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][3] It is given by injection into muscle once every week.[3] Although it was widely used in the past, the drug has mostly been discontinued and hence is now mostly no longer available.[3][11]
Side effects of NPP include symptoms of masculinization like acne, increased hair growth, voice changes, and increased sexual desire.[3] 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).[3][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.[3][12][13] NPP is a nandrolone ester and a long-lasting prodrug of nandrolone in the body.[3]
NPP was first described in 1957 and was introduced for medical use in 1959.[3] 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has been one of the most widely used nandrolone esters.[3][14] However, in more recent times, the drug has been largely superseded by nandrolone decanoate, which is longer-acting and more convenient to use.[3][11] In addition to its medical use, NPP is used to improve physique and performance.[3] The drug is a controlled substance in many countries and so non-medical use is generally illicit.[3]
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 postmenopausalosteoporosis in women.[3] Historically, it has also had a variety of other uses.[3] 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]
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Androgen/anabolic steroid dosages for breast cancer
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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.[3]
Non-medical uses[]
See also: Anabolic steroid § Enhancing performance
NPP is used for physique- and performance-enhancing purposes by competitiveathletes, bodybuilders, and powerlifters.[3] Nandrolone esters have been said to be the most popular AAS used by bodybuilders and in sports.[3][18] This is in part due to the high ratio of anabolic to androgenic effect of nandrolone and its weak propensity for androgenic and estrogenicside effects.[3]
Side effects[]
See also: Anabolic steroid § Adverse 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.[3] However, relative to most other AAS, NPP has a greatly reduced propensity for virilization and such side effects are relatively uncommon at recommended dosages.[3] At higher dosages and/or with long-term treatment they make increase in incidence and magnitude however.[3] A variety of uncommon and rare side effects may also occur.[3]
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.[3]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.[3] 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.[3]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.
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Androgenic vs. anabolic activity of androgens/anabolic steroids
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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][3] As such, it is an androgen and anabolic steroid, or an agonist of the androgen receptor, the biological target of androgens like testosterone.[3][20] Relative to testosterone, NPP has enhanced anabolic effects and reduced androgenic effects.[20][3] In addition to its anabolic and androgenic activity, NPP has low estrogenic activity (via its metaboliteestradiol) and moderate progestogenic activity.[3] Like other AAS, NPP has antigonadotropic effects, which are due to both its androgenic and progestogenic activity.[3]
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Relative affinities (%) of nandrolone and related steroids
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Notes: Values are percentages (%). Reference ligands (100%) were progesterone for the PR, testosterone for the AR, estradiol for the ER, dexamethasone for the GR, aldosterone for the MR, dihydrotestosterone for SHBG, and cortisol for CBG. Sources: See template.
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Relative affinities of nandrolone and related steroids at the androgen receptor
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NPP is converted into nandrolone in the body, which is the active form of the drug.[3] 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.[3] The elimination half-life and duration of action of NPP are much shorter than those of nandrolone decanoate.[3][21]
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Parenteral durations of androgens/anabolic steroids
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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 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.
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Hormone levels with nandrolone esters by intramuscular injection
Nandrolone levels after a single 50, 100, or 150 mg intramuscular injection of nandrolone decanoate in oil solution in men.[22]
Nandrolone levels after a single 100 mg intramuscular injection of nandrolone decanoate or nandrolone phenylpropionate in 4 mL or 1 mL arachis oil solution into gluteal or deltoid muscle in men.[23]
Nandrolone levels with a single 50 mg intramuscular injection of nandrolone decanoate or nandrolone hexyloxyphenylpropionate in oil solution in men.[24]
Dose-normalized nandrolone exposure (serum level divided by dose administered) with nandrolone decanoate in oil solution by intramuscular or subcutaneous injection in men.[25][26]
Chemistry[]
See also: Nandrolone § Chemistry, Androgen ester, and List of androgen esters § Nandrolone esters
Nandrolone phenylpropionate, or nandrolone 17β-phenylpropionate, is a syntheticestranesteroid and a derivative of testosterone.[8][9] It is an androgen ester; specifically, it is the C17β phenylpropionateester of nandrolone (19-nortestosterone), which itself is the 19-demethylatedanalogue of testosterone.[8][9]
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Structural properties of major anabolic steroid estersshow
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 of ester in carbonatoms 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/anabolicpotency). 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.[3][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.[3] Today, NPP is scarcely available.[3] 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 while nandrolone phenpropionate is its USAN.[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, Superanabolon, and Turinabol.[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[]
See also: List of androgens/anabolic steroids available in the 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]
Legal status[]
NPP, along with other AAS, is a schedule IIIcontrolled substance in the United States under the Controlled Substances Act.[29]
References[]
^McEvoy JD, McVeigh CE, McCaughey WJ (1998). "Residues of nortestosterone esters at injection sites. Part 1. Oral bioavailability". Analyst. 123 (12): 2475–8. doi:10.1039/a804919j. PMID10435281.
^ Jump up to: abMinto 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. PMID9103484.
^Charles D. Kochakian (6 December 2012). Anabolic-Androgenic Steroids. Springer Science & Business Media. pp. 401–. ISBN978-3-642-66353-6.
^Walter Sneader (23 June 2005). Drug Discovery: A History. John Wiley & Sons. pp. 206–. ISBN978-0-471-89979-2.
^A. Wayne Meikle (1 June 1999). Hormone Replacement Therapy. Springer Science & Business Media. pp. 271–. ISBN978-1-59259-700-0.
^Wu C, Kovac JR (2016). "Novel Uses for the Anabolic Androgenic Steroids Nandrolone and Oxandrolone in the Management of Male Health". Curr Urol Rep. 17 (10): 72. doi:10.1007/s11934-016-0629-8. PMID27535042. S2CID43199715.
^Carrie Bagatell; William J. Bremner (27 May 2003). Androgens in Health and Disease. Springer Science & Business Media. pp. 25–. ISBN978-1-59259-388-0.
^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. PMID15713722.
^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. PMID9103484.
^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. PMID4010287.
^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. PMID26690043.
^Steven B. Karch, MD, FFFLM (21 December 2006). Drug Abuse Handbook, Second Edition. CRC Press. pp. 30–. ISBN978-1-4200-0346-8.CS1 maint: multiple names: authors list (link)
Wu C, Kovac JR (2016). "Novel Uses for the Anabolic Androgenic Steroids Nandrolone and Oxandrolone in the Management of Male Health". Curr Urol Rep. 17 (10): 72. doi:10.1007/s11934-016-0629-8. PMID27535042. S2CID43199715.
Anabolic steroids (e.g., testosterone and esters, methyltestosterone, metandienone (methandrostenolone), nandrolone and esters, many others; via estrogenic metabolites)