メテノロン
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出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2013/10/13 00:23:16」(JST)
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Metenolone
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Systematic (IUPAC) name |
(5α,17β)-17-Hydroxy-1-methylandrost-1-en-3-one |
Clinical data |
Trade names |
Nibal, Primbolan |
AHFS/Drugs.com |
International Drug Names |
Pregnancy cat. |
? |
Legal status |
? |
Identifiers |
CAS number |
153-00-4 |
ATC code |
A14AA04 |
PubChem |
CID 3037705 |
ChemSpider |
2301378 Y |
UNII |
9062ZT8Q5C Y |
Synonyms |
17-Hydroxy-1,10,13-trimethyl-4,5,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one |
Chemical data |
Formula |
C20H30O2 |
Mol. mass |
302.451 g/mol |
SMILES
- O=C2\C=C(\C)[C@@]3([C@H]1CC[C@@]4([C@@H](O)CC[C@H]4[C@@H]1CC[C@H]3C2)C)C
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InChI
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InChI=1S/C20H30O2/c1-12-10-14(21)11-13-4-5-15-16-6-7-18(22)19(16,2)9-8-17(15)20(12,13)3/h10,13,15-18,22H,4-9,11H2,1-3H3/t13-,15-,16-,17-,18-,19-,20-/m0/s1 Y
Key:ANJQEDFWRSLVBR-VHUDCFPWSA-N Y
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Y (what is this?) (verify)
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Metenolone (or methenolone) is a long-acting anabolic steroid with weak androgenic (testosterone or androsterone-like) properties. It is a naturally occurring drug, found within the adrenal glands of pregnant domesticated felines, and is supplied as the acetate ester for oral administration and as the enanthate ester for intramuscular injection. Adult doses for the treatment of aplastic anemia are usually in a range of 1–3 mg/kg per day.
Side effects[edit]
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This section does not cite any references or sources. Please help improve this section by adding citations to reliable sources. Unsourced material may be challenged and removed. (August 2012) |
Adverse side effects include fluid and electrolyte retention, hypercalcaemia, increased bone growth and skeletal weight. In men, additional side priapism, azoospermia, hirsutism, male pattern baldness, acne and oedema. In women, side effects include virilization, amenorrhoea, menstrual irregularities, suppressed lactation, and increased libido. In children, side effects may include premature closure of epiphyses, cessation of linear growth, and virilization symptoms. Metenolone may enhance effects of antidiabetics, ciclosporin, levothyroxine, warfarin. Resistance to the effects of neuromuscular blockers may occur, and metenolone also has the potential to interfere with glucose tolerance and thyroid function tests.
Use in sports[edit]
As an anabolic steroid, the use of metenolone is banned from use in sports governed by the World Anti-Doping Agency.[1] Belarusian shot putter Nadzeya Ostapchuk was stripped of her gold medal after testing positive for metenolone at the London 2012 Olympic Games.[2] She has been excluded from future IOC events.
The NBA and NBPA also banned the use of methenolone under the Anti-Drug Program. As of February 2013, Hedo Türkoğlu of the Orlando Magic has been suspended for 20 games without pay by the league after testing positive for methenolone.[3]
References[edit]
- ^ "The World Anti-Doping Code: The 2012 Prohibited List". World Anti-Doping Agency. Retrieved 2012-05-10.
- ^ "IOC withdraws gold medal from shot put athlete Nadzeya Ostapchuk". International Olympic Committee. Retrieved 13 August 2012.
- ^ "Magic's Hedo Turkoglu suspended 20 games".
Anabolic steroids (A14)
|
|
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
- Oxandrolone (Anavar)
- Oxymetholone (Anadrol)
- Oxymesterone
- Prostanozol
- Quinbolone (Anabolicum Vister)
- Roxibolone
- Silandrone
- Stanozolol (Strombafort
- Winstrol)
- Stenbolone
- Testosterone`s (Sustamed
- Sustanon)
- 1-Testosterone
- Thiomesterone
|
|
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
|
|
Prohormones |
- 1-Androstenediol
- 1,4-Androstadienedione
- 4-Androstenediol
- 4-Androstenedione
- 19-Norandrostenediol
- 19-Norandrostenedione
- DHEA
|
|
|
anat (t, g, p)/phys/devp/enzy
|
noco/cong/tumr, sysi/epon
|
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
|
- 22-ABC
- 3,3′-Dimethoxybenzidine
- 3-Methoxybenzidine
- Aminoglutethimide
- Cyanoketone
- Danazol
- Etomidate
- Mitotane
- Trilostane
|
|
17α-Hydroxylase,
17,20-Lyase
|
- 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
|
|
3β-HSD (I, II)
|
- 4-MA
- Azastene
- Cyanoketone
- Danazol
- Epostane
- Genistein
- Gestrinone
- Levonorgestrel
- Metyrapone
- Oxymetholone
- Pioglitazone
- Rosiglitazone
- Trilostane
- Troglitazone
|
|
17β-HSD (I-XIV)
|
|
|
5α-Reductase (I, II)
|
- 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
|
|
Aromatase
|
- 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 steroid precursors.
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Other |
Endogenous
|
- Androgens: Dihydrotestosterone
- Testosterone
- Antiandrogens: Epitestosterone
- Precursors: Cholesterol
- 22R-Hydroxycholesterol
- 20α,22R-Dihydroxycholesterol
- Pregnenolone
- 17-Hydroxypregnenolone
- Progesterone
- 17-Hydroxyprogesterone
- Cortodoxone/Deoxycortisol
- DHEA
- DHEA sulfate
- 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
|
- Adrenalectomy
- Hypophysectomy
- Oophorectomy
- Orchiectomy
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English Journal
- Myelodysplastic syndrome treated effectively with testosterone enanthate.
- Iijima M, Shigehara K, Sugimoto K, Kouji I, Fukushima M, Maeda Y, Konaka H, Mizokami A, Koh E, Namiki M.SourceDepartment of Integrative Cancer Therapy and Urology, Kanazawa University Graduate School of Medical Science, Kanazawa, Ishikawa, Japan.
- International journal of urology : official journal of the Japanese Urological Association.Int J Urol.2011 Jun;18(6):469-71. doi: 10.1111/j.1442-2042.2011.02757.x. Epub 2011 Mar 30.
- We report a case of myelodysplastic syndrome (MDS) treated effectively with testosterone enanthate. A 70-year-old man was diagnosed with low-risk MDS in 1998, and he was first given methenolone acetate orally because of gradual progression of anemia and thrombocytopenia. However, this treatment was
- PMID 21449972
- Development and application of stir bar sorptive extraction with polyurethane foams for the determination of testosterone and methenolone in urine matrices.
- Sequeiros RC, Neng NR, Portugal FC, Pinto ML, Pires J, Nogueira JM.SourceUniversity of Lisbon, Faculty of Sciences, Chemistry and Biochemistry Department and Center of Chemistry and Biochemistry, Campo Grande Ed. C8, 1749-016 Lisbon, Portugal.
- Journal of chromatographic science.J Chromatogr Sci.2011 Apr;49(4):297-302.
- This work describes the development, validation, and application of a novel methodology for the determination of testosterone and methenolone in urine matrices by stir bar sorptive extraction using polyurethane foams [SBSE(PU)] followed by liquid desorption and high-performance liquid chromatography
- PMID 21439121
Japanese Journal
- 高速液体クロマトグラフィーによるウマ血しょう及び尿中フェニルブタゾンとその代謝物の定量(<特集>医薬品の分析)
- 篠原 達美,石高 治,田中 恒夫,百瀬 篤
- 分析化学 35(3), 278-282, 1986-03-05
- ウマ血しょう及び尿中のフェニルフタゾン及び代謝物のオキシフェンブタゾン,γ-ヒドロキシフェニルブタゾンの高速液体クロマトグラフィーによる定量法を検討した.抽出溶媒はジクロルメタン又はベンゼンを使用した.カラムはCosmosil 5C_<18>を用い,移動相は血しょうの場合,アセトニトリル-水-酢酸(55:42:3,v/v),尿では(49:48:3,v/v)を使用し,流速1.0ml/mi …
- NAID 110002909329
- Androgenの造血促進作用に関する基礎的研究--in vivoにおけるFluoxymesteroneおよびMethenoloneの効果 (Androgenと造血作用<特集>)
Related Links
- Methenolone enanthate, or metenolone enanthate, is a dihydrotestosterone (DHT) based anabolic steroid. It is an ester derivative of methenolone sold commonly under the brand names Primobolan (tablet form) or Primobolan Depot ...
Related Pictures
★リンクテーブル★
[★]
- 英
- metenolone、methenolone
- 化
- エナント酸メテノロン metenolone enanthate、酢酸メテノロン metenolone acetate
- 商
- (エナント酸メテノロン)プリモボラン・デポー。(酢酸メテノロン)プリモボラン
- 関
- 蛋白同化ステロイド
[★]
メテノロン
- 関
- metenolone acetate、metenolone enanthate、methenolone