as natural methyltestosterone. Like testosterone and other androgenic hormones, fluoxymesterone binds to the androgen receptor. It produces retention of nitrogen, sodium, potassium, and phosphorus; increases protein anabolism; decreases amino acid catabolism and decreased urinary excretion of calcium. The antitumour activity of fluoxymesterone appears related to reduction or competitive inhibition of prolactin receptors or estrogen receptors or production.
Metabolism:
Presence of 17-alpha alkyl group reduces susceptibility to hepatic enzyme degradation, which slows metabolism and allows oral administration. Inactivation of testosterone occurs primarily in the liver
Toxicity:
Side effects include virilization (masculine traits in women), acne, fluid retention, and hypercalcemia.
General Reference:
Miner JN, Chang W, Chapman MS, Finn PD, Hong MH, Lopez FJ, Marschke KB, Rosen J, Schrader W, Turner R, van Oeveren A, Viveros H, Zhi L, Negro-Vilar A: An orally active selective androgen receptor modulator is efficacious on bone, muscle, and sex function with reduced impact on prostate. Endocrinology. 2007 Jan;148(1):363-73. Epub 2006 Oct 5. Pubmed
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