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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H29FO3
Molecular Weight 336.4416
Optical Activity UNSPECIFIED
Defined Stereocenters 7 / 7
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FLUOXYMESTERONE

SMILES

C[C@@]12CCC(=O)C=C2CC[C@@]3([H])[C@]4([H])CC[C@@](C)([C@@]4(C)C[C@@]([H])([C@@]31F)O)O

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

Description
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.3 nM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
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

-4.1696641E11
Primary
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

-4.1696641E11
Primary
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

-4.1696641E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
80 ng/mL
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
306 ng × h/mL
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
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
2 h
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

Doses

DosePopulationAdverse events​
40 mg 1 times / day multiple, oral (max)
Recommended
unhealthy
Health Status: unhealthy
Condition: Conditions associated with a deficiency or absence of endogenous testosterone|Metastatic mammary cancer
Sources:
Disc. AE: Peliosis hepatis...
AEs

AEs

AESignificanceDosePopulation
Peliosis hepatis grade 4-5
Disc. AE
40 mg 1 times / day multiple, oral (max)
Recommended
unhealthy
Health Status: unhealthy
Condition: Conditions associated with a deficiency or absence of endogenous testosterone|Metastatic mammary cancer
Sources:
PubMed

PubMed

TitleDatePubMed
Impotence therapy and cancer of the prostate.
1976 May
Ataxia caused by fluoxymesterone therapy in breast cancer.
1981 Jun
Hormone stimulation and chemotherapy in advanced prostate cancer: preliminary results of a prospective controlled clinical trial.
1985 Mar-Apr
Peliosis hepatis after long-term androgen therapy.
1985 May
Hormone stimulation and chemotherapy in advanced prostate cancer: interim analysis of an ongoing randomized trial.
1986 Mar-Apr
Androgen depletion and repletion as a means of potentiating the effect of cytotoxic chemotherapy in advanced prostate cancer.
1987
Splenic and hepatic peliosis: MR findings.
1992 Jan
Sample size calculations for the two-sample problem using the multiplicative intensity model.
2001 Feb 28
Androgen responsiveness of the pituitary gonadotrope cell line LbetaT2.
2001 Sep
A49T, V89L and TA repeat polymorphisms of steroid 5alpha-reductase type II and breast cancer risk in Japanese women.
2002
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 May
The androgen-regulated gene human kallikrein 15 (KLK15) is an independent and favourable prognostic marker for breast cancer.
2002 Nov 18
Optimization and validation of conventional and micellar LC methods for the analysis of methyltestosterone in sugar-coated pills.
2003 Feb 5
Screening of free 17-alkyl-substituted anabolic steroids in human urine by liquid chromatography-electrospray ionization tandem mass spectrometry.
2004 Feb
Analysis of anabolic steroids by partial filling micellar electrokinetic capillary chromatography and electrospray mass spectrometry.
2004 Jun 18
Mitochondrial function in diaphragm of emphysematous hamsters after treatment with nandrolone.
2006
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 Jul
[Secondary hypogonadism].
2006 Jun 28
Partial filling micellar electrokinetic chromatography analysis of androgens and testosterone derivatives using two sequential pseudostationary phases.
2006 Oct 27
Testosterone depot injection in male hypogonadism: a critical appraisal.
2007
Letrozole in advanced breast cancer: the PO25 trial.
2007
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 Apr
Mini-dose of thalidomide for treatment of primary myelofibrosis. Report of a case with complete reversal of bone marrow fibrosis and splenomegaly.
2007 Feb
How do distress and well-being relate to medical student empathy? A multicenter study.
2007 Feb
An orally active selective androgen receptor modulator is efficacious on bone, muscle, and sex function with reduced impact on prostate.
2007 Jan
Liquid chromatographic method development for steroids determination (corticoids and anabolics). Application to animal feed samples.
2007 Jul 13
Novel series of potent, nonsteroidal, selective androgen receptor modulators based on 7H-[1,4]oxazino[3,2-g]quinolin-7-ones.
2007 May 17
Determination of association constants between steroid compounds and albumins by partial-filling ACE.
2007 Oct
Pharmacogenetics and pharmacogenomics of endocrine agents for breast cancer.
2008
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
Characterization and quantification of fluoxymesterone metabolite in horse urine by gas chromatography/mass spectrometry.
2008 Jul
Elucidation of urinary metabolites of fluoxymesterone by liquid chromatography-tandem mass spectrometry and gas chromatography-mass spectrometry.
2008 Mar
Efficient approach for the comprehensive detection of unknown anabolic steroids and metabolites in human urine by liquid chromatography-electrospray-tandem mass spectrometry.
2008 Mar 1
Liquid chromatographic method development for anabolic androgenic steroids using a monolithic column Application to animal feed samples.
2008 Mar 17
Systematic review of the clinical effect of glucocorticoids on nonhematologic malignancy.
2008 Mar 28
The development of multiple drug use among anabolic-androgenic steroid users: six subjective case reports.
2008 Nov 28
Simultaneous doping analysis of main urinary metabolites of anabolic steroids in horse by ion-trap gas chromatography-tandem mass spectrometry.
2008 Sep
Development of a rapid method for the analysis of synthetic growth promoters in bovine muscle using liquid chromatography tandem mass spectrometry.
2009 Apr 1
Megestrol acetate versus metronomic cyclophosphamide in patients having exhausted all effective therapies under standard care.
2010 Apr 13
Treatment of cachexia in oncology.
2010 Sep
The anabolic androgenic steroid fluoxymesterone inhibits 11β-hydroxysteroid dehydrogenase 2-dependent glucocorticoid inactivation.
2012 Apr
Patents

Patents

Sample Use Guides

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
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.
Name Type Language
FLUOXYMESTERONE
HSDB   INN   MART.   MI   ORANGE BOOK   USP   VANDF   WHO-DD  
INN  
Official Name English
9-FLUORO-11.BETA.,17.BETA.-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
FLUOXYMESTERONE CIII
USP-RS  
Common Name English
FLUOXYMESTERONE [WHO-DD]
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 [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
Created by admin on Fri Jun 25 20:59:44 UTC 2021 , Edited by admin on Fri Jun 25 20:59:44 UTC 2021
DEA NO. 4000
Created by admin on Fri Jun 25 20:59:44 UTC 2021 , Edited by admin on Fri Jun 25 20:59:44 UTC 2021
NCI_THESAURUS C2360
Created by admin on Fri Jun 25 20:59:44 UTC 2021 , Edited by admin on Fri Jun 25 20:59:44 UTC 2021
NDF-RT N0000008241
Created by admin on Fri Jun 25 20:59:44 UTC 2021 , Edited by admin on Fri Jun 25 20:59:44 UTC 2021
NDF-RT N0000000146
Created by admin on Fri Jun 25 20:59:44 UTC 2021 , Edited by admin on Fri Jun 25 20:59:44 UTC 2021
LIVERTOX 425
Created by admin on Fri Jun 25 20:59:44 UTC 2021 , Edited by admin on Fri Jun 25 20:59:44 UTC 2021
WHO-ATC G03BA01
Created by admin on Fri Jun 25 20:59:44 UTC 2021 , Edited by admin on Fri Jun 25 20:59:44 UTC 2021
WHO-VATC QG03BA01
Created by admin on Fri Jun 25 20:59:44 UTC 2021 , Edited by admin on Fri Jun 25 20:59:44 UTC 2021
NDF-RT N0000175824
Created by admin on Fri Jun 25 20:59:44 UTC 2021 , Edited by admin on Fri Jun 25 20:59:44 UTC 2021
Code System Code Type Description
ECHA (EC/EINECS)
200-961-8
Created by admin on Fri Jun 25 20:59:44 UTC 2021 , Edited by admin on Fri Jun 25 20:59:44 UTC 2021
PRIMARY
DRUG BANK
DB01185
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PRIMARY
ChEMBL
CHEMBL1445
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PRIMARY
INN
624
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PRIMARY
NCI_THESAURUS
C507
Created by admin on Fri Jun 25 20:59:44 UTC 2021 , Edited by admin on Fri Jun 25 20:59:44 UTC 2021
PRIMARY
RXCUI
4494
Created by admin on Fri Jun 25 20:59:44 UTC 2021 , Edited by admin on Fri Jun 25 20:59:44 UTC 2021
PRIMARY RxNorm
MESH
D005474
Created by admin on Fri Jun 25 20:59:44 UTC 2021 , Edited by admin on Fri Jun 25 20:59:44 UTC 2021
PRIMARY
WIKIPEDIA
FLUOXYMESTERONE
Created by admin on Fri Jun 25 20:59:44 UTC 2021 , Edited by admin on Fri Jun 25 20:59:44 UTC 2021
PRIMARY
EVMPD
SUB07724MIG
Created by admin on Fri Jun 25 20:59:44 UTC 2021 , Edited by admin on Fri Jun 25 20:59:44 UTC 2021
PRIMARY
CAS
76-43-7
Created by admin on Fri Jun 25 20:59:44 UTC 2021 , Edited by admin on Fri Jun 25 20:59:44 UTC 2021
PRIMARY
PUBCHEM
6446
Created by admin on Fri Jun 25 20:59:44 UTC 2021 , Edited by admin on Fri Jun 25 20:59:44 UTC 2021
PRIMARY
IUPHAR
2861
Created by admin on Fri Jun 25 20:59:44 UTC 2021 , Edited by admin on Fri Jun 25 20:59:44 UTC 2021
PRIMARY
MERCK INDEX
M5488
Created by admin on Fri Jun 25 20:59:44 UTC 2021 , Edited by admin on Fri Jun 25 20:59:44 UTC 2021
PRIMARY Merck Index
HSDB
3333
Created by admin on Fri Jun 25 20:59:44 UTC 2021 , Edited by admin on Fri Jun 25 20:59:44 UTC 2021
PRIMARY
USP_CATALOG
1280009
Created by admin on Fri Jun 25 20:59:44 UTC 2021 , Edited by admin on Fri Jun 25 20:59:44 UTC 2021
PRIMARY USP-RS
FDA UNII
9JU12S4YFY
Created by admin on Fri Jun 25 20:59:44 UTC 2021 , Edited by admin on Fri Jun 25 20:59:44 UTC 2021
PRIMARY
EPA CompTox
76-43-7
Created by admin on Fri Jun 25 20:59:44 UTC 2021 , Edited by admin on Fri Jun 25 20:59:44 UTC 2021
PRIMARY
DRUG CENTRAL
1210
Created by admin on Fri Jun 25 20:59:44 UTC 2021 , Edited by admin on Fri Jun 25 20:59:44 UTC 2021
PRIMARY