Compound: NORETHANDROLONE
SMILES: O=C1C=C2[C@@H]([C@@H]3[C@H]([C@H]4[C@]([C@](O)(CC)CC4)(C)CC3)CC2)CC1
InChIKey: ZDHCJEIGTNNEMY-XGXHKTLJSA-N
Synonyms: NORETHANDROLONE, Pronabol, Nilevar, Solevar, 52-78-8, Noretandrolona, Noretandrolone, Norethandrolonum, NSC-70581, P7W01638W6, DTXSID0023379, Ethylestrenolone, RefChem:166600, DTXCID603379, A14AA09, (1S,2R,10R,11S,14S,15S)-14-ethyl-14-hydroxy-15-methyltetracyclo(8.7.0.0^(2,7).0^(11,15))heptadec-6-en-5-one, 200-153-5, Ethylnortestosterone, 17-Ethyl-19-nortestosterone, 17-ENT, Nileva, 19-Norethyltestosterone, SC 5914, 19-Nortestosterone, 17-ethyl-, NSC 70581, CB 8022, U 6817, (8R,9S,10R,13S,14S,17S)-17-ethyl-17-hydroxy-13-methyl-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one, 8022 C. B., Norethandrolone (INN), 17-Hydroxy-19-norpregn-4-en-3-one, Ethylnortestosteron, NORETHANDROLONE [INN], 17.alpha.-Ethylnortestosterone, Noretandrolone [DCIT], (17-alpha)-17-Hydroxy-19-norpregn-4-en-3-one, 17-alpha-Nortestosterone, 17.alpha.-Ethyl-19-nortestosterone, 17alpha-Ethyl-19-nortestosterone, 17alpha-Ethylnortestosterone, Norethandrolone (1mg/ml in Acetonitrile), Noretandrolona [INN-Spanish], Norethandrolonum [INN-Latin], CCRIS 9066, 19-Norpregn-4-en-3-one, (17.alpha.)-, Estr-4-en-3-one, 17.alpha.-ethyl-17-hydroxy-, 19-Nor-17-alpha-ethyltestosterone, 17.alpha.-Ethyl-17.beta.-hydroxyestr-4-en-3-one, EINECS 200-153-5, 19-Nor-17.alpha.-pregn-4-en-3-one, 17-hydroxy-, Norethandrolone (1.0 mg/mL in 1,2-Dimethoxyethane), 17-alpha-Ethyl-17-hydroxynorandrostenone, Norethandrolone [INN:BAN:NF], UNII-P7W01638W6, Estr-4-en-3-one, 17alpha-ethyl-17-hydroxy-, 17-alpha-Ethyl-17-hydroxy-4-norandrosten-3-one, 17-Hydroxy-19-nor-17-alpha-pregn-4-en-3-one, NSC-9893, 17-alpha-Ethyl-17-hydroxy-19-norandrost-4-en-3-one, 19-Norpregn-4-en-3-one, 17-hydroxy-, (17alpha)-, (17beta)-17-ethyl-17-hydroxyestr-4-en-3-one, 8022 C.B., 17alpha-Ethyl-17beta-hydroxyestr-4-en-3-one, NORETHANDROLONE [MI], 19-Nor-17alpha-pregn-4-en-3-one, 17-hydroxy-, SCHEMBL147638, 19-Nor-17-alpha-pregn-4-en-3-one, 17-hydroxy-, NORETHANDROLONE [MART.], 19-Norpregn-4-en-3-one, 17-hydroxy-, (17-alpha)-, CHEMBL1697845, NORETHANDROLONE [WHO-DD], NSC9893, CHEBI:135282, NSC70581, DB12787, (8R,9S,10R,13S,14S,17S)-17-ethyl-17-hydroxy-13-methyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthren-3-one, Norethandrolone (1 mg/ml in Acetonitrile), Norethandrolone 1.0 mg/ml in Acetonitrile, 17alpha-Ethyl-17-hydroxyestr-4-en-3-one, NS00000172, 17-Hydroxy-17alpha-19-norpregn-4-en-3-one, D07127, Q7050955
Theoretical properties:
molecular_formula: C20H30O2
molecular_weight: 302.5 g/mol
exact_mass: 302.224580195 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 2
rotatable_bond_count: 1
heavy_atom_count: 22
topological_polar_surface_area: 37.3 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Norethandrolone is a corticosteroid hormone.
chembl: NORETHANDROLONE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 3.0.
wikipedia: Norethandrolone, sold under the brand names Nilevar and Pronabol among others, is an androgen and anabolic steroid (AAS) medication which has been used to promote muscle growth and to treat severe burns, physical trauma, and aplastic anemia but has mostly been discontinued. It is still available for use in France however. It is taken by mouth.
Side effects of norethandrolone include symptoms of masculinization like acne, increased hair growth, voice changes, and increased sexual desire. It can also cause estrogenic effects like fluid retention, breast tenderness, and breast enlargement in men and liver damage. The drug is a synthetic androgen and anabolic steroid and hence is an agonist of the androgen receptor (AR), the biological target of androgens like testosterone and dihydrotestosterone (DHT). It has strong anabolic effects relative to its androgenic effects. The drug also has strong progestogenic effects.
Norethandrolone was discovered in 1953 and was introduced for medical use in 1956. It was the first AAS with a favorable separation of anabolic and androgenic effect to be marketed. The drug was mostly withdrawn in the 1980s due to concerns of liver damage. In addition to its medical use, norethandrolone has been used to improve physique and performance. The drug is a controlled substance in many countries and so non-medical use is generally illicit.