Nandrolone

Last updated
Nandrolone
Nandrolone.svg
Nandrolone molecule ball.png
Clinical data
Pronunciation /ˈnændrəloʊn/ [1]
Trade names • Deca-Durabolin (as ND Tooltip nandrolone decanoate)
• Durabolin (as NPP Tooltip 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
Routes of
administration 		• IM injection (esters)
• SC injection (esters)
• Eye drops (NS Tooltip nandrolone sulfate)
Drug class Androgen; Anabolic steroid; Progestogen
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability • Oral: <3% (pigs) [5]
• Intramuscular: high [6]
Metabolism Liver (reduction) [7] [8]
Metabolites • 5α-Dihydronandrolone [7] [9]
• 19-Norandrosterone [7]
• 19-Noretiocholanolone [7]
• Conjugates [8]
Elimination half-life • Nandrolone: <4.3 hours [7]
• ND Tooltip Nandrolone decanoate (IM Tooltip Intramuscular injection): 6–12 days [7] [9] [10]
• NPP Tooltip Nandrolone phenylpropionate: 2.7 days [10]
Duration of action • ND (IM): 2–3 weeks [9] [11]
• NPP (IM): 5–7 days [9] [10]
Excretion Urine [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
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.006.457 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C18H26O2
Molar mass 274.404 g·mol−1
3D model (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 Yes check.svgY
  • Key:NPAGDVCDWIYMMC-IZPLOLCNSA-N Yes check.svgY
   (verify)

Nandrolone, also known as 19-nortestosterone, is an endogenous androgen. It is also an anabolic steroid (AAS) which is medically used in the form of esters such as nandrolone decanoate (brand name Deca-Durabolin) and nandrolone phenylpropionate (brand name Durabolin). [2] [12] [9] [13] Nandrolone esters are used in the treatment of anemias, cachexia (muscle wasting syndrome), osteoporosis, breast cancer, and for other indications. [9] They are now used by oral administration or instead are given by injection into muscle or fat. [9] [13] [14]

Contents

Side effects of nandrolone esters include symptoms of masculinization like acne, increased hair growth, and voice changes. [9] They are synthetic androgens and anabolic steroids and hence are agonists of the androgen receptor (AR), the biological target of androgens like testosterone and dihydrotestosterone (DHT). [9] [15] Nandrolone has strong 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. [9] [15] [16] There are metabolites of Nandrolone that act as long-lasting prodrugs in the body, [9] such as 5α-Dihydronandrolone.

Nandrolone esters were first described and introduced for medical use in the late 1950s. [9] They are among the most widely used anabolic steroid worldwide. [9] 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. [9] [17] The drugs are controlled substances in many countries and so non-medical use is generally illicit. [9]

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 physique- and performance-enhancing purposes by competitive athletes, bodybuilders, and powerlifters. [9]

Side effects

Side effects of nandrolone esters include masculinization among others. [9] In women, nandrolone and nandrolone esters have been reported to produce increased libido, acne, facial and body hair growth, voice changes, and clitoral enlargement. [20] However, the masculinizing effects of nandrolone and its esters are reported to be slighter than those of testosterone. [20] Nandrolone has also been found to produce penile growth in prepubertal boys. [20] Amenorrhea and menorrhagia have been reported as side effects of nandrolone cypionate. [20]

Nandrolone theoretically may produce erectile dysfunction as a side effect, although there is no clinical evidence to support this notion at present. [21] Side effects of high doses of nandrolone may include cardiovascular toxicity as well as hypogonadism and infertility.[ citation needed ] Nandrolone may not produce scalp hair loss, although this is also theoretical. [21]

Pharmacology

Pharmacodynamics

Androgenic vs. anabolic activity ratio
of androgens/anabolic steroids
MedicationRatioa
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
Nandrolone1:3–1:16
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 agonist of the AR, the biological target of androgens like testosterone and DHT Tooltip dihydrotestosterone. Unlike testosterone and certain other anabolic steroids, nandrolone is not potentiated in androgenic tissues like the scalp, skin, and prostate, hence deleterious effects in these tissues are lessened. [22] This is because nandrolone is metabolized by 5α-reductase to the much weaker AR ligand 5α-dihydronandrolone (DHN), which has both reduced 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 progestogen. [24] It binds to the progesterone receptor with approximately 22% of the affinity of progesterone. [24] The progestogenic activity of nandrolone serves to augment its antigonadotropic effects, [25] [9] as antigonadotropic action is a known property of progestogens. [26] [27]

Relative affinities (%) of nandrolone and related steroids
Compound PR Tooltip Progesterone receptor AR Tooltip Androgen receptor ER Tooltip Estrogen receptor GR Tooltip Glucocorticoid receptor MR Tooltip Mineralocorticoid receptor SHBG Tooltip Sex hormone-binding globulin CBG Tooltip Corticosteroid-binding globulin
Nandrolone20154–155<0.10.51.61–160.1
Testosterone 1.0–1.2100<0.10.170.919–823–8
Estradiol 2.67.91000.60.138.7–12<0.1
Notes: Values are percentages (%). Reference ligands (100%) were progesterone for the PR Tooltip progesterone receptor, testosterone for the AR Tooltip androgen receptor, estradiol for the ER Tooltip estrogen receptor, dexamethasone for the GR Tooltip glucocorticoid receptor, aldosterone for the MR Tooltip mineralocorticoid receptor, dihydrotestosterone for SHBG Tooltip sex hormone-binding globulin, and cortisol for 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
CompoundrAR(%)hAR(%)
Testosterone 3838
5α-Dihydrotestosterone 77100
Nandrolone7592
5α-Dihydronandrolone 3550
Ethylestrenol ND2
Norethandrolone ND22
5α-Dihydronorethandrolone ND14
Metribolone 100110
Sources: See template.

Pharmacokinetics

The oral activity of nandrolone has been studied. [28] [29] [30] [31] [5] [32] With oral administration of nandrolone in rodents, it had about one-tenth of the potency of subcutaneous injection of nandrolone. [28] [33] [20]

Nandrolone has very low affinity for human serum sex hormone-binding globulin (SHBG), about 5% of that of testosterone and 1% of that of DHT. [34] It is metabolized by the enzyme 5α-reductase, among others. [35] [ additional citation(s) needed ] Nandrolone is less susceptible to metabolism by 5α-reductase and 17β-hydroxysteroid dehydrogenase than testosterone. [35] This results in it being transformed less in so-called "androgenic" tissues like the skin, hair follicles, and prostate gland and in the kidneys, respectively. [35] Metabolites of nandrolone include 5α-dihydronandrolone, 19-norandrosterone, and 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]

Chemistry

Nandrolone, with the differences from testosterone highlighted in red. The methyl group in testosterone at the C19 position has been removed, and the C17b position is where esters are attached to nandrolone. 19-nortestosterones.svg
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.

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, [43] is a naturally occurring estrane (19-norandrostane) steroid and a derivative of testosterone (androst-4-en-17β-ol-3-one). [2] [12] It is specifically the C19 demethylated (nor) analogue of testosterone. [2] [12] Nandrolone is an endogenous intermediate in the production of estradiol from testosterone via aromatase in mammals including humans and is present in the body naturally in trace amounts. [44] It can be detected during pregnancy in women. [45] Nandrolone esters have an ester such as decanoate or phenylpropionate attached at the C17β position. [2] [12]

Derivatives

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] [9]

Anabolic steroids

Nandrolone is the parent compound of a large group of anabolic steroids. Notable examples include the non-17α-alkylated trenbolone and the 17α-alkylated ethylestrenol (ethylnandrol) and metribolone (R-1881), as well as the 17α-alkylated designer steroids norboletone and tetrahydrogestrinone (THG). The following is list of derivatives of nandrolone that have been developed as anabolic steroids: [9]

Progestins

Nandrolone, together with ethisterone (17α-ethynyltestosterone), is also the parent compound of a large group of 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: alternative: 19-Nortestosterone synthesis.svg
19-Nortestosterone synthesis: alternative:

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 Birch reduction, [51] is typified by the treatment of the monomethyl ether of estradiol (1) with a solution of lithium metal in liquid ammonia in the presence of alcohol as a proton source. Initial reaction constituents of 1,4-dimetalation of the most electron deficient positions of the aromatic ring–in the case of an estrogen, the 1 and 4-positions. Rxn of the intermediate with the proton source leads to a dihydrobenzene; a special virtue of this sequence in steroids is the fact that the double bind at 2 is in effect becomes an enol ether moiety. Treatment of this product (2) with weak acid, oxalic acid for e.g., leads to the hydrolysis of the enol ether, producing β,γ-unconjugated ketone 3. Hydrolysis under more strenuous conditions (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 19-norandrosterone, a metabolite. The International Olympic Committee has set a limit of 2.0 μg/L of 19-norandrosterone in urine as the upper limit, [54] beyond which an 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 athletics occurred in 1999, which included high-profile athletes such as Merlene Ottey, Dieter Baumann, and Linford Christie. [59] However, the following year the detection method for nandrolone at the time was proved to be faulty. 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 lysine (as indicated in the treatment of cold sores) has allegedly shown false positives in some and was cited by American 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. DECA QV 300.jpg
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 generic name of the drug and its INN Tooltip International Nonproprietary Name, BAN Tooltip British Approved Name, DCF Tooltip Dénomination Commune Française, and DCIT Tooltip Denominazione Comune Italiana. [2] [12] [3] [66] The formal generic names of nandrolone esters include nandrolone cyclohexylpropionate (BANM Tooltip British Approved Name), nandrolone cyclotate (USAN Tooltip United States Adopted Name), nandrolone decanoate (USAN Tooltip USAN, USP Tooltip United States Pharmacopeia, BANM Tooltip British Approved Name, JAN Tooltip Japanese Accepted Name), nandrolone laurate (BANM Tooltip British Approved Name), nandrolone phenpropionate (USP Tooltip United States Pharmacopeia), and nandrolone phenylpropionate (BANM Tooltip British Approved Name, JAN Tooltip Japanese Accepted Name). [2] [12] [3] [66]

Doping in sports

Nandrolone was probably among the first anabolic steroids to be used as a doping agent in sports in the 1960s.[ citation needed ] It has been banned at the Olympics since 1974. [18] : 128  There are many known cases of doping in sports with nandrolone esters by professional athletes.

Research

Nandrolone esters have been studied in several indications. They were intensively studied for osteoporosis, and increased calcium uptake and decreased bone loss, but caused virilization in about half of the women who took them and were mostly abandoned for this use when better drugs like the bisphosphonates became available. [21] They have also been studied in clinical trials for chronic kidney failure, aplastic anemia, and as male contraceptives. [18] : 134 

Related Research Articles

<span class="mw-page-title-main">Tetrahydrogestrinone</span> Synthetic and orally active anabolic–androgenic steroid (AAS)

Tetrahydrogestrinone (THG), known by the nickname The Clear, is a synthetic and orally active anabolic–androgenic steroid (AAS) which was never marketed for medical use. It was developed by Patrick Arnold and was used by a number of high-profile athletes such as Barry Bonds and Dwain Chambers.

<span class="mw-page-title-main">Nandrolone decanoate</span> Anabolic steroid

Nandrolone decanoate, sold under the brand names Rolon and Deca-Durabolin, among others, is an androgen and anabolic steroid (AAS) medication which is used primarily in the treatment of anemias and wasting syndromes, as well as osteoporosis in menopausal women. It is given by injection into muscle or fat once every one to four weeks.

<span class="mw-page-title-main">Ethylestrenol</span> Chemical compound

Ethylestrenol, also known as ethyloestrenol or ethylnandrol and sold under the brand names Maxibolin and Orabolin among others, is an androgen and anabolic steroid (AAS) medication which has been used in the past for a variety of indications such as to promote weight gain and to treat anemia and osteoporosis but has been discontinued for use in humans. It is still available for veterinary use in Australia and New Zealand however. It is taken by mouth.

<span class="mw-page-title-main">Norethandrolone</span> Chemical compound

Norethandrolone, sold under the brand names Nilevar and Pronabol among others, is an androgen and anabolic steroid (AAS) medication which has been used to promote muscle growth and to treat severe burns, physical trauma, and aplastic anemia but has mostly been discontinued. It is still available for use in France however. It is taken by mouth.

<span class="mw-page-title-main">Trestolone</span> Chemical compound

Trestolone, also known as 7α-methyl-19-nortestosterone (MENT), is an experimental androgen/anabolic steroid (AAS) and progestogen medication which has been under development for potential use as a form of hormonal birth control for men and in androgen replacement therapy for low testosterone levels in men but has never been marketed for medical use. It is given as an implant that is placed into fat. As trestolone acetate, an androgen ester and prodrug of trestolone, the medication can also be given by injection into muscle.

<span class="mw-page-title-main">Metribolone</span> Chemical compound

Metribolone is a synthetic and orally active anabolic–androgenic steroid (AAS) and a 17α-alkylated nandrolone (19-nortestosterone) derivative which was never marketed for medical use but has been widely used in scientific research as a hot ligand in androgen receptor (AR) ligand binding assays (LBAs) and as a photoaffinity label for the AR. More precisely, metribolone is the 17α-methylated derivative of trenbolone. It was investigated briefly for the treatment of advanced breast cancer in women in the late 1960s and early 1970s, but was found to produce signs of severe hepatotoxicity at very low dosages, and its development was subsequently discontinued.

<span class="mw-page-title-main">Anabolic steroid</span> Steroidal androgen that is structurally related and has similar effects to testosterone

Anabolic steroids, also known as anabolic-androgenic steroids (AAS), are a class of drugs that are structurally related to testosterone, the main male sex hormone, and produce effects by binding to the androgen receptor (AR). Anabolic steroids have a number of medical uses, but are also used by athletes to increase muscle size, strength, and performance.

<span class="mw-page-title-main">Normethandrone</span> Chemical compound

Normethandrone, also known as methylestrenolone or methylnortestosterone and sold under the brand name Metalutin among others, is a progestin and androgen/anabolic steroid (AAS) medication which is used in combination with an estrogen in the treatment of amenorrhea and menopausal symptoms in women. It is taken by mouth.

<span class="mw-page-title-main">Altrenogest</span> Chemical compound

Altrenogest, sold under the brand names Swinemate and Altren manufactured by Aurora Pharmaceutical and Regumate manufactured by Merck, is a progestin of the 19-nortestosterone group which is widely used in veterinary medicine to suppress or synchronize estrus in horses and pigs. It is available for veterinary use in both Europe and the United States.

<span class="mw-page-title-main">Androgen ester</span> Class of chemical compounds

An androgen or anabolic steroid ester is an ester of an androgen/anabolic steroid (AAS) such as the natural testosterone or dihydrotestosterone (DHT) or the synthetic nandrolone (19-nortestosterone). Esterification renders AAS into metabolism-resistant prohormones of themselves, improving oral bioavailability, increasing lipophilicity, and extending the elimination half-life. In addition, with intramuscular injection, AAS esters are absorbed more slowly into the body, further improving the elimination half-life. Aside from differences in pharmacokinetics, these esters essentially have the same effects as the parent drugs. They are used in androgen replacement therapy (ART), among other indications. Examples of androgen esters include testosterone esters such as testosterone cypionate, testosterone enanthate, testosterone propionate, and testosterone undecanoate and nandrolone esters such as nandrolone decanoate and nandrolone phenylpropionate.

<span class="mw-page-title-main">Nandrolone hexyloxyphenylpropionate</span> Chemical compound

Nandrolone hexyloxyphenylpropionate, also known as 19-nortestosterone 17β-(3- phenyl)propionate, is a synthetic androgen and anabolic steroid and a nandrolone ester that is marketed in France, Denmark, Austria, Luxembourg, and Turkey. It has been studied as a potential long-acting injectable male contraceptive, though it has not been marketed for this indication. Approximately 70% of men became azoospermic, while the remaining men all became oligospermic. NHPP has a mean residence time in the body of 29.1 days and an elimination half-life in the body of 20.1 days.

<span class="mw-page-title-main">Nandrolone phenylpropionate</span> Anabolic steroid

Nandrolone phenylpropionate (NPP), or nandrolone phenpropionate, sold under the brand name Durabolin among others, is an androgen and anabolic steroid (AAS) medication which has been used primarily in the treatment of breast cancer and osteoporosis in women. It is given by injection into muscle once every week. Although it was widely used in the past, the drug has mostly been discontinued and hence is now mostly no longer available.

<span class="mw-page-title-main">Dimethandrolone</span> Chemical compound

Dimethandrolone (DMA), also known by its developmental code name CDB-1321, is an experimental androgen/anabolic steroid (AAS) and progestogen medication which is under investigation for potential clinical use.

<span class="mw-page-title-main">Dimethyltrienolone</span> Anabolic–androgenic steroid

Dimethyltrienolone is a synthetic, orally active, and extremely potent anabolic–androgenic steroid (AAS) and 17α-alkylated 19-nortestosterone (nandrolone) derivative which was never marketed for medical use. It has among the highest known affinity of any AAS for the androgen receptors, and has been said to be perhaps the most potent AAS to have ever been developed.

<span class="mw-page-title-main">Boldenone undecylenate</span> Chemical compound

Boldenone undecylenate, or boldenone undecenoate, sold under the brand names Equipoise and Parenabol among others, is an androgen and anabolic steroid (AAS) medication which is used in veterinary medicine, mainly in horses. It was formerly used in humans as well. It is given by injection into muscle.

<span class="mw-page-title-main">11β-Methyl-19-nortestosterone</span> Chemical compound

11β-Methyl-19-nortestosterone (11β-MNT) is a synthetic and orally active anabolic–androgenic steroid (AAS) and a derivative of nandrolone (19-nortestosterone) which was developed by the Contraceptive Development Branch (CDB) of the National Institute of Child Health and Human Development (NICHD) and has not been marketed at this time.

<span class="mw-page-title-main">Structure–activity relationships of anabolic steroids</span>

The structure–activity relationships (SAR) of anabolic steroids (AAS) have been extensively studied.

<span class="mw-page-title-main">Lynestrenol phenylpropionate</span> Chemical compound

Lynestrenol phenylpropionate (LPP), also known as ethynylestrenol phenylpropionate, is a progestin and a progestogen ester which was developed for potential use as a progestogen-only injectable contraceptive by Organon but was never marketed. It was assessed at doses of 25 to 75 mg in an oil solution once a month by intramuscular injection. LPP was associated with high contraceptive failure at the low dose and with poor cycle control. The medication was found to produce estrogenic effects in the endometrium in women due to transformation into estrogenic metabolites.

References

  1. ↑ "Nandrolone Meaning in the Cambridge English Dictionary".
  2. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 Elks J, Ganellin CR, eds. (2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. New York City: Springer. pp. 660–. ISBN   978-1-4757-2085-3. OCLC   1079003025.
  3. 1 2 3 4 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.
  4. ↑ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-15.
  5. 1 2 McEvoy JD, McVeigh CE, McCaughey WJ (December 1998). "Residues of nortestosterone esters at injection sites. Part 1. Oral bioavailability". The Analyst. 123 (12): 2475–8. doi:10.1039/a804919j. PMID   10435281.
  6. ↑ Becker KL (2001). Principles and Practice of Endocrinology and Metabolism. Lippincott Williams & Wilkins. pp. 1185–. ISBN   978-0-7817-1750-2.
  7. 1 2 3 4 5 6 7 "Deca-Durabolin" (PDF). Schering-Plough. Archived from the original (PDF) on 18 December 2010.
  8. 1 2 Thomas JA (6 December 2012). Drugs, Athletes, and Physical Performance. Springer Science & Business Media. pp. 27–29. ISBN   978-1-4684-5499-4.
  9. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 Llewellyn W (2011). Anabolics. Molecular Nutrition Llc. pp. 402–412, 460–467, 193–194. ISBN   978-0-9828280-1-4.
  10. 1 2 3 Minto CF, Howe C, Wishart S, Conway AJ, Handelsman DJ (April 1997). "Pharmacokinetics and pharmacodynamics of nandrolone esters in oil vehicle: effects of ester, injection site and injection volume". The Journal of Pharmacology and Experimental Therapeutics. 281 (1): 93–102. PMID   9103484.
  11. ↑ "Deca-Durabolin" (PDF). Merck Sharp & Dohme (Australia).
  12. 1 2 3 4 5 6 7 8 9 Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 716–. ISBN   978-3-88763-075-1.
  13. 1 2 Sneader W (23 June 2005). Drug Discovery: A History. John Wiley & Sons. pp. 206–. ISBN   978-0-471-89979-2.
  14. ↑ Singh GK, Turner L, Desai R, Jimenez M, Handelsman DJ (July 2014). "Pharmacokinetic-pharmacodynamic study of subcutaneous injection of depot nandrolone decanoate using dried blood spots sampling coupled with ultrapressure liquid chromatography tandem mass spectrometry assays". The Journal of Clinical Endocrinology and Metabolism. 99 (7): 2592–8. doi: 10.1210/jc.2014-1243 . PMID   24684468.
  15. 1 2 3 4 5 Kicman AT (June 2008). "Pharmacology of anabolic steroids". British Journal of Pharmacology. 154 (3): 502–21. doi:10.1038/bjp.2008.165. PMC   2439524 . PMID   18500378.
  16. ↑ Kochakian CD (6 December 2012). Anabolic-Androgenic Steroids. Springer Science & Business Media. pp. 401–. ISBN   978-3-642-66353-6.
  17. ↑ Jameson JL, De Groot LJ (25 February 2015). Endocrinology: Adult and Pediatric E-Book. Elsevier Health Sciences. pp. 2388–. ISBN   978-0-323-32195-2.
  18. 1 2 3 4 Hemmersbach P, Große J (2009). "Nandrolone: A Multi-Faceted Doping Agent". In Thieme D, Hemmersbach P (eds.). Doping in sports. Berlin: Springer. pp. 127–154. ISBN   978-3-540-79088-4.
  19. ↑ Handelsman DJ (2013). "Androgen Physiology, Pharmacology and Abuse". In De Groot LJ (ed.). Endotext. MDText.com. 4.1.2 Pharmacologic Androgen Therapy. PMID   25905160 – via NCBI Bookshelf. Both testosterone and its non-aromatizable derivative nandrolone, produce increased bone density in men with glucocorticoid-induced osteoporosis with minimal short-term side-effects....
  20. 1 2 3 4 5 6 Camerino B, Sala G (1960). "Anabolic Steroids". Fortschritte der Arzneimittelforschung / Progress in Drug Research / Progrès des recherches pharmaceutiques. Vol. 2. pp. 71–134. doi:10.1007/978-3-0348-7038-2_2. ISBN   978-3-0348-7040-5. PMID   14448579.{{cite book}}: |journal= ignored (help)
  21. 1 2 3 Pan MM, Kovac JR (April 2016). "Beyond testosterone cypionate: evidence behind the use of nandrolone in male health and wellness". Translational Andrology and Urology. 5 (2): 213–9. doi: 10.21037/tau.2016.03.03 . PMC   4837307 . PMID   27141449.
  22. 1 2 Bergink EW, Janssen PS, Turpijn EW, van der Vies J (June 1985). "Comparison of the receptor binding properties of nandrolone and testosterone under in vitro and in vivo conditions". Journal of Steroid Biochemistry. 22 (6): 831–6. doi:10.1016/0022-4731(85)90293-6. PMID   4021486.
  23. ↑ Brueggemeier RW (September 16, 2006). "Sex Hormones (Male): Analogs and Antagonists". In Meyers RA (ed.). Encyclopedia of Molecular Cell Biology and Molecular Medicine (abstract). John Wiley & Sons. doi:10.1002/3527600906.mcb.200500066. ISBN   978-3527600908.
  24. 1 2 Kuhl H (August 2005). "Pharmacology of estrogens and progestogens: influence of different routes of administration". Climacteric. 8 (Suppl 1): 3–63. doi:10.1080/13697130500148875. PMID   16112947. S2CID   24616324.
  25. 1 2 3 de Souza GL, Hallak J (December 2011). "Anabolic steroids and male infertility: a comprehensive review". BJU International. 108 (11): 1860–5. doi: 10.1111/j.1464-410X.2011.10131.x . PMID   21682835. S2CID   29035729.
  26. ↑ Couzinet B, Young J, Brailly S, Chanson P, Thomas JL, Schaison G (December 1996). "The antigonadotropic activity of progestins (19-nortestosterone and 19-norprogesterone derivatives) is not mediated through the androgen receptor". The Journal of Clinical Endocrinology and Metabolism. 81 (12): 4218–23. doi: 10.1210/jcem.81.12.8954018 . PMID   8954018.
  27. ↑ Mauvais-Jarvis, P. "Progesterone and progestins: a general overview." (1983): 1-16.
  28. 1 2 Camerino B, Sciaky R (1975). "Structure and effects of anabolic steroids". Pharmacology & Therapeutics B. 1 (2): 233–75. doi:10.1016/0306-039X(75)90007-0. PMID   817322.
  29. ↑ Holtkamp DE, Heming AE, Mansor LF (1955). "Comparison of Oral and Subcutaneous Administration in the Anabolic and Androgenic Effectiveness of 19-Nortestosterone and Testosterone". The Journal of Clinical Endocrinology & Metabolism. 15 (7): 848. doi: 10.1210/jcem-15-7-834 . ISSN   0021-972X.
  30. ↑ Furman RH, Howard RP, Smith CW, Norcia LN (January 1956). "Comparison of the effects of oral methyltestosterone, 19-nortestosterone, and 17-methyl-19-nortestosterone on serum lipids and lipoproteins". Journal of Laboratory and Clinical Medicine. 48 (5): 808–809.
  31. ↑ Furman RH, Howard RP, Norcia LN, Keaty EC (January 1958). "The influence of androgens, estrogens and related steroids on serum lipids and lipoproteins". The American Journal of Medicine. 24 (1): 80–97. doi:10.1016/0002-9343(58)90364-4. PMID   13498038.
  32. ↑ Arnold A, Potts GO (January 1964). "Oral anabolic and androgenic effects of 19-nortestosterone and 17α-methyl-19-nortestosterone". Federation Proceedings. 23 (2): 412.
  33. 1 2 Baker WH, Henneman PH, Baggett B, Engel LL, Tibbetts D, Brown M (January 1955). "Metabolic effect of 19-nortestosterone". Journal of Clinical Endocrinology & Metabolism. 15 (7): 848–849. doi: 10.1210/jcem-15-7-834 . ISSN   0021-972X.
  34. ↑ Saartok T, Dahlberg E, Gustafsson JA (June 1984). "Relative binding affinity of anabolic-androgenic steroids: comparison of the binding to the androgen receptors in skeletal muscle and in prostate, as well as to sex hormone-binding globulin". Endocrinology. 114 (6): 2100–6. doi:10.1210/endo-114-6-2100. PMID   6539197.
  35. 1 2 3 Bergink EW, Geelen JA, Turpijn EW (1985). "Metabolism and receptor binding of nandrolone and testosterone under in vitro and in vivo conditions". Acta Endocrinologica. Supplementum. 271 (3_Suppla): 31–7. doi:10.1530/acta.0.109S0031. PMID   3865479.
  36. ↑ Mottram DR (12 November 2010). Drugs in Sport. Routledge. pp. 63–. ISBN   978-1-135-25825-2.
  37. ↑ Dorfman RI (5 December 2016). Steroidal Activity in Experimental Animals and Man. Elsevier Science. pp. 68–. ISBN   978-1-4832-7300-6.
  38. ↑ Bagchus WM, Smeets JM, Verheul HA, De Jager-Van Der Veen SM, Port A, Geurts TB (2005). "Pharmacokinetic evaluation of three different intramuscular doses of nandrolone decanoate: analysis of serum and urine samples in healthy men". J. Clin. Endocrinol. Metab. 90 (5): 2624–30. doi:10.1210/jc.2004-1526. PMID   15713722.
  39. ↑ Minto CF, Howe C, Wishart S, Conway AJ, Handelsman DJ (1997). "Pharmacokinetics and pharmacodynamics of nandrolone esters in oil vehicle: effects of ester, injection site and injection volume". J. Pharmacol. Exp. Ther. 281 (1): 93–102. PMID   9103484.
  40. ↑ Belkien L, Schürmeyer T, Hano R, Gunnarsson PO, Nieschlag E (May 1985). "Pharmacokinetics of 19-nortestosterone esters in normal men". J. Steroid Biochem. 22 (5): 623–9. doi:10.1016/0022-4731(85)90215-8. PMID   4010287.
  41. ↑ Kalicharan RW, Schot P, Vromans H (February 2016). "Fundamental understanding of drug absorption from a parenteral oil depot". Eur J Pharm Sci. 83: 19–27. doi:10.1016/j.ejps.2015.12.011. PMID   26690043.
  42. ↑ Kalicharan, Raween Wikesh (2017). New Insights into Drug Absorption from Oil Depots (PhD). Utrecht University.
  43. 1 2 Schnitzer R (1 January 1967). Experimental Chemotherapy. Elsevier Science. pp. 165–. ISBN   978-0-323-14611-1.
  44. ↑ Bricout V, Wright F (June 2004). "Update on nandrolone and norsteroids: how endogenous or xenobiotic are these substances?". European Journal of Applied Physiology. 92 (1–2): 1–12. doi:10.1007/s00421-004-1051-3. PMID   15042372. S2CID   6472015.
  45. ↑ Lippi G, Franchini M, Banfi G (May 2011). "Biochemistry and physiology of anabolic androgenic steroids doping". Mini Reviews in Medicinal Chemistry. 11 (5): 362–73. doi:10.2174/138955711795445952. PMID   21443514. S2CID   3862299.
  46. 1 2 3 Schindler AE, Campagnoli C, Druckmann R, Huber J, Pasqualini JR, Schweppe KW, Thijssen JH (December 2003). "Classification and pharmacology of progestins". Maturitas. 46 (Suppl 1): S7–S16. doi:10.1016/j.maturitas.2003.09.014. PMID   14670641.
  47. ↑ Meikle AW (24 April 2003). Endocrine Replacement Therapy in Clinical Practice. Springer Science & Business Media. pp. 489–. ISBN   978-1-59259-375-0. Estranes. Estrane and gonane progestogens are derived from 19-nortestosterone, the progestogenic parent compound used in oral contraceptives in the United States. Estranes are characterized by the presence of an ethinyl group at position 17 and by the absence of a methyl group between the A and B rings (see Fig. 10). The estrane progestogens that are related structurally to norethindrone (norethynodrel, lynestrenol, norethindrone acetate, ethynodiol diacetate) are converted to this parent compound. Norethindrone is the second most commonly used progestogen in the United States for HRT. Gonanes. The gonanes share the structural modifications found in the estranes and also possess an ethinyl group at position 13 and a keto group at position 3 (see Fig. 11). Norgestrel was synthesized in 1963 and is a racemic mixture of dextro and levorotatory forms. The levorotatory form, levonorgestrel, provides the biologic activity. Third-generation gonanes (desogestrel, gestodene, and norgestimate) have been developed to reduce unwanted side effects of progestogens, [...]
  48. ↑ Wilds AL, Nelson NA (1953). "The Facile Synthesis of 19-Nortestosterone and 19-Norandrostenedione from Estrone". Journal of the American Chemical Society. 75 (21): 5366–5369. doi:10.1021/ja01117a065.
  49. ↑ Ueberwasser H, Heusler K, Kalvoda J, Meystre CH, Wieland P, Anner G, Wettstein A (1963). "19-Norsteroide II. Ein einfaches Herstellungsverfahren für 19-Norandrostan-Derivate. Über Steroide, 193. Mitteilung". Helvetica Chimica Acta. 46: 344–352. doi:10.1002/hlca.19630460135.
  50. ↑ Shimizu I, Naito Y, Tsuji J (1980). "Synthesis of optically active (+)-19-nortestosterone by asymmetric bis-annulation reaction". Tetrahedron Letters. 21 (5): 487–490. doi:10.1016/S0040-4039(00)71440-7.
  51. ↑ Birch AJ (1950). "The reduction of organic compounds by metal-ammonia solutions". Quarterly Reviews, Chemical Society. 4: 69. doi:10.1039/QR9500400069.
  52. ↑ US 2998423,DeWytt ED, Overbeek O, Overbeek GA,issued 1961, assigned to Organon .
  53. ↑ CH 206119,issued 1939, assigned to Gesellschaft für Chemische Industrie Basel
  54. ↑ "Clarification about Nandrolone Testing". World Anti-Doping Agency. 2005-05-30. Archived from the original on 2012-09-15. Retrieved 2012-01-31.
  55. ↑ Bresson M, Cirimele V, Villain M, Kintz P (May 2006). "Doping control for metandienone using hair analyzed by gas chromatography-tandem mass spectrometry". Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences. 836 (1–2): 124–8. doi:10.1016/j.jchromb.2006.03.040. PMID   16597518.
  56. ↑ Ueki M, Ikekita A, Takao Y (2000). "[Nandrolone metabolite in urine of Nagano Olympic athlete]". Jap. J. For. Tox. (in Japanese). 18: 198–199.
  57. ↑ Catlin DH, Leder BZ, Ahrens B, Starcevic B, Hatton CK, Green GA, Finkelstein JS (2000). "Trace contamination of over-the-counter androstenedione and positive urine test results for a nandrolone metabolite". JAMA. 284 (20): 2618–21. doi: 10.1001/jama.284.20.2618 . PMID   11086369.
  58. ↑ Baselt RC (2008). Disposition of Toxic Drugs and Chemicals in Man (8th ed.). Foster City, CA: Biomedical Publications. pp. 1078–1080. ISBN   978-0-9626523-7-0. Archived from the original on 2020-12-04. Retrieved 2010-08-19.
  59. ↑ Baron P (19 September 2000). "The Drugs Issue: Baumann to fight all the way" . The Telegraph. Retrieved 2010-11-13.
  60. ↑ Richardson M (2004-02-19). "Athletics: Mark Richardson explains how he felt at his disciplinary hearing". The Guardian . Retrieved 2010-11-13.
  61. ↑ "Track Star Marion Jones to Admit Steroid Use". National Public Radio. 2007-10-05. Retrieved 2009-11-09.
  62. ↑ UK Sport Anti-doping Directorate (January 2000). Nandrolone Review (PDF) (Report). UK Sport. Archived from the original (PDF) on 2005-04-04. Retrieved 2013-02-02.
  63. ↑ Buiarelli F, Giannetti L, Jasionowska R, Cruciani C, Neri B (July 2010). "Determination of nandrolone metabolites in human urine: comparison between liquid chromatography/tandem mass spectrometry and gas chromatography/mass spectrometry". Rapid Communications in Mass Spectrometry. 24 (13): 1881–1894. Bibcode:2010RCMS...24.1881B. doi: 10.1002/rcm.4583 . PMID   20533318.
  64. ↑ Birch AJ (1950). "80. Hydroaromatic steroid hormones. Part I. 10-Nortestosterone". Journal of the Chemical Society (Resumed): 367. doi:10.1039/jr9500000367. ISSN   0368-1769.
  65. ↑ Consolidated List of Products Whose Consumption And/or Sale Have Been Banned, Withdrawn, Severely Restricted Or Not Approved by Governments. United Nations Publications. 1983. pp. 154–. ISBN   978-92-1-130230-1.[ permanent dead link ]
  66. 1 2 "Nandrolone".

Further reading

This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.