Nandrolone undecanoate

Last updated
Nandrolone undecanoate
Nandrolone undecylate.svg
Clinical data
Trade names Dynabolon, Dynabolin, Psychobolan
Other namesNU; Nandrolone undecylate; 19-Nortestosterone 17β-undecanoate
Routes of
administration
Intramuscular injection
Drug class Androgen; Anabolic steroid; Androgen ester; Progestogen
Identifiers
  • [(8R,9S,10R,13S,14S,17S)-13-methyl-3-oxo-2,6,7,8,9,10,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl] undecanoate
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard 100.011.573 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C29H46O3
Molar mass 442.684 g·mol−1
3D model (JSmol)
  • CCCCCCCCCCC(=O)O[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@H]34)C
  • InChI=1S/C29H46O3/c1-3-4-5-6-7-8-9-10-11-28(31)32-27-17-16-26-25-14-12-21-20-22(30)13-15-23(21)24(25)18-19-29(26,27)2/h20,23-27H,3-19H2,1-2H3/t23-,24+,25+,26-,27-,29-/m0/s1
  • Key:GRAAWEGTURLYKP-MVTMSODMSA-N

Nandrolone undecanoate (NU), also known as nandrolone undecylate, and sold under the brand names Dynabolon, Dynabolin, and Psychobolan, is an androgen and anabolic steroid medication and a nandrolone ester. It was developed in the 1960s, and was previously marketed in France, Germany, Italy, and Monaco, but has since been discontinued and is now no longer known to be available. [1] [2] [3] [4] The pharmacokinetics of nandrolone undecanoate alone (Dynabolon) and in combination with other steroid esters (Trophobolene) have been studied and compared. [5]

Relative affinities (%) of nandrolone and related steroids
Compound PR Tooltip Progesterone receptor AR Tooltip Androgen receptor ER Tooltip Estrogen receptor GR Tooltip Glucocorticoid receptor MR Tooltip Mineralocorticoid receptor SHBG Tooltip Sex hormone-binding globulin CBG Tooltip Corticosteroid-binding globulin
Nandrolone 20154–155<0.10.51.61–160.1
Testosterone 1.0–1.2100<0.10.170.919–823–8
Estradiol 2.67.91000.60.138.7–12<0.1
Notes: Values are percentages (%). Reference ligands (100%) were progesterone for the PR Tooltip progesterone receptor, testosterone for the AR Tooltip androgen receptor, estradiol for the ER Tooltip estrogen receptor, dexamethasone for the GR Tooltip glucocorticoid receptor, aldosterone for the MR Tooltip mineralocorticoid receptor, dihydrotestosterone for SHBG Tooltip sex hormone-binding globulin, and cortisol for CBG Tooltip corticosteroid-binding globulin. Sources: See template.

See also

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">Trenbolone</span> Anabolic steroid

Trenbolone is an androgen and anabolic steroid (AAS) of the nandrolone group which itself was never marketed. Trenbolone ester prodrugs, including trenbolone acetate and trenbolone hexahydrobenzylcarbonate, are or have been marketed for veterinary and clinical use. Trenbolone acetate is used in veterinary medicine in livestock to increase muscle growth and appetite, while trenbolone hexahydrobenzylcarbonate was formerly used clinically in humans but is now no longer marketed. In addition, although it is not approved for clinical or veterinary use, trenbolone enanthate is sometimes sold on the black market under the nickname Trenabol.

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

Trenbolone acetate, sold under brand names such as Finajet and Finaplix among others, is an androgen and anabolic steroid (AAS) medication which is used in veterinary medicine, specifically to increase the profitability of livestock by promoting muscle growth in cattle. It is given by injection into muscle.

<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">Hydroxyprogesterone heptanoate</span> Chemical compound

Hydroxyprogesterone heptanoate (OHPH), also known as hydroxyprogesterone enanthate (OHPE) and sold under the brand names H.O.P., Lutogil A.P., and Lutogyl A.P. among others, is a progestin medication used for progestogenic indications. It has been formulated both alone and in together with estrogens, androgens/anabolic steroids, and other progestogens in several combination preparations. OHPH is given by injection into muscle at regular intervals.

<span class="mw-page-title-main">Androgen ester</span> Class of chemical compounds

An androgen or anabolic steroid ester is an ester of an androgen/anabolic steroid (AAS) such as the natural testosterone or dihydrotestosterone (DHT) or the synthetic nandrolone (19-nortestosterone). Esterification renders AAS into metabolism-resistant prohormones of themselves, improving oral bioavailability, increasing lipophilicity, and extending the elimination half-life. In addition, with intramuscular injection, AAS esters are absorbed more slowly into the body, further improving the elimination half-life. Aside from differences in pharmacokinetics, these esters essentially have the same effects as the parent drugs. They are used in androgen replacement therapy (ART), among other indications. Examples of androgen esters include testosterone esters such as testosterone cypionate, testosterone enanthate, testosterone propionate, and testosterone undecanoate and nandrolone esters such as nandrolone decanoate and nandrolone phenylpropionate.

<span class="mw-page-title-main">Nandrolone caproate</span> Synthetic androgen and anabolic steroid

Nandrolone caproate, or nandrolone hexanoate, also known as 19-nortestosterone 17β-hexanoate, is a synthetic androgen and anabolic steroid and a nandrolone ester.

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

Nandrolone cypionate, or nandrolone cipionate, also known as 19-nortestosterone 17β-cyclopentanepropionate, is a synthetic androgen and anabolic steroid and a nandrolone ester.

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

Nandrolone furylpropionate (NFP), also known as 19-nortestosterone 17β-(2-furanyl)propanoate, is a synthetic androgen and anabolic steroid and a nandrolone ester. It was developed and marketed by Mochida Pharmaceutical in Japan in the 1960s.

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

Nandrolone hexyloxyphenylpropionate, also known as 19-nortestosterone 17β-(3- phenyl)propionate, is a synthetic androgen and anabolic steroid and a nandrolone ester that is marketed in France, Denmark, Austria, Luxembourg, and Turkey. It has been studied as a potential long-acting injectable male contraceptive, though it has not been marketed for this indication. Approximately 70% of men became azoospermic, while the remaining men all became oligospermic. NHPP has a mean residence time in the body of 29.1 days and an elimination half-life in the body of 20.1 days.

<span class="mw-page-title-main">Nandrolone hydrogen succinate</span> Chemical compound

Nandrolone hydrogen succinate, or nandrolone hemisuccinate, also known as 19-nortestosterone 17β-(3-carboxy)propionate, is a synthetic androgen and anabolic steroid and a nandrolone ester that is or has been marketed in Italy.

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

Nandrolone laurate, or nandrolone dodecanoate, also known as 19-nortestosterone 17β-laurate, is a synthetic androgen and anabolic steroid and a nandrolone ester. It is used in veterinary medicine in Austria, France, the Netherlands, and Switzerland.

<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">Nandrolone propionate</span> Chemical compound

Nandrolone propionate, or nandrolone propanoate, also known as 19-nortestosterone 17β-propionate, is a synthetic androgen and anabolic steroid and nandrolone ester that is or has been marketed in Spain.

<span class="mw-page-title-main">Nandrolone sulfate</span> Synthetic androgen and anabolic steroid

Nandrolone sulfate, also known as 19-nortestosterone 17β-sulfate and used medically as the sodium salt nandrolone sodium sulfate, is a synthetic androgen and anabolic steroid and a nandrolone ester which is or has been used as an ophthalmic drug in the form of eye drops in Spain, Denmark, Switzerland, France, Portugal, and Belgium.

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

Bolmantalate, also known as 19-nortestosterone 17β-adamantoate, is an androgen and anabolic steroid and a nandrolone ester which was synthesized and developed by Eli Lilly in 1865 but was never marketed.

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

Trenbolone undecanoate, or trenbolone undecylate, is a synthetic and injected anabolic–androgenic steroid (AAS) and a derivative of nandrolone (19-nortestosterone) which was never marketed. It is the C17β undecanoate (undecylate) ester and a long-acting prodrug of trenbolone. The drug was described by Roussel Uclaf in 1967 and was the first long-lasting ester of trenbolone to be developed. Subsequently, trenbolone hexahydrobenzylcarbonate, a roughly equivalent compound, was developed and introduced for use in humans in 1980, though it was discontinued in 1997. Trenbolone enanthate is another long-lasting ester of trenbolone. Similarly to trenbolone undecanoate, it was never marketed, but it has been sold on the black market as a designer steroid for bodybuilders and athletes.

Estrapronicate/hydroxyprogesterone heptanoate/nandrolone undecanoate (EPC/OHPH/NU), tentative brand name Trophobolene or Trophoboline, is an injectable combination medication of estrapronicate, an estrogen, hydroxyprogesterone heptanoate (OHPH), a progestogen, and nandrolone undecanoate (NU), an androgen/anabolic steroid, which was never marketed. It contained 1.3 mg EPC, 80 mg OHPH, and 50 mg NU in oil solution and was administered by intramuscular injection. The medication was developed by Théramex in the mid-to-late 1960s. It was studied for use for a variety of indications, including treatment of coronary insufficiency, growth deficiency, and osteoporosis, as well as hormonal disorders in gonadotropin deficiency.

References

  1. Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 660–. ISBN   978-1-4757-2085-3.
  2. Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 716–717. ISBN   978-3-88763-075-1.
  3. Morton IK, Hall JM (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. ISBN   978-94-011-4439-1.
  4. Llewellyn W (2011). Anabolics. Molecular Nutrition Llc. pp. 477–. ISBN   978-0-9828280-1-4.
  5. Courtot D, Forichon J, Paris J (1983). "Pharmacokinetics of 19-Nortestosterone in Man". Chromatography in Biochemistry, Medicine, and Environmental Research, 1: Proceedings of the 1st International Symposium on Chromatography in Biochemistry, Medicine and Environmental Research, Venice, June 16–17, 1981. Analytical Chemistry Symposia Series. Vol. 13. Amsterdam/Oxford/New York: Elsevier. pp. 95–110.