Nandrolone cyclotate

Chemical compound
Nandrolone cyclotate
Clinical data
Other namesNandrolone ciclotate; RS-3268R; 19-Nortestosterone 17β-ciclotate
Routes of
administration
Intramuscular injection
Drug classAndrogen; 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
  • 22263-51-0
PubChem CID
  • 164526
ChemSpider
  • 32700233
UNII
  • 1MG9GW4ZH8
CompTox Dashboard (EPA)
  • DTXSID2023351 Edit this at Wikidata
Chemical and physical data
FormulaC28H38O3
Molar mass422.609 g·mol−1
3D model (JSmol)
  • Interactive image
  • 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
  • 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 (USANTooltip 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]

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Relative affinities (%) of nandrolone and related steroids
Compound PRTooltip Progesterone receptor ARTooltip Androgen receptor ERTooltip Estrogen receptor GRTooltip Glucocorticoid receptor MRTooltip Mineralocorticoid receptor SHBGTooltip Sex hormone-binding globulin CBGTooltip Corticosteroid-binding globulin
Nandrolone 20 154–155 <0.1 0.5 1.6 1–16 0.1
Testosterone 1.0–1.2 100 <0.1 0.17 0.9 19–82 3–8
Estradiol 2.6 7.9 100 0.6 0.13 8.7–12 <0.1
Notes: Values are percentages (%). Reference ligands (100%) were progesterone for the PRTooltip progesterone receptor, testosterone for the ARTooltip androgen receptor, estradiol for the ERTooltip estrogen receptor, dexamethasone for the GRTooltip glucocorticoid receptor, aldosterone for the MRTooltip mineralocorticoid receptor, dihydrotestosterone for SHBGTooltip sex hormone-binding globulin, and cortisol for CBGTooltip corticosteroid-binding globulin. Sources: See template.

See also

References

  1. ^ a b 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. ^ a b 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. ^ a b 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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ARTooltip Androgen receptor
Agonists
SARMsTooltip Selective androgen receptor modulator
Antagonists
GPRC6A
Agonists
See also
Receptor/signaling modulators
Androgens and antiandrogens
Estrogen receptor modulators
Progesterone receptor modulators
List of androgens and anabolic steroids
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PRTooltip Progesterone receptor
Agonists
Mixed
(SPRMsTooltip Selective progesterone receptor modulators)
Antagonists
mPRTooltip Membrane progesterone receptor
(PAQRTooltip Progestin and adipoQ receptor)
Agonists
Antagonists
See also
Receptor/signaling modulators
Progestogens and antiprogestogens
Androgen receptor modulators
Estrogen receptor modulators
List of progestogens
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