Fluoxymesterone
Clinical data | |
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Trade names | Halotestin, Ora-Testryl, Ultandren, others |
Other names | Fluoxymestrone; Androfluorene; NSC-12165; 9 |
AHFS/Drugs.com | Monograph |
MedlinePlus | a682690 |
Pregnancy category |
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Routes of administration | By mouth[1] |
Drug class | Androgen; Anabolic steroid |
ATC code | |
Legal status | |
Legal status |
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Pharmacokinetic data | |
Bioavailability | Oral: 80%[3] |
Metabolism | Liver (6 |
Metabolites | • 5 • 11-Oxofluoxymesterone[4] |
Elimination half-life | 9.2 hours[5][6] |
Excretion | Urine (<5% unchanged)[3][4] |
Identifiers | |
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CAS Number | |
PubChem CID | |
IUPHAR/BPS | |
DrugBank | |
ChemSpider | |
UNII | |
KEGG | |
ChEBI | |
ChEMBL | |
CompTox Dashboard (EPA) | |
ECHA InfoCard | 100.000.875 |
Chemical and physical data | |
Formula | C20H29FO3 |
Molar mass | 336.447 g·mol−1 |
3D model (JSmol) | |
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Fluoxymesterone, sold under the brand names Halotestin and Ultandren among others, is an androgen and anabolic steroid (AAS) medication which is used in the treatment of low testosterone levels in men, delayed puberty in boys, breast cancer in women, and anemia.[1] It is taken by mouth.[1]
Side effects of fluoxymesterone include symptoms of masculinization like acne, increased hair growth, voice changes, and increased sexual desire.[1] It can also cause liver damage and cardiovascular side effects like high blood pressure.[1][7][8] The drug is a synthetic androgen and anabolic steroid and hence is an agonist of the androgen receptor (AR), the biological target of androgens like testosterone and dihydrotestosterone (DHT).[1][9] It has strong androgenic effects and moderate anabolic effects, which make it useful for producing masculinization.[1][10]
Fluoxymesterone was first described in 1956 and was introduced for medical use in 1957.[1][11] In addition to its medical use, fluoxymesterone is used to improve physique and performance.[1] The drug is a controlled substance in many countries and so non-medical use is generally illicit.[1]
Medical uses[edit]
Fluoxymesterone is or has been used in the treatment of hypogonadism, delayed puberty, and anemia in males and the treatment of breast cancer in women.[1][12] It is specifically approved in one or more countries for the treatment of hypogonadism in men, delayed puberty in boys, and breast cancer in women.[13] Current prescribing guidelines in the United States list only the treatment of androgen deficiency in males and breast cancer in females as indications.[1]
Fluoxymesterone is less effective in inducing masculinization than testosterone, but is useful for maintaining established masculinization in adults.[14]
Route | Medication | Major brand names | Form | Dosage |
---|---|---|---|---|
Oral | Testosteronea | – | Tablet | 400–800 mg/day (in divided doses) |
Testosterone undecanoate | Andriol, Jatenzo | Capsule | 40–80 mg/2–4x day (with meals) | |
Methyltestosteroneb | Android, Metandren, Testred | Tablet | 10–50 mg/day | |
Fluoxymesteroneb | Halotestin, Ora-Testryl, Ultandren | Tablet | 5–20 mg/day | |
Metandienoneb | Dianabol | Tablet | 5–15 mg/day | |
Mesteroloneb | Proviron | Tablet | 25–150 mg/day | |
Sublingual | Testosteroneb | Testoral | Tablet | 5–10 mg 1–4x/day |
Methyltestosteroneb | Metandren, Oreton Methyl | Tablet | 10–30 mg/day | |
Buccal | Testosterone | Striant | Tablet | 30 mg 2x/day |
Methyltestosteroneb | Metandren, Oreton Methyl | Tablet | 5–25 mg/day | |
Transdermal | Testosterone | AndroGel, Testim, TestoGel | Gel | 25–125 mg/day |
Androderm, AndroPatch, TestoPatch | Non-scrotal patch | 2.5–15 mg/day | ||
Testoderm | Scrotal patch | 4–6 mg/day | ||
Axiron | Axillary solution | 30–120 mg/day | ||
Androstanolone (DHT) | Andractim | Gel | 100–250 mg/day | |
Rectal | Testosterone | Rektandron, Testosteronb | Suppository | 40 mg 2–3x/day |
Injection (IM or SC ) | Testosterone | Andronaq, Sterotate, Virosterone | Aqueous suspension | 10–50 mg 2–3x/week |
Testosterone propionateb | Testoviron | Oil solution | 10–50 mg 2–3x/week | |
Testosterone enanthate | Delatestryl | Oil solution | 50–250 mg 1x/1–4 weeks | |
Xyosted | Auto-injector | 50–100 mg 1x/week | ||
Testosterone cypionate | Depo-Testosterone | Oil solution | 50–250 mg 1x/1–4 weeks | |
Testosterone isobutyrate | Agovirin Depot | Aqueous suspension | 50–100 mg 1x/1–2 weeks | |
Testosterone phenylacetateb | Perandren, Androject | Oil solution | 50–200 mg 1x/3–5 weeks | |
Mixed testosterone esters | Sustanon 100, Sustanon 250 | Oil solution | 50–250 mg 1x/2–4 weeks | |
Testosterone undecanoate | Aveed, Nebido | Oil solution | 750–1,000 mg 1x/10–14 weeks | |
Testosterone buciclatea | – | Aqueous suspension | 600–1,000 mg 1x/12–20 weeks | |
Implant | Testosterone | Testopel | Pellet | 150–1,200 mg/3–6 months |
Notes: Men produce about 3 to 11 mg testosterone per day (mean 7 mg/day in young men). Footnotes: a = Never marketed. b = No longer used and/or no longer marketed. Sources: See template. |
Route | Medication | Major brand names | Form | Dosage |
---|---|---|---|---|
Oral | Testosterone undecanoate | Andriol, Jatenzo | Capsule | 40–80 mg 1x/1–2 days |
Methyltestosterone | Metandren, Estratest | Tablet | 0.5–10 mg/day | |
Fluoxymesterone | Halotestin | Tablet | 1–2.5 mg 1x/1–2 days | |
Normethandronea | Ginecoside | Tablet | 5 mg/day | |
Tibolone | Livial | Tablet | 1.25–2.5 mg/day | |
Prasterone (DHEA)b | – | Tablet | 10–100 mg/day | |
Sublingual | Methyltestosterone | Metandren | Tablet | 0.25 mg/day |
Transdermal | Testosterone | Intrinsa | Patch | 150–300 |
AndroGel | Gel, cream | 1–10 mg/day | ||
Vaginal | Prasterone (DHEA) | Intrarosa | Insert | 6.5 mg/day |
Injection | Testosterone propionatea | Testoviron | Oil solution | 25 mg 1x/1–2 weeks |
Testosterone enanthate | Delatestryl, Primodian Depot | Oil solution | 25–100 mg 1x/4–6 weeks | |
Testosterone cypionate | Depo-Testosterone, Depo-Testadiol | Oil solution | 25–100 mg 1x/4–6 weeks | |
Testosterone isobutyratea | Femandren M, Folivirin | Aqueous suspension | 25–50 mg 1x/4–6 weeks | |
Mixed testosterone esters | Climacterona | Oil solution | 150 mg 1x/4–8 weeks | |
Omnadren, Sustanon | Oil solution | 50–100 mg 1x/4–6 weeks | ||
Nandrolone decanoate | Deca-Durabolin | Oil solution | 25–50 mg 1x/6–12 weeks | |
Prasterone enanthatea | Gynodian Depot | Oil solution | 200 mg 1x/4–6 weeks | |
Implant | Testosterone | Testopel | Pellet | 50–100 mg 1x/3–6 months |
Notes: Premenopausal women produce about 230 ± 70 |
Route | Medication | Form | Dosage | |
---|---|---|---|---|
Oral | Methyltestosterone | Tablet | 30–200 mg/day | |
Fluoxymesterone | Tablet | 10–40 mg 3x/day | ||
Calusterone | Tablet | 40–80 mg 4x/day | ||
Normethandrone | Tablet | 40 mg/day | ||
Buccal | Methyltestosterone | Tablet | 25–100 mg/day | |
Injection (IM or SC ) | Testosterone propionate | Oil solution | 50–100 mg 3x/week | |
Testosterone enanthate | Oil solution | 200–400 mg 1x/2–4 weeks | ||
Testosterone cypionate | Oil solution | 200–400 mg 1x/2–4 weeks | ||
Mixed testosterone esters | Oil solution | 250 mg 1x/week | ||
Methandriol | Aqueous suspension | 100 mg 3x/week | ||
Androstanolone (DHT) | Aqueous suspension | 300 mg 3x/week | ||
Drostanolone propionate | Oil solution | 100 mg 1–3x/week | ||
Metenolone enanthate | Oil solution | 400 mg 3x/week | ||
Nandrolone decanoate | Oil solution | 50–100 mg 1x/1–3 weeks | ||
Nandrolone phenylpropionate | Oil solution | 50–100 mg/week | ||
Note: Dosages are not necessarily equivalent. Sources: See template. |
Available forms[edit]
Fluoxymesterone is available in the form of 2, 5, and 10 mg oral tablets.[15]
Non-medical uses[edit]
Fluoxymesterone is used for physique- and performance-enhancing purposes by competitive athletes, bodybuilders, and powerlifters.[1]
Side effects[edit]
Side effects that have been associated with fluoxymesterone include acne, edema, seborrhea/seborrheic dermatitis, alopecia, hirsutism, voice deepening, virilization in general, flushing, gynecomastia, breast pain, menstrual disturbances, hypogonadism, testicular atrophy, clitoral enlargement, penile enlargement, priapism, increased aggressiveness, prostate enlargement, cardiovascular toxicity, and hepatotoxicity, among others.[1][16]
Pharmacology[edit]
Pharmacodynamics[edit]
Medication | Ratioa |
---|---|
Testosterone | ~1:1 |
Androstanolone (DHT) | ~1:1 |
Methyltestosterone | ~1:1 |
Methandriol | ~1:1 |
Fluoxymesterone | 1:1–1:15 |
Metandienone | 1:1–1:8 |
Drostanolone | 1:3–1:4 |
Metenolone | 1:2–1:30 |
Oxymetholone | 1:2–1:9 |
Oxandrolone | 1:3–1:13 |
Stanozolol | 1:1–1:30 |
Nandrolone | 1:3–1:16 |
Ethylestrenol | 1:2–1:19 |
Norethandrolone | 1:1–1:20 |
Notes: In rodents. Footnotes: a = Ratio of androgenic to anabolic activity. Sources: See template. |
As an AAS, fluoxymesterone is an agonist of the androgen receptor (AR), similarly to androgens like testosterone and DHT.[1][17] It is a substrate for 5
Fluoxymesterone has been reported to be non-aromatizable due to steric hindrance by its C11
Because of the presence of its 17
11β -HSD inhibition[edit]
Fluoxymesterone has been found to act as a potent inhibitor of 11
Glucocorticoid activity[edit]
Unlike other AAS, fluoxymesterone has structural features in common with corticosteroids, including its C9
Pharmacokinetics[edit]
Fluoxymesterone has approximately 80% oral bioavailability, unlike testosterone, as the C17
Chemistry[edit]
Fluoxymesterone, also known as 9
Synthesis[edit]
Step one: The first step in the synthesis of fluoxymesterone is the microbiological oxidation of commercially available androstenedione (1.11) by Actinomyces; this introduces a hydroxyl group to the 11
Step two: The 11
Detection in body fluids[edit]
Detection of halotestin and other such illegal anabolic steroids in sports is achieved by GS-MS identification of urinary excreted anabolic steroids and their metabolites. In a test for halotestin, a dry residue obtained from a urine sample is dissolved in dimethylformamide and a sulfur trioxide-pyridine complex and is heated with 1% potassium carbonate solution. Halotestin and many of its metabolites contain two polar hydroxyl groups, leading to intermolecular hydrogen bonding that increases their boiling point and reduces volatility. In order to attain a gaseous sample for GC-MS, the products of hydrolysis are extracted, dissolved in methanol and derivatised to form volatile trimethylsilyl (TMS) esters by adding N-methyl-N-trimethylsilyl-trifluoroacetamide (MSTFA) and trimethylsilylimidazole (TMSImi).[27]
History[edit]
Fluoxymesterone was first described in 1956 and was introduced for medical use in the United States in 1957.[1][11] Over time the use of fluoxymesterone has become increasingly controversial and limited.[1]
Society and culture[edit]
Generic names[edit]
Fluoxymesterone is the generic name of the drug and its INN , USP , BAN , DCIT , and JAN , while fluoxymestérone is its DCF .[25][26][28][29]
Brand names[edit]
Brand names of fluoxymesterone include Android-F, Androxy, Halotestin, Ora-Testryl, and Ultandren among others.[25][26][28][29]
Availability[edit]
United States[edit]
Fluoxymesterone is one of the few AAS that remains available for medical use in the United States.[30] The others (as of August 2023) are testosterone, testosterone cypionate, testosterone enanthate, testosterone undecanoate, methyltestosterone, and oxymetholone.[30]
Other countries[edit]
Availability of fluoxymesterone aside from the United States remains scarce, but it is marketed in some other countries such as Mexico, Moldova, and Taiwan.[1][29]
Legal status[edit]
Fluoxymesterone, along with other AAS, is a schedule III controlled substance in the United States under the Controlled Substances Act.[31]
References[edit]
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β -hydroxysteroid dehydrogenase 2-dependent glucocorticoid inactivation". Toxicol. Sci. 126 (2): 353–61. doi:10.1093/toxsci/kfs022. PMID 22273746. - ^ a b c d Joseph JF, Parr MK (2015). "Synthetic androgens as designer supplements". Curr Neuropharmacol. 13 (1): 89–100. doi:10.2174/1570159X13666141210224756. PMC 4462045. PMID 26074745.
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- ^ Lo TE, Andal ZC, Lantion-Ang FL (2015). "Fluoxymesterone-induced gynaecomastia in a patient with childhood aplastic anaemia". BMJ Case Rep. 2015: bcr2014207474. doi:10.1136/bcr-2014-207474. PMC 4434366. PMID 25948845.
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