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LS-1727

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LS-1727
Clinical data

Other names	LEO-1727; 19-Nortestosterone 17β-N-(2-chloroethyl)-N-nitrosocarbamate; Nandrolone chloroethylnitrosocarbamate
Routes of administration	Intramuscular injection
Drug class	Cytostatic antineoplastic agent; 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] N-(2-chloroethyl)-N-nitrosocarbamate
CAS Number	54025-36-4
PubChem CID	320801
ChemSpider	283976
CompTox Dashboard (EPA)	DTXSID20968855
Chemical and physical data
Formula	C₂₁H₂₉ClN₂O₄
Molar mass	408.92 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2OC(=O)N(CCCl)N=O)CCC4=CC(=O)CC[C@H]34
InChI InChI=1S/C21H29ClN2O4/c1-21-9-8-16-15-5-3-14(25)12-13(15)2-4-17(16)18(21)6-7-19(21)28-20(26)24(23-27)11-10-22/h12,15-19H,2-11H2,1H3/t15-,16+,17+,18-,19-,21-/m0/s1 Key:KTQUNVRSLAGBSY-RRFJAZBJSA-N

LS-1727 (also known as nandrolone 17β-N-(2-chloroethyl)-N-nitrosocarbamate) is a synthetic, injected anabolic–androgenic steroid (AAS) and a nitrosocarbamate esterofnandrolone (19-nortestosterone) which was developed as a cytostatic antineoplastic agent but was never marketed.^[1]^[2]^[3]^[4]

v

t

e
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.

References

[edit]

^ Reynolds RC, Tiwari A, Harwell JE, Gordon DG, Garrett BD, Gilbert KS, Schmid SM, Waud WR, Struck RF (2000). "Synthesis and evaluation of several new (2-chloroethyl)nitrosocarbamates as potential anticancer agents". J. Med. Chem. 43 (8): 1484–8. doi:10.1021/jm990417j. PMID 10780904.

^ J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 660–. ISBN 978-1-4757-2085-3.

^ Müntzing J, Kirdani RY, Williams PD, Murphy GP (1981). "Effect of LS 1727, a nitrosocarbamate of 19-nortestosterone, on the R-3327 rat prostatic adenocarcinoma". Res. Commun. Chem. Pathol. Pharmacol. 32 (2): 309–16. PMID 7244365.

^ Hartley-Asp B, Wilkinson R, Venitt S, Harrap KR (1981). "Studies on the mechanism of action of LS 1727, a nitrosocarbamate of 19-nortestosterone". Acta Pharmacol Toxicol (Copenh). 48 (2): 129–38. doi:10.1111/j.1600-0773.1981.tb01598.x. PMID 6167141.