Nandrolone

Source: Wikipedia, the free encyclopedia.
Nandrolone
Clinical data
Pronunciation/ˈnændrəloʊn/[1]
Trade names• Deca-Durabolin (as NDTooltip nandrolone decanoate)
• Durabolin (as NPPTooltip nandrolone phenylpropionate)
• Many others (see here)
Other names• 19-Nortestosterone[2][3]
• 10-Nortestosterone
• Estr-4-en-17β-ol-3-one
• Estrenolone
• Oestrenolone
• 19-Norandrost-4-en-17β-ol-3-one
• Norandrostenolone[2]
• Nortestrionate[2]
• Nortestonate[2]
• Norandroone
• SG-4341[2][3]
Pregnancy
category
  • AU: D
esters)
• Eye drops (NSTooltip nandrolone sulfate)
Drug classAndrogen; Anabolic steroid; Progestogen
ATC code
Legal status
Legal status
Conjugates[9]
Elimination half-life• Nandrolone: <4.3 hours[7]
• NDTooltip Nandrolone decanoate (IMTooltip Intramuscular injection): 6–12 days[7][8][10]
• NPPTooltip Nandrolone phenylpropionate: 2.7 days[10]
Duration of action• ND (IM): 2–3 weeks[8][11]
• NPP (IM): 5–7 days[8][10]
ExcretionUrine[7]
Identifiers
  • (8R,9S,10R,13S,14S,17S)-17-hydroxy-13-methyl-2,6,7,8,9,10,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-one
JSmol)
  • O=C4\C=C2/[C@@H]([C@H]1CC[C@@]3([C@@H](O)CC[C@H]3[C@@H]1CC2)C)CC4
  • InChI=1S/C18H26O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h10,13-17,20H,2-9H2,1H3/t13-,14+,15+,16-,17-,18-/m0/s1 checkY
  • Key:NPAGDVCDWIYMMC-IZPLOLCNSA-N checkY
  (verify)

Nandrolone, also known as 19-nortestosterone, is an

fat.[8][13][14]

anabolic effects and weak androgenic effects, which give them a mild side effect profile and make them especially suitable for use in women and children.[8][15][16] There are metabolites of Nandrolone that act as long-lasting prodrugs in the body,[8] such as 5α-Dihydronandrolone
.

Nandrolone esters were first described and introduced for medical use in the late 1950s.[8] They are among the most widely used anabolic steroid worldwide.[8] In addition to their medical use, nandrolone esters are used to improve physique and performance, and are said to be the most widely used anabolic steroid for such purposes.[8][17] The drugs are controlled substances in many countries and so non-medical use is generally illicit.[8]

Medical uses

Nandrolone esters are used clinically, although increasingly rarely, for people in catabolic states with major burns, cancer, and AIDS, and an ophthalmological formulation was available to support cornea healing.[18]: 134 

The positive effects of nandrolone esters include muscle growth, appetite stimulation and increased red blood cell production,[medical citation needed] and bone density.[19] Clinical studies have shown them to be effective in treating anemia, osteoporosis, and breast cancer.

Nandrolone sulfate has been used in an eye drop formulation as an ophthalmic medication.[2][12]

Non-medical uses

Nandrolone esters are used for

powerlifters.[8]

Side effects

See also: Anabolic steroid § Adverse effects

menorrhagia have been reported as side effects of nandrolone cypionate.[20]

Nandrolone theoretically may produce

scalp hair loss, although this is also theoretical.[21]

Pharmacology

Pharmacodynamics

Androgenic vs. anabolic activity ratio
of androgens/anabolic steroids
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 1:2–1:30
Oxymetholone 1:2–1:9
Oxandrolone 1:3–1:13
Stanozolol 1:1–1:30
Nandrolone 1:3–1:16
Ethylestrenol 1:2–1:19
Norethandrolone 1:1–1:20
Notes: In rodents. Footnotes: a = Ratio of androgenic to anabolic activity. Sources: See template.

Nandrolone is an

affinity for the androgen receptor (AR) relative to nandrolone in vitro and weaker AR agonistic potency in vivo.[22] The lack of alkylation on the 17α-carbon drastically reduces the hepatotoxic potential of nandrolone.[medical citation needed] Estrogen effects resulting from reaction with aromatase are also reduced due to lessened enzyme interaction,[23] but effects such as gynecomastia and reduced libido may still occur at sufficiently high doses.[citation needed
]

In addition to its AR agonistic activity, unlike many other anabolic steroids, nandrolone is also a potent

antigonadotropic effects,[25][8] as antigonadotropic action is a known property of progestogens.[26][27]

Relative affinities (%) of nandrolone and related steroids
Compound PRTooltip Progesterone receptor ARTooltip Androgen receptor ERTooltip Estrogen receptor GRTooltip Glucocorticoid receptor MRTooltip Mineralocorticoid receptor SHBGTooltip Sex hormone-binding globulin
CBG
Tooltip 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 (%). Reference
CBG
Tooltip corticosteroid-binding globulin. Sources: See template.

Anabolic and androgenic activity

Nandrolone has a very high ratio of anabolic to androgenic activity.[15] In fact, many nandrolone-like anabolic steroids and even nandrolone itself are said to have among the highest ratio of anabolic to androgenic effect of all anabolic steroids.[25] This is attributed to the fact that whereas testosterone is potentiated via conversion into dihydrotestosterone (DHT) in androgenic tissues, the opposite is true with nandrolone and similar anabolic steroids (i.e., other 19-nortestosterone derivatives).[15] As such, nandrolone-like anabolic steroids, namely nandrolone esters, are the most frequently used anabolic steroids in clinical settings in which anabolic effects are desired; for instance, in the treatment of AIDS-associated cachexia, severe burns, and chronic obstructive pulmonary disease.[25] However, anabolic steroids with a very high ratio of anabolic to androgenic action like nandrolone still have significant androgenic effects and can produce symptoms of masculinization like hirsutism and voice deepening in women and children with extended use.[15]

Relative affinities of nandrolone and related steroids at the androgen receptor
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.

Pharmacokinetics

The

subcutaneous injection of nandrolone.[28][33][20]

Nandrolone has very low

19-noretiocholanolone, and these metabolites may be detected in urine.[36]

Single intramuscular injections of 100 mg nandrolone phenylpropionate or nandrolone decanoate have been found to produce an anabolic effect for 10 to 14 days and 20 to 25 days, respectively.[37] Conversely, unesterified nandrolone has been used by intramuscular injection once daily.[20][33]

Hormone levels with nandrolone esters by intramuscular injection

Chemistry

Nandrolone, with the differences from testosterone highlighted in red. The methyl group in testosterone at the C19 position has been removed, and the C17β position is where esters are attached to nandrolone.
See also:
List of androgens/anabolic steroids

Nandrolone, also known as 19-nortestosterone (19-NT) or as estrenolone, as well as estra-4-en-17β-ol-3-one or 19-norandrost-4-en-17β-ol-3-one,

phenylpropionate attached at the C17β position.[2][12]

Derivatives

Esters

See also: List of androgen esters § Nandrolone esters

A variety of esters of nandrolone have been marketed and used medically.[2][12] The most commonly used esters are nandrolone decanoate and to a lesser extent nandrolone phenylpropionate. Examples of other nandrolone esters that have been marketed and used medically include nandrolone cyclohexylpropionate, nandrolone cypionate, nandrolone hexyloxyphenylpropionate, nandrolone laurate, nandrolone sulfate, and nandrolone undecanoate.[2][12][8]

Anabolic steroids

See also:
List of androgens/anabolic steroids and List of androgen esters § Esters of synthetic anabolic steroids

Nandrolone is the parent compound of a large group of anabolic steroids. Notable examples include the non-17α-alkylated

designer steroids norboletone and tetrahydrogestrinone (THG). The following is list of derivatives of nandrolone that have been developed as anabolic steroids:[8]

Progestins

See also: List of progestogens § Testosterone derivatives

Nandrolone, together with

progestins, the norethisterone (17α-ethynyl-19-nortestosterone) derivatives.[46][47] This family is subdivided into two groups: the estranes and the gonanes.[46] The estranes include norethisterone (norethindrone), norethisterone acetate, norethisterone enanthate, lynestrenol, etynodiol diacetate, and noretynodrel, while the gonanes include norgestrel, levonorgestrel, desogestrel, etonogestrel, gestodene, norgestimate, dienogest (actually a 17α-cyanomethyl-19-nortestosterone derivative), and norelgestromin.[46]

Synthesis

19-Nortestosterone synthesis:[48] alternative:[49][50]

The elaboration of a method for the reduction of aromatic rings to the corresponding dihydrobenzenes under controlled conditions by A. J. Birch opened a convenient route to compounds related to the putative

19-norprogesterone
.

This reaction, now known as the

mineral acids
) results in migration/conjugation of the olefin to yield nandrolone (4).

Esters

  • Treatment of 4 with decanoic anhydride and pyridine affords nandrolone decanoate.[52]
  • Acylation of 4 with phenylpropionyl chloride yields nandrolone phenpropionate.[53]

Detection in body fluids

Nandrolone use is directly detectable in hair or indirectly detectable in urine by testing for the presence of

athlete is suspected of doping. In the largest nandrolone study performed on 621 athletes at the 1998 Nagano Olympic Games, no athlete tested over 0.4 μg/L. 19-Norandrosterone was identified as a trace contaminant in commercial preparations of androstenedione, which until 2004 was available without a prescription as a dietary supplement in the U.S.[55][56][57][58]

A number of nandrolone cases in

Mark Richardson, a British Olympic relay runner who tested positive for the substance, gave a significant amount of urine samples in a controlled environment and delivered a positive test for the drug, demonstrating that false positives could occur, which led to an overhaul of his competitive ban.[60]

Heavy consumption of the essential amino acid

shotputter C. J. Hunter as the reason for his positive test, though in 2004 he admitted to a federal grand jury that he had injected nandrolone.[61] A possible cause of incorrect urine test results is the presence of metabolites from other anabolic steroids, though modern urinalysis can usually determine the exact anabolic steroid used by analyzing the ratio of the two remaining nandrolone metabolites. As a result of the numerous overturned verdicts, the testing procedure was reviewed by UK Sport. In October 2007, three-time Olympic gold medalist for track and field Marion Jones admitted to use of the drug, and was sentenced to six months in jail for lying to a federal grand jury in 2000.[62]

Mass spectrometry is also used to detect small amounts of nandrolone in urine samples.[63]

History

QV Nandrolone Deca, a form of nandrolone used by athletes.

Nandrolone was first synthesized in 1950.[2][43][18]: 130 [64] It was first introduced, as nandrolone phenylpropionate, in 1959, and then as nandrolone decanoate in 1962, followed by additional esters.[65]

Society and culture

Generic names

Nandrolone is the

nandrolone phenpropionate (USPTooltip United States Pharmacopeia), and nandrolone phenylpropionate (BANMTooltip British Approved Name, JANTooltip Japanese Accepted Name).[2][12][3][66]

Doping in sports

See also:
List of doping in sport cases § Nandrolone esters

Nandrolone was probably among the first anabolic steroids to be used as a doping agent in sports in the 1960s.[

doping in sports with nandrolone esters by professional athletes
.

Research

Nandrolone esters have been studied in several indications. They were intensively studied for

chronic kidney failure, aplastic anemia, and as male contraceptives.[18]
: 134 

References

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Further reading