Nandrolone nonanoate

Chemical compound

Nandrolone nonanoate

Clinical data
Other names| 19-Nortestosterone 17β-nonanoate; Nandrolone pelargonate; 19-Nortestosterone 17β-pelargonate
Drug class| Androgen; Anabolic steroid; Androgen ester; Progestogen
Identifiers

IUPAC name

* [(8R,9S,10R,13S,14S,17S)-13-methyl-3-oxo-2,6,7,8,9,10,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl] nonanoate

CAS Number|

* 52230-64-5 Y

UNII|

* 2B78GY4XY5

Chemical and physical data
Formula| C27H42O3
Molar mass| 414.630 g·mol−1
3D model (JSmol)|

* Interactive image

SMILES

* CCCCCCCCC(=O)O[C@H]1CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@@H]4[C@H]3CC[C@]12C

InChI

* InChI=1S/C27H42O3/c1-3-4-5-6-7-8-9-26(29)30-25-15-14-24-23-12-10-19-18-20(28)11-13-21(19)22(23)16-17-27(24,25)2/h18,21-25H,3-17H2,1-2H3/t21-,22+,23+,24-,25-,27-/m0/s1 AuxInfo=1/0/N:1,30,2,3,4,5,6,7,8,18,23,17,24,14,13,27,28,20,19,21,25,26,16,15,12,9,29,22,10,11/it:im/rA:30CCCCCCCCCOOCCCCCCCCCCOCCCCCCCC/rB:s1;s2;s3;s4;s5;s6;s7;s8;d9;s9;p11;s12;s13;p14;s15;N16;s17;s18;d19;s20;d21;s21;s23;s19n24;s16s25;P26;s27;s12s15s28;P29;/rC:-11.2241,.7601,0;-9.8904,-.0099,0;-8.5567,.7601,0;-7.223,-.0099,0;-5.8893,.7601,0;-4.5557,-.0099,0;-3.222,.7601,0;-1.8883,-.0099,0;-.5546,.7601,0;-.5546,2.3001,0;.7791,-.0099,0;2.1127,.7601,0;2.2737,2.2917,0;3.7801,2.6118,0;4.5501,1.2782,0;6.0564,.958,0;7.0869,2.1024,0;8.5932,1.7822,0;9.0691,.3176,0;10.5754,-.0026,0;11.0513,-1.4672,0;12.5577,-1.7874,0;10.0209,-2.6117,0;8.5145,-2.2915,0;8.0386,-.8268,0;6.5323,-.5067,0;5.5018,-1.6511,0;3.9955,-1.3309,0;3.5196,.1337,0;2.3751,-.8967,0;

* Key:UVVFTQBZOQSECA-QNTYDACNSA-N

Nandrolone nonanoate, also known as nandrolone pelargonate or as 19-nortestosterone 17β-nonanoate, is an androgen and anabolic steroid and an androgen ester—specifically, the C17β nonanoate (pelargonate) ester of nandrolone (19-nortestosterone)—which was studied but was never marketed.[1][2][3][4][5][6][7]

## References[edit]

1. ^ Chaudry AQ, James KC (February 1974). "A Hansch analysis of the anabolic activities of some nandrolone esters". J Med Chem. 17 (2): 157–61. doi:10.1021/jm00248a003. PMID 4809250.
2. ^ Chaudry MA, James KC, Ng CT, Nicholls PJ (December 1976). "Anabolic and androgenic activities, in rat, of some nandrolone and androstanolone esters". J Pharm Pharmacol. 28 (12): 882–5. doi:10.1111/j.2042-7158.1976.tb04085.x. PMID 12263. S2CID 20546783.
3. ^ Chaudry MA (1983). "Preparation and characterization some of anabolic steroids". Journal of Pharmacy (Lahore). 4 (1–2): 13–17. ISSN 0253-8288. "Butyrate, hexanoate, heptanoate, octanoate, nonanoate, decanoate, and undecanoate esters of testosterone and nandrolone were prepd. and characterized."
4. ^ Chaudry MA (1983). "A realistic method for the evaluation of anabolic androgenic activity of some nandrolone esters". Journal of Pharmacy (Lahore). 4 (1–2): 51–62. ISSN 0253-8288. "The short-comings of the various methods used for detg. anabolic-androgenic activities were discussed, and a realistic method was developed for the comparative studies. The limitation of using the wt. gain of the target organs after administration of the hormone, which is time-dependent, was highlighted. The cumulative wt. (mg day) was recommended; it is independent of time, provided the expt. is carried out until the sample response reaches a plateau. This method provides a basis for obtaining anabolic-androgenic percentage dissocn. The method is applied to a no. of nandrolone esters."
5. ^ Ruelle P, Farina-Cuendet A, Kesselring UW (November 1997). "The mobile order solubility equation applied to polyfunctional molecules: The non-hydroxysteroids in aqueous and non aqueous solvents". Int J Pharm. 157 (2): 219–232. doi:10.1016/s0378-5173(97)00240-8. PMID 10477819.
6. ^ Joseph R. Robinson (1978). Sustained and Controlled Release Drug Delivery Systems. M. Dekker. p. 428\. ISBN 978-0-8247-6715-0.
7. ^ Chien YW (1981). "Long-acting parenteral drug formulations". J Parenter Sci Technol. 35 (3): 106–139. PMID 6113276.

* v
* t
* e

Androgen receptor modulators

ARTooltip Androgen receptor|

| 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

* 5α-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
* 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

* 5α-Dihydro-19-nortestosterone derivatives: 5α-Dihydronandrolone
* 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 5α-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-Alkylated 5α-dihydro-19-nortestosterone derivatives: 5α-Dihydronorethandrolone
* 5α-Dihydronormethandrone

* 17α-Vinyltestosterone derivatives: Norvinisterone (vinylnortestosterone)

* 17α-Vinyl-19-nortestosterone derivatives: Vinyltestosterone

* 17α-Ethynyltestosterone derivatives: Danazol
* Ethinylandrostenediol
* Ethandrostate
* Ethisterone (ethynyltestosterone)

* 5α-Dihydro-17α-ethynyltestosterone derivatives: 17α-Ethynyl-3α-androstanediol
* 17α-Ethynyl-3β-androstanediol
* Dihydroethisterone

* 17α-Ethynyl-19-nortestosterone derivatives: Δ4-Tibolone
* Desogestrel
* 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

* 5α-Dihydro-17α-ethynyl-19-nortestosterone derivatives: 5α-Dihydrolevonorgestrel
* 5α-Dihydronorethisterone

* Progesterone derivatives: 6α-Methylprogesterone
* Medroxyprogesterone acetate
* Megestrol acetate

* Others/unsorted: 3-Keto-5α-abiraterone
* 5α-Androstane
* Alternariol
* Cl-4AS-1
* Drupanol
* Trilostane
* ZM-182345

|

SARMsTooltip Selective androgen receptor modulator|

* Nonsteroidal: 198RL26
* ACP-105
* AC-262,536
* Acetothiolutamide
* Acetoxolutamide
* Andarine (acetamidoxolutamide, androxolutamide, GTx-007, S-4)
* BMS-564,929
* DTIB
* Enobosarm (ostarine, MK-2866, GTx-024, S-22)
* FTBU-1
* GLPG-0492
* GSK2881078
* GSK-4336A
* GSK-8698
* LG121071 (LGD-121071)
* LGD-2226
* LGD-2941 (LGD-122941)
* LGD-3303
* LGD-4033
* LY305
* JNJ-26146900
* JNJ-28330835
* JNJ-37654032
* OPK-88004 (LY-2452473, TT-701)
* ORM-11984
* PF-06260414
* R-1
* RU-59063
* S-1
* S-23
* S-40503
* S-101479
* Vosilasarm

* 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
* Ludaterone
* 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
* Bavdegalutamide
* 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
* EPI-7386
* 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
* Pyrilutamide
* Ralaniten (EPI-002)
* Ralaniten acetate (EPI-506)
* RD-162
* Rezvilutamide
* 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. aluminium, calcium, gadolinium, magnesium, strontium, zinc)
* Dehydroandrosterone
* Dihydrotestosterone
* Estradiol
* L-α-Amino acids (incl. L-arginine, L-lysine, L-ornithine)
* Osteocalcin
* SHBGTooltip Sex hormone-binding globulin
* Testosterone

|

See also
Receptor/signaling modulators
Androgens and antiandrogens
Estrogen receptor modulators
Progesterone receptor modulators
List of androgens and anabolic steroids
*[v]: View this template
*[t]: Discuss this template
*[e]: Edit this template
*[AR]: Androgen receptor
*[SARMs]: Selective androgen receptor modulator
*[SHBG]: Sex hormone-binding globulin