From Wikipedia, the free encyclopedia
LS-1727 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
[(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 ) Formula C 21 H 29 Cl N 2 O 4 Molar mass 408.92 g·mol−1 3D model (JSmol )
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=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 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
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.
See also [ ]
References [ ]
^ 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 .
AR
Agonists
Testosterone derivatives: 4-Androstenediol
4-Dehydroepiandrosterone (4-DHEA)
4-Hydroxytestosterone
5-Androstenedione
11-Ketotestosterone
11β-Hydroxyandrostenedione
Adrenosterone (11-ketoandrostenedione, 11-oxoandrostenedione)
Androstenediol (5-androstenediol)
Androstenedione (4-androstenedione)
Atamestane
Boldenone
Boldione (1,4-androstadienedione)
Clostebol
Clostebol acetate
Clostebol caproate
Clostebol propionate
Cloxotestosterone
Cloxotestosterone acetate
Dehydroandrosterone
DHEA (androstenolone, prasterone; 5-DHEA)
DHEA enanthate (prasterone enanthate)
DHEA sulfate
Exemestane
Formestane
Plomestane
Quinbolone
Silandrone
Testosterone # (+dutasteride )
17α-Ethynyl-19-nortestosterone derivatives: Δ4 -Tibolone
Desogestrel
Etonogestrel
Etynodiol
Gestodene
Gestrinone
Levonorgestrel
Levonorgestrel esters (e.g., levonorgestrel butanoate )
Lynestrenol
Lynestrenol phenylpropionate
Norethisterone
Norethisterone esters (e.g., norethisterone acetate , norethisterone enanthate )
Norgestrel
Norgestrienone
Quingestanol
Tibolone
Mixed (SARMs )
Steroidal:
MK-0773
TFM-4AS-1
YK-11
Antagonists
Nonsteroidal: 5N -Bicalutamide
AA560
Apalutamide
Atraric acid
Bakuchiol
Bicalutamide
Bisphenols (e.g., BADGE , , bisphenol A , bisphenol F , bisphenol S )
BMS-641988
Cimetidine
Cioteronel
Cyanonilutamide
Darolutamide
DDT (via metabolite p,p’-DDE )
Dieldrin
DIMP
Endosulfan
Enzalutamide
EPI-001
EPI-7386
Fenarimol
Flutamide
Hydroxyflutamide
Inocoterone
Inocoterone acetate
Ketoconazole
Ketodarolutamide
Lavender oil
LG-120907
Linuron
Methiocarb
N -Desmethylapalutamide
N -Desmethylenzalutamide
Nilutamide
Pentomone
Phenothrin
Prochloraz
Procymidone
Proxalutamide
Ralaniten (EPI-002)
Ralaniten acetate (EPI-506)
RD-162
Rezvilutamide
RU-22930
RU-56187
RU-57073
RU-58642
RU-58841
Seviteronel
Thalidomide
Topilutamide (fluridil)
Valproic acid
Vinclozolin
GPRC6A
Agonists
Cations (incl. aluminum , calcium , gadolinium , magnesium , strontium , zinc )
Dehydroandrosterone
Dihydrotestosterone
Estradiol
L -α-Amino acids (incl. L -arginine , L -lysine , L -ornithine )
Osteocalcin
SHBG
Testosterone
See also
Receptor/signaling modulators
Androgens and antiandrogens
Estrogen receptor modulators
Progesterone receptor modulators
List of androgens/anabolic steroids
PR
Agonists
Testosterone derivatives: Progestins: 6,6-Difluoronorethisterone
6,6-Difluoronorethisterone acetate
17α-Allyl-19-nortestosterone
Allylestrenol
Altrenogest
Chloroethynylnorgestrel
Cingestol
Danazol
Desogestrel
Dienogest
Ethinylandrostenediol
Ethisterone
Ethynerone
Etonogestrel
Etynodiol
Etynodiol diacetate
Gestodene
Gestrinone
Levonorgestrel
Levonorgestrel esters (e.g., levonorgestrel butanoate )
Lynestrenol
Lynestrenol phenylpropionate
Metynodiol
Metynodiol diacetate
Norelgestromin
Norethisterone (norethindrone)
Norethisterone esters (e.g., norethisterone acetate , norethisterone enanthate )
Noretynodrel
Norgesterone
Norgestimate
Norgestrel
Norgestrienone
Norvinisterone
Oxendolone
Quingestanol
Quingestanol acetate
Tibolone
Tigestol
Tosagestin ; Anabolic–androgenic steroids: 11β-Methyl-19-nortestosterone
11β-Methyl-19-nortestosterone dodecylcarbonate
19-Nor-5-androstenediol
19-Nor-5-androstenedione
19-Nordehydroepiandrosterone
Bolandiol
Bolandiol dipropionate
Bolandione
Dimethisterone
Dienedione
Dienolone
Dimethandrolone
Dimethandrolone buciclate
Dimethandrolone dodecylcarbonate
Dimethandrolone undecanoate
Dimethyldienolone
Dimethyltrienolone
Ethyldienolone
Ethylestrenol (ethylnandrol)
Methyldienolone
Metribolone (R-1881)
Methoxydienone (methoxygonadiene)
Mibolerone
Nandrolone
Nandrolone esters (e.g., nandrolone decanoate , nandrolone phenylpropionate )
Norethandrolone
Normethandrone (methylestrenolone, normethandrolone, normethisterone)
RU-2309
Tetrahydrogestrinone
Trenbolone (trienolone)
Trenbolone esters (e.g., trenbolone acetate , trenbolone enanthate )
Trendione
Trestolone
Trestolone acetate
Spirolactone derivatives: Canrenoic acid
Canrenone
Drospirenone
Mespirenone
Potassium canrenoate
Prorenone
SC-5233 (spirolactone)
SC-8109
Spironolactone
Spirorenone
Mixed (SPRMs )
Nonsteroidal: Apigenin
Kaempferol
Naringenin
Syringic acid
Antagonists
Nonsteroidal: Darolutamide
Valproic acid
mPR (PAQR )
See also
Receptor/signaling modulators
Progestogens and antiprogestogens
Androgen receptor modulators
Estrogen receptor modulators
List of progestogens
Categories :
Abandoned drugs Androgens and anabolic steroids Antineoplastic drugs Estranes Hormonal antineoplastic drugs Nandrolone esters Nitrogen mustards Organochlorides Prodrugs Progestogens Chloroethyl compounds Nitrosocarbamates Genito-urinary system drug stubs Antineoplastic and immunomodulating drug stubs Steroid stubs Hidden categories:
Articles without EBI source Chemical pages without DrugBank identifier Articles without KEGG source Articles without UNII source Drugs missing an ATC code Drugs with no legal status Articles containing unverified chemical infoboxes All stub articles