メテノロン。酢酸メテノロン
WordNet
- a salt or ester of acetic acid (同)ethanoate
PrepTutorEJDIC
- 酢酸(さくさん)塩;アセテート(酢酸人造絹糸)
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2017/01/16 12:00:41」(JST)
[Wiki en表示]
Metenolone acetate
Clinical data |
Trade names |
Primobolan, Primobolan S, Primonabol, Nibal |
Routes of
administration |
Oral |
Identifiers |
IUPAC name
- [(5S,8R,9S,10S,13S,14S,17S)-1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl] acetate
|
Synonyms |
NSC-74226; SH-567; SQ-16496 |
CAS Number |
434-05-9 |
PubChem (CID) |
252372 |
ChemSpider |
3946 |
UNII |
W75590VPKQ |
Chemical and physical data |
Formula |
C22H32O3 |
Molar mass |
344.495 g/mol |
3D model (Jmol) |
Interactive image |
SMILES
-
CC1=CC(=O)C[C@H]2[C@]1([C@H]3CC[C@]4([C@H]([C@@H]3CC2)CC[C@@H]4OC(=O)C)C)C
|
InChI
-
InChI=1S/C22H32O3/c1-13-11-16(24)12-15-5-6-17-18-7-8-20(25-14(2)23)21(18,3)10-9-19(17)22(13,15)4/h11,15,17-20H,5-10,12H2,1-4H3/t15-,17-,18-,19-,20-,21-,22-/m0/s1
-
Key:PGAUJQOPTMSERF-QWQRBHLCSA-N
|
Metenolone acetate (INN), or methenolone acetate (USAN, BANM) (brand names Primobolan, Primobolan S, Primonabol, Nibal), also known as 1-methyl-4,5α-dihydro-δ1-testosterone 17β-acetate (1-methyl-δ1-DHT 17β-acetate) or 1-methylandrost-1,4-dien-17β-ol-3-one 17β-acetate, is a synthetic, orally active anabolic-androgenic steroid (AAS) and derivative of dihydrotestosterone (DHT) that is marketed in Europe, Australia, and Mexico.[1][2][3] It has been used in the treatment of bone marrow diseases and anemia.[3] Metenolone acetate is the C17β acetate ester and a prodrug of metenolone,[1][2] and is the form of metenolone that is used orally; the form that is used via depot intramuscular injection is metenolone enanthate.[2] Along with mesterolone, metenolone acetate is one of the few AAS that is orally active but is not 17α-alkylated.[4]
References
- ^ a b J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 784–. ISBN 978-1-4757-2085-3.
- ^ a b c Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 660–661. ISBN 978-3-88763-075-1.
- ^ a b I.K. Morton; Judith M. Hall (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 178–. ISBN 978-94-011-4439-1.
- ^ Kicman AT (June 2008). "Pharmacology of anabolic steroids". British Journal of Pharmacology. 154 (3): 502–21. doi:10.1038/bjp.2008.165. PMC 2439524. PMID 18500378.
Androgens and antiandrogens
|
|
Androgens
(incl. AAS) |
AR agonists |
- Testosterone derivatives: Androstenediol dipropionate
- Boldenone undecylenate
- Clostebol
- Clostebol acetate
- Clostebol caproate
- Clostebol propionate
- Cloxotestosterone acetate
- Dehydroepiandrosterone (DHEA) (androstenolone, prasterone)
- DHEA enanthate (prasterone enanthate)
- Quinbolone
- Testosterone#
- Testosterone acetate
- Testosterone capropate
- Testosterone cyclohexylpropionate
- Testosterone cypionate
- Testosterone decanoate
- Testosterone enanthate
- Testosterone ester mixtures (Deposterona, Omnadren, Sustanon)
- Testosterone furoate
- Testosterone hexahydrobenzoate
- Testosterone hexahydrobenzylcarbonate
- Testosterone hexyloxyphenylpropionate
- Testosterone isobutyrate
- Testosterone isocaproate
- Testosterone ketolaurate
- Testosterone nicotinate
- Testosterone phenylacetate
- Testosterone phenylpropionate
- Testosterone phosphate
- Testosterone propionate
- Testosterone undecanoate
- Testosterone valerate
- Dihydrotestosterone derivatives: Bolazine capronate
- Dihydrotestosterone (DHT) (androstanolone, stanolone)
- Dihydrotestosterone acetate
- Dihydrotestosterone benzoate
- Dihydrotestosterone butyrate
- Dihydrotestosterone enanthate
- Dihydrotestosterone formate
- Dihydrotestosterone propionate
- Dihydrotestosterone valerate
- Drostanolone propionate (dromostanolone propionate)
- Epitiostanol
- Mepitiostane
- Mesterolone
- Metenolone acetate (methenolone acetate)
- Metenolone enanthate (methenolone enanthate)
- Stenbolone acetate
- 19-Nortestosterone derivatives: Bolandiol dipropionate
- Nandrolone caproate
- Nandrolone cypionate
- Nandrolone cyclohexanecarboxylate
- Nandrolone cyclohexylpropionate
- Nandrolone decanoate
- Nandrolone furylpropionate
- Nandrolone hexyloxyphenylpropionate
- Nandrolone hydrogen succinate
- Nandrolone laurate
- Nandrolone phenylpropionate
- Nandrolone propionate
- Nandrolone sulfate sodium
- Nandrolone undecanoate
- Norclostebol
- Norclostebol acetate
- Oxabolone cipionate (oxabolone cypionate)
- Trenbolone acetate
- Trenbolone hexahydrobenzylcarbonate (trenbolone cyclohexylmethylcarbonate)
- 17α-Alkylated testosterone derivatives: Bolasterone
- Calusterone
- Chlorodehydromethyltestosterone (CDMT)
- Fluoxymesterone
- Formebolone
- Metandienone (methandienone, methandrostenolone)
- Methandriol (methylandrostenediol)
- Methandriol bisenanthoyl acetate
- Methandriol dipropionate
- Methandriol propionate
- Methyltestosterone
- Methyltestosterone 3-hexyl ether
- Oxymesterone
- Penmesterol
- Tiomesterone (thiomesterone)
- 17α-Alkylated dihydrotestosterone derivatives: Androisoxazole
- Furazabol
- Mebolazine (dimethazine)
- Mestanolone
- Oxandrolone
- Oxymetholone
- Stanozolol
- 17α-Alkylated 19-nortestosterone derivatives: Ethylestrenol
- Mibolerone
- Norethandrolone
- Normethandrone (methylestrenolone, normethisterone)
- Propetandrol (propethandrol)
- 17α-Vinyltestosterone derivatives: Norvinisterone (vinylnortestosterone)
- 17α-Ethynyltestosterone derivatives: Danazol
- Gestrinone
- Progestins (e.g., ethisterone (ethynyltestosterone), levonorgestrel, norgestrel, norethisterone (norethindrone), lynestrenol, norgestrienone)
- Tibolone
- Progesterone derivatives: Medroxyprogesterone acetate
|
|
Progonadotropins |
- Antiestrogens (e.g., tamoxifen, clomifene)
- GnRH agonists (e.g., GnRH (gonadorelin), leuprorelin)
- Gonadotropins (e.g., LH, hCG)
|
|
|
Antiandrogens |
AR antagonists |
- Steroidal: Abiraterone acetate
- Canrenone
- Chlormadinone acetate
- Cyproterone acetate
- Dienogest
- Drospirenone
- Medrogestone
- Megestrol acetate
- Nomegestrol acetate
- Osaterone acetate
- Oxendolone
- Potassium canrenoate
- Spironolactone
- Non-steroidal: Apalutamide†
- Bicalutamide
- Cimetidine
- Darolutamide†
- Enzalutamide
- Flutamide
- Ketoconazole
- Nilutamide
- Seviteronel†
- Topilutamide (fluridil)
|
|
Steroidogenesis
inhibitors |
5α-Reductase |
- Alfatradiol
- Dutasteride
- Epristeride
- Finasteride
- Saw palmetto extract
|
|
Others |
- Abiraterone acetate
- Aminoglutethimide
- Bifluranol
- Cyproterone acetate
- Flutamide
- Ketoconazole
- Nilutamide
- Seviteronel†
- Spironolactone
|
|
|
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 |
- Androstenedione immunogens: Androvax (androstenedione albumin)
- Ovandrotone albumin (Fecundin)
|
|
|
- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
See also: Estrogens and antiestrogens • Progestogens and antiprogestogens • Glucocorticoids and antiglucocorticoids • Mineralocorticoids and antimineralocorticoids • Gonadotropins and GnRH
|
Androgen receptor modulators
|
|
AR |
Agonists
|
- Testosterone derivatives: 4-Androstenediol
- 4-Dehydroepiandrosterone (4-DHEA)
- 4-Hydroxytestosterone
- 5-Androstenedione
- 11-Ketotestosterone
- 11β-Hydroxyandrostenedione
- Adrenosterone (11-ketoandrostenedione, 11-oxoandrostenedione)
- Androstenediol (5-androstenediol)
- Androstenediol 3β-acetate
- Androstenediol 17β-acetate
- Androstenediol diacetate
- Androstenediol dipropionate
- Androstenedione (4-androstenedione)
- Atamestane
- Boldenone
- Boldione (1,4-androstadienedione)
- Clostebol
- Clostebol acetate
- Clostebol caproate
- Clostebol propionate
- Cloxotestosterone
- Cloxotestosterone acetate
- Dehydroandrosterone
- DHEA (androstenolone, prasterone; 5-DHEA)
- DHEA enanthate (prasterone enanthate)
- DHEA sulfate
- Exemestane
- Formestane
- Plomestane
- Quinbolone
- Silandrone
- Testosterone#
- Testosterone acetate
- Testosterone acetate butyrate
- Testosterone acetate propionate
- Testosterone benzoate
- Testosterone butyrate
- Testosterone buciclate
- Testosterone capropate
- Testosterone cyclohexylpropionate
- Testosterone cypionate
- Testosterone decanoate
- Testosterone diacetate
- Testosterone dipropionate
- Testosterone enanthate
- Testosterone enanthate benziloylhydrazone
- Testosterone formate
- Testosterone furoate
- Testosterone hexahydrobenzoate
- Testosterone hexahydrobenzylcarbonate
- Testosterone hexyloxyphenylpropionate
- Testosterone isobutyrate
- Testosterone isocaproate
- Testosterone isovalerate
- Testosterone ketolaurate
- Testosterone nicotinate
- Testosterone palmitate
- Testosterone phenylacetate
- Testosterone phenylbutyrate
- Testosterone phenylpropionate
- Testosterone phosphate
- Testosterone propionate
- Testosterone stearate
- Testosterone sulfate
- Testosterone undecanoate
- Testosterone valerate
- Dihydrotestosterone derivatives: 1-Androstenediol
- 1-Androstenedione
- 1-Androsterone (1-andro, 1-DHEA)
- 1-Testosterone
- 3α-Androstanediol
- 5α-Androst-2-en-17-one
- 7β-Hydroxyepiandrosterone
- 11-Ketodihydrotestosterone
- Androsterone
- Bolazine
- Dihydrotestosterone (androstanolone, stanolone)
- Dihydrotestosterone acetate
- Dihydrotestosterone benzoate
- Dihydrotestosterone butyrate
- Dihydrotestosterone enanthate
- Dihydrotestosterone formate
- Dihydrotestosterone propionate
- Dihydrotestosterone valerate
- Drostanolone
- Epiandrosterone
- Epitiostanol
- Mepitiostane
- Mesabolone
- Mesterolone
- Nisterime
- Prostanozol
- Stenbolone
- Testifenon (testiphenon, testiphenone)
- 19-Nortestosterone derivatives: 7α-Methyl-19-norandrostenedione (MENT dione, trestione)
- 11β-Methyl-19-nortestosterone
- 11β-Methyl-19-nortestosterone dodecylcarbonate
- 19-Nor-5-androstenediol
- 19-Nor-5-androstenedione
- Bolandiol
- Bolandione (19-nor-4-androstenedione)
- Bolmantalate (nandrolone adamantoate)
- Dienedione
- Dienolone
- Dimethandrolone
- Dimethandrolone buciclate
- Dimethandrolone dodecylcarbonate
- Dimethandrolone undecanoate
- LS-1727 (nandrolone 17β-N-(2-chloroethyl)-N-nitrosocarbamate)
- Methoxydienone (methoxygonadiene)
- Nandrolone
- Nandrolone acetate
- Nandrolone caproate
- Nandrolone cypionate
- Nandrolone cyclohexanecarboxylate
- Nandrolone cyclohexylpropionate
- Nandrolone cyclotate
- Nandrolone decanoate
- Nandrolone formate
- Nandrolone furylpropionate
- Nandrolone hexyloxyphenylpropionate
- Nandrolone hydrogen succinate
- Nandrolone laurate
- Nandrolone phenylpropionate
- Nandrolone propionate
- Nandrolone sulfate
- Nandrolone sulfate sodium
- Nandrolone undecanoate
- Norclostebol
- Normethandrone (methylestrenolone, normethisterone)
- Oxabolone
- Oxabolone cipionate (oxabolone cypionate)
- Trenbolone
- Trenbolone acetate
- Trenbolone enanthate
- Trenbolone hexahydrobenzylcarbonate
- Trestolone (MENT)
- Dihydrotestosterone and 19-nortestosterone derivatives: 5α-Dihydronandrolone
- 19-Norandrosterone
- 17α-Alkylated testosterone derivatives:
- Bolasterone
- Calusterone
- Chlorodehydromethylandrostenediol (CDMA)
- Chlorodehydromethyltestosterone (CDMT)
- Chloromethylandrostenediol (CMA)
- Enestebol
- Ethyltestosterone
- Fluoxymesterone
- Formebolone
- Hydroxystenozole
- Metandienone (methandrostenolone)
- Methandriol (methylandrostenediol)
- Methandriol bisenanthoyl acetate
- Methandriol diacetate
- Methandriol dipropionate
- Methandriol propionate
- Methylclostebol (chloromethyltestosterone)
- Methyltestosterone
- Methyltestosterone 3-hexyl ether
- Oxymesterone
- Penmesterol
- Tiomesterone
- 17α-Alkylated dihydrotestosterone derivatives: Androisoxazole
- Desoxymethyltestosterone
- Furazabol
- Mebolazine (dimethazine)
- Mestanolone
- Metenolone
- Metenolone acetate
- Metenolone enanthate
- Methasterone
- Methyl-1-testosterone
- Methylepitiostanol
- Methylstenbolone
- Oxandrolone
- Oxymetholone
- Stanozolol
- 17α-Alkylated 19-nortestosterone derivatives: Bolenol
- Dimethyltrienolone (7α-methylmetribolone, 7α,17α-dimethyltrenbolone)
- Ethyldienolone
- Ethylestrenol
- Methyldienolone
- Methylhydroxynandrolone (MOHN, MHN)
- Metribolone
- Mibolerone
- Norboletone
- Norethandrolone
- Propetandrol
- Tetrahydrogestrinone
- 17α-Vinyltestosterone derivatives: Norvinisterone (vinylnortestosterone)
- Vinyltestosterone
- 17α-Ethynyltestosterone derivatives: Δ4-Tibolone
- Danazol
- Desogestrel
- Ethisterone (ethynyltestosterone)
- Etonogestrel
- Etynodiol
- Etynodiol diacetate
- Gestodene
- Gestrinone
- Levonorgestrel
- Levonorgestrel butanoate
- Lynestrenol
- Norethisterone
- Norethisterone acetate
- Norethisterone acetate oxime
- Norethisterone enanthate
- Norgestrel
- Norgestrienone
- Quingestanol
- Quingestanol acetate
- Tibolone
- Progesterone derivatives: Medroxyprogesterone acetate
- Others/unsorted: Cl-4AS-1
- Drupanol
- ZM-182345
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Mixed (SARMs)
|
- Non-steroidal: 198RL26
- ACP-105
- AC-262,356
- Acetothiolutamide
- Andarine (acetamidoxolutamide, androxolutamide, GTx-007, S-4)
- BMS-564,929
- Enobosarm (ostarine, MK-2866, GTx-024, S-22)
- FTBU-1
- GSK-4336A
- GSK-8698
- LG-121071 (LGD-121071)
- LGD-2226
- LGD-2941 (LGD-122941)
- LGD-3303
- LGD-4033
- JNJ-26146900
- JNJ-28330835
- JNJ-37654032
- ORM-11984
- RAD140
- R-1
- R-2
- R-3
- S-1
- S-23
- S-40503
- S-101479
- Steroidal: MK-0773
- TFM-4AS-1
- YK-11
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Antagonists
|
- Steroidal: 9,11-Dehydrocortexolone 17α-butyrate (CB-03-04)
- 11α-Hydroxyprogesterone
- 15β-Hydroxycyproterone acetate
- Abiraterone
- Abiraterone acetate
- Allyltestosterone
- Benorterone
- BOMT
- Canrenoic acid
- Canrenone
- Chlormadinone acetate
- Clometerone
- Cortexolone 17α-propionate (CB-03-01)
- Cyproterone
- Cyproterone acetate
- Delanterone
- Dienogest
- Drospirenone
- Edogestrone
- Epitestosterone
- Galeterone
- Guggulsterone
- Medrogestone
- Megestrol acetate
- Mespirenone
- Metogest
- Mexrenone
- Mifepristone
- Nomegestrol acetate
- Nordinone
- Osaterone
- Osaterone acetate
- Oxendolone
- Potassium canrenoate
- Prorenone
- Rosterolone
- SC-5233 (spirolactone)
- Spironolactone
- Spirorenone
- Topterone
- Trimethyltrienolone (R-2956)
- Zanoterone
- Non-steroidal: AA560
- Apalutamide
- Atraric acid
- AZD-3514
- Bakuchiol
- BAY-1024767
- Bicalutamide
- Bisphenols (e.g., BADGE, BFDGE, bisphenol A, bisphenol F, bisphenol S)
- BMS-641,988
- Cimetidine
- Cioteronel
- Darolutamide
- DDT (via metabolite p,p’-DDE)
- Dieldrin
- DIMP
- Endosulfan
- Enzalutamide
- EPI-001
- EPI-506
- Fenarimol
- Flutamide
- Hydroxyflutamide
- Inocoterone
- Inocoterone acetate
- Ketoconazole
- Lavender oil
- LG-105
- LG-120907
- Linuron
- Methiocarb
- N-Butylbenzenesulfonamide
- N-Desmethylenzalutamide
- Nilutamide
- ONC1-13B
- ORM-15341
- Pentomone
- PF-998425
- Phenothrin
- Prochloraz
- Procymidone
- RU-22930
- RU-58642
- RU-58841
- Seviteronel
- Thalidomide
- Topilutamide (fluridil)
- Valproic acid
- Vinclozolin
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|
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GPRC6A |
Agonists
|
- Cations (incl. aluminum, calcium, gadolinium, magnesium, strontium)
- Dehydroandrosterone
- Dihydrotestosterone
- Estradiol
- L-α-Amino acids (incl. L-arginine, L-lysine, L-ornithine)
- Osteocalcin
- Testosterone
|
|
|
See also: Estrogenics • Glucocorticoidics • Mineralocorticoidics • Progestogenics • Steroid hormone metabolism modulators • List of androgens/anabolic steroids
|
UpToDate Contents
全文を閲覧するには購読必要です。 To read the full text you will need to subscribe.
English Journal
- Chronic anabolic androgenic steroid usage associated with acute coronary syndrome in bodybuilder.
- Sonmez E1, Turkdogan KA1, Yilmaz C1, Kucukbuzcu S2, Ozkan A1, Sogutt O1.
- Turkish journal of emergency medicine.Turk J Emerg Med.2016 Mar 10;16(1):35-7. doi: 10.1016/j.tjem.2014.11.001. eCollection 2016 Mar.
- PMID 27239638
- [Clinical aspects of primary myelofibrosis in Japan].
- Shimoda K, Takenaka K, Kitanaka A, Akashi K.
- [Rinsho ketsueki] The Japanese journal of clinical hematology.Rinsho Ketsueki.2014 Mar;55(3):289-94.
- PMID 24681931
- In vitro metabolic studies using homogenized horse liver in place of horse liver microsomes.
- Wong JK1, Tang FP, Wan TS.
- Drug testing and analysis.Drug Test Anal.2011 Jun;3(6):393-9. doi: 10.1002/dta.273. Epub 2011 Mar 5.
- PMID 21381223
Japanese Journal
- メテノロン酢酸エステルの投与中にもかかわらず Meibom 腺機能不全を発症した1例
- 眼科臨床紀要 = Folia Japonica de ophthalmologica clinica 3(3), 233-235, 2010-03-15
- NAID 10030250170
- Endocrinological and Pathological Effects of Anabolic-androgenic Steroid in Male Rats
Related Links
- メテノロン酢酸エステル(Metenolone Acetate) 化学名 1-Methyl-3-oxo-5α-androst-1-en-17β-yl acetate 分子式 C 22 H 32 O 3 分子量 344.49 性状 本品は白色〜微黄白色の結晶性の粉末で,においはない. 本品はアセトン,1,4 ...
- (Methenolone Acetate) Primobolan is an oral anabolic steroid that is a little unique compared to many oral anabolic steroids. Before we go any further, it’s important we distinguish the difference between Primobolan and Primobolan ...
★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