Nandrolone cyclotate

Nandrolone cyclotate (USAN) (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	AR	ER	GR	MR	SHBG	CBG
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 PR, testosterone for the AR, estradiol for the ER, dexamethasone for the GR, aldosterone for the MR, dihydrotestosterone for SHBG, and cortisol for CBG. Sources: See template.

Nandrolone cyclotate

Clinical data
Other names	Nandrolone ciclotate; RS-3268R; 19-Nortestosterone 17β-ciclotate
Routes of administration	Intramuscular injection
Drug class	Androgen; Anabolic steroid; Androgen ester; Progestogen
Identifiers
IUPAC name [(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
Chemical and physical data
Formula	C28H38O3
Molar mass	422.609 g·mol^−1
3D model (JSmol)	Interactive image
SMILES 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

See also

• List of androgen esters § Nandrolone esters

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. 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.