Clinical data | |
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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 |
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CompTox Dashboard (EPA) | |
Chemical and physical data | |
Formula | C21H29ClN2O4 |
Molar mass | 408.92 g·mol−1 |
3D model (JSmol) | |
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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. [1] [2] [3] [4]
Compound | PR Tooltip Progesterone receptor | AR Tooltip Androgen receptor | ER Tooltip Estrogen receptor | GR Tooltip Glucocorticoid receptor | MR Tooltip Mineralocorticoid receptor | SHBG Tooltip Sex hormone-binding globulin | CBG Tooltip Corticosteroid-binding globulin |
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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 Tooltip progesterone receptor, testosterone for the AR Tooltip androgen receptor, estradiol for the ER Tooltip estrogen receptor, dexamethasone for the GR Tooltip glucocorticoid receptor, aldosterone for the MR Tooltip mineralocorticoid receptor, dihydrotestosterone for SHBG Tooltip sex hormone-binding globulin, and cortisol for CBG Tooltip corticosteroid-binding globulin. Sources: See template. |
Nandrolone, also known as 19-nortestosterone, is an endogenous androgen which exists in the male body at a ratio of 1:50 compared to testosterone. It is also an anabolic steroid (AAS) which is medically used in the form of esters such as nandrolone decanoate and nandrolone phenylpropionate. Nandrolone esters are used in the treatment of anemias, cachexia, osteoporosis, breast cancer, and for other indications. They are not used by mouth and instead are given by injection into muscle or fat.
Atrimustine, also known as bestrabucil or busramustine, is a cytostatic antineoplastic agent which was under development in Japan by Kureha Chemicals for the treatment of breast cancer and non-Hodgkin's lymphoma as well as for the prevention of graft-versus-host disease in bone marrow transplant recipients. It is the benzoate ester of an ester conjugate of estradiol and chlorambucil, which results in targeted/site-directed cytostatic activity toward estrogen receptor-positive tissues such as breast and bone. It reached preregistration for the treatment of cancer but was ultimately discontinued. Estrogenicic side effects of atrimustine in clinical trials included vaginal bleeding and gynecomastia. The drug was first patented in 1980.
Alestramustine, also known as estradiol 3-(bis carbamate) 17β-(L-alaninate), is a cytostatic antineoplastic agent which was never marketed. It is the L-alanine ester of estramustine, which is a combination of the nitrogen mustard normustine coupled via a carbamate to the estrogen estradiol. Alestramustine acts as a prodrug to estramustine, and also forms estradiol as a byproduct. The drug, via its active metabolites, binds to microtubule-associated proteins and β-tubulin and interferes with microtubule function, thereby inhibiting cell division. Due to its estrogen moiety, alestramustine is selectively concentrated in estrogen receptor-positive cells such as prostate and breast.
Nandrolone cyclotate, 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. It is an androgen ester – specifically, the C17β ciclotate (4-methylbicyclo[2.2.2]oct-2-ene-1-carboxylate) ester of nandrolone. 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.
Nandrolone hexyloxyphenylpropionate, also known as 19-nortestosterone 17β-(3- phenyl)propionate, is a synthetic androgen and anabolic steroid and a nandrolone ester that is marketed in France, Denmark, Austria, Luxembourg, and Turkey. It has been studied as a potential long-acting injectable male contraceptive, though it has not been marketed for this indication. Approximately 70% of men became azoospermic, while the remaining men all became oligospermic. NHPP has a mean residence time in the body of 29.1 days and an elimination half-life in the body of 20.1 days.
Nandrolone phenylpropionate (NPP), or nandrolone phenpropionate, sold under the brand name Durabolin among others, is an androgen and anabolic steroid (AAS) medication which has been used primarily in the treatment of breast cancer and osteoporosis in women. It is given by injection into muscle once every week. Although it was widely used in the past, the drug has mostly been discontinued and hence is now mostly no longer available.
Bolmantalate, also known as 19-nortestosterone 17β-adamantoate, is an androgen and anabolic steroid and a nandrolone ester which was synthesized and developed by Eli Lilly in 1865 but was never marketed.
ICI-85966, also known as diethylstilbestrol (DES) bis(di carbamate), is a synthetic, nonsteroidal estrogen and cytostatic antineoplastic agent of the stilbestrol group and a nitrogen mustard ester of diethylstilbestrol (DES) which was developed for the treatment of breast cancer and prostate cancer but was never marketed.
Estromustine, also known as estrone 17β-3-N-bis(2-chloroethyl)carbamate or estrone–cytostatic complex, is a major active metabolite of the cytostatic antineoplastic agent and estrogen estramustine phosphate, a medication used in the treatment of prostate cancer.
Phenestrol, or fenestrol, also known as hexestrol bis[4-[bis(2-chloroethyl)amino]phenylacetate, is a synthetic, nonsteroidal estrogen and cytostatic antineoplastic agent and a chlorphenacyl nitrogen mustard ester of hexestrol which was developed in the early 1960s for the treatment of hormone-dependent tumors but was never marketed.
Estradiol mustard, also known as chlorphenacyl estradiol diester, as well as estradiol 3,17β-bis(4- phenyl)acetate, is a synthetic, steroidal estrogen and cytostatic antineoplastic agent and a chlorphenacyl nitrogen mustard-coupled estrogen ester that was never marketed. It is selectively distributed into estrogen receptor (ER)-positive tissues such as ER-expressing tumors like those seen in breast and prostate cancers. For this reason, estradiol mustard and other cytostatic-linked estrogens like estramustine phosphate have reduced toxicity relative to non-linked nitrogen mustard cytostatic antineoplastic agents. However, they may stimulate breast tumor growth due to their inherent estrogenic activity and are said to be devoid of major therapeutic efficacy in breast cancer, although estramustine phosphate has been approved for and is used in the treatment of prostate cancer.
Nandrolone acetate, also known as 19-nortestosterone 17β-acetate or as estr-4-en-17β-ol-3-one 17β-acetate, is a synthetic, injected anabolic–androgenic steroid (AAS) and a derivative of 19-nortestosterone (nandrolone) that was never marketed. It is an androgen ester – specifically, the C17β acetate ester of nandrolone.
Nandrolone formate, also known as nandrolone carboxylate or nandrolone methanoate, as well as 19-nortestosterone 17β-formate or estr-4-en-17β-ol-3-one 17β-formate, is a synthetic, injected anabolic–androgenic steroid (AAS) and a derivative of 19-nortestosterone (nandrolone) that was never marketed. It is an androgen ester – specifically, the C17β formate ester of nandrolone.
Cytestrol acetate is a steroidal antiestrogen and a cytostatic antineoplastic agent which was developed for the treatment of breast cancer but was never marketed.
Testifenon, also known as testiphenon, testiphenone, chlorphenacyl dihydrotestosterone ester, or dihydrotestosterone 17β-(4- phenyl)acetate, is a synthetic anabolic–androgenic steroid (AAS) and a cytostatic antineoplastic agent that was never marketed. It is an androgen ester – specifically, a chlorphenacyl nitrogen mustard ester of dihydrotestosterone (DHT) – and acts as a prodrug of these two components in the body. The drug was developed in Russia as a tissue-selective cytostatic drug for the treatment of various cancers occurring in androgen receptor-expressing tissues that would have reduced side effects and toxicity relative to other chemotherapy drugs.
Sturamustine, also known as dehydroepiandrosterone (DHEA) 17β-N-(2-chloroethyl)-N-nitrosourea, is a synthetic androstane steroid and a C17β nitrosourea conjugate of dehydroepiandrosterone (DHEA) which was developed as a cytostatic antineoplastic agent for the treatment of hormone-dependent tumors but was never marketed. It was synthesized in 1982.
Nandrolone nonanoate, also known as nandrolone pelargonate or as 19-nortestosterone 17β-nonanoate, is an androgen and anabolic steroid and an androgen ester—specifically, the C17β nonanoate (pelargonate) ester of nandrolone (19-nortestosterone)—which was studied but was never marketed.