 | |
 | |
| Clinical data | |
|---|---|
| Trade names | Rolon, Deca-Durabolin, others |
| Other names | • Nandrolone decylate • 19-Nortestosterone 17β-decanoate |
| Pregnancy category |
|
| Routes of administration | Intramuscular injection,subcutaneous injection |
| Drug class | Androgen;Anabolic steroid;Androgen ester;Progestogen |
| Legal status | |
| Legal status |
|
| Pharmacokinetic data | |
| Bioavailability | Intramuscular: 53–73%[1] |
| Metabolism | Blood (hydrolysis),liver (reduction)[2][4] |
| Metabolites | •Nandrolone[2][3] •5α-Dihydronandrolone[2][3] •19-Norandrosterone[2] •19-Noretiocholanolone[2] •Conjugates[4] |
| Eliminationhalf-life | • Intramuscular: 6–12 days[2][5] • Nandrolone: <4.3 hours[2] |
| Duration of action | • Intramuscular: 2–3 weeks[3][6] |
| Excretion | Urine[2] |
| Identifiers | |
| |
| CAS Number | |
| PubChemCID | |
| DrugBank | |
| ChemSpider | |
| UNII | |
| CompTox Dashboard(EPA) | |
| ECHA InfoCard | 100.006.037 |
| Chemical and physical data | |
| Formula | C28H44O3 |
| Molar mass | 428.657 g·mol−1 |
| 3D model (JSmol) | |
| |
| |
Nandrolone decanoate, sold under the brand namesRolon[7] andDeca-Durabolin, among others, is anandrogen andanabolic steroid (AAS) medication which is used primarily in the treatment ofanemias andwasting syndromes, as well asosteoporosis inmenopausal women.[8][9][10][11][3] It is given byinjection into muscle orfat once every one to four weeks.[3][12]
Side effects of nandrolone decanoate may includesymptoms ofmasculinization likeacne,increased hair growth, andvoice changes.[3] The medication is asynthetic androgen and anabolic steroid and hence is anagonist of theandrogen receptor (AR), thebiological target of androgens liketestosterone anddihydrotestosterone (DHT).[3][13] It has stronganabolic effects and weakandrogenic effects, which give it a mild side effect profile and make it especially suitable for use in women and children.[3][13][14] Nandrolone decanoate is anandrolone ester and a long-lastingprodrug ofnandrolone in the body.[3][15]
Nandrolone decanoate was first described in 1960 and was introduced for medical use in 1962.[3] It was the second nandrolone ester to be introduced, followingnandrolone phenylpropionate (NPP) in 1959, and is one of the most widely used nandrolone esters.[3][16] It is also one of the most widely used AAS worldwide.[3] In addition to its medical use, nandrolone decanoate is used toimprove physique and performance, and is said to be the most widely used AAS for such purposes.[3][17] The drug is acontrolled substance in many countries and so non-medical use is generally illicit.[3]
Nandrolone decanoate is approved in theUnited States specifically for the treatment ofanemia ofchronic kidney disease and in theUnited Kingdom specifically for the treatment ofosteoporosis inpostmenopausal women.[3][18][19] InAustralia, it is approved specifically for the treatment ofkidney failure,chronic kidney disease,anemia of kidney failure,aplastic anemia, osteoporosis (in women in whomestrogens arecontraindicated), inoperablebreast cancer, and for patients on long-termcorticosteroid therapy.[6] InNew Zealand, it is approved for osteoporosis, inoperable breast cancer, and as anadjunct to therapy for conditions characterized by a negativenitrogen balance.[2] The drug is often used off-label to preservelean mass inHIV/AIDS patients and in otherwasting syndromes.[3]
In the past, nandrolone decanoate has also been indicated and used for a variety of other conditions and situations including pre- and postoperative use for increasing lean mass, treatingweight loss due toconvalescence or disease,geriatric states (e.g., generalweakness,fatigue),burns, severetrauma,ulcers, and selected cases ofgrowth failure in children.[3] Starting in the 1970s, the indications of nandrolone decanoate were refined and use of the drug became more selective and restricted.[3] Its use in medicine continues to decline and has become limited, with its sale having been discontinued in many countries.[3]
Nandrolone esters can be used as a form ofandrogen replacement therapy for treatment ofandrogen deficiency in men.[20] However, they have not generally been used for this purpose, and have instead mostly been used only as anabolic agents.[20][21][22] In any case, nandrolone decanoate has widely been used at low doses as a means of androgen replacement in postmenopausal women, for instance to maintain or increasebone mineral density and decrease the risk of osteoporosis.[23][24][25][26] It is one of only three androgens approved for androgen replacement in postmenopausal women, the others beingtestosterone (andesters) andmethyltestosterone.[26] Nandrolone esters have more recently been proposed for more widespread treatment of androgen deficiency in men due to favorable properties including their high ratio of anabolic to androgenic effect and hence lower or negligible risk ofscalp hair loss,prostate enlargement, andprostate cancer relative to testosterone.[20][27][28] Nandrolone esters and related compounds such astrestolone anddimethandrolone undecanoate have also been studied as means of androgen replacement in investigationalmale contraceptive regimens.[20][29][30]
It has also been proposed formasculinizing hormone therapy in some nonbinary peopleassigned female at birth who want the body shape effects of testosterone withoutandrogenic hair growth.[31]
A dosage of nandrolone decanoate of 25 to 50 mg once every 6 to 12 weeks (working out to an average exposure of about 2 to 8 mg per week) by intramuscular injection is considered to be appropriate for general androgen replacement therapy in women.[32][33][20] A dosage of 50 mg once every 2 to 4 weeks by intramuscular injection is used in the prevention and treatment of postmenopausal osteoporosis and in the palliative treatment of inoperative breast cancer.[2][6][34] For children aged 2 to 13 years, the average dosage for anemia of chronic kidney disease is 25 to 50 mg every 3 to 4 weeks by intramuscular injection.[18] Dosages in men and for other uses have also been described.[18][19][6][2][3]
| Route | Medication | Major brand names | Form | Dosage |
|---|---|---|---|---|
| Oral | Testosterone undecanoate | Andriol, Jatenzo | Capsule | 40–80 mg 1x/1–2 days |
| Methyltestosterone | Metandren, Estratest | Tablet | 0.5–10 mg/day | |
| Fluoxymesterone | Halotestin | Tablet | 1–2.5 mg 1x/1–2 days | |
| Normethandronea | Ginecoside | Tablet | 5 mg/day | |
| Tibolone | Livial | Tablet | 1.25–2.5 mg/day | |
| Prasterone (DHEA)b | – | Tablet | 10–100 mg/day | |
| Sublingual | Methyltestosterone | Metandren | Tablet | 0.25 mg/day |
| Transdermal | Testosterone | Intrinsa | Patch | 150–300 μg/day |
| AndroGel | Gel, cream | 1–10 mg/day | ||
| Vaginal | Prasterone (DHEA) | Intrarosa | Insert | 6.5 mg/day |
| Injection | Testosterone propionatea | Testoviron | Oil solution | 25 mg 1x/1–2 weeks |
| Testosterone enanthate | Delatestryl, Primodian Depot | Oil solution | 25–100 mg 1x/4–6 weeks | |
| Testosterone cypionate | Depo-Testosterone, Depo-Testadiol | Oil solution | 25–100 mg 1x/4–6 weeks | |
| Testosterone isobutyratea | Femandren M, Folivirin | Aqueous suspension | 25–50 mg 1x/4–6 weeks | |
| Mixed testosterone esters | Climacterona | Oil solution | 150 mg 1x/4–8 weeks | |
| Omnadren, Sustanon | Oil solution | 50–100 mg 1x/4–6 weeks | ||
| Nandrolone decanoate | Deca-Durabolin | Oil solution | 25–50 mg 1x/6–12 weeks | |
| Prasterone enanthatea | Gynodian Depot | Oil solution | 200 mg 1x/4–6 weeks | |
| Implant | Testosterone | Testopel | Pellet | 50–100 mg 1x/3–6 months |
| Notes:Premenopausal women produce about 230 ± 70 μgtestosterone per day (6.4 ± 2.0 mg testosterone per 4 weeks), with a range of 130 to 330 μg per day (3.6–9.2 mg per 4 weeks).Footnotes:a = Mostly discontinued or unavailable.b =Over-the-counter.Sources: See template. | ||||
| Route | Medication | Form | Dosage | |
|---|---|---|---|---|
| Oral | Methyltestosterone | Tablet | 30–200 mg/day | |
| Fluoxymesterone | Tablet | 10–40 mg 3x/day | ||
| Calusterone | Tablet | 40–80 mg 4x/day | ||
| Normethandrone | Tablet | 40 mg/day | ||
| Buccal | Methyltestosterone | Tablet | 25–100 mg/day | |
| Injection (IMTooltip intramuscular injection orSCTooltip subcutaneous injection) | Testosterone propionate | Oil solution | 50–100 mg 3x/week | |
| Testosterone enanthate | Oil solution | 200–400 mg 1x/2–4 weeks | ||
| Testosterone cypionate | Oil solution | 200–400 mg 1x/2–4 weeks | ||
| Mixed testosterone esters | Oil solution | 250 mg 1x/week | ||
| Methandriol | Aqueous suspension | 100 mg 3x/week | ||
| Androstanolone (DHT) | Aqueous suspension | 300 mg 3x/week | ||
| Drostanolone propionate | Oil solution | 100 mg 1–3x/week | ||
| Metenolone enanthate | Oil solution | 400 mg 3x/week | ||
| Nandrolone decanoate | Oil solution | 50–100 mg 1x/1–3 weeks | ||
| Nandrolone phenylpropionate | Oil solution | 50–100 mg/week | ||
| Note: Dosages are not necessarily equivalent.Sources: See template. | ||||
Nandrolone decanoate has been available in 25 mg/mL, 50 mg/mL, 100 mg/mL, and 200 mg/mL formulations inoil solution forintramuscular injection.[21][3]
Nandrolone decanoate is used forphysique- and performance-enhancing purposes by competitive athletes,bodybuilders, andpowerlifters.[3] It is consumed by bodybuilders as per 8–12 weeks bulking cycles with some form oftestosterone as a base[35] because, according to the studies if consumed solo (i.e., without a base) it shuts down the natural production of testosterone by altering blood–testis barrier components.[36] Despite this fact, nandrolone decanoate is one of the most popular injectable AAS worldwide, and nandrolone esters have been said to be the most popular AAS used by bodybuilders and in sports.[3][17] This is in part due to the high ratio of anabolic to androgenic effect of nandrolone and its weak propensity forandrogenic andestrogenic side effects.[3][37]
Contraindications for nandrolone decanoate includepregnancy,breastfeeding,prostate cancer,male breast cancer,breast cancer in women withhypercalcemia,hypersensitivity (to nandrolone decanoate orexcipients such asarachis (peanut) oil; includes those withpeanut andsoy allergies),nephrosis ornephritis,liver disease with impairedbilirubinexcretion, andheart failure.[6][18] High dosages may also be considered contraindicated in women due to their high potential forvirilization.[3][6]
Theside effects of nandrolone decanoate are dependent ondosage, duration of treatment, andindividual sensitivity.[6][19] A number of common, uncommon, and rare side effects have been observed with the medication at recommended dosages.[6][19] While less common or severe than with many other AAS, the most common side effect of nandrolone decanoate isvirilization (masculinization) in women.[6][19] Uncommon side effects of nandrolone decanoate at recommended dosages includefluid retention, inhibition ofspermatogenesis,testicular atrophy,erectile dysfunction,gynecomastia, increased frequency ofpenile erections, increasedpenis size in pre-pubertal boys,clitoral hypertrophy, increasedpubic hair growth,oligomenorrhea,amenorrhea,hyperlipidemia, decreasedHDL cholesterol, increasedhemoglobin (to abnormal high levels),hypertension,nausea,epididymitis,bladder irritability, reducedurine flow,benign prostatic hyperplasia,priapism, prematureepiphyseal closure (in children), and acne.[6] Rare side effects include abnormalliver function,jaundice,peliosis hepatis,liver tumors,oily skin,greasy hair,rash,pruritus,exanthema,urticaria at the injection site, andfurunculosis.[6] Localinjection site reactions may also occur.[19]
Unlike17α-alkylated AAS such asmethyltestosterone, nandrolone decanoate is not associated withliver toxicity.[3][38]
Nandrolone decanoate causesvirilization as a common side effect in women, includingacne,hoarseness of the voice,hirsutism (excessivefacial/body hair growth), andlibido changes, among others.[6]Clitoral enlargement is an uncommon symptom of virilization that can occur.[6] Virilization is especially prevalent and marked at high dosages of nandrolone decanoate and/or with long-term treatment, and some aspects of virilization likevoice deepening can be irreversible.[6][19][3] Hoarseness is often the first sign of voice changes.[6] Although said to be only slightly androgenic, nandrolone decanoate may still occasionally cause virilization at recommended dosages in women, especially with long-term treatment.[3] A minor though statistically insignificant incidence of virilization has been observed in women treated with nandrolone decanoate short-term at a dosage of 100 mg every 2 weeks for 12 weeks.[3] Conversely, long-term (>1 year) studies have shown significant virilization in women even at a dosage of 50 mg every 2 or 3 weeks.[3]
The acutetoxicity of nandrolone esters in animals is very low and there are no reports of acuteoverdosage with nandrolone decanoate in humans.[2][6] There are no specific recommendations for the management of nandrolone decanoate.[6]
Antiestrogens likearomatase inhibitors (e.g.,anastrozole) andselective estrogen receptor modulators (e.g.,tamoxifen,raloxifene) can interfere with and prevent theestrogenic effects of nandrolone decanoate.[3]5α-Reductase inhibitors likefinasteride anddutasteride can prevent the inactivation of nandrolone in so-called "androgenic"tissues like theskin,hair follicles, andprostate gland, and may therefore considerably increase its androgenic side effects.[3] This is opposite to the case of most other AAS, which are either potentiated by5α-reductase in such tissues or are notsubstrates of 5α-reductase.[3]Antiandrogens likecyproterone acetate,spironolactone, andbicalutamide can block both the anabolic and androgenic effects of AAS like nandrolone decanoate.[20]
| Medication | Ratioa |
|---|---|
| Testosterone | ~1:1 |
| Androstanolone (DHT) | ~1:1 |
| Methyltestosterone | ~1:1 |
| Methandriol | ~1:1 |
| Fluoxymesterone | 1:1–1:15 |
| Metandienone | 1:1–1:8 |
| Drostanolone | 1:3–1:4 |
| Metenolone | 1:2–1:3 |
| Oxymetholone | 1:2–1:9 |
| Oxandrolone | 1:13–1:3 |
| Stanozolol | 1:1–1:3 |
| Nandrolone | 1:3–1:16 |
| Ethylestrenol | 1:2–1:19 |
| Norethandrolone | 1:1–1:2 |
| Notes: In rodents.Footnotes:a = Ratio of androgenic to anabolic activity.Sources: See template. | |
Nandrolone decanoate is anandrolone ester, or aprodrug ofnandrolone.[6][39][3][13] As such, it is anandrogen andanabolic steroid, or anagonist of the AR, thebiological target of androgens like testosterone and DHT.[6][3][13][39] Relative to testosterone, nandrolone decanoate has enhancedanabolic effects and reducedandrogenic effects.[6][39][13] It is considered to have strong anabolic effects but weak androgenic effects, with respectivepotency ratios of 3.29–4.92 and 0.31–0.41 (index value 10.6–12.1 or about an 11:1 ratio ofmyotrophic to androgenic effect) relative totestosterone propionate.[3][13][28] This is defined specifically on the basis of a rodent model in which change in the weights of the ratbulbocavernosus/levator ani muscle ("anabolic" or "myotrophic" activity) and the ratventral prostate orseminal vesicles ("androgenic" activity) are compared with testosterone and then used to form a ratio.[13] Along withoxandrolone (which has a ratio of about 10:1), nandrolone esters are thought to have the highest ratio of anabolic to androgenic effect of any other AAS.[3][27] For this reason, they are considered to be among the most appropriate AAS for use in women and children.[3][14]
Androgenic effects likevirilization are relatively uncommon with nandrolone decanoate at recommended dosages, though may still occur especially at higher dosages or with extended use.[3][6] The low androgenicity of nandrolone decanoate is thought to be due to the fact that whereas many other AAS like testosterone are potentiated viatransformation by5α-reductase into more potent AR agonists like DHT in specifictissues including theskin,hair follicles,prostate gland,liver, andbrain, nandrolone is instead inactivated by 5α-reductase via transformation into the low-affinity AR ligand5α-dihydronandrolone in such tissues.[4][3][13] This is thought to result in a much lower incidence and magnitude offacial/body hair growth,scalp hair loss, and possiblyprostate issues likeprostate enlargement andprostate cancer with nandrolone esters relative to testosterone.[3][27][28]
In addition to its anabolic and androgenic activity, nandrolone decanoate has lowestrogenic activity (via itsmetaboliteestradiol) and moderateprogestogenic activity.[3] This may result in side effects such asfluid retention andgynecomastia.[3] Like other AAS, nandrolone decanoate hasantigonadotropic effects.[3] It has been found to suppress testosterone levels by 57% at a dosage of 100 mg/week and by 70% at a dosage of 300 mg/week in men following 6 weeks of treatment.[3] Both the androgenic activity and the progestogenic activity of nandrolone decanoate may contribute to its antigonadotropic potency.[3] Relative to testosterone, due to its lower estrogenic potency, much less of the antigonadotropic potency of nandrolone decanoate is derived from its estrogenic activity.[3]
| Compound | PRTooltip Progesterone receptor | ARTooltip Androgen receptor | ERTooltip Estrogen receptor | GRTooltip Glucocorticoid receptor | MRTooltip Mineralocorticoid receptor | SHBGTooltip Sex hormone-binding globulin | CBGTooltip Corticosteroid-binding globulin |
|---|---|---|---|---|---|---|---|
| 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 (%). Referenceligands (100%) wereprogesterone for thePRTooltip progesterone receptor,testosterone for theARTooltip androgen receptor,estradiol for theERTooltip estrogen receptor,dexamethasone for theGRTooltip glucocorticoid receptor,aldosterone for theMRTooltip mineralocorticoid receptor,dihydrotestosterone forSHBGTooltip sex hormone-binding globulin, andcortisol forCBGTooltip corticosteroid-binding globulin.Sources: See template. | |||||||
| Compound | rAR(%) | hAR(%) | ||||||
|---|---|---|---|---|---|---|---|---|
| Testosterone | 38 | 38 | ||||||
| 5α-Dihydrotestosterone | 77 | 100 | ||||||
| Nandrolone | 75 | 92 | ||||||
| 5α-Dihydronandrolone | 35 | 50 | ||||||
| Ethylestrenol | ND | 2 | ||||||
| Norethandrolone | ND | 22 | ||||||
| 5α-Dihydronorethandrolone | ND | 14 | ||||||
| Metribolone | 100 | 110 | ||||||
| Sources: See template. | ||||||||
Uponintramuscular injection inoil, which results in the formation of a long-lastingdepot in themuscle, nandrolone decanoate is stored unchanged and is slowlyabsorbed into the body.[4] Once in thecirculation, it is converted intonandrolone, which is the active form of the drug.[2] There is a sharp spike in nandrolone levels 24 to 48 hours after an intramuscular injection of nandrolone decanoate, followed by a steady decline to baseline levels within approximately two or three weeks.[3][6] Thebioavailability of nandrolone decanoate is 53 to 73% with intramuscular injection and varies with the site of injection, with the highest bioavailability seen when injected into thegluteal muscle.[1] Like testosterone, nandrolone is highlyprotein-bound and is present in the blood in both bound and free fractions.[4] It has very lowaffinity forsex hormone-binding globulin (SHBG), about 5% of that of testosterone and 1% of that of DHT.[4][40]
Nandrolone decanoate is rapidlyhydrolyzed in the blood byesterases into nandrolone, with aterminal half-life of one hour or less.[4][2] It does not appear to be hydrolyzed in muscle or fat.[41] Themetabolism of nandrolone occurs in theliver and is very similar to that of testosterone, includingreduction by5α-reductase and5β-reductase,dehydrogenation by3α-hydroxysteroid dehydrogenase,3β-hydroxysteroid dehydrogenase, and17β-hydroxysteroid dehydrogenase, andconjugation.[4] Themetabolites of nandrolone include5α-dihydronandrolone,19-norandrosterone, and19-noretiocholanolone, with 19-norandrosterone being the major metabolite.[4] Other metabolites include19-norandrostenedione, 19-norandrostanediols, 19-norepiandrosterone, andconjugates.[4] Nandrolone also undergoesaromatization intoestradiol similarly to testosterone, though at a rate of only about 20% of that of testosterone or possibly even less; one study found virtually no aromatization of nandrolone in men.[3][17][4][42]
Theelimination half-life of nandrolone decanoate administered byintramuscular injection is approximately 6 to 12 days.[2][3] Studies that have assessed theduration of nandrolone decanoate via its anabolic effects, for instance on nitrogen balance, have found that a single 50 to 100 mg intramuscular injection had a duration of about 18 to 25 days.[43][44] The blood half-life for the combined process of hydrolysis into nandrolone andelimination of nandrolone is 4.3 hours.[2] Nandrolone and its metabolites areexcreted in theurine, mainly in the form of conjugates.[4]
Although nandrolone decanoate is usually administered by intramuscular injection, it has been found to be similarly effective when administered bysubcutaneous injection.[45] Thepharmacokinetics of nandrolone decanoate via subcutaneous injection closely resemble those of intramuscular injection.[45] However, subcutaneous injection is considered to be easier, more convenient, and less painful compared to intramuscular injection.[45] In addition, research suggests that most intramuscular injections in practice are in fact subcutaneous injections.[45]
| 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 | 14–28 days |
| Testosterone cypionate | Oil solution | Depovirin | 14–28 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 | 21–28 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 viai.m. injection.Footnotes:a =TP,TV, andTUe.b =TP andTKL.c =TP,TPP,TiCa, andTD.d = Studied but never marketed.e = Developmental code names.Sources: See template. | |||
Nandrolone decanoate, or nandrolone 17β-decanoate, is asyntheticestranesteroid and aderivative oftestosterone.[8][9] It is anandrogen ester; specifically, it is the C17βdecylate (decanoate)ester ofnandrolone (19-nortestosterone), which itself is the 19-demethylatedanalogue of testosterone.[8][9]
| Anabolic steroid | Structure | Ester | Relative mol. weight | Relative AAS contentb | Durationc | ||||
|---|---|---|---|---|---|---|---|---|---|
| Position | Moiety | Type | Lengtha | ||||||
| Boldenone undecylenate |  | C17β | Undecylenic acid | Straight-chain fatty acid | 11 | 1.58 | 0.63 | Long | |
| Drostanolone propionate |  | C17β | Propanoic acid | Straight-chain fatty acid | 3 | 1.18 | 0.84 | Short | |
| Metenolone acetate |  | C17β | Ethanoic acid | Straight-chain fatty acid | 2 | 1.14 | 0.88 | Short | |
| Metenolone enanthate |  | C17β | Heptanoic acid | Straight-chain fatty acid | 7 | 1.37 | 0.73 | Long | |
| Nandrolone decanoate | | C17β | Decanoic acid | Straight-chain fatty acid | 10 | 1.56 | 0.64 | Long | |
| Nandrolone phenylpropionate |  | C17β | Phenylpropanoic acid | Aromatic fatty acid | – (~6–7) | 1.48 | 0.67 | Long | |
| Trenbolone acetate |  | C17β | Ethanoic acid | Straight-chain fatty acid | 2 | 1.16 | 0.87 | Short | |
| Trenbolone enanthated |  | C17β | Heptanoic acid | Straight-chain fatty acid | 7 | 1.41 | 0.71 | Long | |
| Footnotes:a = Length ofester incarbonatoms forstraight-chain fatty acids or approximate length of ester in carbon atoms foraromatic fatty acids.b = Relative androgen/anabolic steroid content by weight (i.e., relativeandrogenic/anabolicpotency).c =Duration byintramuscular orsubcutaneous injection inoil solution.d = Never marketed.Sources: See individual articles. | |||||||||
Nandrolone decanoate was first described in the literature in 1960.[3] It was developed byOrganon and was introduced for medical use under the brand name Deca-Durabolin in 1962.[3][51] Shortly thereafter it became one of the most widely used AAS in the world.[3] Nandrolone decanoate was the second form of nandrolone to be introduced, having been preceded by nandrolone phenylpropionate in 1959.[51]
Nandrolone decanoate is thegeneric name of the drug and itsUSANTooltip United States Adopted Name andBANTooltip British Approved Name.[8][9][10][11] It has also been referred to asnandrolone decylate.[8][9][10][11]
Nandrolone decanoate is or has been marketed under the brand names Deca-Durabolin, Deca-Durabol, Decaneurabol, Metadec, and Retabolil, among others.[8][9][10][11]
Nandrolone decanoate is available widely throughout the world, including in theUnited Kingdom, otherEuropean countries,Australia,New Zealand,Latin America,Asia, and elsewhere in the world.[9][11][3][16] It has been discontinued inUnited States andCanada.[52][53] Its availability is becoming increasingly limited with time.[3]
Nandrolone decanoate, along with other AAS, is aschedule IIIcontrolled substance in theUnited States under theControlled Substances Act.[54]
Nandrolone decanoate has been studied in the treatment of bone loss in men, but in contrast totestosterone esters, was found to be ineffective.[55][56] In short-term (6- to 8-week) studies in healthy male bodybuilders, nandrolone decanoate did not alter bone mineral density.[57][58][59] However, the short duration of these studies limits conclusions on the influence of nandrolone decanoate on bone in men.[58][59]