ノルエタンドロロン
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出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2014/07/23 23:09:37」(JST)
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Norethandrolone
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Systematic (IUPAC) name |
(17β)-17-ethyl-17-hydroxyester-4-en-3-one |
Clinical data |
AHFS/Drugs.com |
International Drug Names |
Legal status |
? |
Identifiers |
CAS number |
52-78-8 |
ATC code |
A14AA09 |
PubChem |
CID 5858 |
ChemSpider |
5649 Y |
UNII |
P7W01638W6 Y |
KEGG |
D07127 Y |
Synonyms |
(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 |
Chemical data |
Formula |
C20H30O2 |
Mol. mass |
302.451 g/mol |
SMILES
- O=C4\C=C3/[C@@H]([C@H]2CC[C@]1([C@@H](CC[C@@]1(O)CC)[C@@H]2CC3)C)CC4
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InChI
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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
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Y (what is this?) (verify) |
Norethandrolone is an anabolic steroid. This drug was approved for sale by the U.S. Food and Drug Administration (FDA) in 1965 under the trade name Nilevar[1] and finds legitimate use as an androgen for cases of hormonal deficiency, treatment of patients with severe burns, after severe trauma and for certain forms of aplastic anemia. It is now only marketed in Australia, France and Switzerland, and as with all 17-alpha alkylated oral steroids, long-term use in high doses result in elevated liver enzymes and consequently cirrhosis.[2]
References
- ^ W., Llewellyn. (2005). Anabolics. p. 156.
- ^ D., Lednicer. (2011). Steroid Chemistry at Glance. Wiley. p. 67.
Anabolic steroids (A14)
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Androstane (carbon 19 present) |
- Adrenosterone
- Androisoxazole
- Bolasterone (Myagen)
- Bolazine
- Boldione
- Boldenone undecylenate (Equipoise)
- 4-Chlordehydromethyltestosterone (Turinabol)
- 4-Hydroxytestosterone
- Calusterone
- Clostebol
- Danazol
- Desoxymethyltestosterone (Madol)
- DHT
- Drostanolone (Masteron)
- Enestebol
- Epitiostanol
- Fluoxymesterone (Halotestin)
- Formebolone
- Furazabol (Miotolan)
- Hydroxystenozole
- Mebolazine
- Mesabolone
- Mestanolone
- Mesterolone (Proviron)
- Methandriol
- Methandrostenolone (Dianabol)
- Metenolone
- Methenolone enanthate (Primobolan)
- Methasterone (Superdrol)
- Methyltestosterone
- Methyldiazirinol
- Oxandrolone (Anavar)
- Oxymetholone (Anadrol)
- Oxymesterone
- Prostanozol
- Quinbolone (Anabolicum Vister)
- Roxibolone
- Silandrone
- Stanozolol (Strombafort
- Winstrol)
- Stenbolone
- Testosterone`s (Sustamed
- Sustanon)
- 1-Testosterone
- Thiomesterone
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Estrene (carbon 19 absent) |
- Bolenol
- Ethyldienolone
- Ethylestrenol
- Mibolerone (Cheque Drops)
- Methylnortestosterone
- Metribolone (R1881)
- Nandrolone (Deca Durabolin)
- Norboletone (Genabol)
- Norclostebol
- Norethandrolone
- Normethandrone
- Oxabolone cipionate
- Propetandrol
- Tetrahydrogestrinone (The Clear)
- Trenbolone (Fina)
- Trestolone
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Prohormones |
- 1-Androstenediol
- 1,4-Androstadienedione
- 4-Androstenediol
- 4-Androstenedione
- 19-Norandrostenediol
- 19-Norandrostenedione
- DHEA
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anat (t, g, p)/phys/devp/enzy
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noco/cong/tumr, sysi/epon
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proc, drug (A2A/2B/3/4/5/6/7/14/16), blte
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Androgenics
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Receptor |
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Enzyme
(inhibitors) |
20,22-Desmolase
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- 22-ABC
- 3,3′-Dimethoxybenzidine
- 3-Methoxybenzidine
- Aminoglutethimide
- Cyanoketone
- Danazol
- Etomidate
- Mitotane
- Trilostane
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17α-Hydroxylase,
17,20-Lyase
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- 22-ABC
- 22-Oxime
- Abiraterone
- Bifonazole
- Clotrimazole
- Cyanoketone
- Cyproterone acetate
- Danazol
- Econazole
- Galeterone
- Gestrinone
- Isoconazole
- Ketoconazole
- L-39
- Levonorgestrel
- Liarozole
- LY-207,320
- MDL-27,302
- Miconazole
- Mifepristone
- Orteronel
- Pioglitazone
- Rosiglitazone
- Spironolactone
- Stanozolol
- SU-10,603
- TGF-β
- Tioconazole
- Troglitazone
- VN/87-1
- YM116
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3β-HSD (I, II)
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- 4-MA
- Azastene
- Cyanoketone
- Danazol
- Epostane
- Genistein
- Gestrinone
- Levonorgestrel
- Metyrapone
- Oxymetholone
- Pioglitazone
- Rosiglitazone
- Trilostane
- Troglitazone
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17β-HSD (I-XIV)
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5α-Reductase (I, II)
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- 22-Oxime
- Alfatradiol
- Azelaic acid
- β-Sitosterol
- Bexlosteride
- Dutasteride
- Epitestosterone
- Epristeride
- Finasteride
- gamma-Linolenic acid
- Ganoderic acid
- Izonsteride
- L-39
- Lapisteride
- Polyunsaturated fatty acids (α-linolenic acid, linoleic acid, γ-linolenic acid, oleic acid)
- Saw palmetto
- Turosteride
- Vitamin B6
- Zinc
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Aromatase
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- 1,4,6-Androstatriene-3,17-dione
- 4-Androstene-3,6,17-trione
- 4-Cyclohexylaniline
- 4-Hydroxytestosterone
- 5α-DHNET
- Abyssinone II
- Aminoglutethimide
- Anastrozole
- Ascorbic acid (Vitamin C)
- Atamestane
- Bifonazole
- CGP-45,688
- CGS-47,645
- Clotrimazole
- DHT
- Difeconazole
- Econazole
- Exemestane
- Fadrozole
- Fenarimol
- Finrozole
- Formestane
- Imazalil
- Isoconazole
- Ketoconazole
- Letrozole
- Liarozole
- MEN-11066
- Miconazole
- Minamestane
- Nimorazole
- NKS01
- ORG-33,201
- Penconazole
- Plomestane
- Prochloraz
- Propioconazole
- Pyridoglutethimide
- Rogletimide
- Rotenone
- Talarozole
- Testolactone
- Tioconazole
- Triadimefon
- Triadimenol
- Troglitazone
- Vorozole
- YM511
- Zinc
Note: 21-Hydroxylase inhibitors may also affect androgen levels as they prevent metabolism of androgen precursors.
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Other |
Endogenous
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- Androgens: Dihydrotestosterone
- Testosterone
- Antiandrogens: Epitestosterone
- Precursors: Cholesterol
- 22R-Hydroxycholesterol
- 20α,22R-Dihydroxycholesterol
- Pregnenolone
- 17-Hydroxypregnenolone
- Progesterone
- 17-Hydroxyprogesterone
- Cortodoxone/Deoxycortisol
- DHEA
- Androstenediol
- Androstenedione
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Indirect
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- Estrogens/Antiestrogens (see here)
- GnRH agonists/antagonists (see here)
- Gonadotropins/Antigonadotropins (see here)
- Plasma proteins (SHBG, ABP, Albumin)
- Progestogens/Antiprogestins (see here)
- Prolactin
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Procedures
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- Adrenalectomy
- Hypophysectomy
- Oophorectomy
- Orchiectomy
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UpToDate Contents
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English Journal
- Rate-dependent effects of monoamine releasers on intracranial self-stimulation in rats: implications for abuse liability assessment.
- Bauer CT1, Banks ML, Blough BE, Negus SS.
- Behavioural pharmacology.Behav Pharmacol.2013 Sep;24(5-6):448-58. doi: 10.1097/FBP.0b013e328363d1a4.
- 'Rate dependency' in the discipline of behavioral pharmacology describes a phenomenon wherein the effect of a drug on the rate of a behavior varies systematically as a function of the baseline, predrug rate of that behavior. Historically, rate-dependency studies have compared drug effects on differe
- PMID 23851484
- The metabolism of anabolic-androgenic steroids in the greyhound.
- McKinney AR1, Cawley AT, Young EB, Kerwick CM, Cunnington K, Stewart RT, Ambrus JI, Willis AC, McLeod MD.
- Bioanalysis.Bioanalysis.2013 Apr;5(7):769-81. doi: 10.4155/bio.13.40.
- BACKGROUND: Effective control of the use of anabolic-androgenic steroids (AASs) in animal sports is essential in order to ensure both animal welfare and integrity. In order to better police their use in Australian and New Zealand greyhound racing, thorough metabolic studies have been carried out on
- PMID 23534422
- In vitro study methodologies to investigate genetic aspects and effects of drugs used in attention-deficit hyperactivity disorder.
- Grünblatt E1, Bartl J, Marinova Z, Walitza S.
- Journal of neural transmission (Vienna, Austria : 1996).J Neural Transm (Vienna).2013 Jan;120(1):131-9. doi: 10.1007/s00702-012-0869-9. Epub 2012 Jul 26.
- Attention-deficit/hyperactivity disorder (ADHD) is one of the most common psychiatric disorders in children and adolescents, with up to 5 % affected worldwide. Twin and family studies on ADHD show its high familiality with heritability estimated around 70 %, but, to date, no specific polymorphism or
- PMID 22833045
Japanese Journal
- 17α-Ethyl-5β-estrane-3α, 17β-diol, a biological marker for the abuse of norethandrolone and ethylestrenol in slaughter cattle
- VAN PUYMBROECK M.,KUILMAN M. E. M.,MAAS R. F. M.,WITKAMP R. F.,LEYSSENS L.,VAN MIERT A. S. J. P. A. M.,HENDRIKS L.,VANDERZANDE D.,ADRIAENSENS P.,JACOBS M.-P.,RAUS J.
- Journal of chromatography. B, Biomedical sciences and applications 728(2), 217-232, 1999-05-28
- NAID 10024537314
- Quantitative Evaluation of Fetal Virilization by Steroids. Anogenital Distance Method
- 川島 邦夫,中浦 槙介,長尾 重之,田中 悟,桑村 司,大森 義仁
- 先天異常 : 日本先天異常学会会報 : official journal of Congeital Anomalies Research Association of Japan 17(1), 47-51, 1977-03-30
- NAID 110002726591
- Quantitative Evaluation of Virilizing Activity of Steroids by Measuring Morphological Changes in Uro-genital Region of Rats
- [他], , , , ,
- Endocrinologia Japonica 22(5), 439-444, 1975
- … Among these three parameters the abridgment in urovaginal septum was shown to be the most sensitive.<BR>A quantitative assay of virilizing activity of steroids in female fetuses was examined on rats treated subcutaneously with 17α-methyltestosterone and norethandrolone. … The relative potency of norethandrolone to 17α-methyltestosterone calculated on urovaginal septum length was 0.354 with fiducial limits of 0.293-0.446, and it was suggested that the virilizing activities of steroids can be evaluated quantitatively. …
- NAID 130000956193
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