Short description: Chemical compound
Androstanolone benzoate |
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| Clinical data |
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| Trade names | Ermalone-Amp, Hermalone, Sarcosan |
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| Other names | Stanolone benzoate; Dihydrotestosterone benzoate; DHT benzoate; DHTB; 5α-Androstan-17β-ol-3-one 17β-benzoate |
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Routes of administration | Intramuscular injection |
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| Drug class | Androgen; Anabolic steroid; Androgen ester |
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| Identifiers |
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IUPAC name
[(5S,8R,9S,10S,13S,14S,17S)-10,13-dimethyl-3-oxo-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl] benzoate
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| Chemical and physical data |
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| Formula | C26H34O3 |
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| Molar mass | 394.555 g·mol−1 |
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| 3D model (JSmol) | |
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SMILES
C[C@]12CCC(=O)C[C@@H]1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CC[C@@H]4OC(=O)C5=CC=CC=C5)C
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InChI
InChI=1S/C26H34O3/c1-25-14-12-19(27)16-18(25)8-9-20-21-10-11-23(26(21,2)15-13-22(20)25)29-24(28)17-6-4-3-5-7-17/h3-7,18,20-23H,8-16H2,1-2H3/t18-,20-,21-,22-,23-,25-,26-/m0/s1 Key:ZGDZDAPCWHIIKB-LVYWIKMTSA-N
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Androstanolone benzoate (brand names Ermalone-Amp, Hermalone, Sarcosan), also known as stanolone benzoate or dihydrotestosterone benzoate (DHTB), as well as 5α-androstan-17β-ol-3-one 17β-benzoate, is a synthetic androgen and anabolic steroid and a dihydrotestosterone ester.[1][2] It is used as an injectable and acts as a prodrug of androstanolone (stanolone, dihydrotestosterone, DHT).
See also
- List of androgen esters § Dihydrotestosterone esters
References
- ↑ The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. 14 November 2014. pp. 640–. ISBN 978-1-4757-2085-3. https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA640.
- ↑ Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. 6 December 2012. pp. 261–. ISBN 978-94-011-4439-1. https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA261.
{{Navbox
| name = Androgens and antiandrogens
| title = Androgens and antiandrogens
| state = collapsed
| listclass = hlist
| groupstyle = text-align:center;
| group1 = Androgens
(incl. AAS)
| list1 =
| AR agonists |
- Testosterone derivatives: Androstenediol dipropionate
- Boldenone undecylenate
- Clostebol
- Clostebol acetate
- Clostebol caproate
- Clostebol propionate
- Cloxotestosterone acetate
- Prasterone (dehydroepiandrosterone, DHEA)
- Prasterone enanthate (DHEA enanthate)
- Prasterone sulfate (DHEA sulfate)
- Quinbolone
- Testosterone#
- Testosterone esters (e.g., testosterone cypionate, testosterone enanthate]], testosterone propionate]], testosterone undecanoate]], testosterone ester mixture]]s (Deposterona, Omnadren, Sustanon, Testoviron Depot))
- Dihydrotestosterone derivatives: Androstanolone (stanolone, dihydrotestosterone, DHT)
- Androstanolone esters
- Bolazine capronate
- Drostanolone propionate (dromostanolone propionate)
- Epitiostanol
- Mepitiostane
- Mesterolone
- Metenolone acetate (methenolone acetate)
- Metenolone enanthate (methenolone enanthate)
- Stenbolone acetate
- 19-Nortestosterone derivatives: Bolandiol dipropionate
- Nandrolone esters (e.g., nandrolone decanoate, nandrolone phenylpropionate)
- 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), [[Chemistry:Lynestrlynestrenol, Norgestrienone|norgestrienone]])
- Tibolone
- Progesterone derivatives: Medroxyprogesterone acetate
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| Progonadotropins |
- Antiestrogens (e.g., tamoxifen, Chemistry:Clomifene
|
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| group2 = Antiandrogens
| list2 = {{Navbox|child
| groupstyle = text-align:center;
| groupwidth = 9em;
| group1 = AR antagonists
| list1 =
- Steroidal: Abiraterone acetate
- Canrenone
- Chlormadinone acetate
- Cyproterone acetate
- Delmadinone acetate
- Dienogest
- Drospirenone
- Medrogestone
- Megestrol acetate
- Nomegestrol acetate
- Osaterone acetate
- Oxendolone
- Potassium canrenoate
- Spironolactone
- Nonsteroidal: Apalutamide
- Bicalutamide
- Cimetidine
- Darolutamide
- Enzalutamide
- Flutamide
- Ketoconazole
- Nilutamide
- Seviteronel†
- Topilutamide (fluridil)
| group2 = Steroidogenesis
inhibitors
| list2 =
| 5α-Reductase |
- Alfatradiol
- Dutasteride
- Epristeride
- Finasteride
- Saw palmetto extract
|
|---|
| Others |
- Abiraterone acetate
- Aminoglutethimide
- Bifluranol
- Cyproterone acetate
- Flutamide
- Ketoconazole
- Nilutamide
- Seviteronel†
- Spironolactone
|
|---|
| group3 = Antigonadotropins
| list3 =
- 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, [[Chemistry:Medroxyprogesterone medroxyprogesterone acetate, Chemistry:Megestrol acetate|megestrol acetate]])
| group4 = Others
| list4 =
- Androstenedione immunogens: Androvax (androstenedione albumin)
- Ovandrotone albumin (Fecundin)
}}
| liststyle = background:#DDDDFF;
| list3 =
- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
- See also
- Androgen receptor modulators
- Estrogens and antiestrogens
- Progestogens and antiprogestogens
- List of androgens/anabolic steroids
}}
Androgen receptor modulators |
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| AR | | Agonists |
- Testosterone derivatives: 4-Androstenediol
- 4-Dehydroepiandrosterone (4-DHEA)
- 4-Hydroxytestosterone
- 4,17α-Dimethyltestosterone
- 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# (+dutasteride)
- Testosterone esters
- Polytestosterone phloretin phosphate
- 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
- Dihydroethisterone
- Dihydroethyltestosterone
- Dihydrofluoxymesterone
- Dihydromethylandrostenediol
- Dihydrotestosterone (DHT) (androstanolone, stanolone)
- Dihydrotestosterone esters
- Drostanolone
- Epiandrosterone
- Epitiostanol
- Mepitiostane
- Mesabolone
- Mesterolone
- Methyldiazinol
- 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
- 19-Nordehydroepiandrosterone
- 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
- Norclostebol
- Normethandrone (methylestrenolone, normethisterone)
- Oxabolone
- Oxabolone cipionate (oxabolone cypionate)
- Trenbolone
- Trenbolone acetate
- Trenbolone enanthate
- Trenbolone hexahydrobenzylcarbonate
- Trenbolone undecanoate
- Trendione
- Trestolone (MENT)
- Trestolone acetate
- Trestolone enanthate
- Dihydrotestosterone and 19-nortestosterone derivatives: 5α-Dihydrolevonorgestrel
- 5α-Dihydronandrolone
- 5α-Dihydronorethandrolone
- 5α-Dihydronorethisterone
- 5α-Dihydronormethandrone
- 5α-Dihydrotrestolone
- 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 (+esterified estrogens)
- 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
- Dimethyldienolone
- Dimethyltrienolone
- Ethyldienolone
- Ethylestrenol
- Methyldienolone
- Methylhydroxynandrolone (MOHN, MHN)
- Metribolone
- Mibolerone
- Norboletone
- Norethandrolone
- Propetandrol
- RU-2309
- Tetrahydrogestrinone
- 17α-Vinyltestosterone derivatives: Norvinisterone (vinylnortestosterone)
- Vinyltestosterone
- 17α-Ethynyltestosterone derivatives: Δ4-Tibolone
- Danazol
- Desogestrel
- Ethisterone (ethynyltestosterone)
- Etonogestrel
- Etynodiol
- Etynodiol diacetate
- Gestodene
- Gestrinone
- Levonorgestrel
- Levonorgestrel esters (e.g., levonorgestrel butanoate)
- Lynestrenol
- Lynestrenol phenylpropionate
- Norethisterone
- Norethisterone esters (e.g., norethisterone acetate, norethisterone enanthate)
- Norgestrel
- Norgestrienone
- Quingestanol
- Quingestanol acetate
- Tibolone
- Progesterone derivatives: Medroxyprogesterone acetate
- Megestrol acetate
- Others/unsorted: 3-Keto-5α-abiraterone
- 5α-Androstane
- Alternariol
- Cl-4AS-1
- Drupanol
- ZM-182345
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Mixed (SARMs) |
- Nonsteroidal: 198RL26
- ACP-105
- AC-262536
- Acetothiolutamide
- Andarine (acetamidoxolutamide, androxolutamide, GTx-007, S-4)
- BMS-564929
- DTIB
- 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
- R-1
- RAD140
- RU-59063
- S-1
- S-23
- S-40503
- S-101479
- Triclosan
- Steroidal: EM-9017
- MK-0773
- TFM-4AS-1
- YK-11
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| Antagonists | |
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| GPRC6A | | Agonists |
- Cations (incl. aluminum, calcium, Gadolinium
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- See also
- Receptor/signaling modulators
- Androgens and antiandrogens
- Estrogen receptor modulators
- Progesterone receptor modulators
- List of androgens/anabolic steroids
|
 | Original source: https://en.wikipedia.org/wiki/Androstanolone benzoate. Read more |