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Nandrolone phenylpropionate

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]

Nandrolone phenylpropionate
Nandrolone phenylpropionate.svg
Nandrolone phenylpropionate molecule ball.png
Clinical data
Trade namesDurabolin, others
Other names• NPP
• Nandrolone phenpropionate
• 19-Nortestosterone phenylpropionate
• Nandrolone hydrocinnamate
• 19-Nortestosterone 17β-phenylpropionate
• NSC-23162
Pregnancy
category
  • AU: D
  • US: X (Contraindicated)
Routes of
administration
Intramuscular injection
Drug classAndrogen; Anabolic steroid; Androgen ester; Progestogen
Legal status
Legal status
Pharmacokinetic data
BioavailabilityOral: 0.3–2.9% (pigs)[3]
Intramuscular: high[4]
MetabolismBlood (hydrolysis), liver (reduction)[1][2]
MetabolitesNandrolone[5]
5α-Dihydronandrolone[5]
19-Norandrosterone[6]
19-Noretiocholanolone[6]
Conjugates[2]
Elimination half-life• Intramuscular: 2.7 days[7]
• Nandrolone: <4.3 hours[1]
Duration of action• Intramuscular: 5–7 days[5][7]
ExcretionUrine[1]
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.000.502 Edit this at Wikidata
Chemical and physical data
FormulaC27H34O3
Molar mass406.566 g·mol−1
3D model (JSmol)

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 usesEdit

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.[4][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

Route/form Androgen Dosage
Oral Methyltestosterone 30–200 mg/day
Fluoxymesterone 10–40 mg 3x/day
Calusterone 40 mg 4x/day
Normethandrone 40 mg/day
IM injection Testosterone propionate 50–100 mg 3x/week
Testosterone enanthate 200–400 mg 1x/2–4 weeks
Testosterone cypionate 200–400 mg 1x/2–4 weeks
Methandriol (aq. susp.) 100 mg 3x/week
Androstanolone (aq. susp.) 300 mg 3x/week
Drostanolone propionate 100 mg 3x/week
Nandrolone decanoate 50–100 mg 1x/1–3 weeks
Nandrolone phenylpropionate 50–100 mg/week
Notes: Dosages are not necessarily equivalent. Sources: See template.

Available formsEdit

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

Non-medical usesEdit

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 effectsEdit

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]

InteractionsEdit

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]

PharmacologyEdit

PharmacodynamicsEdit

Androgenic vs. anabolic activity
of androgens/anabolic steroids

Medication Ratioa
Testosterone 2:1–1:2
Dihydrotestosterone 3:1–1:2
Methyltestosterone ~1:1
Fluoxymesterone 2:1–1:15
Metandienone 2:1–1:8
Drostanolone 1:3
Metenolone 1:2–1:30
Oxymetholone 1:2–1:9
Oxandrolone 1:3–1:13
Stanozolol 2:1–1:30
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 AR ER GR MR SHBG CBG
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 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.

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.

PharmacokineticsEdit

 
Nandrolone levels over 32 days after a single 100 mg intramuscular injection of nandrolone phenylpropionate or nandrolone decanoate at a volume of 4 mL or 1 mL in arachis oil into gluteal or deltoid muscle.[7]

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

Compound Brand name(s) Type Duration
Testosterone (aq. susp.) Andronaq, Sterotate, Virosterone Androgen 2–3 days
Testosterone propionate Androteston, Perandren, Testoviron Androgen 3–4 days
Testosterone phenylpropionate Testolent Androgen 8 days
Testosterone isobutyrate (aq. susp.) Agovirin Depot, Perandren M Androgen 14 days
Mixed testosterone estersa Triolandren Androgen 10–20 days
Mixed testosterone estersb Testosid Depot Androgen 14–20 days
Testosterone enanthate Delatestryl Androgen 14–20 days
Testosterone cypionate Depovirin Androgen 14–20 days
Mixed testosterone estersc Sustanon 250 Androgen 28 days
Testosterone undecanoate Aveed, Nebido Androgen 100 days
Testosterone buciclate (aq. susp.)d 20 Aet-1, CDB-1781e Androgen 90–120 days
Nandrolone phenylpropionate Durabolin Anabolic 10 days
Nandrolone decanoate Deca Durabolin Anabolic 21 days
Methandriol (aq. susp.) Notandron, Protandren Androgen 8 days
Methandriol bisenanthoyl acetate Notandron Depot Androgen 16 days
Metenolone acetate Primobolan Anabolic 3 days
Metenolone enanthate Primobolan Depot Anabolic 14 days
Note: All are via i.m. injection of oil solution unless noted otherwise. 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.

ChemistryEdit

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 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 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.

HistoryEdit

NPP was first described in 1957 and was introduced for medical use in 1959.[5][22] 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.[22]

Society and cultureEdit

Generic namesEdit

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 namesEdit

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]

AvailabilityEdit

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 StatesEdit

NPP was marketed previously in the United States but is no longer available in this country.[23] Nandrolone decanoate, conversely, is one of the few AAS that remains available for medical use in this country.[23]

Legal statusEdit

NPP, along with other AAS, is a schedule III controlled substance in the United States under the Controlled Substances Act.[24]

ReferencesEdit

  1. ^ a b c http://www.medsafe.govt.nz/profs/Datasheet/d/Decadurabolininj.pdf
  2. ^ a b John A. Thomas (6 December 2012). Drugs, Athletes, and Physical Performance. Springer Science & Business Media. pp. 27–29. ISBN 978-1-4684-5499-4.
  3. ^ 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. PMID 10435281.
  4. ^ a b Kenneth L. Becker (2001). Principles and Practice of Endocrinology and Metabolism. Lippincott Williams & Wilkins. pp. 1185–. ISBN 978-0-7817-1750-2.
  5. ^ a b c d e f g h i j k l m n o p q r s t u v w x y z aa ab ac ad ae af ag ah ai aj ak al am William Llewellyn (2011). Anabolics. Molecular Nutrition Llc. pp. 460–467, 193–194. ISBN 978-0-9828280-1-4.
  6. ^ a b Victor A. Rogozkin (14 June 1991). Metabolism of Anabolic-Androgenic Steroids. CRC Press. pp. 108–. ISBN 978-0-8493-6415-0.
  7. ^ a b c 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.
  8. ^ a b c d e f J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 660–. ISBN 978-1-4757-2085-3.
  9. ^ a b c d e f g Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 716–717. ISBN 978-3-88763-075-1.
  10. ^ a b c d I.K. Morton; Judith M. Hall (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. ISBN 978-94-011-4439-1.
  11. ^ a b c d e f g https://www.drugs.com/international/nandrolone.html
  12. ^ a b Kicman AT (2008). "Pharmacology of anabolic steroids". Br. J. Pharmacol. 154 (3): 502–21. doi:10.1038/bjp.2008.165. PMC 2439524. PMID 18500378.
  13. ^ Charles D. Kochakian (6 December 2012). Anabolic-Androgenic Steroids. Springer Science & Business Media. pp. 401–. ISBN 978-3-642-66353-6.
  14. ^ Walter Sneader (23 June 2005). Drug Discovery: A History. John Wiley & Sons. pp. 206–. ISBN 978-0-471-89979-2.
  15. ^ A. Wayne Meikle (1 June 1999). Hormone Replacement Therapy. Springer Science & Business Media. pp. 271–. ISBN 978-1-59259-700-0.
  16. ^ 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. PMID 27535042.
  17. ^ Pan MM, Kovac JR (2016). "Beyond testosterone cypionate: evidence behind the use of nandrolone in male health and wellness". Transl Androl Urol. 5 (2): 213–9. doi:10.21037/tau.2016.03.03. PMC 4837307. PMID 27141449.
  18. ^ J. Larry Jameson; Leslie J. De Groot (25 February 2015). Endocrinology: Adult and Pediatric E-Book. Elsevier Health Sciences. pp. 2388–. ISBN 978-0-323-32195-2.
  19. ^ Carrie Bagatell; William J. Bremner (27 May 2003). Androgens in Health and Disease. Springer Science & Business Media. pp. 25–. ISBN 978-1-59259-388-0.
  20. ^ a b c d Gao W, Bohl CE, Dalton JT (2005). "Chemistry and structural biology of androgen receptor". Chem. Rev. 105 (9): 3352–70. doi:10.1021/cr020456u. PMC 2096617. PMID 16159155.
  21. ^ Thomas L. Lemke; David A. Williams (24 January 2012). Foye's Principles of Medicinal Chemistry. Lippincott Williams & Wilkins. pp. 1362–. ISBN 978-1-60913-345-0.
  22. ^ a b 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. 153–154. ISBN 978-92-1-130230-1.
  23. ^ a b "Drugs@FDA: FDA Approved Drug Products". United States Food and Drug Administration. Retrieved 17 December 2016.
  24. ^ Steven B. Karch, MD, FFFLM (21 December 2006). Drug Abuse Handbook, Second Edition. CRC Press. pp. 30–. ISBN 978-1-4200-0346-8.CS1 maint: multiple names: authors list (link)

Further readingEdit

External linksEdit