Nandrolone phenylpropionate

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Nandrolone phenylpropionate
Nandrolone phenylpropionate.svg
Nandrolone phenylpropionate molecule ball.png
Clinical data
Trade names Durabolin, others
Other names• NPP
• Nandrolone phenpropionate
• 19-Nortestosterone phenylpropionate
• Nandrolone hydrocinnamate
• 19-Nortestosterone 17β-phenylpropionate
• NSC-23162
Pregnancy
category
  • AU:D
Routes of
administration
Intramuscular injection
Drug class Androgen; Anabolic steroid; Androgen ester; Progestogen
Legal status
Legal status
Pharmacokinetic data
Bioavailability Oral: 0.3–2.9% (pigs) [1]
Intramuscular: high [2]
Metabolism Blood (hydrolysis), liver (reduction) [3] [4]
Metabolites Nandrolone [5]
5α-Dihydronandrolone [5]
19-Norandrosterone [6]
19-Noretiocholanolone [6]
Conjugates [4]
Elimination half-life • Intramuscular: 2.7 days [7]
• Nandrolone: <4.3 hours [3]
Duration of action • Intramuscular: 5–7 days [5] [7]
Excretion Urine [3]
Identifiers
  • [(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] 3-phenylpropanoate
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard 100.000.502 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C27H34O3
Molar mass 406.566 g·mol−1
3D model (JSmol)
  • C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2OC(=O)CCC4=CC=CC=C4)CCC5=CC(=O)CC[C@H]35
  • InChI=1S/C27H34O3/c1-27-16-15-22-21-11-9-20(28)17-19(21)8-10-23(22)24(27)12-13-25(27)30-26(29)14-7-18-5-3-2-4-6-18/h2-6,17,21-25H,7-16H2,1H3/t21-,22+,23+,24-,25-,27-/m0/s1
  • Key:UBWXUGDQUBIEIZ-QNTYDACNSA-N

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. [8] [9] [10] [11] [5] It is given by injection into muscle once every week. [5] Although it was widely used in the past, the drug has mostly been discontinued and hence is now mostly no longer available. [5] [11]

Contents

Side effects of NPP include symptoms of masculinization like acne, increased hair growth, voice changes, and increased sexual desire. [5] The drug is a synthetic androgen and anabolic steroid and hence is an agonist of the androgen receptor (AR), the biological target of androgens like testosterone and dihydrotestosterone (DHT). [5] [12] It has strong anabolic effects and weak androgenic effects, which give it a mild side effect profile and make it especially suitable for use in women and children. [5] [12] [13] NPP is a nandrolone ester and a long-lasting prodrug of nandrolone in the body. [5]

NPP was first described in 1957 and was introduced for medical use in 1959. [5] It was the first nandrolone ester to be introduced, followed by nandrolone decanoate in 1962, and has been one of the most widely used nandrolone esters. [5] [14] However, in more recent times, the drug has been largely superseded by nandrolone decanoate, which is longer-acting and more convenient to use. [5] [11] In addition to its medical use, NPP is used to improve physique and performance. [5] The drug is a controlled substance in many countries and so non-medical use is generally illicit. [5]

Medical uses

NPP has been used mainly in the treatment of advanced breast cancer in women and as an adjunct therapy for the treatment of senile or postmenopausal osteoporosis in women. [5] Historically, it has also had a variety of other uses. [5] Because of its reduced androgenic effects, the drug has not generally been used in androgen replacement therapy for androgen deficiency in men and has instead been used for solely for anabolic indications. [2] [15] However, nandrolone esters have more recently been proposed for the treatment of androgen deficiency in men due to favorable properties including their high ratio of anabolic to androgenic effects and consequent much lower risk of prostate enlargement, prostate cancer, and scalp hair loss relative to testosterone. [16] [17]

Androgen/anabolic steroid dosages for breast cancer
RouteMedicationFormDosage
Oral Methyltestosterone Tablet30–200 mg/day
Fluoxymesterone Tablet10–40 mg 3x/day
Calusterone Tablet40–80 mg 4x/day
Normethandrone Tablet40 mg/day
Buccal Methyltestosterone Tablet25–100 mg/day
Injection (IM Tooltip intramuscular injection or SC Tooltip subcutaneous injection) Testosterone propionate Oil solution50–100 mg 3x/week
Testosterone enanthate Oil solution200–400 mg 1x/2–4 weeks
Testosterone cypionate Oil solution200–400 mg 1x/2–4 weeks
Mixed testosterone esters Oil solution250 mg 1x/week
Methandriol Aqueous suspension100 mg 3x/week
Androstanolone (DHT) Aqueous suspension300 mg 3x/week
Drostanolone propionate Oil solution100 mg 1–3x/week
Metenolone enanthate Oil solution400 mg 3x/week
Nandrolone decanoate Oil solution50–100 mg 1x/1–3 weeks
Nandrolone phenylpropionateOil solution50–100 mg/week
Note: Dosages are not necessarily equivalent. Sources: See template.

Available forms

NPP is or has been available 25 mg/mL and 50 mg/mL formulations in oil solution for intramuscular injection. [5]

Non-medical uses

NPP is used for physique- and performance-enhancing purposes by competitive athletes, bodybuilders, and powerlifters. [5] Nandrolone esters have been said to be the most popular AAS used by bodybuilders and in sports. [5] [18] This is in part due to the high ratio of anabolic to androgenic effect of nandrolone and its weak propensity for androgenic and estrogenic side effects. [5]

Side effects

The most common side effects of NPP consist of virilization (masculinization) in women, including symptoms such as acne, hirsutism (increased body/facial hair growth), hoarseness of the voice, and voice deepening. [5] However, relative to most other AAS, NPP has a greatly reduced propensity for virilization and such side effects are relatively uncommon at recommended dosages. [5] At higher dosages and/or with long-term treatment they make increase in incidence and magnitude however. [5] A variety of uncommon and rare side effects may also occur. [5]

Interactions

Antiestrogens like aromatase inhibitors (e.g., anastrozole) and selective estrogen receptor modulators (e.g., tamoxifen, raloxifene) can interfere with and prevent the estrogenic effects of NPP. [5] 5α-Reductase inhibitors like finasteride and dutasteride can prevent the inactivation of nandrolone in so-called "androgenic" tissues like the skin, hair follicles, and prostate gland and may therefore considerably increase its androgenic side effects. [5] This is opposite to the case of most other AAS, which are either potentiated by 5α-reductase in such tissues or are not metabolized by 5α-reductase. [5] Antiandrogens like cyproterone acetate, spironolactone, and bicalutamide can block both the anabolic and androgenic effects of NPP. [19]

Pharmacology

Pharmacodynamics

Nandrolone, the active form of NPP. Nandrolone.svg
Nandrolone, the active form of NPP.
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
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.

NPP is a nandrolone ester, or a prodrug of nandrolone. [20] [5] As such, it is an androgen and anabolic steroid, or an agonist of the androgen receptor, the biological target of androgens like testosterone. [5] [20] Relative to testosterone, NPP has enhanced anabolic effects and reduced androgenic effects. [20] [5] In addition to its anabolic and androgenic activity, NPP has low estrogenic activity (via its metabolite estradiol) and moderate progestogenic activity. [5] Like other AAS, NPP has antigonadotropic effects, which are due to both its androgenic and progestogenic activity. [5]

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
Nandrolone 20154–155<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.
Relative affinities of nandrolone and related steroids at the androgen receptor
CompoundrAR(%)hAR(%)
Testosterone 3838
5α-Dihydrotestosterone 77100
Nandrolone 7592
5α-Dihydronandrolone 3550
Ethylestrenol ND2
Norethandrolone ND22
5α-Dihydronorethandrolone ND14
Metribolone 100110
Sources: See template.

Pharmacokinetics

NPP is converted into nandrolone in the body, which is the active form of the drug. [5] It has an extended elimination half-life in the body when administered via intramuscular injection. [20] Its duration of action is approximately one week and it is administered once every few days to once per week. [5] The elimination half-life and duration of action of NPP are much shorter than those of nandrolone decanoate. [5] [21]

Parenteral durations of androgens/anabolic steroids
MedicationFormMajor brand namesDuration
Testosterone Aqueous suspensionAndronaq, Sterotate, Virosterone2–3 days
Testosterone propionate Oil solutionAndroteston, Perandren, Testoviron3–4 days
Testosterone phenylpropionate Oil solutionTestolent8 days
Testosterone isobutyrate Aqueous suspensionAgovirin Depot, Perandren M14 days
Mixed testosterone esters aOil solutionTriolandren10–20 days
Mixed testosterone esters bOil solutionTestosid Depot14–20 days
Testosterone enanthate Oil solutionDelatestryl14–28 days
Testosterone cypionate Oil solutionDepovirin14–28 days
Mixed testosterone esters cOil solutionSustanon 25028 days
Testosterone undecanoate Oil solutionAveed, Nebido100 days
Testosterone buciclate dAqueous suspension20 Aet-1, CDB-1781e90–120 days
Nandrolone phenylpropionateOil solutionDurabolin10 days
Nandrolone decanoate Oil solutionDeca Durabolin21–28 days
Methandriol Aqueous suspensionNotandron, Protandren8 days
Methandriol bisenanthoyl acetate Oil solutionNotandron Depot16 days
Metenolone acetate Oil solutionPrimobolan3 days
Metenolone enanthate Oil solutionPrimobolan Depot14 days
Note: All are via i.m. injection. Footnotes:a = TP, TV, and TUe. b = TP and TKL. c = TP, TPP, TiCa, and TD. d = Studied but never marketed. e = Developmental code names. Sources: See template.

Chemistry

Nandrolone phenylpropionate, or nandrolone 17β-phenylpropionate, is a synthetic estrane steroid and a derivative of testosterone. [8] [9] It is an androgen ester; specifically, it is the C17β phenylpropionate ester of nandrolone (19-nortestosterone), which itself is the 19-demethylated analogue of testosterone. [8] [9]

Structural properties of major anabolic steroid esters
Anabolic steroidStructureEsterRelative
mol. weight
Relative
AAS contentb
Durationc
PositionMoietyTypeLengtha
Boldenone undecylenate
Boldenone undecylenate.svg
C17β Undecylenic acid Straight-chain fatty acid111.580.63Long
Drostanolone propionate
Drostanolone propionate.svg
C17β Propanoic acid Straight-chain fatty acid31.180.84Short
Metenolone acetate
Metenolone acetate.svg
C17β Ethanoic acid Straight-chain fatty acid21.140.88Short
Metenolone enanthate
Metenolone enanthate.png
C17β Heptanoic acid Straight-chain fatty acid71.370.73Long
Nandrolone decanoate
Nandrolone decanoate.svg
C17β Decanoic acid Straight-chain fatty acid101.560.64Long
Nandrolone phenylpropionate
Nandrolone phenylpropionate.svg
C17β Phenylpropanoic acid Aromatic fatty acid– (~6–7)1.480.67Long
Trenbolone acetate
Trenbolone acetate.svg
C17β Ethanoic acid Straight-chain fatty acid21.160.87Short
Trenbolone enanthate d
Trenbolone enanthate.svg
C17β Heptanoic acid Straight-chain fatty acid71.410.71Long
Footnotes:a = Length of ester in carbon atoms for straight-chain fatty acids or approximate length of ester in carbon atoms for aromatic fatty acids. b = Relative androgen/anabolic steroid content by weight (i.e., relative androgenic/anabolic potency). c = Duration by intramuscular or subcutaneous injection in oil solution. d = Never marketed. Sources: See individual articles.

History

NPP was first described in 1957 and was introduced for medical use in 1959. [5] [27] It was initially used for a wide variety of indications, but starting in the 1970s its use became more restricted and its main uses became the treatment of breast cancer and osteoporosis in women. [5] Today, NPP is scarcely available. [5] The drug was the first form of nandrolone to be introduced, and was followed by nandrolone decanoate in 1962, which has been more widely used in comparison. [27]

Society and culture

Generic names

Nandrolone phenylpropionate is the generic name of the drug and its BAN Tooltip British Approved Name while nandrolone phenpropionate is its USAN Tooltip United States Adopted Name. [8] [9] [10] [11] It has also been referred to as nandrolone phenylpropanoate or as nandrolone hydrocinnamate. [8] [9] [10] [11]

Brand names

NPP is or has been marketed under a variety of brand names including Durabolin, Fenobolin, Activin, Deca-Durabolin, Evabolin, Grothic, Hybolin Improved, Metabol, Nerobolil, Neurabol, Norabol, Noralone, Sintabolin, Strabolene, and Superanabolon. [8] [9] [10] [11]

Availability

NPP is or has been marketed in many countries throughout the world, including in the United States, the United Kingdom, and Canada. [9] [11]

United States

NPP was marketed previously in the United States but is no longer available in this country. [28] Nandrolone decanoate, conversely, is one of the few AAS that remains available for medical use in this country. [28]

NPP, along with other AAS, is a schedule III controlled substance in the United States under the Controlled Substances Act. [29]

Related Research Articles

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

Nandrolone, also known as 19-nortestosterone, is an endogenous androgen which exists in the male body at a ratio of 1:50 compared to testosterone. It is also an anabolic steroid (AAS) which is medically used in the form of esters such as nandrolone decanoate and nandrolone phenylpropionate. Nandrolone esters are used in the treatment of anemias, cachexia, osteoporosis, breast cancer, and for other indications. They are now used by oral administration or instead are given by injection into muscle or fat.

<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">Testosterone cypionate</span> Chemical compound

Testosterone cypionate, sold under the brand name Depo-Testosterone among others, is an androgen and anabolic steroid (AAS) medication which is used mainly in the treatment of low testosterone levels in men, including hormone therapy for transgender men. It is given by injection into muscle or subcutaneously, once every one to four weeks, depending on clinical indication.

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

Testosterone propionate, sold under the brand name Testoviron among others, is an androgen and anabolic steroid (AAS) medication which is used mainly in the treatment of low testosterone levels in men. It has also been used to treat breast cancer in women. It is given by injection into muscle usually once every two to three days.

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

Metenolone enanthate, or methenolone enanthate, sold under the brand names Primobolan Depot and Nibal Injection, is an androgen and anabolic steroid (AAS) medication which is used mainly in the treatment of anemia due to bone marrow failure. It is given by injection into muscle. Although it was widely used in the past, the drug has mostly been discontinued and hence is now mostly only available on the black market. A related drug, metenolone acetate, is taken by mouth.

<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">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">Testosterone phenylpropionate</span> Chemical compound

Testosterone phenylpropionate, or testosterone phenpropionate, also known as testosterone hydrocinnamate, is a synthetic anabolic-androgenic steroid (AAS) and an androgen ester – specifically, the C17β phenylpropionate ester of testosterone – which was formerly marketed in Romania. It was first synthesized in 1951 and was first described in the literature by 1953. The medication was an ingredient of several isolated AAS commercial products, but was never widely used. Testosterone phenylpropionate was also notably a component of Sustanon and Omnadren, as well as of Estandron Prolongatum, Lynandron Prolongatum, and Mixogen. TPP was previously available in Great Britain.

<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 cyclotate</span> Chemical compound

Nandrolone cyclotate, or nandrolone ciclotate, also known as 19-nortestosterone 17β-ciclotate, is a synthetic and injected anabolic–androgenic steroid (AAS) of the nandrolone (19-nortestosterone) group which was never marketed. It is an androgen ester – specifically, the C17β ciclotate (4-methylbicyclo[2.2.2]oct-2-ene-1-carboxylate) ester of nandrolone. Nandrolone cyclotate has potent and prolonged activity as an AAS when administered by intramuscular injection and is reported to have a similar duration of action to that of nandrolone decanoate via this route.

<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">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">Androstanolone</span> Androgenic and anabolic steroid medication

Androstanolone, or stanolone, also known as dihydrotestosterone (DHT) and sold under the brand name Andractim among others, is an androgen and anabolic steroid (AAS) medication and hormone which is used mainly in the treatment of low testosterone levels in men. It is also used to treat breast development and small penis in males. Compared to testosterone, androstanolone (DHT) is less likely to aromatize into estrogen, and therefore it shows less pronounced estrogenic side effects, such as gynecomastia and water retention. On the other hand, androstanolone (DHT) show more significant androgenic side effects, such as acne, hair loss and prostate enlargement.

<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.

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