Norethandrolone

Last updated
Norethandrolone
Norethandrolone structure.png
Clinical data
Trade names Nilevar, Pronabol
Other namesNoretandrolone; CB-8022; 3-Ketoethylestrenol; Ethylestrenolone; 17α-Ethyl-19-nortestosterone; 17α-Ethylestr-4-en-17β-ol-3-one; 17α-Ethyl-19-norandrost-4-en-17β-ol-3-one; Ethylnandrolone; Ethylnortestosterone
AHFS/Drugs.com International Drug Names
Routes of
administration 		By mouth
Drug class Androgen; Anabolic steroid; Progestin; Progestogen
ATC code
Legal status
Legal status
Identifiers
  • (8R,9S,10R,13S,14S,17S)-17-ethyl-17-hydroxy-13-methyl-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
ECHA InfoCard 100.000.140 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C20H30O2
Molar mass 302.458 g·mol−1
3D model (JSmol)
  • O=C4\C=C3/[C@@H]([C@H]2CC[C@]1([C@@H](CC[C@@]1(O)CC)[C@@H]2CC3)C)CC4
  • InChI=1S/C20H30O2/c1-3-20(22)11-9-18-17-6-4-13-12-14(21)5-7-15(13)16(17)8-10-19(18,20)2/h12,15-18,22H,3-11H2,1-2H3/t15-,16+,17+,18-,19-,20-/m0/s1 Yes check.svgY
  • Key:ZDHCJEIGTNNEMY-XGXHKTLJSA-N Yes check.svgY
   (verify)

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. [2] [3] [4] It is still available for use in France however. [3] [4] It is taken by mouth. [3]

Contents

Side effects of norethandrolone include symptoms of masculinization like acne, increased hair growth, voice changes, and increased sexual desire. [3] It can also cause estrogenic effects like fluid retention, breast tenderness, and breast enlargement in men and liver damage. [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). [3] [5] It has strong anabolic effects relative to its androgenic effects. [3] The drug also has strong progestogenic effects. [3]

Norethandrolone was discovered in 1953 and was introduced for medical use in 1956. [6] [7] It was the first AAS with a favorable separation of anabolic and androgenic effect to be marketed. [7] [8] The drug was mostly withdrawn in the 1980s due to concerns of liver damage. [9] In addition to its medical use, norethandrolone has been used to improve physique and performance. [3] The drug is a controlled substance in many countries and so non-medical use is generally illicit. [3]

Medical uses

Norethandrolone has been used in the treatment of muscle wasting, [9] patients with severe burns, after severe trauma, and for certain forms of aplastic anemia among other indications. [3]

Side effects

Side effects of norethandrolone include virilization among others. [3] It has estrogenic effects and can cause gynecomastia and fluid retention. [3] As with all 17α-alkylated AAS, long-term use of norethandrolone in high doses may result in hepatotoxicity including elevated liver enzymes and cirrhosis. [10]

Pharmacology

Pharmacodynamics

Androgenic vs. anabolic activity
of androgens/anabolic steroids
MedicationRatioa
Testosterone ~1:1
Androstanolone (DHT) ~1:1
Methyltestosterone ~1:1
Methandriol ~1:1
Fluoxymesterone 1:1–1:15
Metandienone 1:1–1:8
Drostanolone 1:3–1:4
Metenolone 1:2–1:30
Oxymetholone 1:2–1:9
Oxandrolone 1:3–1:13
Stanozolol 1:1–1:30
Nandrolone 1:3–1:16
Ethylestrenol 1:2–1:19
Norethandrolone1:1–1:20
Notes: In rodents. Footnotes:a = Ratio of androgenic to anabolic activity. Sources: See template.

Norethandrolone is an androgen and anabolic steroid and hence is an agonist of the androgen receptor, the biological target of androgens like testosterone and dihydrotestosterone. [3] It has a high ratio of anabolic to androgenic activity. [3] Analogously to the case of nandrolone and 5α-dihydronandrolone, 5α-dihydronorethandrolone, the 5α-reduced metabolite of norethandrolone, shows diminished affinity for the androgen receptor relative to norethandrolone. [3] [11] This is likely related to the high ratio of anabolic to androgenic activity observed with norethandrolone. [3] [11] Norethandrolone has relatively high estrogenic activity via transformation by aromatase into the potent estrogen ethylestradiol. [3] It also has strong progestogenic activity. [3] The progestogenic potency of norethandrolone is similar to that of norethisterone in terms of endometrial changes in women. [12] In addition, norethandrolone is hepatotoxic. [3]

Relative affinities of nandrolone and related steroids at the androgen receptor
CompoundrAR(%)hAR(%)
Testosterone 3838
5α-Dihydrotestosterone 77100
Nandrolone 7592
5α-Dihydronandrolone 3550
Ethylestrenol ND2
NorethandroloneND22
5α-Dihydronorethandrolone ND14
Metribolone 100110
Sources: See template.

Pharmacokinetics

The pharmacokinetics of norethandrolone have been reviewed. [13]

Chemistry

Norethandrolone, also known as 17α-ethyl-19-nortestosterone or as 17α-ethylestr-4-en-17β-ol-3-one, is a synthetic estrane steroid and a 17α-alkylated derivative of testosterone and 19-nortestosterone (nandrolone). [2] [3] It is closely related to normethandrone (17α-methyl-19-nortestosterone) and to ethylestrenol (3-deketo-17α-ethyl-19-nortestosterone). [2] [3]

Synthesis

Chemical syntheses of norethandrolone have been published. [13]

History

Norethandrolone was synthesized at G. D. Searle & Company in 1953 and was originally studied as a progestin, along with norethisterone and noretynodrel, but ultimately was not marketed as such. [6] In 1955, it was re-examined for testosterone-like activity and was found to have similar anabolic activity to testosterone but only one-sixteenth the androgenic potency. [6] [9] Norethandrolone was introduced for medical use as an AAS in 1956 and was the first so-called "anabolic steroid", or AAS with a favorable separation of anabolic and androgenic effect, to be marketed. [7] [8] It was followed by normethandrone as a progestin in 1957 and by the more well-known AAS nandrolone phenylpropionate in 1959. [14] [8] Norethandrolone was introduced in the United States in the late 1950s under the brand name Nilevar but was discontinued in this country in the 1960s due to limited sales. [3] Although it was also introduced into Europe and certain other markets, [3] it was withdrawn in many countries in the 1980s due to concerns of cholestatic jaundice. [9] Today, the drug remains available only in France. [3] [4]

Society and culture

Generic names

Norethandrolone is the generic name of the drug and its INN Tooltip International Nonproprietary Name and BAN Tooltip British Approved Name. [2] [4] It has also been referred to as noretandrolone, ethylnandrolone, and ethylnortestosterone, as well as by its developmental code name CB-8022. [2] [4]

Brand names

Norethandrolone is marketed under the brand names Nilevar and Pronabol. [2] [3] [4]

Availability

Norethandrolone is available today only in France. [4] [15]

Research

Norethandrolone has been studied for use in male hormonal contraception. [16] [17] [18]

Related Research Articles

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

Nandrolone, also known as 19-nortestosterone, is an endogenous androgen which exists in the male body at a ratio of 1:50 compared to testosterone. It is also an anabolic steroid (AAS) which is medically used in the form of esters such as nandrolone decanoate and nandrolone phenylpropionate. Nandrolone esters are used in the treatment of anemias, cachexia, osteoporosis, breast cancer, and for other indications. They are not used by mouth and instead are given by injection into muscle or fat.

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

Nandrolone decanoate, sold under the brand name ROLON among others, is an androgen and anabolic steroid (AAS) medication which is used primarily in the treatment of anemias and wasting syndromes, as well as osteoporosis in menopausal women. It is given by injection into muscle or fat once every one to four weeks.

<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">Ethylestrenol</span> Chemical compound

Ethylestrenol, also known as ethyloestrenol or ethylnandrol and sold under the brand names Maxibolin and Orabolin among others, is an androgen and anabolic steroid (AAS) medication which has been used in the past for a variety of indications such as to promote weight gain and to treat anemia and osteoporosis but has been discontinued for use in humans. It is still available for veterinary use in Australia and New Zealand however. It is taken by mouth.

<span class="mw-page-title-main">Norethisterone</span> Progestin medication

Norethisterone, also known as norethindrone and sold under many brand names, is a progestin medication used in birth control pills, menopausal hormone therapy, and for the treatment of gynecological disorders. The medication is available in both low-dose and high-dose formulations and both alone and in combination with an estrogen. It is used by mouth or, as norethisterone enanthate, by injection into muscle.

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

Ethisterone, also known as ethinyltestosterone, pregneninolone, and anhydrohydroxyprogesterone and formerly sold under the brand names Proluton C and Pranone among others, is a progestin medication which was used in the treatment of gynecological disorders but is now no longer available. It was used alone and was not formulated in combination with an estrogen. The medication is taken by mouth.

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

Trestolone, also known as 7α-methyl-19-nortestosterone (MENT), is an experimental androgen/anabolic steroid (AAS) and progestogen medication which has been under development for potential use as a form of hormonal birth control for men and in androgen replacement therapy for low testosterone levels in men but has never been marketed for medical use. It is given as an implant that is placed into fat. As trestolone acetate, an androgen ester and prodrug of trestolone, the medication can also be given by injection into muscle.

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

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. It is still available for use in Japan however. It is taken by mouth.

<span class="mw-page-title-main">Anabolic steroid</span> Steroidal androgen that is structurally related and has similar effects to testosterone

Anabolic steroids, also known as anabolic-androgenic steroids (AAS), are a class of drugs that are structurally related to testosterone, the main male sex hormone, and produce effects by binding to the androgen receptor. Anabolic steroids have a number of medical uses, but are also used by athletes to increase muscle size, strength, and performance.

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

Normethandrone, also known as methylestrenolone or methylnortestosterone and sold under the brand name Metalutin among others, is a progestin and androgen/anabolic steroid (AAS) medication which is used in combination with an estrogen in the treatment of amenorrhea and menopausal symptoms in women. It is taken by mouth.

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

Nandrolone phenylpropionate (NPP), or nandrolone phenpropionate, sold under the brand name Durabolin among others, is an androgen and anabolic steroid (AAS) medication which has been used primarily in the treatment of breast cancer and osteoporosis in women. It is given by injection into muscle once every week. Although it was widely used in the past, the drug has mostly been discontinued and hence is now mostly no longer available.

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

Dimethandrolone (DMA), also known by its developmental code name CDB-1321, is an experimental androgen/anabolic steroid (AAS) and progestogen medication which is under investigation for potential clinical use.

<span class="mw-page-title-main">Dimethyltrienolone</span> Anabolic–androgenic steroid

Dimethyltrienolone is a synthetic, orally active, and extremely potent anabolic–androgenic steroid (AAS) and 17α-alkylated 19-nortestosterone (nandrolone) derivative which was never marketed for medical use. It has among the highest known affinity of any AAS for the androgen receptors, and has been said to be perhaps the most potent AAS to have ever been developed.

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

Methylhydroxynandrolone, also known as 4-hydroxy-17α-methyl-19-nortestosterone (HMNT), as well as 4,17β-dihydroxy-17α-methylestr-4-en-3-one, is a synthetic, orally active anabolic–androgenic steroid (AAS) and a 17α-alkylated derivative of nandrolone (19-nortestosterone) which was never marketed. It was first described in 1964 and was studied in the treatment of breast cancer, but was not introduced for clinical use. The drug re-emerged in 2004 when it started being sold on the Internet as a "dietary supplement". MOHN joined other AAS as a controlled substance in the United States on 20 January 2005.

<span class="mw-page-title-main">5α-Dihydronandrolone</span> Chemical compound

5α-Dihydronandrolone is a naturally occurring anabolic–androgenic steroid (AAS) and a 5α-reduced derivative of nandrolone (19-nortestosterone). It is a major metabolite of nandrolone and is formed from it by the actions of the enzyme 5α-reductase analogously to the formation of dihydrotestosterone (DHT) from testosterone.

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

Dimethandrolone undecanoate (DMAU), also known by its developmental code name CDB-4521, is an experimental androgen/anabolic steroid (AAS) and progestogen medication which is under development as a potential birth control pill for men. It is taken by mouth, but can also be given by injection into muscle.

<span class="mw-page-title-main">11β-Methyl-19-nortestosterone</span> Chemical compound

11β-Methyl-19-nortestosterone (11β-MNT) is a synthetic and orally active anabolic–androgenic steroid (AAS) and a derivative of nandrolone (19-nortestosterone) which was developed by the Contraceptive Development Branch (CDB) of the National Institute of Child Health and Human Development (NICHD) and has not been marketed at this time.

<span class="mw-page-title-main">5α-Dihydronorethisterone</span> Chemical compound

5α-Dihydronorethisterone is a major active metabolite of norethisterone (norethindrone). Norethisterone is a progestin with additional weak androgenic and estrogenic activity. 5α-DHNET is formed from norethisterone by 5α-reductase in the liver and other tissues.

<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.

References

  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.
  2. 1 2 3 4 5 6 J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 885–. ISBN   978-1-4757-2085-3.
  3. 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 William Llewellyn (2011). Anabolics. Molecular Nutrition Llc. pp. 575–583. ISBN   978-0-9828280-1-4.
  4. 1 2 3 4 5 6 7 "List of Androgens and anabolic steroids".
  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. 1 2 3 Charles D. Kochakian (6 December 2012). Anabolic-Androgenic Steroids. Springer Science & Business Media. pp. 380–. ISBN   978-3-642-66353-6.
  7. 1 2 3 Camille Georges Wermuth (2 May 2011). The Practice of Medicinal Chemistry. Academic Press. pp. 34–. ISBN   978-0-08-056877-5.
  8. 1 2 3 James Edward Wright (1994). Altered States: The Use and Abuse of Anabolic Steroids. Masters Press. p. 33. ISBN   978-1-57028-013-9.
  9. 1 2 3 4 Walter Sneader (23 June 2005). Drug Discovery: A History. John Wiley & Sons. pp. 206–. ISBN   978-0-471-89979-2.
  10. ↑ Daniel Lednicer (20 June 2011). Steroid Chemistry at a Glance. John Wiley & Sons. pp. 67–. ISBN   978-1-119-95729-4.
  11. 1 2 Bergink EW, Geelen JA, Turpijn EW (1985). "Metabolism and receptor binding of nandrolone and testosterone under in vitro and in vivo conditions". Acta Endocrinol Suppl (Copenh). 271 (3_Suppla): 31–7. doi:10.1530/acta.0.109S0031. PMID   3865479.
  12. ↑ Boschann HW (July 1958). "Observations of the role of progestational agents in human gynecologic disorders and pregnancy complications". Ann. N. Y. Acad. Sci. 71 (5): 727–52. Bibcode:1958NYASA..71..727B. doi:10.1111/j.1749-6632.1958.tb46803.x. PMID   13583829.
  13. 1 2 Die Gestagene. Springer-Verlag. 27 November 2013. pp. 13, 282–283. ISBN   978-3-642-99941-3.
  14. ↑ United States. Patent Office (1957). Official Gazette of the United States Patent Office. U.S. Patent Office.
  15. ↑ "IBM Watson Health Products".
  16. ↑ Schearer SB, Alvarez-Sanchez F, Anselmo J, Brenner P, Coutinho E, Latham-Faundes A, et al. (1978). "Hormonal Contraception for Men". International Journal of Andrology. 1 (s2b): 680–712. doi: 10.1111/j.1365-2605.1978.tb00517.x . ISSN   0105-6263.
  17. ↑ Neumann F, Diallo FA, Hasan SH, Schenck B, Traore I (1976). "The influence of pharmaceutical compounds on male fertility". Andrologia. 8 (3): 203–35. doi: 10.1111/j.1439-0272.1976.tb02137.x . PMID   793446. S2CID   24859886.
  18. ↑ Brenner PF, Bernstein GS, Roy S, Jecht EW, Mishell DR (February 1975). "Administration of norethandrolone and testosterone as a contraceptive agent for men". Contraception. 11 (2): 193–207. doi:10.1016/0010-7824(75)90030-x. PMID   1112088.


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