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Mesterolone

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Not to be confused with Mestanolone.
Mesterolone
Clinical data
Trade namesProviron, others
Other namesNSC-75054; SH-60723; SH-723; 1α-Methyl-4,5α-dihydrotestosterone; 1α-Methyl-DHT; 1α-Methyl-5α-androstan-17β-ol-3-one
AHFS/Drugs.comInternational Drug Names
Routes of
administration		By mouth
Drug classAndrogen; Anabolic steroid
ATC code
Legal status
Legal status
Pharmacokinetic data
BioavailabilityLow[1]
MetabolismLiver
ExcretionUrine
Identifiers
  • (1S,5S,8R,9S,10S,13S,14S,17S)-17-hydroxy-1,10,13-trimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.014.397 Edit this at Wikidata
Chemical and physical data
FormulaC20H32O2
Molar mass304.467 g/mol g·mol−1
3D model (JSmol)
  • O=C4C[C@@H]3CC[C@@H]2[C@H](CC[C@]1(C)[C@@H](O)CC[C@H]12)[C@@]3(C)[C@@H](C)C4
  • InChI=1S/C20H32O2/c1-12-10-14(21)11-13-4-5-15-16-6-7-18(22)19(16,2)9-8-17(15)20(12,13)3/h12-13,15-18,22H,4-11H2,1-3H3/t12-,13-,15-,16-,17-,18-,19-,20-/m0/s1 checkY
  • Key:UXYRZJKIQKRJCF-TZPFWLJSSA-N checkY
 ☒NcheckY (what is this?)  (verify)

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.[1][2] It has also been used to treat male infertility, although this use is controversial.[1][3][4] It is taken by mouth.[1]

Side effects of mesterolone include symptoms of masculinization like acne, increased hair growth, voice changes, and increased sexual desire.[1] It has no risk of liver damage.[1][2] 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][5] It has strong androgenic effects and weak anabolic effects, which make it useful for producing masculinization.[1] The drug has no estrogenic effects.[1][2]

Mesterolone was discovered and introduced for medical use in 1934.[1][6] 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.[1] The drug is a controlled substance in many countries and so non-medical use is generally illicit.[1][7]

Medical uses

Mesterolone is used in the treatment of androgen deficiency in male hypogonadism, anemia, and to support male fertility among other indications.[1][8][9] It has also been used to treat delayed puberty in boys.[10] Because it lacks estrogenic effects, mesterolone may be indicated for treating cases of androgen deficiency in which breast tenderness or gynecomastia is also present.[11] 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.[1][9][12][2]

Non-medical uses

Mesterolone has been used for physique- and performance-enhancing purposes by competitive athletes, bodybuilders, and powerlifters.[1]

Side effects

See also: Anabolic steroid § Adverse effects

Side effects of mesterolone include virilization among others.[1]

Pharmacology

Pharmacodynamics

Like other AAS, mesterolone is an agonist of the androgen receptor (AR).[1] It 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.[1] 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).[1] In contrast, testosterone is a very poor substrate for 3α-HSD, and so is not similarly inactivated in skeletal muscle.[1] 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.[1] However, it does still show a greater ratio of anabolic activity to androgenic activity relative to testosterone.[1]

Mesterolone is not a substrate for aromatase, and so cannot be converted into an estrogen.[1] As such, it has no propensity for producing estrogenic side effects such as gynecomastia and fluid retention.[1] It also has no progestogenic activity.[1]

Because mesterolone is not 17α-alkylated, it has little or no potential for hepatotoxicity.[1] However, its risk of deleterious effects on the cardiovascular system is comparable to that of several other oral AAS.[1]

Pharmacokinetics

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.[1] In any case, mesterolone is one of the few non-17α-alkylated AAS that is active with oral ingestion.[1] 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.[13][1][14] 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.[1]

Chemistry

See also: List of androgens/anabolic steroids

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.[15][16][1] It is specifically DHT with a methyl group at the C1α position.[15][16][1] Closely related AAS include metenolone and its esters metenolone acetate and metenolone enanthate.[15][16][1] The antiandrogen rosterolone (17α-propylmesterolone) is also closely related to mesterolone.[17]

History

Mesterolone was synthesized and introduced for medical use in 1934 and was the first AAS to be marketed.[1][6] It was followed by methyltestosterone in 1936 and testosterone propionate in 1937.[6][18][1][19] The drug continues to be widely available and used today.[1][20]

Society and culture

Generic names

Mesterolone is the generic name of the drug and its INNTooltip International Nonproprietary Name, USANTooltip United States Adopted Name, BANTooltip British Approved Name, and DCITTooltip Denominazione Comune Italiana, while mestérolone is its DCFTooltip Dénomination Commune Française.[15][16][21][20]

Brand names

Mesterolone is marketed mainly under the brand name Proviron.[15][16][20][1]

Availability

Mesterolone is available widely throughout the world, including in the United Kingdom, Australia, and South Africa, as well as many non-English-speaking countries.[16][20] It is not available in the United States, Canada, or New Zealand.[16][20] The drug has never been marketed in the United States.[6]

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.[7][22]

Research

In one small scale clinical trial of depressed patients, an improvement of symptoms which included anxiety, lack of drive and desire was observed.[23] In patients with dysthymia, unipolar, and bipolar depression significant improvement was observed.[23] In this series of studies, mesterolone lead to a significant decrease in luteinizing hormone and testosterone levels.[23] In another study, 100 mg mesterolone cipionate was administered twice monthly.[24] With regards to plasma testosterone levels, there was no difference between the treated versus untreated group, and baseline luteinizing hormone levels were minimally affected.[24]

References

  1. ^ a b c d e f g h i j k l m n o p q r s t u v w x y z aa ab ac ad ae af ag ah ai aj ak al William Llewellyn (2011). Anabolics. Molecular Nutrition Llc. pp. 641–. ISBN 978-0-9828280-1-4.
  2. ^ a b c d E. Nieschlag; H. M. Behre (1 April 2004). Testosterone: Action, Deficiency, Substitution. Cambridge University Press. pp. 411–. ISBN 978-1-139-45221-2.
  3. ^ T.B. Hargreave (6 December 2012). Male Infertility. Springer Science & Business Media. pp. 398–399. ISBN 978-1-4471-1029-3.
  4. ^ Larry I. Lipshultz; Stuart S. Howards; Craig S. Niederberger (24 September 2009). Infertility in the Male. Cambridge University Press. pp. 445–446. ISBN 978-0-521-87289-8.
  5. ^ Kicman AT (2008). "Pharmacology of anabolic steroids". Br. J. Pharmacol. 154 (3): 502–21. doi:10.1038/bjp.2008.165. PMC 2439524. PMID 18500378.
  6. ^ a b c d Alexandre Hohl (6 April 2017). Testosterone: From Basic to Clinical Aspects. Springer. pp. 204–. ISBN 978-3-319-46086-4.
  7. ^ a b Steven B. Karch, MD, FFFLM (21 December 2006). Drug Abuse Handbook, Second Edition. CRC Press. pp. 30–. ISBN 978-1-4200-0346-8.{{cite book}}: CS1 maint: multiple names: authors list (link)
  8. ^ Gautam N. Allahbadia; Rita Basuray Das (12 November 2004). The Art and Science of Assisted Reproductive Techniques. CRC Press. pp. 824–. ISBN 978-0-203-64051-7.
  9. ^ a b Kenneth L. Becker (2001). Principles and Practice of Endocrinology and Metabolism. Lippincott Williams & Wilkins. pp. 1186–. ISBN 978-0-7817-1750-2.
  10. ^ I. Hart; R.W. Newton (6 December 2012). Endocrinology. Springer Science & Business Media. pp. 119–. ISBN 978-94-010-9298-2.
  11. ^ Corona G, Rastrelli G, Vignozzi L, Maggi M (2012). "Emerging medication for the treatment of male hypogonadism". Expert Opin Emerg Drugs. 17 (2): 239–59. doi:10.1517/14728214.2012.683411. PMID 22612692.
  12. ^ Nieschlag E, Behre HM, Bouchard P, et al. (2004). "Testosterone replacement therapy: current trends and future directions". Hum. Reprod. Update. 10 (5): 409–19. doi:10.1093/humupd/dmh035. PMID 15297434.
  13. ^ Saartok T, Dahlberg E, Gustafsson JA (1984). "Relative binding affinity of anabolic-androgenic steroids: comparison of the binding to the androgen receptors in skeletal muscle and in prostate, as well as to sex hormone-binding globulin". Endocrinology. 114 (6): 2100–6. doi:10.1210/endo-114-6-2100. PMID 6539197.
  14. ^ Pugeat MM, Dunn JF, Nisula BC (July 1981). "Transport of steroid hormones: interaction of 70 drugs with testosterone-binding globulin and corticosteroid-binding globulin in human plasma". J. Clin. Endocrinol. Metab. 53 (1): 69–75. doi:10.1210/jcem-53-1-69. PMID 7195405.
  15. ^ a b c d e J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 775–. ISBN 978-1-4757-2085-3.
  16. ^ a b c d e f g Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 656–. ISBN 978-3-88763-075-1.
  17. ^ Brooks, J. R.; Primka, R. L.; Berman, C; Krupa, D. A.; Reynolds, G. F.; Rasmusson, G. H. (1991). "Topical anti-androgenicity of a new 4-azasteroid in the hamster". Steroids. 56 (8): 428–33. doi:10.1016/0039-128x(91)90031-p. PMID 1788861.
  18. ^ N.A.R.D. journal. National Association of Retail Druggists. July 1956.
  19. ^ William Llewellyn (2011). Anabolics. Molecular Nutrition Llc. pp. 413, 426, 607. ISBN 978-0-9828280-1-4.
  20. ^ a b c d e https://www.drugs.com/international/mesterolone.html
  21. ^ I.K. Morton; Judith M. Hall (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 176–177. ISBN 978-94-011-4439-1.
  22. ^ Linda Lane Lilley; Julie S. Snyder; Shelly Rainforth Collins (5 August 2016). Pharmacology for Canadian Health Care Practice. Elsevier Health Sciences. pp. 50–. ISBN 978-1-77172-066-3.
  23. ^ a b c Itil TM, Michael ST, Shapiro DM, Itil KZ (June 1984). "The effects of mesterolone, a male sex hormone in depressed patients (a double blind controlled study)". Methods Find Exp Clin Pharmacol. 6 (6): 331–7. PMID 6431212.
  24. ^ a b Kövary PM, Lenau H, Niermann H, Zierden E, Wagner H (May 1977). "Testosterone levels and gonadotrophins in Klinefelter's patients treated with injections of mesterolone cipionate". Arch Dermatol Res. 258 (3): 289–94. doi:10.1007/bf00561132. PMID 883846.

Further reading

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