Chemical compound
Pharmaceutical compound
Norethandrolone Clinical data Trade names Nilevar, Pronabol Other names Noretandrolone; CB-8022; 3-Ketoethylestrenol; Ethylestrenolone; 17α-Ethyl-19-nortestosterone; 17α-Ethylestr-4-en-17β-ol-3-one; 17α-Ethyl-19-norandrost-4-en-17β-ol-3-one; Ethylnandrolone; Ethylnortestosterone AHFS /Drugs.com International Drug Names Routes of By mouth Drug class Androgen ;Anabolic steroid ;Progestin ;Progestogen ATC code Legal status Legal status Identifiers (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
CAS Number PubChem CID ChemSpider UNII KEGG CompTox Dashboard (EPA) ECHA InfoCard 100.000.140 Chemical and physical data Formula C 20 H 30 O 2 Molar mass −1 3D model (JSmol ) InChI=1S/C20H30O2/c1-3-20(22)11-9-18-17-6-4-13-12-14(21)5-7-15(13)16(17)8-10-19(18,20)2/h12,15-18,22H,3-11H2,1-2H3/t15-,16+,17+,18-,19-,20-/m0/s1
Y Key:ZDHCJEIGTNNEMY-XGXHKTLJSA-N
Y (verify)
Norethandrolone , sold under the brand namesNilevar andPronabol among others, is anandrogen andanabolic steroid (AAS) medication which has been used to promotemuscle growth and to treat severeburns ,physical trauma , andaplastic anemia but has mostly been discontinued.[ 2] [ 3] [ 4] France however.[ 3] [ 4] by mouth .[ 3]
Side effects of norethandrolone includesymptoms ofmasculinization likeacne ,increased hair growth ,voice changes , and increasedsexual desire .[ 3] estrogenic effects likefluid retention ,breast tenderness , andbreast enlargement in men andliver damage .[ 3] synthetic androgen and anabolic steroid and hence is anagonist of theandrogen receptor (AR), thebiological target of androgens liketestosterone anddihydrotestosterone (DHT).[ 3] [ 5] anabolic effects relative to itsandrogenic effects.[ 3] progestogenic effects.[ 3]
Norethandrolone was discovered in 1953 and was introduced for medical use in 1956.[ 6] [ 7] [ 7] [ 8] [ 9] improve physique and performance .[ 3] controlled substance in many countries and so non-medical use is generally illicit.[ 3]
Norethandrolone has been used in the treatment ofmuscle wasting ,[ 9] burns , after severetrauma , and for certain forms ofaplastic anemia among other indications.[ 3]
Side effects of norethandrolone includevirilization among others.[ 3] estrogenic effects and can causegynecomastia andfluid retention .[ 3] 17α-alkylated AAS , long-term use of norethandrolone in high doses may result inhepatotoxicity includingelevated liver enzymes andcirrhosis .[ 10]
Norethandrolone is anandrogen andanabolic steroid and hence is anagonist of theandrogen receptor , thebiological target of androgens liketestosterone anddihydrotestosterone .[ 3] anabolic toandrogenic activity.[ 3] nandrolone and5α-dihydronandrolone ,5α-dihydronorethandrolone , the5α-reduced metabolite of norethandrolone, shows diminishedaffinity for the androgen receptor relative to norethandrolone.[ 3] [ 11] [ 3] [ 11] estrogenic activity via transformation byaromatase into the potentestrogen ethylestradiol .[ 3] progestogenic activity.[ 3] potency of norethandrolone is similar to that ofnorethisterone in terms ofendometrial changes in women.[ 12] hepatotoxic .[ 3]
Thepharmacokinetics of norethandrolone have been reviewed.[ 13]
Norethandrolone, also known as 17α-ethyl-19-nortestosterone or as 17α-ethylestr-4-en-17β-ol-3-one, is asynthetic estrane steroid and a17α-alkylated derivative oftestosterone and19-nortestosterone (nandrolone).[ 2] [ 3] normethandrone (17α-methyl-19-nortestosterone) and toethylestrenol (3-deketo-17α-ethyl-19-nortestosterone).[ 2] [ 3]
Chemical syntheses of norethandrolone have been published.[ 13]
Norethandrolone was synthesized atG. D. Searle & Company in 1953 and was originally studied as aprogestin , along withnorethisterone andnoretynodrel , but ultimately was not marketed as such.[ 6] testosterone -like activity and was found to have similaranabolic activity to testosterone but only one-sixteenth theandrogenic potency.[ 6] [ 9] [ 7] [ 8] normethandrone as a progestin in 1957 and by the more well-known AASnandrolone phenylpropionate in 1959.[ 14] [ 8] United States in the late 1950s under the brand name Nilevar but was discontinued in this country in the 1960s due to limited sales.[ 3] Europe and certain other markets,[ 3] cholestatic jaundice .[ 9] France .[ 3] [ 4]
Society and culture [ edit ] Norethandrolone is thegeneric name of the drug and itsINN Tooltip International Nonproprietary Name andBAN Tooltip British Approved Name .[ 2] [ 4] noretandrolone ,ethylnandrolone , andethylnortestosterone , as well as by its developmental code nameCB-8022 .[ 2] [ 4]
Norethandrolone is marketed under the brand names Nilevar and Pronabol.[ 2] [ 3] [ 4]
Norethandrolone is available today only inFrance .[ 4] [ 15]
Norethandrolone has been studied for use inmale hormonal contraception .[ 16] [ 17] [ 18]
^ Anvisa (2023-03-31)."RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese).Diário Oficial da União (published 2023-04-04).Archived from the original on 2023-08-03. Retrieved2023-08-15 .^a b c d e f J. Elks (14 November 2014).The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies ISBN 978-1-4757-2085-3 ^a b c d e f g h i j k l m n o p q r s t u v w x y z William Llewellyn (2011).Anabolics 575– 583.ISBN 978-0-9828280-1-4 ^a b c d e f g "List of Androgens and anabolic steroids" .^ Kicman AT (2008)."Pharmacology of anabolic steroids" .Br. J. Pharmacol .154 (3):502– 21.doi :10.1038/bjp.2008.165 .PMC 2439524 PMID 18500378 . ^a b c Charles D. Kochakian (6 December 2012).Anabolic-Androgenic Steroids ISBN 978-3-642-66353-6 ^a b c Camille Georges Wermuth (2 May 2011).The Practice of Medicinal Chemistry ISBN 978-0-08-056877-5 ^a b c James Edward Wright (1994).Altered States: The Use and Abuse of Anabolic Steroids ISBN 978-1-57028-013-9 ^a b c d Walter Sneader (23 June 2005).Drug Discovery: A History ISBN 978-0-471-89979-2 ^ Daniel Lednicer (20 June 2011).Steroid Chemistry at a Glance ISBN 978-1-119-95729-4 ^a b Bergink EW, Geelen JA, Turpijn EW (1985). "Metabolism and receptor binding of nandrolone and testosterone under in vitro and in vivo conditions".Acta Endocrinol Suppl (Copenh) .271 (3_Suppla):31– 7.doi :10.1530/acta.0.109S0031 .PMID 3865479 . ^ Boschann HW (July 1958). "Observations of the role of progestational agents in human gynecologic disorders and pregnancy complications".Ann. N. Y. Acad. Sci .71 (5):727– 52.Bibcode :1958NYASA..71..727B .doi :10.1111/j.1749-6632.1958.tb46803.x .PMID 13583829 . ^a b Die Gestagene 282– 283.ISBN 978-3-642-99941-3 ^ United States. Patent Office (1957).Official Gazette of the United States Patent Office ^ "IBM Watson Health Products" .^ Schearer SB, Alvarez-Sanchez F, Anselmo J, Brenner P, Coutinho E, Latham-Faundes A, et al. (1978)."Hormonal Contraception for Men" .International Journal of Andrology .1 (s2b):680– 712.doi :10.1111/j.1365-2605.1978.tb00517.x ISSN 0105-6263 . ^ Neumann F, Diallo FA, Hasan SH, Schenck B, Traore I (1976)."The influence of pharmaceutical compounds on male fertility" .Andrologia .8 (3):203– 35.doi :10.1111/j.1439-0272.1976.tb02137.x PMID 793446 .S2CID 24859886 . ^ Brenner PF, Bernstein GS, Roy S, Jecht EW, Mishell DR (February 1975). "Administration of norethandrolone and testosterone as a contraceptive agent for men".Contraception .11 (2):193– 207.doi :10.1016/0010-7824(75)90030-x .PMID 1112088 .
Androgens AAS Tooltip anabolic–androgenic steroid )
Antiandrogens
AR Tooltip Androgen receptor antagonists Steroidogenesis
Antigonadotropins D2 receptor antagonists (prolactin releasers ) (e.g.,domperidone ,metoclopramide ,risperidone ,haloperidol ,chlorpromazine ,sulpiride )Estrogens (e.g.,bifluranol ,diethylstilbestrol ,estradiol ,estradiol esters ,ethinylestradiol ,ethinylestradiol sulfonate ,paroxypropione )GnRH agonists (e.g.,leuprorelin )GnRH antagonists (e.g.,cetrorelix )Progestogens (incl.,chlormadinone acetate ,cyproterone acetate ,hydroxyprogesterone caproate ,gestonorone caproate ,medroxyprogesterone acetate ,megestrol acetate )Others
Estrogens
ER Tooltip Estrogen receptor agonistsSteroidal: Alfatradiol Certainandrogens /anabolic steroids (e.g.,testosterone ,testosterone esters ,methyltestosterone ,metandienone ,nandrolone esters ) (via estrogenic metabolites) Certainprogestins (e.g.,norethisterone ,noretynodrel ,etynodiol diacetate ,tibolone ) Clomestrone Cloxestradiol acetate Conjugated estriol Conjugated estrogens Epiestriol Epimestrol Esterified estrogens Estetrol † Estradiol Estradiol esters (e.g.,estradiol acetate ,estradiol benzoate ,estradiol cypionate ,estradiol enanthate ,estradiol undecylate ,estradiol valerate ,polyestradiol phosphate ,estradiol ester mixtures (Climacteron ))Estramustine phosphate Estriol Estriol esters (e.g.,estriol succinate ,polyestriol phosphate )Estrogenic substances Estrone Estrone esters Ethinylestradiol # Hydroxyestrone diacetate Mestranol Methylestradiol Moxestrol Nilestriol Prasterone (dehydroepiandrosterone; DHEA) Promestriene Quinestradol Quinestrol Progonadotropins
Antiestrogens
ER Tooltip Estrogen receptor antagonistsSERMs Tooltip selective estrogen receptor modulators /SERDs Tooltip selective estrogen receptor downregulators )Aromatase inhibitors Antigonadotropins Androgens /anabolic steroids (e.g.,testosterone ,testosterone esters ,nandrolone esters ,oxandrolone ,fluoxymesterone )D2 receptor antagonists (prolactin releasers) (e.g.,domperidone ,metoclopramide ,risperidone ,haloperidol ,chlorpromazine ,sulpiride )GnRH agonists (e.g.,leuprorelin ,goserelin )GnRH antagonists (e.g.,cetrorelix ,elagolix )Progestogens (e.g.,chlormadinone acetate ,cyproterone acetate ,gestonorone caproate ,hydroxyprogesterone caproate ,medroxyprogesterone acetate ,megestrol acetate )Others
ER Tooltip Estrogen receptor
Agonists Steroidal: 2-Hydroxyestradiol 2-Hydroxyestrone 3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol 3α-Androstanediol 3α,5α-Dihydrolevonorgestrel 3β,5α-Dihydrolevonorgestrel 3α-Hydroxytibolone 3β-Hydroxytibolone 3β-Androstanediol 4-Androstenediol 4-Androstenedione 4-Fluoroestradiol 4-Hydroxyestradiol 4-Hydroxyestrone 4-Methoxyestradiol 4-Methoxyestrone 5-Androstenediol 7-Oxo-DHEA 7α-Hydroxy-DHEA 7α-Methylestradiol 7β-Hydroxyepiandrosterone 8,9-Dehydroestradiol 8,9-Dehydroestrone 8β-VE2 10β,17β-Dihydroxyestra-1,4-dien-3-one (DHED) 11β-Chloromethylestradiol 11β-Methoxyestradiol 15α-Hydroxyestradiol 16-Ketoestradiol 16-Ketoestrone 16α-Fluoroestradiol 16α-Hydroxy-DHEA 16α-Hydroxyestrone 16α-Iodoestradiol 16α-LE2 16β-Hydroxyestrone 16β,17α-Epiestriol (16β-hydroxy-17α-estradiol) 17α-Estradiol (alfatradiol )17α-Dihydroequilenin 17α-Dihydroequilin 17α-Epiestriol (16α-hydroxy-17α-estradiol) 17α-Ethynyl-3α-androstanediol 17α-Ethynyl-3β-androstanediol 17β-Dihydroequilenin 17β-Dihydroequilin 17β-Methyl-17α-dihydroequilenin Abiraterone Abiraterone acetate Alestramustine Almestrone Anabolic steroids (e.g.,testosterone andesters ,methyltestosterone ,metandienone (methandrostenolone) ,nandrolone andesters , many others; via estrogenic metabolites)Atrimustine Bolandiol Bolandiol dipropionate Butolame Clomestrone Cloxestradiol Conjugated estriol Conjugated estrogens Cyclodiol Cyclotriol DHEA DHEA-S ent -EstradiolEpiestriol (16β-epiestriol, 16β-hydroxy-17β-estradiol) Epimestrol Equilenin Equilin ERA-63 (ORG-37663) Esterified estrogens Estetrol Estradiol Estramustine Estramustine phosphate Estrapronicate Estrazinol Estriol Estrofurate Estrogenic substances Estromustine Estrone Etamestrol (eptamestrol) Ethinylandrostenediol Ethinylestradiol Ethinylestriol Ethylestradiol Etynodiol Etynodiol diacetate Hexolame Hippulin Hydroxyestrone diacetate Lynestrenol Lynestrenol phenylpropionate Mestranol Methylestradiol Moxestrol Mytatrienediol Nilestriol Norethisterone Noretynodrel Orestrate Pentolame Prodiame Prolame Promestriene RU-16117 Quinestradol Quinestrol Tibolone Xenoestrogens: Anise -related (e.g.,anethole ,anol ,dianethole ,dianol ,photoanethole )Chalconoids (e.g.,isoliquiritigenin ,phloretin ,phlorizin (phloridzin) ,wedelolactone )Coumestans (e.g.,coumestrol ,psoralidin )Flavonoids (incl.7,8-DHF ,8-prenylnaringenin ,apigenin ,baicalein ,baicalin ,biochanin A ,calycosin ,catechin ,daidzein ,daidzin ,ECG ,EGCG ,epicatechin ,equol ,formononetin ,glabrene ,glabridin ,genistein ,genistin ,glycitein ,kaempferol ,liquiritigenin ,mirificin ,myricetin ,naringenin ,penduletin ,pinocembrin ,prunetin ,puerarin ,quercetin ,tectoridin ,tectorigenin )Lavender oil Lignans (e.g.,enterodiol ,enterolactone ,nyasol (cis -hinokiresinol) )Metalloestrogens (e.g.,cadmium )Pesticides (e.g.,alternariol ,dieldrin ,endosulfan ,fenarimol ,HPTE ,methiocarb ,methoxychlor ,triclocarban ,triclosan )Phytosteroids (e.g.,digitoxin (digitalis ),diosgenin ,guggulsterone )Phytosterols (e.g.,β-sitosterol ,campesterol ,stigmasterol )Resorcylic acid lactones (e.g.,zearalanone ,α-zearalenol ,β-zearalenol ,zearalenone ,zeranol (α-zearalanol) ,taleranol (teranol, β-zearalanol) )Steroid -like (e.g.,deoxymiroestrol ,miroestrol )Stilbenoids (e.g.,resveratrol ,rhaponticin )Synthetic xenoestrogens (e.g.,alkylphenols ,bisphenols (e.g.,BPA ,BPF ,BPS ),DDT ,parabens ,PBBs ,PHBA ,phthalates ,PCBs )Others (e.g.,agnuside ,rotundifuran ) MixedSERMs Tooltip Selective estrogen receptor modulators ) Antagonists Coregulator-binding modulators: ERX-11
GPER Tooltip G protein-coupled estrogen receptor
Agonists Antagonists Unknown
PR Tooltip Progesterone receptor
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 MixedSPRMs Tooltip Selective progesterone receptor modulators ) Antagonists
mPR Tooltip Membrane progesterone receptor PAQR Tooltip Progestin and adipoQ receptor )
