Nandrolone cyclotate

Last updated
Nandrolone cyclotate
Nandrolone cyclotate.svg
Clinical data
Other namesNandrolone ciclotate; RS-3268R; 19-Nortestosterone 17β-ciclotate
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] 1-methylbicyclo[2.2.2]oct-2-ene-4-carboxylate
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
Formula C28H38O3
Molar mass 422.609 g·mol−1
3D model (JSmol)
  • C[C@@]12C=C[C@@](CC1)(CC2)C(=O)O[C@@H]3[C@@]4([C@H]([C@H]5[C@@H]([C@@H]6C(=CC(=O)CC6)CC5)CC4)CC3)C
  • InChI=1S/C28H38O3/c1-26-11-14-28(15-12-26,16-13-26)25(30)31-24-8-7-23-22-5-3-18-17-19(29)4-6-20(18)21(22)9-10-27(23,24)2/h11,14,17,20-24H,3-10,12-13,15-16H2,1-2H3/t20-,21+,22+,23-,24-,26-,27-,28-/m0/s1
  • Key:REACBNMPQDINOF-ZDMPKJLCSA-N

Nandrolone cyclotate (USAN Tooltip United States Adopted Name) (developmental code name RS-3268R), or nandrolone ciclotate, also known as 19-nortestosterone 17β-ciclotate, is a synthetic and injected anabolic–androgenic steroid (AAS) of the nandrolone (19-nortestosterone) group which was never marketed. [1] [2] [3] [4] It is an androgen ester – specifically, the C17β ciclotate (4-methylbicyclo[2.2.2]oct-2-ene-1-carboxylate) ester of nandrolone. [1] [2] Nandrolone cyclotate has potent and prolonged activity as an AAS when administered by intramuscular injection and is reported to have a similar duration of action to that of nandrolone decanoate via this route. [4]

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

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

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

Trestolone acetate is a synthetic and injected anabolic–androgenic steroid (AAS) and a derivative of nandrolone (19-nortestosterone) which was never marketed. It is an androgen ester – specifically, the C17 acetate ester of trestolone. The medication was first described in 1963.

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

Oxabolone is a synthetic anabolic-androgenic steroid (AAS) of the nandrolone (19-nortestosterone) group which was never marketed. It can be formulated as the cipionate ester prodrug oxabolone cipionate, which, in contrast, has been marketed for medical use.

<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

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<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

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

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. The pharmacokinetics of nandrolone undecanoate alone (Dynabolon) and in combination with other steroid esters (Trophobolene) have been studied and compared.

<span class="mw-page-title-main">LS-1727</span> Chemical compound

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

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<span class="mw-page-title-main">Norclostebol acetate</span> Synthetic, injectable anabolic-androgenic steroid

Norclostebol acetate, or norchlorotestosterone acetate (NClTA), also known as 4-chloro-19-nortestosterone 17β-acetate or as 4-chloroestr-4-en-17β-ol-3-one, is a synthetic, injectable anabolic-androgenic steroid (AAS) and derivative of 19-nortestosterone (nandrolone). It is an androgen ester – specifically, the C17β acetate ester of norclostebol (4-chloro-19-nortestosterone).

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

Ciclotic acid, or cyclotic acid, systematic name 4-methylbicyclo[2.2.2]oct-2-ene-1-carboxylic acid, is a bicyclic carboxylic acid. The salts and esters of ciclotic acid are known as ciclotates (cyclotates). An example is nandrolone cyclotate, a long-acting ester prodrug of the anabolic-androgenic steroid nandrolone.

References

  1. 1 2 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. 1 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. 1 2 van Wayjen RG, van den Ende A (May 1973). "Clinical-pharmacological investigation of the nitrogen-retaining effect of nandrolone cyclotate". Acta Endocrinologica. 73 (1): 171–8. doi:10.1530/acta.0.0730171. PMID   4740146.
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