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| Clinical data | |
|---|---|
| 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 | |
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| Pharmacokinetic data | |
| Bioavailability | 3% |
| Protein binding | 98% (40% toAlbumin, 58% toSHBG) |
| Metabolism | Liver |
| Eliminationhalf-life | 12-13 hours |
| Excretion | Urine |
| Identifiers | |
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| CAS Number | |
| PubChemCID | |
| ChemSpider |
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| UNII | |
| KEGG |
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| 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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 N Y (what is this?) (verify) | |
Mesterolone, sold under the brand nameProviron among others, is anandrogen andanabolic steroid (AAS) medication which is used mainly in the treatment oflow testosterone levels.[2][3] It has also been used to treatmale infertility, although this use is controversial.[2][4][5] It is takenby mouth.[2]
Side effects of mesterolone includesymptoms ofmasculinization likeacne,scalp hair loss,increased body hair growth,voice changes, and increasedsexual desire.[2] It has no risk ofliver damage.[2][3] The drug is asynthetic androgen and anabolic steroid and hence is anagonist of theandrogen receptor (AR), thebiological target of androgens liketestosterone anddihydrotestosterone (DHT).[2][6] It has strongandrogenic effects and weakanabolic effects, which make it useful for producing masculinization.[2] The drug has noestrogenic 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 toimprove physique and performance, although it is not commonly used for such purposes due to its weak anabolic effects.[2] The drug is acontrolled substance in many countries and so non-medical use is generally illicit.[2][10]
Mesterolone is used in the treatment ofandrogen deficiency in malehypogonadism,anemia, and to supportmale fertility among other indications.[2][11][12] It has also been used to treatdelayed puberty in boys.[13] Because it lacks estrogenic effects, mesterolone may be indicated for treating cases of androgen deficiency in whichbreast tenderness orgynecomastia is also present.[14] The drug is described as a relatively weak androgen with partial activity and is rarely used for the purpose ofandrogen replacement therapy, but is still widely used in medicine.[2][12][15][3]
Mesterolone is used inandrogen 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/2–4× 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 1–4×/day |
| Methyltestosteroneb | Metandren, Oreton Methyl | Tablet | 10–30 mg/day | |
| Buccal | Testosterone | Striant | Tablet | 30 mg 2×/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 2–3×/day |
| Injection (IMTooltip intramuscular injection orSCTooltip subcutaneous injection) | Testosterone | Andronaq, Sterotate, Virosterone | Aqueous suspension | 10–50 mg 2–3×/week |
| Testosterone propionateb | Testoviron | Oil solution | 10–50 mg 2–3×/week | |
| Testosterone enanthate | Delatestryl | Oil solution | 50–250 mg 1x/1–4 weeks | |
| Xyosted | Auto-injector | 50–100 mg 1×/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 1×/3–5 weeks | |
| Mixed testosterone esters | Sustanon 100, Sustanon 250 | Oil solution | 50–250 mg 1×/2–4 weeks | |
| Testosterone undecanoate | Aveed, Nebido | Oil solution | 750–1,000 mg 1×/10–14 weeks | |
| Testosterone buciclatea | – | Aqueous suspension | 600–1,000 mg 1×/12–20 weeks | |
| Implant | Testosterone | Testopel | Pellet | 150–1,200 mg/3–6 months |
| Notes: Men produce about 3 to 11 mg of 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 forphysique- and performance-enhancing purposes bycompetitiveathletes,bodybuilders, andpowerlifters.[2]
Side effects of mesterolone includevirilization among others.[2]
Like other AAS, mesterolone is anagonist of theandrogen receptor (AR).[2] Mesterolone is described as a very pooranabolic agent due to inactivation by3α-hydroxysteroid dehydrogenase (3α-HSD) inskeletal muscletissue, similarly to DHT andmestanolone (17α-methyl-DHT).[2] In contrast,testosterone is a very poorsubstrate 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 itsandrogenicpotency 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 asubstrate for5α-reductase, as it is already 5α-reduced, and hence is not potentiated in so-called "androgenic"tissues such as theskin,hair follicles, andprostate gland.[2]
Mesterolone is not a substrate foraromatase, and so cannot be converted into anestrogen.[2] As such, it has no propensity for producing estrogenicside effects such asgynecomastia andfluid retention.[2] It also has noprogestogenic activity.[2]
Because mesterolone is not17α-alkylated, it has little or no potential forhepatotoxicity.[2] However, its risk of deleterious effects on thecardiovascular system is comparable to that of several other oral AAS.[2]
The C1αmethyl group of mesterolone inhibits itshepaticmetabolism and thereby confers significantoral activity, although its oralbioavailability 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 highaffinity for human serumsex 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 displaceendogenous 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 asyntheticandrostanesteroid andderivative of DHT.[19][20][2] It is specifically DHT with amethyl group at the C1α position.[19][20][2] Closely related AAS includemetenolone and itsestersmetenolone acetate andmetenolone enanthate.[19][20][2] Theantiandrogenrosterolone (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 bySchering under the brand name Proviron by 1967.[8][9] The well-established brand name Proviron had previously been used by Schering fortestosterone 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 thegeneric name of the drug and itsINNTooltip International Nonproprietary Name,USANTooltip United States Adopted Name,BANTooltip British Approved Name, andDCITTooltip Denominazione Comune Italiana, whilemestérolone is itsDCFTooltip Dénomination Commune Française.[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 theUnited Kingdom,Australia, andSouth Africa, as well as many non-English-speaking countries.[20][30] It is not available in theUnited States,Canada, orNew Zealand.[20][30] The drug has never been marketed in the United States.[27]
Mesterolone, along with other AAS, is aschedule IIIcontrolled substance in theUnited States under theControlled Substances Act and aschedule IV controlled substance inCanada under theControlled 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 withdysthymia,unipolar, andbipolar depression significant improvement was observed.[32] In this series of studies, mesterolone lead to a significant decrease inluteinizing hormone andtestosterone levels.[32] In another study, 100 mgmesterolone 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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