Mesterolone

Mesterolone
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	G03BB01 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); BR: Class C5 (Anabolic steroids); CA: Schedule IV; US: Schedule III;
Pharmacokinetic data
Bioavailability	3%
Protein binding	98% (40% to Albumin, 58% to SHBG)
Metabolism	Liver
Elimination half-life	12-13 hours
Excretion	Urine
Identifiers
	IUPAC name (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	1424-00-6 ;
PubChem CID	15020;
ChemSpider	14296 ;
UNII	0SRQ75X9I9;
KEGG	D04947 ;
ChEMBL	ChEMBL258918 ;
CompTox Dashboard (EPA)	DTXSID90878533 ;
ECHA InfoCard	100.014.397
Chemical and physical data
Formula	C20H32O2
Molar mass	304.474 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES 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 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 ; Key:UXYRZJKIQKRJCF-TZPFWLJSSA-N ;
	(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.^[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]

Medical uses

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]

v
t
e
Androgen replacement therapy formulations and dosages used in men
Route	Medication	Major brand names	Form	Dosage
Oral	Testosterone^a	–	Tablet	400–800 mg/day (in divided doses)
	Testosterone undecanoate	Andriol, Jatenzo	Capsule	40–80 mg/2–4x day (with meals)
	Methyltestosterone^b	Android, Metandren, Testred	Tablet	10–50 mg/day
	Fluoxymesterone^b	Halotestin, Ora-Testryl, Ultandren	Tablet	5–20 mg/day
	Metandienone^b	Dianabol	Tablet	5–15 mg/day
	Mesterolone^b	Proviron	Tablet	25–150 mg/day
Sublingual	Testosterone^b	Testoral	Tablet	5–10 mg 1–4x/day
Sublingual	Methyltestosterone^b	Metandren, Oreton Methyl	Tablet	10–30 mg/day
Buccal	Testosterone	Striant	Tablet	30 mg 2x/day
Buccal	Methyltestosterone^b	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, Testosteron^b	Suppository	40 mg 2–3x/day
Injection (IMTooltip intramuscular injection or SCTooltip subcutaneous injection)	Testosterone	Andronaq, Sterotate, Virosterone	Aqueous suspension	10–50 mg 2–3x/week
	Testosterone propionate^b	Testoviron	Oil solution	10–50 mg 2–3x/week
	Testosterone enanthate	Delatestryl	Oil solution	50–250 mg 1x/1–4 weeks
	Testosterone enanthate	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 phenylacetate^b	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 buciclate^a	–	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.

Non-medical uses

Mesterolone has been used for physique- and performance-enhancing purposes by competitive athletes, bodybuilders, and powerlifters.^[2]

Side effects

Side effects of mesterolone include virilization among others.^[2]

Pharmacology

Pharmacodynamics

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]

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.^[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]

Chemistry

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]

History

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]

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.^[19]^[20]^[29]^[30]

Brand names

Mesterolone is marketed mainly under the brand name Proviron.^[19]^[20]^[30]^[2]

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.^[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]

Legal status

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]

Research

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]

References

^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-15.
^ ^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 Llewellyn W (2011). Anabolics. Molecular Nutrition Llc. pp. 641–. ISBN 978-0-9828280-1-4.
^ ^a ^b ^c ^d Nieschlag E, Behre HM (1 April 2004). Testosterone: Action, Deficiency, Substitution. Cambridge University Press. pp. 411–. ISBN 978-1-139-45221-2.
^ Hargreave TB (6 December 2012). Male Infertility. Springer Science & Business Media. pp. 398–399. ISBN 978-1-4471-1029-3.
^ Lipshultz LI, Howards SS, Niederberger CS (24 September 2009). Infertility in the Male. Cambridge University Press. pp. 445–446. ISBN 978-0-521-87289-8.
^ Kicman AT (June 2008). "Pharmacology of anabolic steroids". British Journal of Pharmacology. 154 (3): 502–521. doi:10.1038/bjp.2008.165. PMC 2439524. PMID 18500378.
^ ^a ^b Behre HM, Wang C, Handelsman DJ, Nieschlag E (2004). "Pharmacology of testosterone preparations". Testosterone. Cambridge University Press. pp. 405–444. doi:10.1017/CBO9780511545221.015. ISBN 9780521833806.
^ ^a ^b Rausch-Stroomann JG, Petry R, Hienz HA (1967). "The influence of mesterolone on testicular function". Research on Steroids. 3. Pergamon: 181–184.
^ ^a ^b Tausk M (1968). "Practically Applicable Results of Twenty Years of Research in Endocrinology". Progress in Drug Research / Fortschritte der Arzneimittelforschung / Progrès des recherches pharmaceutiques. Vol. 12. pp. 137–164. doi:10.1007/978-3-0348-7065-8_3. ISBN 978-3-0348-7067-2. PMID 4307936. {{cite book}}: |journal= ignored (help)
^ ^a ^b Karch SB (21 December 2006). Drug Abuse Handbook, Second Edition. CRC Press. pp. 30–. ISBN 978-1-4200-0346-8.
^ Allahbadia GN, Das RB (12 November 2004). The Art and Science of Assisted Reproductive Techniques. CRC Press. pp. 824–. ISBN 978-0-203-64051-7.
^ ^a ^b Becker KL (2001). Principles and Practice of Endocrinology and Metabolism. Lippincott Williams & Wilkins. pp. 1186–. ISBN 978-0-7817-1750-2.
^ Hart I, Newton RW (6 December 2012). Endocrinology. Springer Science & Business Media. pp. 119–. ISBN 978-94-010-9298-2.
^ Corona G, Rastrelli G, Vignozzi L, Maggi M (June 2012). "Emerging medication for the treatment of male hypogonadism". Expert Opinion on Emerging Drugs. 17 (2): 239–259. doi:10.1517/14728214.2012.683411. PMID 22612692. S2CID 22068249.
^ Nieschlag E, Behre HM, Bouchard P, Corrales JJ, Jones TH, Stalla GK, et al. (2004). "Testosterone replacement therapy: current trends and future directions". Human Reproduction Update. 10 (5): 409–419. doi:10.1093/humupd/dmh035. PMID 15297434.
^ Rastrelli G, Reisman Y, Ferri S, Prontera O, Sforza A, Maggi M, Corona G (2019). "Testosterone Replacement Therapy". Sexual Medicine. Springer. pp. 79–93. doi:10.1007/978-981-13-1226-7_8. ISBN 978-981-13-1225-0.
^ Saartok T, Dahlberg E, Gustafsson JA (June 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): 2100–2106. doi:10.1210/endo-114-6-2100. PMID 6539197.
^ 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". The Journal of Clinical Endocrinology and Metabolism. 53 (1): 69–75. doi:10.1210/jcem-53-1-69. PMID 7195405.
^ ^a ^b ^c ^d ^e Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 775–. ISBN 978-1-4757-2085-3.
^ ^a ^b ^c ^d ^e ^f ^g Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 656–. ISBN 978-3-88763-075-1.
^ Brooks JR, Primka RL, Berman C, Krupa DA, Reynolds GF, Rasmusson GH (August 1991). "Topical anti-androgenicity of a new 4-azasteroid in the hamster". Steroids. 56 (8): 428–433. doi:10.1016/0039-128x(91)90031-p. PMID 1788861. S2CID 21500107.
^ ^a ^b Carruthers M (2006). Androgen Deficiency in the Adult Male: Causes, Diagnosis and Treatment. CRC Press. pp. 137–178. ISBN 978-0-367-80018-5.
^ Neumann F, Wiechert R, Kramer M, Raspé G (April 1966). "[Experimental animal studies with a new androgen--mesterolone (1-alpha-methyl-5-alpha-androstan-17-beta-ol-one)]". Arzneimittel-Forschung (in German). 16 (4): 455–458. PMID 6014248.
^ Laschet U, Niermann H, Laschet L, Paarmann HF (1967). "Mesterolone, a potent oral active androgen without gonadotropin inhibition". Acta Endocrinologica. 56 (1_Suppl): S55. doi:10.1530/acta.0.056S055. ISSN 0804-4643.
^ Tausk M (1968). "Practically Applicable Results of Twenty Years of Research in Endocrinology". Progress in Drug Research / Fortschritte der Arzneimittelforschung / Progrès des recherches pharmaceutiques. Vol. 12. pp. 137–164. doi:10.1007/978-3-0348-7065-8_3. ISBN 978-3-0348-7067-2. PMID 4307936. {{cite book}}: |journal= ignored (help)
^ ^a ^b Nieschlag E, Nieschlag S (2017). "The History of Testosterone and The Testes: From Antiquity to Modern Times". Testosterone. Springer. pp. 1–19. doi:10.1007/978-3-319-46086-4_1. ISBN 978-3-319-46084-0.
^ ^a ^b Hohl A (6 April 2017). Testosterone: From Basic to Clinical Aspects. Springer. pp. 204–. ISBN 978-3-319-46086-4.
^ Kalinchenko S, Tyuzikov I, Mskhalaya G, Tishova Y (2017). "Testosterone Therapy: Oral Androgens". Testosterone. Springer. pp. 203–224. doi:10.1007/978-3-319-46086-4_10. ISBN 978-3-319-46084-0.
^ Morton IK, Hall JM (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 176–177. ISBN 978-94-011-4439-1.
^ ^a ^b ^c ^d "Mesterolone".
^ Lilley LL, Snyder JS, Collins SR (5 August 2016). Pharmacology for Canadian Health Care Practice. Elsevier Health Sciences. pp. 50–. ISBN 978-1-77172-066-3.
^ ^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 and Findings in Experimental and Clinical Pharmacology. 6 (6): 331–337. PMID 6431212.
^ ^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". Archives for Dermatological Research. 258 (3): 289–294. doi:10.1007/bf00561132. PMID 883846. S2CID 1222130.

External links

Proviron (mesterolone) - William Llewellyn's Anabolic.org Archived 2016-09-23 at the Wayback Machine.

[1] Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-15.

[Llewellyn2011-2] ^ ^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 Llewellyn W (2011). Anabolics. Molecular Nutrition Llc. pp. 641–. ISBN 978-0-9828280-1-4.

[NieschlagBehre2004-3] Nieschlag E, Behre HM (1 April 2004). Testosterone: Action, Deficiency, Substitution. Cambridge University Press. pp. 411–. ISBN 978-1-139-45221-2.

[Hargreave2012-4] Hargreave TB (6 December 2012). Male Infertility. Springer Science & Business Media. pp. 398–399. ISBN 978-1-4471-1029-3.

[LipshultzHowards2009-5] Lipshultz LI, Howards SS, Niederberger CS (24 September 2009). Infertility in the Male. Cambridge University Press. pp. 445–446. ISBN 978-0-521-87289-8.

[pmid18500378-6] Kicman AT (June 2008). "Pharmacology of anabolic steroids". British Journal of Pharmacology. 154 (3): 502–521. doi:10.1038/bjp.2008.165. PMC 2439524. PMID 18500378.

[BehreWang2004-7] Behre HM, Wang C, Handelsman DJ, Nieschlag E (2004). "Pharmacology of testosterone preparations". Testosterone. Cambridge University Press. pp. 405–444. doi:10.1017/CBO9780511545221.015. ISBN 9780521833806.

[Pergamon1967-8] Rausch-Stroomann JG, Petry R, Hienz HA (1967). "The influence of mesterolone on testicular function". Research on Steroids. 3. Pergamon: 181–184.

[Tausk1968-9] Tausk M (1968). "Practically Applicable Results of Twenty Years of Research in Endocrinology". Progress in Drug Research / Fortschritte der Arzneimittelforschung / Progrès des recherches pharmaceutiques. Vol. 12. pp. 137–164. doi:10.1007/978-3-0348-7065-8_3. ISBN 978-3-0348-7067-2. PMID 4307936. {{cite book}}: |journal= ignored (help)

[FFFLM2006-10] Karch SB (21 December 2006). Drug Abuse Handbook, Second Edition. CRC Press. pp. 30–. ISBN 978-1-4200-0346-8.

[AllahbadiaDas2004-11] Allahbadia GN, Das RB (12 November 2004). The Art and Science of Assisted Reproductive Techniques. CRC Press. pp. 824–. ISBN 978-0-203-64051-7.

[Becker2001-12] Becker KL (2001). Principles and Practice of Endocrinology and Metabolism. Lippincott Williams & Wilkins. pp. 1186–. ISBN 978-0-7817-1750-2.

[HartNewton2012-13] Hart I, Newton RW (6 December 2012). Endocrinology. Springer Science & Business Media. pp. 119–. ISBN 978-94-010-9298-2.

[pmid22612692-14] Corona G, Rastrelli G, Vignozzi L, Maggi M (June 2012). "Emerging medication for the treatment of male hypogonadism". Expert Opinion on Emerging Drugs. 17 (2): 239–259. doi:10.1517/14728214.2012.683411. PMID 22612692. S2CID 22068249.

[pmid15297434-15] Nieschlag E, Behre HM, Bouchard P, Corrales JJ, Jones TH, Stalla GK, et al. (2004). "Testosterone replacement therapy: current trends and future directions". Human Reproduction Update. 10 (5): 409–419. doi:10.1093/humupd/dmh035. PMID 15297434.

[RastrelliReisman2019-16] Rastrelli G, Reisman Y, Ferri S, Prontera O, Sforza A, Maggi M, Corona G (2019). "Testosterone Replacement Therapy". Sexual Medicine. Springer. pp. 79–93. doi:10.1007/978-981-13-1226-7_8. ISBN 978-981-13-1225-0.

[pmid6539197-17] Saartok T, Dahlberg E, Gustafsson JA (June 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): 2100–2106. doi:10.1210/endo-114-6-2100. PMID 6539197.

[pmid7195405-18] 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". The Journal of Clinical Endocrinology and Metabolism. 53 (1): 69–75. doi:10.1210/jcem-53-1-69. PMID 7195405.

[Elks2014-19] Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 775–. ISBN 978-1-4757-2085-3.

[IndexNominum2000-20] ^ ^a ^b ^c ^d ^e ^f ^g Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 656–. ISBN 978-3-88763-075-1.

[pmid1788861-21] Brooks JR, Primka RL, Berman C, Krupa DA, Reynolds GF, Rasmusson GH (August 1991). "Topical anti-androgenicity of a new 4-azasteroid in the hamster". Steroids. 56 (8): 428–433. doi:10.1016/0039-128x(91)90031-p. PMID 1788861. S2CID 21500107.

[Carruthers2006-22] Carruthers M (2006). Androgen Deficiency in the Adult Male: Causes, Diagnosis and Treatment. CRC Press. pp. 137–178. ISBN 978-0-367-80018-5.

[pmid6014248-23] Neumann F, Wiechert R, Kramer M, Raspé G (April 1966). "[Experimental animal studies with a new androgen--mesterolone (1-alpha-methyl-5-alpha-androstan-17-beta-ol-one)]". Arzneimittel-Forschung (in German). 16 (4): 455–458. PMID 6014248.

[LaschetNiermann1967-24] Laschet U, Niermann H, Laschet L, Paarmann HF (1967). "Mesterolone, a potent oral active androgen without gonadotropin inhibition". Acta Endocrinologica. 56 (1_Suppl): S55. doi:10.1530/acta.0.056S055. ISSN 0804-4643.

[pmid4307936-25] Tausk M (1968). "Practically Applicable Results of Twenty Years of Research in Endocrinology". Progress in Drug Research / Fortschritte der Arzneimittelforschung / Progrès des recherches pharmaceutiques. Vol. 12. pp. 137–164. doi:10.1007/978-3-0348-7065-8_3. ISBN 978-3-0348-7067-2. PMID 4307936. {{cite book}}: |journal= ignored (help)

[NieschlagNieschlag2017-26] Nieschlag E, Nieschlag S (2017). "The History of Testosterone and The Testes: From Antiquity to Modern Times". Testosterone. Springer. pp. 1–19. doi:10.1007/978-3-319-46086-4_1. ISBN 978-3-319-46084-0.

[Hohl2017-27] Hohl A (6 April 2017). Testosterone: From Basic to Clinical Aspects. Springer. pp. 204–. ISBN 978-3-319-46086-4.

[KalinchenkoTyuzikov2017-28] Kalinchenko S, Tyuzikov I, Mskhalaya G, Tishova Y (2017). "Testosterone Therapy: Oral Androgens". Testosterone. Springer. pp. 203–224. doi:10.1007/978-3-319-46086-4_10. ISBN 978-3-319-46084-0.

[MortonHall2012-29] Morton IK, Hall JM (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 176–177. ISBN 978-94-011-4439-1.

[Drugs.com-30] "Mesterolone".

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[pmid883846-33] 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". Archives for Dermatological Research. 258 (3): 289–294. doi:10.1007/bf00561132. PMID 883846. S2CID 1222130.

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Mesterolone

Medical uses

Non-medical uses

Side effects

Pharmacology

Pharmacodynamics

Pharmacokinetics

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