Clinical data | |
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Trade names | Proviron, others |
Other names | NSC-75054; SH-60723; SH-723; 1α-Methyl-4,5α-dihydrotestosterone; 1α-Methyl-DHT; 1α-Methyl-5α-androstan-17β-ol-3-one |
AHFS/ Drugs.com | International Drug Names |
Routes of administration | By mouth |
Drug class | Androgen; Anabolic steroid |
ATC code | |
Legal status | |
Legal status |
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Pharmacokinetic data | |
Bioavailability | 3% |
Protein binding | 98% (40% to Albumin, 58% to SHBG) |
Metabolism | Liver |
Elimination half-life | 12-13 hours |
Excretion | Urine |
Identifiers | |
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CAS Number | |
PubChem CID | |
ChemSpider | |
UNII | |
KEGG | |
ChEMBL | |
CompTox Dashboard ( EPA) | |
ECHA InfoCard | 100.014.397 |
Chemical and physical data | |
Formula | C20H32O2 |
Molar mass | 304.474 g·mol−1 |
3D model ( JSmol) | |
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Mesterolone, sold under the brand name Proviron among others, is an androgen and anabolic steroid (AAS) medication which is used mainly in the treatment of low testosterone levels. [2] [3] It has also been used to treat male infertility, although this use is controversial. [2] [4] [5] It is taken by mouth. [2]
Side effects of mesterolone include symptoms of masculinization like acne, scalp hair loss, increased body hair growth, voice changes, and increased sexual desire. [2] It has no risk of liver damage. [2] [3] 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). [2] [6] It has strong androgenic effects and weak anabolic effects, which make it useful for producing masculinization. [2] The drug has no estrogenic effects. [2] [3]
Mesterolone was first described by 1966 [7] and introduced for medical use by 1967. [8] [9] In addition to its medical use, mesterolone has been used to improve physique and performance, although it is not commonly used for such purposes due to its weak anabolic effects. [2] The drug is a controlled substance in many countries and so non-medical use is generally illicit. [2] [10]
Mesterolone is used in the treatment of androgen deficiency in male hypogonadism, anemia, and to support male fertility among other indications. [2] [11] [12] It has also been used to treat delayed puberty in boys. [13] Because it lacks estrogenic effects, mesterolone may be indicated for treating cases of androgen deficiency in which breast tenderness or gynecomastia is also present. [14] The drug is described as a relatively weak androgen with partial activity and is rarely used for the purpose of androgen replacement therapy, but is still widely used in medicine. [2] [12] [15] [3]
Mesterolone is used in androgen replacement therapy at a dosage of 50 to 100 mg 2 to 3 times per day. [16]
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. |
Mesterolone has been used for physique- and performance-enhancing purposes by competitive athletes, bodybuilders, and powerlifters. [2]
Side effects of mesterolone include virilization among others. [2]
Like other AAS, mesterolone is an agonist of the androgen receptor (AR). [2] Mesterolone is described as a very poor anabolic agent due to inactivation by 3α-hydroxysteroid dehydrogenase (3α-HSD) in skeletal muscle tissue, similarly to DHT and mestanolone (17α-methyl-DHT). [2] In contrast, testosterone is a very poor substrate for 3α-HSD, and so is not similarly inactivated in skeletal muscle. [2] Because of its lack of potentiation by 5α-reductase in "androgenic" tissues and its inactivation by 3α-HSD in skeletal muscle, mesterolone is relatively low in both its androgenic potency and its anabolic potency. [2] However, it does still show a greater ratio of anabolic activity to androgenic activity relative to testosterone. [2]
Mesterolone is not a substrate for 5α-reductase, as it is already 5α-reduced, and hence is not potentiated in so-called "androgenic" tissues such as the skin, hair follicles, and prostate gland. [2]
Mesterolone is not a substrate for aromatase, and so cannot be converted into an estrogen. [2] As such, it has no propensity for producing estrogenic side effects such as gynecomastia and fluid retention. [2] It also has no progestogenic activity. [2]
Because mesterolone is not 17α-alkylated, it has little or no potential for hepatotoxicity. [2] However, its risk of deleterious effects on the cardiovascular system is comparable to that of several other oral AAS. [2]
The C1α methyl group of mesterolone inhibits its hepatic metabolism and thereby confers significant oral activity, although its oral bioavailability is still much lower than that of 17α-alkylated AAS. [2] In any case, mesterolone is one of the few non-17α-alkylated AAS that is active with oral ingestion. [2] Uniquely among AAS, mesterolone has very high affinity for human serum sex hormone-binding globulin (SHBG), about 440% that of DHT in one study and 82% of that of DHT in another study. [17] [2] [18] As a result, it may displace endogenous testosterone from SHBG and thereby increase free testosterone concentrations, which may in part be involved in its effects. [2]
Mesterolone, also known as 1α-methyl-4,5α-dihydrotestosterone (1α-methyl-DHT) or as 1α-methyl-5α-androstan-17β-ol-3-one, is a synthetic androstane steroid and derivative of DHT. [19] [20] [2] It is specifically DHT with a methyl group at the C1α position. [19] [20] [2] Closely related AAS include metenolone and its esters metenolone acetate and metenolone enanthate. [19] [20] [2] The antiandrogen rosterolone (17α-propylmesterolone) is also closely related to mesterolone. [21]
Mesterolone was developed in the 1960s [22] and was first described by 1966. [7] [23] [24] [25] It was introduced for medical use by Schering under the brand name Proviron by 1967. [8] [9] The well-established brand name Proviron had previously been used by Schering for testosterone propionate starting in 1936. [26] Following the introduction of mesterolone as Proviron, Schering continued to market testosterone propionate under the brand name Testoviron. [26] A number of sources incorrectly state that mesterolone was synthesized or introduced for medical use in 1934. [22] [2] [27] [28]
Mesterolone is the generic name of the drug and its INN , USAN , BAN , and DCIT , while mestérolone is its DCF . [19] [20] [29] [30]
Mesterolone is marketed mainly under the brand name Proviron. [19] [20] [30] [2]
Mesterolone is available widely throughout the world, including in the United Kingdom, Australia, and South Africa, as well as many non- English-speaking countries. [20] [30] It is not available in the United States, Canada, or New Zealand. [20] [30] The drug has never been marketed in the United States. [27]
Mesterolone, along with other AAS, is a schedule III controlled substance in the United States under the Controlled Substances Act and a schedule IV controlled substance in Canada under the Controlled Drugs and Substances Act. [10] [31]
In one small scale clinical trial of depressed patients, an improvement of symptoms which included anxiety, lack of drive and desire was observed. [32] In patients with dysthymia, unipolar, and bipolar depression significant improvement was observed. [32] In this series of studies, mesterolone lead to a significant decrease in luteinizing hormone and testosterone levels. [32] In another study, 100 mg mesterolone cipionate was administered twice monthly. [33] With regards to plasma testosterone levels, there was no difference between the treated versus untreated group, and baseline luteinizing hormone levels were minimally affected. [33]
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