Nandrolone undecanoate Trade names Dynabolon, Dynabolin, Psychobolan Other names NU; Nandrolone undecylate; 19-Nortestosterone 17β-undecanoate Routes of administration Intramuscular injection Drug class Androgen ; Anabolic steroid ; Androgen ester ; Progestogen
[(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] undecanoate
CAS Number PubChem CID ChemSpider UNII CompTox Dashboard (EPA ) ECHA InfoCard 100.011.573 Formula C 29 H 46 O 3 Molar mass 442.684 g·mol−1 3D model (JSmol )
CCCCCCCCCCC(=O)O[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@H]34)C
InChI=1S/C29H46O3/c1-3-4-5-6-7-8-9-10-11-28(31)32-27-17-16-26-25-14-12-21-20-22(30)13-15-23(21)24(25)18-19-29(26,27)2/h20,23-27H,3-19H2,1-2H3/t23-,24+,25+,26-,27-,29-/m0/s1
Key:GRAAWEGTURLYKP-MVTMSODMSA-N
Nandrolone undecanoate (NU ), also known as nandrolone undecylate , and sold under the brand names Dynabolon , Dynabolin , and Psychobolan , is an androgen and anabolic steroid medication and a nandrolone ester . It was developed in the 1960s, and was previously marketed in France , Germany , Italy , and Monaco , but has since been discontinued and is now no longer known to be available.[1] [2] [3] [4] The pharmacokinetics of nandrolone undecanoate alone (Dynabolon) and in combination with other steroid esters (Trophobolene ) have been studied and compared.[5]
Relative affinities (%) of nandrolone and related steroids
Compound
PR
AR
ER
GR
MR
SHBG
CBG
Nandrolone
20
154–155
<0.1
0.5
1.6
1–16
0.1
Testosterone
1.0–1.2
100
<0.1
0.17
0.9
19–82
3–8
Estradiol
2.6
7.9
100
0.6
0.13
8.7–12
<0.1
Notes: Values are percentages (%). Reference ligands (100%) were progesterone for the PR , testosterone for the AR , estradiol for the ER , dexamethasone for the GR , aldosterone for the MR , dihydrotestosterone for SHBG , and cortisol for CBG . Sources: See template.
See also [ ]
List of androgen esters § Nandrolone esters
Estrapronicate/hydroxyprogesterone heptanoate/nandrolone undecanoate
References [ ]
^ Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies . Springer. pp. 660–. ISBN 978-1-4757-2085-3 .
^ Index Nominum 2000: International Drug Directory . Taylor & Francis. January 2000. pp. 716–717. ISBN 978-3-88763-075-1 .
^ Morton IK, Hall JM (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms . Springer Science & Business Media. ISBN 978-94-011-4439-1 .
^ Llewellyn W (2011). Anabolics . Molecular Nutrition Llc. pp. 477–. ISBN 978-0-9828280-1-4 .
^ Courtot, D; Forichon, J; Paris, J (1983). "Pharmacokinetics of 19-Nortestosterone in Man". Chromatography in Biochemistry, Medicine, and Environmental Research, 1: Proceedings of the 1st International Symposium on Chromatography in Biochemistry, Medicine and Environmental Research, Venice, June 16–17, 1981 . Analytical Chemistry Symposia Series. Vol. 13. Amsterdam/Oxford/New York: Elsevier. pp. 95–110.
Androgens and antiandrogens
Androgens (incl. AAS )
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 mixtures (Deposterona , Omnadren , Sustanon , Testoviron Depot ))
17α-Alkylated 19-nortestosterone derivatives: Ethylestrenol
Mibolerone
Norethandrolone
Normethandrone (methylestrenolone, normethisterone)
Propetandrol (propethandrol)
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
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)
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
# 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
Progestogens and antiprogestogens
Progestogens (and progestins )
PR agonists
Retroprogesterone derivatives: Dydrogesterone
Trengestone
Testosterone derivatives: Estranes: Danazol
Dimethisterone
Ethisterone
19-Nortestosterone derivatives: Estranes: Allylestrenol
Altrenogest
Dienogest
Etynodiol diacetate
Lynestrenol
Norethisterone (norethindrone) #
Norethisterone acetate
Norethisterone enanthate
Noretynodrel
Norgesterone
Norgestrienone
Normethandrone (methylestrenolone)
Norvinisterone
Oxendolone
Quingestanol acetate
Tibolone ; Gonanes: Desogestrel
Etonogestrel
Gestodene
Gestrinone
Levonorgestrel #
Norelgestromin
Norgestimate
Norgestrel
Spirolactone derivatives: Drospirenone
Antiprogestogens
SPRMs PR antagonists
Aglepristone
Mifepristone
# WHO-EM
‡ Withdrawn from market
Clinical trials :
† Phase III
§ Never to phase III
See also
Progesterone receptor modulators
Androgens and antiandrogens
Estrogens and antiestrogens
List of progestogens
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)
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 )
17α-Ethynyl-19-nortestosterone derivatives: Δ4 -Tibolone
Desogestrel
Etonogestrel
Etynodiol
Gestodene
Gestrinone
Levonorgestrel
Levonorgestrel esters (e.g., levonorgestrel butanoate )
Lynestrenol
Lynestrenol phenylpropionate
Norethisterone
Norethisterone esters (e.g., norethisterone acetate , norethisterone enanthate )
Norgestrel
Norgestrienone
Quingestanol
Tibolone
Mixed (SARMs )
Steroidal:
MK-0773
TFM-4AS-1
YK-11
Antagonists
Nonsteroidal: 5N -Bicalutamide
AA560
Apalutamide
Atraric acid
Bakuchiol
Bicalutamide
Bisphenols (e.g., BADGE , , bisphenol A , bisphenol F , bisphenol S )
BMS-641988
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-120907
Linuron
Methiocarb
N -Desmethylapalutamide
N -Desmethylenzalutamide
Nilutamide
Pentomone
Phenothrin
Prochloraz
Procymidone
Proxalutamide
Ralaniten (EPI-002)
Ralaniten acetate (EPI-506)
RD-162
Rezvilutamide
RU-22930
RU-56187
RU-57073
RU-58642
RU-58841
Seviteronel
Thalidomide
Topilutamide (fluridil)
Valproic acid
Vinclozolin
GPRC6A
Agonists
Cations (incl. aluminum , calcium , gadolinium , magnesium , strontium , zinc )
Dehydroandrosterone
Dihydrotestosterone
Estradiol
L -α-Amino acids (incl. L -arginine , L -lysine , L -ornithine )
Osteocalcin
SHBG
Testosterone
See also
Receptor/signaling modulators
Androgens and antiandrogens
Estrogen receptor modulators
Progesterone receptor modulators
List of androgens/anabolic steroids
PR
Agonists
Testosterone derivatives: Progestins: 6,6-Difluoronorethisterone
6,6-Difluoronorethisterone acetate
17α-Allyl-19-nortestosterone
Allylestrenol
Altrenogest
Chloroethynylnorgestrel
Cingestol
Danazol
Desogestrel
Dienogest
Ethinylandrostenediol
Ethisterone
Ethynerone
Etonogestrel
Etynodiol
Etynodiol diacetate
Gestodene
Gestrinone
Levonorgestrel
Levonorgestrel esters (e.g., levonorgestrel butanoate )
Lynestrenol
Lynestrenol phenylpropionate
Metynodiol
Metynodiol diacetate
Norelgestromin
Norethisterone (norethindrone)
Norethisterone esters (e.g., norethisterone acetate , norethisterone enanthate )
Noretynodrel
Norgesterone
Norgestimate
Norgestrel
Norgestrienone
Norvinisterone
Oxendolone
Quingestanol
Quingestanol acetate
Tibolone
Tigestol
Tosagestin ; Anabolic–androgenic steroids: 11β-Methyl-19-nortestosterone
11β-Methyl-19-nortestosterone dodecylcarbonate
19-Nor-5-androstenediol
19-Nor-5-androstenedione
19-Nordehydroepiandrosterone
Bolandiol
Bolandiol dipropionate
Bolandione
Dimethisterone
Dienedione
Dienolone
Dimethandrolone
Dimethandrolone buciclate
Dimethandrolone dodecylcarbonate
Dimethandrolone undecanoate
Dimethyldienolone
Dimethyltrienolone
Ethyldienolone
Ethylestrenol (ethylnandrol)
Methyldienolone
Metribolone (R-1881)
Methoxydienone (methoxygonadiene)
Mibolerone
Nandrolone
Nandrolone esters (e.g., nandrolone decanoate , nandrolone phenylpropionate )
Norethandrolone
Normethandrone (methylestrenolone, normethandrolone, normethisterone)
RU-2309
Tetrahydrogestrinone
Trenbolone (trienolone)
Trenbolone esters (e.g., trenbolone acetate , trenbolone enanthate )
Trendione
Trestolone
Trestolone acetate
Spirolactone derivatives: Canrenoic acid
Canrenone
Drospirenone
Mespirenone
Potassium canrenoate
Prorenone
SC-5233 (spirolactone)
SC-8109
Spironolactone
Spirorenone
Mixed (SPRMs )
Nonsteroidal: Apigenin
Kaempferol
Naringenin
Syringic acid
Antagonists
Nonsteroidal: Darolutamide
Valproic acid
mPR (PAQR )
See also
Receptor/signaling modulators
Progestogens and antiprogestogens
Androgen receptor modulators
Estrogen receptor modulators
List of progestogens