Mestanolone

Last updated
Mestanolone
Mestanolone Structural Formula V2.svg
Clinical data
Trade names Androstalone, Ermalone, others
Other namesRU-143; Methylandrostanolone; Methyldihydrotestosterone; Methyl-DHT; 17α-Methyl-4,5α-dihydrotestosterone; 17α-Methyl-DHT; 17α-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
  • None
Legal status
Legal status
Pharmacokinetic data
Metabolism Liver
Excretion Urine
Identifiers
  • (5S,8R,9S,10S,13S,14S,17S)-17-hydroxy-10,13,17-trimethyl-2,4,5,6,7,8,9,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-3-one
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.007.549 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C20H32O2
Molar mass 304.474 g·mol−1
3D model (JSmol)
  • O=C2C[C@@H]1CC[C@@H]3[C@@H]([C@@]1(C)CC2)CC[C@]4([C@H]3CC[C@@]4(O)C)C
  • InChI=1S/C20H32O2/c1-18-9-6-14(21)12-13(18)4-5-15-16(18)7-10-19(2)17(15)8-11-20(19,3)22/h13,15-17,22H,4-12H2,1-3H3/t13-,15+,16-,17-,18-,19-,20-/m0/s1 Yes check.svgY
  • Key:WYZDXEKUWRCKOB-YDSAWKJFSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Mestanolone, also known as methylandrostanolone and sold under the brand names Androstalone and Ermalone among others, is an androgen and anabolic steroid (AAS) medication which is mostly no longer used. [1] [2] [3] [4] It is still available for use in Japan however. [2] [3] It is taken by mouth. [4]

Contents

Side effects of mestanolone include symptoms of masculinization like acne, increased hair growth, voice changes, and increased sexual desire. [4] It can also cause liver damage. [4] 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). [4] [5] It has strong androgenic effects and weak anabolic effects, which make it useful for producing masculine psychological and behavioral effects. [4] The drug has no estrogenic effects. [4]

Mestanolone was discovered in 1935 and was introduced for medical use in the 1950s. [6] [7] [8] [4] In addition to its medical use, mestanolone has been used to improve physique and performance. [4] It was used in East Germany in Olympic athletes as part of a state-sponsored doping program in the 1970s and 1980s. [4] The drug is a controlled substance in many countries and so non-medical use is generally illicit. [4]

Medical uses

Available forms

Mestanolone was available in the form of 25 mg sublingual tablets (brand name Ermalone). [9]

Pharmacology

Pharmacodynamics

Mestanolone is an AAS, with both androgenic and anabolic effects. [4] It is very similar in its effects to androstanolone (dihydrotestosterone; DHT), and can be thought of as an orally active version of this AAS. [4] Due to inactivation by 3α-hydroxysteroid dehydrogenase (3α-HSD) in skeletal muscle, mestanolone is described as a very poor anabolic agent, similarly to androstanolone and mesterolone. [4] As mestanolone is 5α-reduced, it cannot be aromatized and hence has no propensity for estrogenic side effects such as gynecomastia. [4] The drug also has no progestogenic activity. [4] Like other 17α-alkylated AAS, mestanolone is hepatotoxic. [4]

Pharmacokinetics

Due to its C17α methyl group, unlike androstanolone, mestanolone is orally active. [4]

Chemistry

Mestanolone, also known as 17α-methyl-4,5α-dihydrotestosterone (17α-methyl-DHT) or as 17α-methyl-5α-androstan-17β-ol-3-one, is a synthetic androstane steroid and a 17α-alkylated derivative of dihydrotestosterone (DHT). [1] [4] It differs from DHT only by the presence of the methyl group at the C17α position. [1] [4] Close synthetic relatives of mestanolone include oxandrolone (2-oxa-17α-methyl-DHT), oxymetholone (2-hydroxymethylene-17α-methyl-DHT), and stanozolol (a derivative of 17α-methyl-DHT (mestanolone) with a pyrazole ring fused to the A ring). [1] [4]

Side effects

Side effects of mestanolone include virilization and hepatotoxicity among others. [4]

History

Mestanolone was first synthesized in 1935 along with methyltestosterone and methandriol. [6] [7] It was developed by Roussel in the 1950s and was introduced for medical use, under the brand names Androstalone and Ermalone, by at least 1960. [4] [10] [8] It was marketed in Germany. [4] The drug was originally thought to be a potent anabolic agent, but subsequent research showed that it actually has relatively weak anabolic effects and is mostly an androgen. [4] Mestanolone was used as a doping agent in athletes competing in the Olympics from East Germany due to a state-sponsored doping program in the 1970s and 1980s. [4] Its value is said to have been less as a muscle-builder and more as an androgen in the central nervous system and neuromuscular interaction, improving speed, strength, aggression, focus, endurance, and stress resilience. [4] Today, mestanolone has mostly been discontinued in medicine, though it is still available in Japan. [2] [3] [4]

Society and culture

Generic names

Mestanolone is the generic name of the drug and its INN Tooltip International Nonproprietary Name, BAN Tooltip British Approved Name, and JAN Tooltip Japanese Accepted Name. [1] [11]

Brand names

Mestanolone was marketed under the brand names Andoron, Androstalone, Ermalone, Mesanolon, and Notandron among many others. [4] [2] [12] [3]

Availability

Mestanolone has mostly been discontinued but remains available in Japan. [2] [3] [4]

Related Research Articles

<span class="mw-page-title-main">Metenolone</span> Chemical compound

Metenolone, or methenolone, is an androgen and anabolic steroid (AAS) which is used in the form of esters such as metenolone acetate and metenolone enanthate. Metenolone esters are used mainly in the treatment of anemia due to bone marrow failure. Metenolone acetate is taken by mouth, while metenolone enanthate is given by injection into muscle.

<span class="mw-page-title-main">Oxandrolone</span> Androgen and anabolic steroid

Oxandrolone, sold under the brand names Oxandrin and Anavar, among others, is an androgen and anabolic steroid (AAS) medication which is used to help promote weight gain in various situations, to help offset protein catabolism caused by long-term corticosteroid therapy, to support recovery from severe burns, to treat bone pain associated with osteoporosis, to aid in the development of girls with Turner syndrome, and for other indications. It is taken by mouth.

<span class="mw-page-title-main">Oxymetholone</span> Androgen and anabolic steroid

Oxymetholone, sold under the brand names Anadrol and Anapolon among others, is an androgen and anabolic steroid (AAS) medication which is used primarily in the treatment of anemia. It is also used to treat osteoporosis, HIV/AIDS wasting syndrome, and to promote weight gain and muscle growth in certain situations. It is taken by mouth.

<span class="mw-page-title-main">Metandienone</span> Androgen and anabolic steroid

Metandienone, also known as methandienone or methandrostenolone and sold under the brand name Dianabol (D-Bol) among others, is an androgen and anabolic steroid (AAS) medication which is still quite often used because of its affordability and effectiveness for bulking cycles. It is also used non-medically for physique- and performance-enhancing purposes. It is often taken by mouth.

<span class="mw-page-title-main">Norethandrolone</span> Chemical compound

Norethandrolone, sold under the brand names Nilevar and Pronabol among others, is an androgen and anabolic steroid (AAS) medication which has been used to promote muscle growth and to treat severe burns, physical trauma, and aplastic anemia but has mostly been discontinued. It is still available for use in France however. It is taken by mouth.

<span class="mw-page-title-main">Mesterolone</span> Chemical compound

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. It has also been used to treat male infertility, although this use is controversial. It is taken by mouth.

<span class="mw-page-title-main">Fluoxymesterone</span> Chemical compound

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. It is taken by mouth.

<span class="mw-page-title-main">Drostanolone propionate</span> Chemical compound

Drostanolone propionate, or dromostanolone propionate, sold under the brand names Drolban, Masteril, and Masteron among others, is an androgen and anabolic steroid (AAS) medication which was used to treat breast cancer in women but is now no longer marketed. It is given by injection into muscle.

<span class="mw-page-title-main">Desoxymethyltestosterone</span> Chemical compound

Desoxymethyltestosterone (DMT), known by the nicknames Madol and Pheraplex, is a synthetic and orally active anabolic–androgenic steroid (AAS) and a 17α-methylated derivative of dihydrotestosterone (DHT) which was never marketed for medical use. It was one of the first designer steroids to be marketed as a performance-enhancing drug to athletes and bodybuilders.

<span class="mw-page-title-main">Metribolone</span> Chemical compound

Metribolone is a synthetic and orally active anabolic–androgenic steroid (AAS) and a 17α-alkylated nandrolone (19-nortestosterone) derivative which was never marketed for medical use but has been widely used in scientific research as a hot ligand in androgen receptor (AR) ligand binding assays (LBAs) and as a photoaffinity label for the AR. More precisely, metribolone is the 17α-methylated derivative of trenbolone. It was investigated briefly for the treatment of advanced breast cancer in women in the late 1960s and early 1970s, but was found to produce signs of severe hepatotoxicity at very low dosages, and its development was subsequently discontinued.

<span class="mw-page-title-main">Drostanolone</span> Chemical compound

Drostanolone, or dromostanolone, is an anabolic–androgenic steroid (AAS) of the dihydrotestosterone (DHT) group which was never marketed. An androgen ester prodrug of drostanolone, drostanolone propionate, was formerly used in the treatment of breast cancer in women under brand names such as Drolban, Masteril, and Masteron. This has also been used non-medically for physique- or performance-enhancing purposes.

<span class="mw-page-title-main">Methasterone</span> Chemical compound

Methasterone, also known as methyldrostanolone and known by the nickname Superdrol, is a synthetic and orally active anabolic–androgenic steroid (AAS) which was never marketed for medical use. It was sold legally for 9 years as a body building supplement. Because of this lengthy time being legal it has more studies and references than most other designer steroids.

<span class="mw-page-title-main">Epitiostanol</span> Chemical compound

Epitiostanol, sold under the brand name Thiodrol, is an injected antiestrogen and anabolic–androgenic steroid (AAS) of the dihydrotestosterone (DHT) group which was described in the literature in 1965 and has been marketed in Japan as an antineoplastic agent for the treatment of breast cancer since 1977.

<span class="mw-page-title-main">Methylstenbolone</span> Chemical compound

Methylstenbolone, known by the nicknames M-Sten, Methyl-Sten, and Ultradrol, is a synthetic and orally active anabolic–androgenic steroid (AAS) and a 17α-methylated derivative of dihydrotestosterone (DHT) which was never introduced for medical use. It is a designer steroid and has been sold via the internet marketed as a dietary/nutritional supplement.

<span class="mw-page-title-main">Methylepitiostanol</span> Chemical compound

Methylepitiostanol, known by the nicknames Epistane, Hemapolin, Havoc, and Epi Plex, is a synthetic and orally active anabolic–androgenic steroid (AAS) of the dihydrotestosterone (DHT) group which was first described in the literature in 1974 but was never marketed for medical use. It is the 17α-methylated derivative of epitiostanol, an AAS and antiestrogen which was formerly used in the treatment of breast cancer in Japan. Similarly to mepitiostane, methylepitiostanol is an orally active variant of epitiostanol. Due to its C17α methyl group, the drug is considered to have a high potential for hepatotoxicity.

A 17α-alkylated anabolic steroid is a synthetic anabolic–androgenic steroid (AAS) that features an alkyl group, specifically a methyl or ethyl group, at the C17α position. Unlike many other AAS, 17α-alkylated AAS are orally active and do not require intramuscular injection. However, they uniquely possess a high potential for hepatotoxicity, which simultaneously limits their use. In addition, some have a high risk of gynecomastia due to uniquely high estrogenic activity, although this does not apply to 17α-alkylated AAS that are also 4,5α-reduced or 19-demethylated. The prototypical example of a 17α-alkylated AAS is methyltestosterone (17α-methyltestosterone).

<span class="mw-page-title-main">Boldenone undecylenate</span> Chemical compound

Boldenone undecylenate, or boldenone undecenoate, sold under the brand names Equipoise and Parenabol among others, is an androgen and anabolic steroid (AAS) medication which is used in veterinary medicine, mainly in horses. It was formerly used in humans as well. It is given by injection into muscle.

<span class="mw-page-title-main">Androstanolone</span> Androgenic and anabolic steroid medication

Androstanolone, or stanolone, also known as dihydrotestosterone (DHT) and sold under the brand name Andractim among others, is an androgen and anabolic steroid (AAS) medication and hormone which is used mainly in the treatment of low testosterone levels in men. It is also used to treat breast development and small penis in males. Compared to testosterone, androstanolone (DHT) is less likely to aromatize into estrogen, and therefore it shows less pronounced estrogenic side effects, such as gynecomastia and water retention. On the other hand, androstanolone (DHT) show more significant androgenic side effects, such as acne, hair loss and prostate enlargement.

<span class="mw-page-title-main">Structure–activity relationships of anabolic steroids</span>

The structure–activity relationships (SAR) of anabolic steroids (AAS) have been extensively studied.

<span class="mw-page-title-main">Methyldiazinol</span> Anabolic steroid

Methyldiazinol is a synthetic and orally active androgen/anabolic steroid (AAS) which was never marketed. It is a 17α-methylated derivative of dihydrotestosterone (DHT); specifically, it is the C3 azi analogue of mestanolone (17α-methyl-DHT). The drug has been found to possess a high ratio and dissociation of myotrophic to androgenic activity; relative to methyltestosterone, its ratio was 15 (3:0.2), among the highest observed.

References

  1. 1 2 3 4 5 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.
  2. 1 2 3 4 5 "Mestanolone". Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 655–. ISBN   978-3-88763-075-1.
  3. 1 2 3 4 5 "S1. Anabolic Agents". Drugs in Sport: Anti-Doping Prohibited List– via Drugs.com.
  4. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 Llewellyn W (2009). Anabolics. Molecular Nutrition Llc. p. 241. ISBN   978-0967930473.
  5. ↑ 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.
  6. 1 2 Schänzer W (July 1996). "Metabolism of anabolic androgenic steroids". Clinical Chemistry. 42 (7): 1001–1020. doi: 10.1093/clinchem/42.7.1001 . PMID   8674183.
  7. 1 2 Ruzicka L, Goldberg MW, Rosenberg HR (1935). "Sexualhormone X. Herstellung des 17-Methyl-testosterons und anderer Androsten- und Androstanderivate. Zusammenhänge zwischen chemischer Konstitution und männlicher Hormonwirkung". Helvetica Chimica Acta. 18 (1): 1487–1498. doi:10.1002/hlca.193501801203. ISSN   0018-019X.
  8. 1 2 Arnold A, Potts GO, Beyler AL (December 1963). "The Ratio of Anabolic to Androgenic Activity of 7: 17-Dimethyltestosterone, Oxymesterone, Mestanolone and Fluoxymesterone". The Journal of Endocrinology. 28: 87–92. doi:10.1677/joe.0.0280087. PMID   14086172.
  9. ↑ Krüskemper HL (22 October 2013). Anabolic Steroids. Elsevier. pp. 196–. ISBN   978-1-4832-6504-9.
  10. ↑ Bishop PM (January 1960). "Male sex hormones". British Medical Journal. 1 (5167): 184–186. doi:10.1136/bmj.1.5167.184. PMC   1966335 . PMID   13800998.
  11. ↑ "Mestanolone [INN:BAN:JAN]". ChemIDplus. U.S. National Library of Medicine.
  12. ↑ Negwer M (1987). Organic-chemical Drugs and Their Synonyms: (an International Survey). VCH Publishers. ISBN   978-0-89573-552-2. Anavormol, Andoron, Androne, Androstalone, Antalon "Kobayashi K.", Assimil, Ermalone, Etnabolate, Hermalone-Glosset, Macrobin (Tabl. -- Syrup), Mesanolon, Mestalone, Mestanolone", Methyantalon, Methybol, 172-Methylandrostanolone, Preroide,. 1045.
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