Testosterone butyrate

Short description: Chemical compound

Testosterone butyrate

Clinical data
Routes of
administration| Intramuscular injection
Identifiers

IUPAC name

* [(8R,9S,10R,13S,14S,17S)-10,13-Dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl] butanoate

CAS Number|

* 3410-54-6

PubChem CID|

* 102409

ChemSpider|

* 92494

UNII|

* 9RD3X2793Y

Chemical and physical data
Formula| C23H34O3
Molar mass| 358.522 g·mol−1
3D model (JSmol)|

* Interactive image

SMILES

* CCCC(=O)O[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@]34C)C

InChI

* InChI=1S/C23H34O3/c1-4-5-21(25)26-20-9-8-18-17-7-6-15-14-16(24)10-12-22(15,2)19(17)11-13-23(18,20)3/h14,17-20H,4-13H2,1-3H3/t17-,18-,19-,20-,22-,23-/m0/s1

* Key:OMPTUWYLCDEFSJ-WAUHAFJUSA-N

Testosterone butyrate, or testosterone butanoate, also known as androst-4-en-17β-ol-3-one 17β-butanoate, is a synthetic, steroidal androgen and an androgen ester – specifically, the C17β butanoate ester of testosterone – which was first synthesized in the 1930s and was never marketed.[1][2][3][4] Its ester side-chain length and duration of effect are intermediate between those of testosterone propionate and testosterone valerate.[2]

v * d * e Parenteral durations of androgens/anabolic steroids  Medication | Form | Major brand names | Duration

|
|
|

Testosterone | Aqueous suspension | Andronaq, Sterotate, Virosterone | 2–3 days
Testosterone propionate | Oil solution | Androteston, Perandren, Testoviron | 3–4 days
Testosterone phenylpropionate | Oil solution | Testolent | 8 days
Testosterone isobutyrate | Aqueous suspension | Agovirin Depot, Perandren M | 14 days
Mixed testosterone estersa | Oil solution | Triolandren | 10–20 days
Mixed testosterone estersb | Oil solution | Testosid Depot | 14–20 days
Testosterone enanthate | Oil solution | Delatestryl | 14–20 days
Testosterone cypionate | Oil solution | Depovirin | 14–20 days
Mixed testosterone estersc | Oil solution | Sustanon 250 | 28 days
Testosterone undecanoate | Oil solution | Aveed, Nebido | 100 days
Testosterone buciclated | Aqueous suspension | 20 Aet-1, CDB-1781e | 90–120 days
Nandrolone phenylpropionate | Oil solution | Durabolin | 10 days
Nandrolone decanoate | Oil solution | Deca Durabolin | 21 days
Methandriol | Aqueous suspension | Notandron, Protandren | 8 days
Methandriol bisenanthoyl acetate | Oil solution | Notandron Depot | 16 days
Metenolone acetate | Oil solution | Primobolan | 3 days
Metenolone enanthate | Oil solution | Primobolan Depot | 14 days
Note: All are via i.m. injection. Footnotes: a = TP, TV, and TUe. b = TP and TKL. c = TP, TPP, TiCa, and TD. d = Studied but never marketed. e = Developmental code names. Sources: See template.

## See also

* Testosterone acetate
* Testosterone caproate
* Testosterone enanthate

## References

1. ↑ Handbook of Aqueous Solubility Data (Second ed.). CRC Press. 19 April 2016. pp. 1288–. ISBN 978-1-4398-0246-5. https://books.google.com/books?id=cfFzJFthLCIC&pg=PA1288.
2. ↑ 2.0 2.1 Androgens: biochemistry, physiology, and clinical significance. Wiley. 1956. p. 119. https://archive.org/details/in.ernet.dli.2015.548094.
3. ↑ "Recent advances in the field of androgens.". Cold Spring Harbor Symposia on Quantitative Biology (Cold Spring Harbor Laboratory Press) 5: 34–43. January 1937. doi:10.1101/SQB.1937.005.01.004.
4. ↑ "Crystallographic data for some testosterone esters". Acta Crystallographica 19 (1): 149–150. 1965. doi:10.1107/S0365110X65002918. ISSN 0365-110X. Bibcode: 1965AcCry..19..149G.

* v
* t
* e

Androgen receptor modulators

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
* Boldenone undecylenate
* 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
* Bolazine capronate
* Dihydroethisterone
* Dihydroethyltestosterone
* Dihydrofluoxymesterone
* Dihydromethylandrostenediol
* Dihydrotestosterone (DHT) (androstanolone, stanolone)
* Dihydrotestosterone esters
* Drostanolone
* Drostanolone propionate
* Epiandrosterone
* Epitiostanol
* Mepitiostane
* Mesabolone
* Mesterolone
* Mesterolone cipionate
* Methyldiazinol
* Nisterime
* Nisterime acetate
* Prostanozol
* Stenbolone
* Stenbolone acetate
* 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
* Bolandiol dipropionate
* 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 esters
* Norclostebol
* Norclostebol acetate
* 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

|

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

Antagonists|

* Steroidal: 7α-Thioprogesterone
* 7α-Thiospironolactone
* 7α-Thiomethylspironolactone
* 11α-Hydroxyprogesterone
* 15β-Hydroxycyproterone acetate
* Abiraterone
* Abiraterone acetate
* Allyltestosterone
* Benorterone
* BOMT
* Canrenoic acid
* Canrenone
* Chlormadinone acetate
* Clascoterone
* Clometerone
* Cyproheptadine
* Cyproterone
* Cyproterone acetate
* Delanterone
* Delmadinone acetate
* Dicirenone
* Dienogest
* Drospirenone
* DU-41165
* Edogestrone
* EM-4350
* EM-5854
* EM-5855
* EM-6537
* Epitestosterone
* Galeterone
* Guggulsterone
* Medrogestone
* Megestrol acetate
* Mespirenone
* Metogest
* Mexrenone
* Mifepristone
* Nomegestrol acetate
* Nordinone
* Osaterone
* Osaterone acetate
* Oxendolone
* Potassium canrenoate
* Promegestone
* Prorenone
* Rosterolone
* RU-15328
* SC-5233 (spirolactone)
* Spironolactone
* Spirorenone
* Spiroxasone
* Topterone
* Trimegestone
* Trimethyltrienolone (R-2956)
* Zanoterone

* Nonsteroidal: 5N-Bicalutamide
* AA560
* Antarlides
* Arabilin
* Apalutamide
* Atraric acid
* AZD-3514
* Bakuchiol
* BAY-1024767
* Bicalutamide
* Bisphenols (e.g., BADGE, BFDGE, bisphenol A, bisphenol F, bisphenol S)
* BMS-501949
* BMS-570511
* BMS-641988
* CH5137291
* Cimetidine
* Cioteronel
* Cyanonilutamide
* Darolutamide
* DDT (via metabolite p,p’-DDE)
* Dieldrin
* DIMP
* Endosulfan
* Enzalutamide
* EPI-001
* Fenarimol
* Flutamide
* Hydroxyflutamide
* Inocoterone
* Inocoterone acetate
* Ketoconazole
* Ketodarolutamide
* Lavender oil
* LG-105
* LG-120907
* LGD-1331
* Linuron
* Methiocarb
* N-Butylbenzenesulfonamide
* N-Desmethylapalutamide
* N-Desmethylenzalutamide
* Nilutamide
* ONC1-13B
* Pentomone
* PF-998425
* Phenothrin
* Prochloraz
* Procymidone
* Proxalutamide
* Ralaniten (EPI-002)
* Ralaniten acetate (EPI-506)
* RD-162
* Ro 2-7239
* Ro 5-2537
* RU-22930
* RU-56187
* RU-57073
* RU-58642
* RU-58841
* Seviteronel
* Thalidomide
* Topilutamide (fluridil)
* Valproic acid
* Vinclozolin
* YM-580
* YM-92088
* YM-175735

GPRC6A|

| Agonists|

* Cations (incl. aluminum, calcium, Gadolinium

|

See also
Receptor/signaling modulators
Androgens and antiandrogens
Estrogen receptor modulators
Progesterone receptor modulators
List of androgens/anabolic steroids

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Original source: https://en.wikipedia.org/wiki/Testosterone butyrate. Read more

|

Retrieved from "https://handwiki.org/wiki/index.php?title=Chemistry:Testosterone_butyrate&oldid=543938"
*[CID]: Compound ID
*[i.m.]: intramuscular
*[TP]: Testosterone propionate
*[TV]: Testosterone valerate
*[TUe]: Testosterone undecylenate
*[TKL]: Testosterone ketolaurate
*[TPP]: Testosterone phenylpropionate
*[TiCa]: Testosterone isocaproate
*[TD]: Testosterone decanoate
*[v]: View this template
*[t]: Discuss this template
*[e]: Edit this template
*[AR]: Androgen receptor
*[SARMs]: Selective androgen receptor modulator
*[GPRC6A]: G protein-coupled receptor family C group 6 member A