FLUOXYMESTERONE

US Previously Marketed

First approved in 1956

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C20H29FO3
Molecular Weight	336.4409
Optical Activity	UNSPECIFIED
Defined Stereocenters	7 / 7
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

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

InChI

InChIKey=YLRFCQOZQXIBAB-RBZZARIASA-N

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

HIDE SMILES / InChI

Molecular Formula	C20H29FO3
Molecular Weight	336.4409
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	7 / 7
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.drugs.com/ppa/fluoxymesterone.html
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/17439112 | http://reference.staging.medscape.com/drug/androxy-fluoxymesterone-342776

Fluoxymesterone, sold under the brand names Halotestin and Ultandren among others, is a synthetic, orally active androgenic-anabolic steroid (AAS) and a 17α-alkylated derivative of testosterone developed by Pharmacia & Upjohn Company LLC, approved by FDA at 1956. Fluoxymesterone is used in the treatment of hypogonadism in males and breast cancer in women. Fluoxymesterone has a relatively high ratio of androgenic to anabolic activity similarly to testosterone. Like many 17α-alkylated AAS, it has a relatively low affinity for the androgen receptor (AR). However, its actions are mediated by the AR, most likely due to its relatively long elimination half-life of approximately 9.2 hours.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Androgen Receptor 169 Target ID: CHEMBL1871 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17439112	Agonist 2752		0.3 nM [EC50]

Conditions

Condition	Modality	Highest Phase	Product
Male hypogonadism 1 Sources: https://www.drugs.com/ppa/fluoxymesterone.html	Primary	Approved 8583	HALOTESTIN Approved Use Males ANDROXY™ Tablets are indicated for replacement therapy in conditions associated with a deficiency or absence of endogenous testosterone. Primary hypogonadism (congenital or acquired) Testicular failure due to cryptorchidism, bilateral torsion, orchitis, vanishing testis syndrome, or orchidectomy. Hypogonadotropic hypogonadism (congenital or acquired) Idiopathic gonadotropin or luteinizing hormone-releasing hormone (LHRH) deficiency, or pituitary-hypothalamic injury from tumors, trauma, or radiation. (Appropriate adrenal cortical and thyroid hormone replacement therapy are still necessary, however, and are actually of primary importance.) If the above conditions occur prior to puberty, androgen replacement therapy will be needed during the adolescent years for development of secondary sexual characteristics. Prolonged androgen treatment will be required to maintain sexual characteristics in these and other males who develop testosterone deficiency after puberty. Delayed puberty ANDROXY™ (Fluoxymesterone Tablets, USP) may be used to stimulate puberty in carefully selected males with clearly delayed puberty. These patients usually have a familial pattern of delayed puberty that is not secondary to a pathological disorder; puberty is expected to occur spontaneously at a relatively late date. Brief treatment with conservative doses may occasionally be justified in these patients if they do not respond to psychological support. The potential adverse effect on bone maturation should be discussed with the patient and parents prior to androgen administration. An X-ray of the hand and wrist to determine bone age should be obtained every six months to assess the effect of treatment on the epiphyseal centers (see WARNINGS). Females Metastatic mammary cancer ANDROXY™ (Fluoxymesterone Tablets, USP) may be used secondarily in women with advancing inoperable metastatic (skeletal) mammary cancer who are one to five years postmenopausal. Primary goals of therapy in these women include ablation of the ovaries. Other methods of counteracting estrogen activity are adrenalectomy, hypophysectomy, and/or antiestrogen therapy. This treatment has been used in premenopausal women with breast cancer who have benefited from oophorectomy and are considered to have a hormone-responsive tumor. Judgment concerning androgen therapy should be made by an oncologist with expertise in this field. Launch Date 1956
Delayed male puberty 1 Sources: https://www.drugs.com/ppa/fluoxymesterone.html	Primary	Approved 8583	HALOTESTIN Approved Use Males ANDROXY™ Tablets are indicated for replacement therapy in conditions associated with a deficiency or absence of endogenous testosterone. Primary hypogonadism (congenital or acquired) Testicular failure due to cryptorchidism, bilateral torsion, orchitis, vanishing testis syndrome, or orchidectomy. Hypogonadotropic hypogonadism (congenital or acquired) Idiopathic gonadotropin or luteinizing hormone-releasing hormone (LHRH) deficiency, or pituitary-hypothalamic injury from tumors, trauma, or radiation. (Appropriate adrenal cortical and thyroid hormone replacement therapy are still necessary, however, and are actually of primary importance.) If the above conditions occur prior to puberty, androgen replacement therapy will be needed during the adolescent years for development of secondary sexual characteristics. Prolonged androgen treatment will be required to maintain sexual characteristics in these and other males who develop testosterone deficiency after puberty. Delayed puberty ANDROXY™ (Fluoxymesterone Tablets, USP) may be used to stimulate puberty in carefully selected males with clearly delayed puberty. These patients usually have a familial pattern of delayed puberty that is not secondary to a pathological disorder; puberty is expected to occur spontaneously at a relatively late date. Brief treatment with conservative doses may occasionally be justified in these patients if they do not respond to psychological support. The potential adverse effect on bone maturation should be discussed with the patient and parents prior to androgen administration. An X-ray of the hand and wrist to determine bone age should be obtained every six months to assess the effect of treatment on the epiphyseal centers (see WARNINGS). Females Metastatic mammary cancer ANDROXY™ (Fluoxymesterone Tablets, USP) may be used secondarily in women with advancing inoperable metastatic (skeletal) mammary cancer who are one to five years postmenopausal. Primary goals of therapy in these women include ablation of the ovaries. Other methods of counteracting estrogen activity are adrenalectomy, hypophysectomy, and/or antiestrogen therapy. This treatment has been used in premenopausal women with breast cancer who have benefited from oophorectomy and are considered to have a hormone-responsive tumor. Judgment concerning androgen therapy should be made by an oncologist with expertise in this field. Launch Date 1956
Inoperable metastatic female breast cancer 1 Sources: https://www.drugs.com/ppa/fluoxymesterone.html	Primary	Approved 8583	HALOTESTIN Approved Use Males ANDROXY™ Tablets are indicated for replacement therapy in conditions associated with a deficiency or absence of endogenous testosterone. Primary hypogonadism (congenital or acquired) Testicular failure due to cryptorchidism, bilateral torsion, orchitis, vanishing testis syndrome, or orchidectomy. Hypogonadotropic hypogonadism (congenital or acquired) Idiopathic gonadotropin or luteinizing hormone-releasing hormone (LHRH) deficiency, or pituitary-hypothalamic injury from tumors, trauma, or radiation. (Appropriate adrenal cortical and thyroid hormone replacement therapy are still necessary, however, and are actually of primary importance.) If the above conditions occur prior to puberty, androgen replacement therapy will be needed during the adolescent years for development of secondary sexual characteristics. Prolonged androgen treatment will be required to maintain sexual characteristics in these and other males who develop testosterone deficiency after puberty. Delayed puberty ANDROXY™ (Fluoxymesterone Tablets, USP) may be used to stimulate puberty in carefully selected males with clearly delayed puberty. These patients usually have a familial pattern of delayed puberty that is not secondary to a pathological disorder; puberty is expected to occur spontaneously at a relatively late date. Brief treatment with conservative doses may occasionally be justified in these patients if they do not respond to psychological support. The potential adverse effect on bone maturation should be discussed with the patient and parents prior to androgen administration. An X-ray of the hand and wrist to determine bone age should be obtained every six months to assess the effect of treatment on the epiphyseal centers (see WARNINGS). Females Metastatic mammary cancer ANDROXY™ (Fluoxymesterone Tablets, USP) may be used secondarily in women with advancing inoperable metastatic (skeletal) mammary cancer who are one to five years postmenopausal. Primary goals of therapy in these women include ablation of the ovaries. Other methods of counteracting estrogen activity are adrenalectomy, hypophysectomy, and/or antiestrogen therapy. This treatment has been used in premenopausal women with breast cancer who have benefited from oophorectomy and are considered to have a hormone-responsive tumor. Judgment concerning androgen therapy should be made by an oncologist with expertise in this field. Launch Date 1956

C_max

Value	Dose	Co-administered	Analyte	Population
80 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4009439	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:		FLUOXYMESTERONE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
100 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4009439	10 mg single, buccal dose: 10 mg route of administration: Buccal experiment type: SINGLE co-administered:		FLUOXYMESTERONE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
306 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4009439	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:		FLUOXYMESTERONE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
391 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4009439	10 mg single, buccal dose: 10 mg route of administration: Buccal experiment type: SINGLE co-administered:		FLUOXYMESTERONE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4009439	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:		FLUOXYMESTERONE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

Doses

Dose	Population	Adverse events
40 mg 1 times / day multiple, oral Recommended Dose: 40 mg, 1 times / day Route: oral Route: multiple Dose: 40 mg, 1 times / day Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=5328c194-5650-4d1f-9e28-8cea038cce81&type=display https://pubmed.ncbi.nlm.nih.gov/577673	unhealthy Health Status: unhealthy Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=5328c194-5650-4d1f-9e28-8cea038cce81&type=display https://pubmed.ncbi.nlm.nih.gov/577673	Disc. AE: Peliosis hepatis... AEs leading to discontinuation/dose reduction: Peliosis hepatis (grade 4-5) Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=5328c194-5650-4d1f-9e28-8cea038cce81&type=display https://pubmed.ncbi.nlm.nih.gov/577673

AEs

AE	Significance	Dose	Population
Peliosis hepatis	grade 4-5 Disc. AE	40 mg 1 times / day multiple, oral Recommended Dose: 40 mg, 1 times / day Route: oral Route: multiple Dose: 40 mg, 1 times / day Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=5328c194-5650-4d1f-9e28-8cea038cce81&type=display https://pubmed.ncbi.nlm.nih.gov/577673	unhealthy Health Status: unhealthy Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=5328c194-5650-4d1f-9e28-8cea038cce81&type=display https://pubmed.ncbi.nlm.nih.gov/577673

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:5120	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:5120
ChemicalBook	CB9258118	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB9258118
ZINC	ZINC000003875484	http://zinc15.docking.org/substances/ZINC000003875484

PubMed

Title	Date	PubMed
The anabolic androgenic steroid fluoxymesterone inhibits 11β-hydroxysteroid dehydrogenase 2-dependent glucocorticoid inactivation.	2012-04	22273746
Treatment of cachexia in oncology.	2010-09	21218002
Megestrol acetate versus metronomic cyclophosphamide in patients having exhausted all effective therapies under standard care.	2010-04-13	20354522
Development of a rapid method for the analysis of synthetic growth promoters in bovine muscle using liquid chromatography tandem mass spectrometry.	2009-04-01	19286019
The development of multiple drug use among anabolic-androgenic steroid users: six subjective case reports.	2008-11-28	19040748
Simultaneous doping analysis of main urinary metabolites of anabolic steroids in horse by ion-trap gas chromatography-tandem mass spectrometry.	2008-09	18781036
Characterization and quantification of fluoxymesterone metabolite in horse urine by gas chromatography/mass spectrometry.	2008-07	18614835
Systematic review of the clinical effect of glucocorticoids on nonhematologic malignancy.	2008-03-28	18373855
Liquid chromatographic method development for anabolic androgenic steroids using a monolithic column Application to animal feed samples.	2008-03-17	18298974
Efficient approach for the comprehensive detection of unknown anabolic steroids and metabolites in human urine by liquid chromatography-electrospray-tandem mass spectrometry.	2008-03-01	18220370
Elucidation of urinary metabolites of fluoxymesterone by liquid chromatography-tandem mass spectrometry and gas chromatography-mass spectrometry.	2008-03	18035854
Pharmacogenetics and pharmacogenomics of endocrine agents for breast cancer.	2008	19128430
1,1-dichloro-2,2-bis(p-chlorophenyl)ethylene (p,p'-DDE) disrupts the estrogen-androgen balance regulating the growth of hormone-dependent breast cancer cells.	2008	18275596
Determination of association constants between steroid compounds and albumins by partial-filling ACE.	2007-10	17893945
Liquid chromatographic method development for steroids determination (corticoids and anabolics). Application to animal feed samples.	2007-07-13	17451720
Novel series of potent, nonsteroidal, selective androgen receptor modulators based on 7H-[1,4]oxazino[3,2-g]quinolin-7-ones.	2007-05-17	17439112
Phase III study of standard combination versus rotating regimen of induction chemotherapy in patients with hormone insensitive metastatic breast cancer: an Eastern Cooperative Oncology Group Intergroup Study (E3185).	2007-04	17414459
Mini-dose of thalidomide for treatment of primary myelofibrosis. Report of a case with complete reversal of bone marrow fibrosis and splenomegaly.	2007-02	17405746
How do distress and well-being relate to medical student empathy? A multicenter study.	2007-02	17356983
An orally active selective androgen receptor modulator is efficacious on bone, muscle, and sex function with reduced impact on prostate.	2007-01	17023534
Testosterone depot injection in male hypogonadism: a critical appraisal.	2007	18225458
Letrozole in advanced breast cancer: the PO25 trial.	2007	17333340
Partial filling micellar electrokinetic chromatography analysis of androgens and testosterone derivatives using two sequential pseudostationary phases.	2006-10-27	16949594
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.	2006-07	16538529
[Secondary hypogonadism].	2006-06-28	16817386
Mitochondrial function in diaphragm of emphysematous hamsters after treatment with nandrolone.	2006	18046906
Analysis of anabolic steroids by partial filling micellar electrokinetic capillary chromatography and electrospray mass spectrometry.	2004-06-18	15248432
Screening of free 17-alkyl-substituted anabolic steroids in human urine by liquid chromatography-electrospray ionization tandem mass spectrometry.	2004-02	15013688
Optimization and validation of conventional and micellar LC methods for the analysis of methyltestosterone in sugar-coated pills.	2003-02-05	12560066
The androgen-regulated gene human kallikrein 15 (KLK15) is an independent and favourable prognostic marker for breast cancer.	2002-11-18	12439720
Factors affecting progression-free survival in hormone-dependent metastatic breast cancer patients receiving high-dose chemotherapy and hematopoietic progenitor cell transplantation: role of maintenance endocrine therapy.	2002-05	12058236
A49T, V89L and TA repeat polymorphisms of steroid 5alpha-reductase type II and breast cancer risk in Japanese women.	2002	12100746
Androgen responsiveness of the pituitary gonadotrope cell line LbetaT2.	2001-09	11524240
Sample size calculations for the two-sample problem using the multiplicative intensity model.	2001-02-28	11223901
Splenic and hepatic peliosis: MR findings.	1992-01	1727362
Androgen depletion and repletion as a means of potentiating the effect of cytotoxic chemotherapy in advanced prostate cancer.	1987	3695494
Hormone stimulation and chemotherapy in advanced prostate cancer: interim analysis of an ongoing randomized trial.	1986-03-01	3518596
Peliosis hepatis after long-term androgen therapy.	1985-05	3992778
Hormone stimulation and chemotherapy in advanced prostate cancer: preliminary results of a prospective controlled clinical trial.	1985-03-01	3888046
Ataxia caused by fluoxymesterone therapy in breast cancer.	1981-06	7235823
Impotence therapy and cancer of the prostate.	1976-05	58562

Patents

Sample Use Guides

In Vivo Use Guide

Hypogonadism (Males): 5-20 mg daily Delayed puberty (Males): 2.5-20 mg daily for 4-6 months Inoperable breast carcinoma (Females): 10-40 mg daily in divided doses for ≥3 months

Route of Administration: Oral

In Vitro Use Guide

MDA-MB-453 cells were used for Androgen Receptor binding assays. Media containing 0.3 nM [3H]DHT and Fluoxymesterone in concentrations ranging from 10-10 to 10-6 M were added to the cells. Three replicates were used for each sample. After 3 h at 37 C, an aliquot of the total binding media at each concentration was removed to determine the amount of free [3H]DHT.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:33:49 GMT 2025` Edited by `admin` on `Mon Mar 31 17:33:49 GMT 2025`
Record UNII	9JU12S4YFY
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

FLUOXYMESTERONE

Official Name

English

FLUOXYMESTERONE CIII

Preferred Name

English

9-Fluoro-11?,17?-dihydroxy-17-methylandrost-4-en-3-one

Common Name

English

ANDROST-4-EN-3-ONE, 9-FLUORO-11,17-DIHYDROXY-17-METHYL-, (11.BETA.,17.BETA.)-

Common Name

English

FLUOXYMESTERONE [HSDB]

Common Name

English

FLUOXYMESTERONE [VANDF]

Common Name

English

ANDROID-F

Brand Name

English

FLUOXYMESTERONE [USP MONOGRAPH]

Common Name

English

FLUOXYMESTERONE [MI]

Common Name

English

NSC-12165

Code

English

ORA-TESTRYL

Brand Name

English

FLUOXYMESTERONE CIII [USP-RS]

Common Name

English

FLUOXYMESTERONE [JAN]

Common Name

English

NSC-10704

Code

English

Fluoxymesterone [WHO-DD]

Common Name

English

FLUOXYMESTERONE [ORANGE BOOK]

Common Name

English

HALOTESTIN

Brand Name

English

FLUOXYMESTERONE [MART.]

Common Name

English

fluoxymesterone [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C243