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
SMILES
[H][C@@]12CC[C@](C)(O)[C@@]1(C)C[C@H](O)[C@@]3(F)[C@@]2([H])CCC4=CC(=O)CC[C@]34C
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
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 |
DescriptionSources: https://www.drugs.com/ppa/fluoxymesterone.htmlCurator'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
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 |
---|---|---|---|
Target ID: CHEMBL1871 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17439112 |
0.3 nM [EC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | HALOTESTIN Approved UseMales 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 |
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Primary | HALOTESTIN Approved UseMales 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 |
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Primary | HALOTESTIN Approved UseMales 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
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 |
T1/2
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 (max) Recommended Dose: 40 mg, 1 times / day Route: oral Route: multiple Dose: 40 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Condition: Conditions associated with a deficiency or absence of endogenous testosterone|Metastatic mammary cancer Sources: |
Disc. AE: Peliosis hepatis... AEs leading to discontinuation/dose reduction: Peliosis hepatis (grade 4-5) Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Peliosis hepatis | grade 4-5 Disc. AE |
40 mg 1 times / day multiple, oral (max) Recommended Dose: 40 mg, 1 times / day Route: oral Route: multiple Dose: 40 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Condition: Conditions associated with a deficiency or absence of endogenous testosterone|Metastatic mammary cancer Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
Ataxia caused by fluoxymesterone therapy in breast cancer. | 1981 Jun |
|
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 |
|
Testosterone depot injection in male hypogonadism: a critical appraisal. | 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 |
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An orally active selective androgen receptor modulator is efficacious on bone, muscle, and sex function with reduced impact on prostate. | 2007 Jan |
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Elucidation of urinary metabolites of fluoxymesterone by liquid chromatography-tandem mass spectrometry and gas chromatography-mass spectrometry. | 2008 Mar |
|
Development of a rapid method for the analysis of synthetic growth promoters in bovine muscle using liquid chromatography tandem mass spectrometry. | 2009 Apr 1 |
|
Treatment of cachexia in oncology. | 2010 Sep |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/ppa/fluoxymesterone.html
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17439112
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
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on
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on
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Record UNII |
9JU12S4YFY
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Record Status |
Validated (UNII)
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Record Version |
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NCI_THESAURUS |
C243
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DEA NO. |
4000
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NCI_THESAURUS |
C2360
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WIKIPEDIA |
Designer-drugs-Fluoxymesterone
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NDF-RT |
N0000008241
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NDF-RT |
N0000000146
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LIVERTOX |
425
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WHO-ATC |
G03BA01
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WHO-VATC |
QG03BA01
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NDF-RT |
N0000175824
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DB01185
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CHEMBL1445
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624
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C507
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1280009
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4494
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12165
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D005474
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FLUOXYMESTERONE
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SUB07724MIG
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76-43-7
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5120
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6446
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2861
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10704
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M5488
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3333
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9JU12S4YFY
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DTXSID8033512
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9JU12S4YFY
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1210
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ACTIVE MOIETY |
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Biological Half-life | PHARMACOKINETIC |
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