Fluoxymesterone

Identification

Summary

Fluoxymesterone is a synthetic androgenic anabolic steroid that used in the treatment of hypogonadism and delayed puberty in males, as well as breast neoplasms in women.

Brand Names
Androxy, Halotestin
Generic Name
Fluoxymesterone
DrugBank Accession Number
DB01185
Background

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.

Type
Small Molecule
Groups
Approved, Illicit
Structure
Weight
Average: 336.4409
Monoisotopic: 336.210072999
Chemical Formula
C20H29FO3
Synonyms
  • 11β,17β-Dihydroxy-9α-fluoro-17α-methyl-4-androster-3-one
  • 17α-Methyl-9α-fluoro-11β-hydroxytesterone
  • 9-Fluoro-11β,17β-dihydroxy-17-methylandrost-4-en-3-one
  • 9α-Fluoro-11β-hydroxy-17-methyltestosterone
  • Fluoximesterona
  • Fluoxymesterone
  • Fluoxymestérone
  • Fluoxymesteronum
External IDs
  • NSC-12165

Pharmacology

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.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Management ofDelayed puberty••••••••••••
Treatment ofGonadotropin deficiency••••••••••••
Management ofHypogonadotropic hypogonadism••••••••••••
Treatment ofLhrh deficiency••••••••••••
Management ofPrimary hypogonadism••••••••••••
Contraindications & Blackbox Warnings
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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.

Mechanism 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.

TargetActionsOrganism
AAndrogen receptor
agonist
Humans
AEstrogen receptor alpha
antagonist
Humans
UGlucocorticoid receptor
antagonist
Humans
UCorticosteroid 11-beta-dehydrogenase isozyme 2
inhibitor
Humans
Absorption

Oral absorption is less than 44%.

Volume of distribution

Not Available

Protein binding

Very high (99%) with 80% to sex hormone binding globulin, 19% to albumin.

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

Route of elimination

Not Available

Half-life

9.2 hours

Clearance

Not Available

Adverse Effects
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Toxicity

Side effects include virilization (masculine traits in women), acne, fluid retention, and hypercalcemia.

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AcarboseFluoxymesterone may increase the hypoglycemic activities of Acarbose.
AcenocoumarolFluoxymesterone may increase the anticoagulant activities of Acenocoumarol.
AcetohexamideFluoxymesterone may increase the hypoglycemic activities of Acetohexamide.
AlbiglutideFluoxymesterone may increase the hypoglycemic activities of Albiglutide.
AlogliptinFluoxymesterone may increase the hypoglycemic activities of Alogliptin.
Food Interactions
  • Take with food.

Products

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International/Other Brands
Ora-Testryl (Bristol-Myers Squibb) / Testoral (Midy) / U-Gono (Upjohn) / UItandren (Ciba)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
HalotestinTablet5 mg/1OralUNSPECIFIED2006-02-06Not applicableUS flag
HalotestinTablet2 mg/1OralUNSPECIFIED2006-02-06Not applicableUS flag
HalotestinTablet10 mg/1OralUNSPECIFIED2006-02-06Not applicableUS flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
AndroxyTablet10 mg/1OralUpsher-Smith Laboratories, LLC1983-10-21Not applicableUS flag

Categories

ATC Codes
G03BA01 — Fluoxymesterone
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Androstane steroids
Direct Parent
Androgens and derivatives
Alternative Parents
Halogenated steroids / 3-oxo delta-4-steroids / 17-hydroxysteroids / 11-beta-hydroxysteroids / Delta-4-steroids / Cyclohexenones / Tertiary alcohols / Secondary alcohols / Fluorohydrins / Cyclic alcohols and derivatives
show 4 more
Substituents
11-beta-hydroxysteroid / 11-hydroxysteroid / 17-hydroxysteroid / 3-oxo-delta-4-steroid / 3-oxosteroid / 9-halo-steroid / Alcohol / Aliphatic homopolycyclic compound / Alkyl fluoride / Alkyl halide
show 20 more
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
11beta-hydroxy steroid, 3-oxo Delta(4)-steroid, 17beta-hydroxy steroid, fluorinated steroid, anabolic androgenic steroid (CHEBI:5120) / C19 steroids (androgens) and derivatives (LMST02020025)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
9JU12S4YFY
CAS number
76-43-7
InChI Key
YLRFCQOZQXIBAB-RBZZARIASA-N
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
IUPAC Name
(1S,3aS,3bS,9aS,9bR,10S,11aS)-9b-fluoro-1,10-dihydroxy-1,9a,11a-trimethyl-1H,2H,3H,3aH,3bH,4H,5H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-one
SMILES
[H][C@@]12CC[C@](C)(O)[C@@]1(C)C[C@H](O)[C@@]1(F)[C@@]2([H])CCC2=CC(=O)CC[C@]12C

References

Synthesis Reference

U.S. Patent 2,793,218 U.S. Patent 2,813,881

General References
  1. 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. [Article]
Human Metabolome Database
HMDB0015316
KEGG Drug
D00327
PubChem Compound
6446
PubChem Substance
46508867
ChemSpider
6205
BindingDB
18189
RxNav
4494
ChEBI
5120
ChEMBL
CHEMBL1445
ZINC
ZINC000003875484
Therapeutic Targets Database
DAP000904
PharmGKB
PA164744518
Guide to Pharmacology
GtP Drug Page
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Fluoxymesterone
MSDS
Download (75.7 KB)

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount
2TerminatedTreatmentMetastatic Breast Cancer1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Major Pharmaceuticals
  • Qualitest
  • Spectrum Pharmaceuticals
  • USL Pharma Inc.
  • Valeant Ltd.
Dosage Forms
FormRouteStrength
TabletOral10 mg/1
TabletOral2 mg/1
TabletOral5 mg/1
TabletOral5 mg
Prices
Unit descriptionCostUnit
Fluoxymesterone powder391.79USD g
Android 10 mg capsule11.35USD each
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)265U.S. Patent 2,793,218 U.S. Patent 2,813,881
water solubility67.5 mg/LNot Available
logP2.38HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.0452 mg/mLALOGPS
logP2.5ALOGPS
logP2.38Chemaxon
logS-3.9ALOGPS
pKa (Strongest Acidic)13.6Chemaxon
pKa (Strongest Basic)-3Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area57.53 Å2Chemaxon
Rotatable Bond Count0Chemaxon
Refractivity90.19 m3·mol-1Chemaxon
Polarizability36.65 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9633
Caco-2 permeable+0.8586
P-glycoprotein substrateSubstrate0.7505
P-glycoprotein inhibitor INon-inhibitor0.7583
P-glycoprotein inhibitor IINon-inhibitor0.87
Renal organic cation transporterNon-inhibitor0.8136
CYP450 2C9 substrateNon-substrate0.862
CYP450 2D6 substrateNon-substrate0.8773
CYP450 3A4 substrateSubstrate0.7669
CYP450 1A2 substrateNon-inhibitor0.9041
CYP450 2C9 inhibitorNon-inhibitor0.8159
CYP450 2D6 inhibitorNon-inhibitor0.9286
CYP450 2C19 inhibitorNon-inhibitor0.917
CYP450 3A4 inhibitorNon-inhibitor0.8354
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8585
Ames testNon AMES toxic0.8777
CarcinogenicityNon-carcinogens0.9242
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.7028 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.943
hERG inhibition (predictor II)Non-inhibitor0.5784
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0ab9-1934000000-8eb342128d6bf9311319
Mass Spectrum (Electron Ionization)MSsplash10-006x-5951000000-4c37d94fe4ed0b343941
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-014j-0059000000-14539957649e4eb13d07
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0009000000-627cfea04e4bf20417a9
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-014r-1498000000-0c10c9dbf69f23e09abe
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0019000000-547934e293669e9fbc86
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-052r-0719000000-ef3d33b7e8379d43ae3c
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-2390000000-97e9ab04112881d64ea3
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-183.7069268
predicted
DarkChem Lite v0.1.0
[M-H]-178.8683
predicted
DeepCCS 1.0 (2019)
[M+H]+185.4897268
predicted
DarkChem Lite v0.1.0
[M+H]+180.83336
predicted
DeepCCS 1.0 (2019)
[M+Na]+184.1047268
predicted
DarkChem Lite v0.1.0
[M+Na]+187.62178
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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Details
1. Androgen receptor
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Zinc ion binding
Specific Function
Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription ...
Gene Name
AR
Uniprot ID
P10275
Uniprot Name
Androgen receptor
Molecular Weight
98987.9 Da
References
  1. Fernandez L, Chirino R, Boada LD, Navarro D, Cabrera N, del Rio I, Diaz-Chico BN: Stanozolol and danazol, unlike natural androgens, interact with the low affinity glucocorticoid-binding sites from male rat liver microsomes. Endocrinology. 1994 Mar;134(3):1401-8. doi: 10.1210/endo.134.3.8119180. [Article]
  2. Kasperk CH, Wergedal JE, Farley JR, Linkhart TA, Turner RT, Baylink DJ: Androgens directly stimulate proliferation of bone cells in vitro. Endocrinology. 1989 Mar;124(3):1576-8. [Article]
  3. Smallridge RC, Vigersky R, Glass AR, Griffin JE, White BJ, Eil C: Androgen receptor abnormalities in identical twins with oligospermia. Clinical and biochemical studies. Am J Med. 1984 Dec;77(6):1049-54. [Article]
  4. 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. [Article]
  5. Kemppainen JA, Langley E, Wong CI, Bobseine K, Kelce WR, Wilson EM: Distinguishing androgen receptor agonists and antagonists: distinct mechanisms of activation by medroxyprogesterone acetate and dihydrotestosterone. Mol Endocrinol. 1999 Mar;13(3):440-54. [Article]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
Zinc ion binding
Specific Function
Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissu...
Gene Name
ESR1
Uniprot ID
P03372
Uniprot Name
Estrogen receptor
Molecular Weight
66215.45 Da
References
  1. Ingle JN, Suman VJ, Mailliard JA, Kugler JW, Krook JE, Michalak JC, Pisansky TM, Wold LE, Donohue JH, Goetz MP, Perez EA: Randomized trial of tamoxifen alone or combined with fluoxymesterone as adjuvant therapy in postmenopausal women with resected estrogen receptor positive breast cancer. North Central Cancer Treatment Group Trial 89-30-52. Breast Cancer Res Treat. 2006 Jul;98(2):217-22. Epub 2006 Mar 15. [Article]
  2. Sledge GW Jr, Hu P, Falkson G, Tormey D, Abeloff M: Comparison of chemotherapy with chemohormonal therapy as first-line therapy for metastatic, hormone-sensitive breast cancer: An Eastern Cooperative Oncology Group study. J Clin Oncol. 2000 Jan;18(2):262-6. [Article]
  3. Pearson OH, Manni A, Arafah BM: Antiestrogen treatment of breast cancer: an overview. Cancer Res. 1982 Aug;42(8 Suppl):3424s-3429s. [Article]
  4. Perloff M, Norton L, Korzun AH, Wood WC, Carey RW, Gottlieb A, Aust JC, Bank A, Silver RT, Saleh F, Canellos GP, Perry MC, Weiss RB, Holland JF: Postsurgical adjuvant chemotherapy of stage II breast carcinoma with or without crossover to a non-cross-resistant regimen: a Cancer and Leukemia Group B study. J Clin Oncol. 1996 May;14(5):1589-98. [Article]
  5. Swain SM, Steinberg SM, Bagley C, Lippman ME: Tamoxifen and fluoxymesterone versus tamoxifen and danazol in metastatic breast cancer--a randomized study. Breast Cancer Res Treat. 1988 Sep;12(1):51-7. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Zinc ion binding
Specific Function
Receptor for glucocorticoids (GC). Has a dual mode of action: as a transcription factor that binds to glucocorticoid response elements (GRE), both for nuclear and mitochondrial DNA, and as a modula...
Gene Name
NR3C1
Uniprot ID
P04150
Uniprot Name
Glucocorticoid receptor
Molecular Weight
85658.57 Da
References
  1. Mayer M, Rosen F: Interaction of anabolic steroids with glucocorticoid receptor sites in rat muscle cytosol. Am J Physiol. 1975 Nov;229(5):1381-6. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid binding
Specific Function
Catalyzes the conversion of cortisol to the inactive metabolite cortisone. Modulates intracellular glucocorticoid levels, thus protecting the nonselective mineralocorticoid receptor from occupation...
Gene Name
HSD11B2
Uniprot ID
P80365
Uniprot Name
Corticosteroid 11-beta-dehydrogenase isozyme 2
Molecular Weight
44126.06 Da
References
  1. Furstenberger C, Vuorinen A, Da Cunha T, Kratschmar DV, Saugy M, Schuster D, Odermatt A: The anabolic androgenic steroid fluoxymesterone inhibits 11beta-hydroxysteroid dehydrogenase 2-dependent glucocorticoid inactivation. Toxicol Sci. 2012 Apr;126(2):353-61. doi: 10.1093/toxsci/kfs022. Epub 2012 Jan 23. [Article]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Androgen binding
Specific Function
Functions as an androgen transport protein, but may also be involved in receptor mediated processes. Each dimer binds one molecule of steroid. Specific for 5-alpha-dihydrotestosterone, testosterone...
Gene Name
SHBG
Uniprot ID
P04278
Uniprot Name
Sex hormone-binding globulin
Molecular Weight
43778.755 Da
References
  1. Smallridge RC, Vigersky R, Glass AR, Griffin JE, White BJ, Eil C: Androgen receptor abnormalities in identical twins with oligospermia. Clinical and biochemical studies. Am J Med. 1984 Dec;77(6):1049-54. [Article]
  2. Pugeat MM, Dunn JF, Nisula BC: Transport of steroid hormones: interaction of 70 drugs with testosterone-binding globulin and corticosteroid-binding globulin in human plasma. J Clin Endocrinol Metab. 1981 Jul;53(1):69-75. [Article]
  3. Vigersky RA, Easley RB, Loriaux DL: Effect of fluoxymesterone on the pituitary-gonadal axis: the role of testosterone-estradiol-binding globulin. J Clin Endocrinol Metab. 1976 Jul;43(1):1-9. [Article]

Drug created at June 13, 2005 13:24 / Updated at May 07, 2021 21:26