(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

• ChemBase ID: 1056
• Molecular Formular: C20H29FO3
• Molecular Mass: 336.4408632
• Monoisotopic Mass: 336.21007301
• SMILES: F[C@]12[C@H]([C@H]3[C@@]([C@@](O)(CC3)C)(C[C@@H]2O)C)CCC2=CC(=O)CC[C@]12C
• Canonical SMILES: O=C1CC[C@]2(C(=C1)CC[C@@H]1[C@]2(F)[C@@H](O)C[C@]2([C@H]1CC[C@]2(C)O)C)C
• InChI: InChI=1S/C20H29FO3/c1-17-8-6-13(22)10-12(17)4-5-15-14-7-9-19(3,24)18(14,2)11-16(23)20(15,17)21/h10,14-16,23-24H,4-9,11H2,1-3H3/t14-,15-,16-,17-,18-,19-,20-/m0/s1
• InChIKey: YLRFCQOZQXIBAB-RBZZARIASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (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; (1R,2S,10S,11S,14S,15S,17S)-1-fluoro-14,17-dihydroxy-2,14,15-trimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-5-one
• IUPAC Traditional name: fluoxymesterone
• Brand Name: Anadroid-F; Android-f; Androsterolo; Fluosterone; Fluotestin; Flusteron; Flutestos; Halotestin; Neo-Ormonal; Ora Testryl; Ora-testryl; Oralsterone; Oratestin; Testoral; Ultandren; Ultandrene
• Synonyms: Fluossimesterone [DCIT]; Fluoximesterona [INN-Spanish]; Fluoximesterone; Fluoximesteronum; Fluoxymesteronum [INN-Latin]; Fluoxymestrone; Androfluorene; Androfluorone; FXM; Fluoxymesterone; 11β,17β-Dihydroxy-9α-fluoro-17α-methyl-4-androsten-3-one; 9α-Fluoro-11β,17β-dihydroxy-17α-methylandrost-4-en-3-one; 9α-Fluoro-11β-hydroxy-17α-methyltestosterone; Fluoxymesterone

Database IDs

• CAS Number: 76-43-7
• EC Number: 200-961-8
• MDL Number: MFCD00010480
• PubChem SID: 46508867; 160964519; 24894947
• PubChem CID: 6446
• CHEBI ID: 5120
• ATC CODE: G03BA01
• CHEMBL: 1445
• Chemspider ID: 6205
• DrugBank ID: DB01185
• IUPHAR ligand ID: 2861
• KEGG ID: D00327
• Unique Ingredient Identifier: 9JU12S4YFY
• Wikipedia Title: Fluoxymesterone
• Medline Plus: a682690

CALCULATED PROPERTIES

JChem

• Acid pKa: 13.601727
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 2.3808422
• LogD (pH = 7.4): 2.3808417
• Log P: 2.3808422
• Molar Refractivity: 90.1885 cm^3
• Polarizability: 35.430447 Å^3
• Polar Surface Area: 57.53 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.5
• LOG S: -3.87
• Solubility (Water): 4.52e-02 g/l

PROPERTIES

Physical Property

• Solubility: 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: soluble6.4 mg/mL; 67.5 mg/L; ethanol: soluble7.3 mg/mL; H2O: ≤0.5 mg/mL
• Apperance: white solid (photosensitive)
• Hydrophobicity(logP): 2

Safety Information

• RTECS: BV8390000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 63
• Safety Statements: 22-36
• GHS Pictograms: GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H361
• GHS Precautionary statements: P281
• Personal Protective Equipment: Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• Drug Control: USDEA Schedule III; Home Office Schedule 4.2; regulated under CDSA - not available from Sigma-Aldrich Canada

Pharmacology Properties

• Bioavailability: 100% Oral
• Excretion: urine
• Half Life: 9.5 hours
• Metabolism: Hepatic
• Legal Status: Schedule III Controlled Substance
• Pregnancy Category: X
• Gene Information: human ... AR(367), ESR1(2099), PRLR(5618)

Product Information

• Purity: 95%

DETAILS

DrugBank - DB01185

• Drug Groups: illicit; approved
• Description: An anabolic steroid that has been used in the treatment of male hypogonadism, delayed puberty in males, and in the treatment of breast neoplasms in women. [PubChem]
• 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.
• Pharmacology: 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.
• Toxicity: Side effects include virilization (masculine traits in women), acne, fluid retention, and hypercalcemia.
• Affected Organisms: Humans and other mammals
• Biotransformation: 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
• Absorption: Oral absorption is less than 44%.
• Half Life: 9.2 hours
• Protein Binding: Very high (99%) with 80% to sex hormone binding globulin, 19% to albumin.
• References: 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]
• External Links: Wikipedia; RxList; Drugs.com

Sigma Aldrich - F7751

Biochem/physiol Actions
Fluoxymesterone is an androgen and anabolic steroid.

REFERENCES

• 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