LS-1727

LS-1727
Clinical data
Other namesLEO-1727; 19-Nortestosterone 17β-N-(2-chloroethyl)-N-nitrosocarbamate; Nandrolone chloroethylnitrosocarbamate
Routes of
administration
Intramuscular injection
Drug classCytostatic 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
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC21H29ClN2O4
Molar mass408.92 g·mol−1
3D model (JSmol)
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 ester of nandrolone (19-nortestosterone) which was developed as a cytostatic antineoplastic agent but was never marketed.[1][2][3][4]

Relative affinities (%) of nandrolone and related steroids
CompoundPRARERGRMRSHBGCBG
Nandrolone20154–155<0.10.51.61–160.1
Testosterone1.0–1.2100<0.10.170.919–823–8
Estradiol2.67.91000.60.138.7–12<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.

See also

References

  1. 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.
  2. 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.
  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.
  4. 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.
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