LS-1727

{{Short description|Chemical compound}}

{{Drugbox

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| 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

| image = LS-1727.svg

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| routes_of_administration = Intramuscular injection

| class = Cytostatic antineoplastic agent; Androgen; Anabolic steroid; Androgen ester; Progestogen

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| CAS_number = 54025-36-4

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| PubChem = 320801

| ChemSpiderID = 283976

| synonyms = LEO-1727; 19-Nortestosterone 17β-N-(2-chloroethyl)-N-nitrosocarbamate; Nandrolone chloroethylnitrosocarbamate

| C=21| H=29 | N=2 | O=4 | Cl=1

| 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

| StdInChI = 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

| StdInChIKey = KTQUNVRSLAGBSY-RRFJAZBJSA-N

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LS-1727 (also known as nandrolone 17β-N-(2-chloroethyl)-N-nitrosocarbamate) is a synthetic, injected anabolic–androgenic steroid (AAS) and a nitrosocarbamate ester of nandrolone (19-nortestosterone) which was developed as a cytostatic antineoplastic agent but was never marketed.{{cite journal |vauthors=Reynolds RC, Tiwari A, Harwell JE, Gordon DG, Garrett BD, Gilbert KS, Schmid SM, Waud WR, Struck RF |title=Synthesis and evaluation of several new (2-chloroethyl)nitrosocarbamates as potential anticancer agents |journal=J. Med. Chem. |volume=43 |issue=8 |pages=1484–8 |year=2000 |pmid=10780904 |doi= 10.1021/jm990417j}}{{cite book|author=J. Elks|title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA660|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=660–}}{{cite journal |vauthors=Müntzing J, Kirdani RY, Williams PD, Murphy GP |title=Effect of LS 1727, a nitrosocarbamate of 19-nortestosterone, on the R-3327 rat prostatic adenocarcinoma |journal=Res. Commun. Chem. Pathol. Pharmacol. |volume=32 |issue=2 |pages=309–16 |year=1981 |pmid=7244365 }}{{cite journal |vauthors=Hartley-Asp B, Wilkinson R, Venitt S, Harrap KR |title=Studies on the mechanism of action of LS 1727, a nitrosocarbamate of 19-nortestosterone |journal=Acta Pharmacol Toxicol (Copenh) |volume=48 |issue=2 |pages=129–38 |year=1981 |pmid=6167141 |doi= 10.1111/j.1600-0773.1981.tb01598.x}}

{{Relative affinities of nandrolone and related steroids}}