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Nandrolone phenylpropionate

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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]

Nandrolone phenylpropionate
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
Routes of
administration		Intramuscular injection
Drug classAndrogen; Anabolic steroid; Androgen ester; Progestogen
Legal status
Legal status
Pharmacokinetic data
Bioavailability• Oral: 0.3–2.9% (pigs)[1]
• Intramuscular: high[2]
MetabolismBlood (hydrolysis), liver (reduction)[7][5]
Metabolites• Nandrolone[3]
• 5α-Dihydronandrolone[3]
• 19-Norandrosterone[4]
• 19-Noretiocholanolone[4]
• Conjugates[5]
Elimination half-life• Intramuscular: 2.7 days[6]
• Nandrolone: <4.3 hours[7]
Duration of action• Intramuscular: 5–7 days[3][6]
ExcretionUrine[7]
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 InfoCard100.000.502 Edit this at Wikidata
Chemical and physical data
FormulaC27H34O3
Molar mass406.566 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

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]

Medical uses

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See also: Anabolic steroid § Medical

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.[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]

Androgen/anabolic steroid dosages for breast cancer
Route Medication Form Dosage
Oral Methyltestosterone Tablet 30–200 mg/day
Fluoxymesterone Tablet 10–40 mg 3x/day
Calusterone Tablet 40–80 mg 4x/day
Normethandrone Tablet 40 mg/day
Buccal Methyltestosterone Tablet 25–100 mg/day
Injection (IMTooltip intramuscular injection or SCTooltip subcutaneous injection) Testosterone propionate Oil solution 50–100 mg 3x/week
Testosterone enanthate Oil solution 200–400 mg 1x/2–4 weeks
Testosterone cypionate Oil solution 200–400 mg 1x/2–4 weeks
Mixed testosterone esters Oil solution 250 mg 1x/week
Methandriol Aqueous suspension 100 mg 3x/week
Androstanolone (DHT) Aqueous suspension 300 mg 3x/week
Drostanolone propionate Oil solution 100 mg 1–3x/week
Metenolone enanthate Oil solution 400 mg 3x/week
Nandrolone decanoate Oil solution 50–100 mg 1x/1–3 weeks
Nandrolone phenylpropionate Oil solution 50–100 mg/week
Note: Dosages are not necessarily equivalent. Sources: See template.

Available forms

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NPP is or has been available 25 mg/mL and 50 mg/mL formulations in oil solution for intramuscular injection.[3]

Non-medical uses

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See also: Anabolic steroid § Enhancing performance

NPP is used for physique- and performance-enhancing purposes by competitive athletes, 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 estrogenic side effects.[3]

Side effects

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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

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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

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Pharmacodynamics

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Nandrolone, the active form of NPP.
Androgenic vs. anabolic activity ratio
of androgens/anabolic steroids
Medication Ratioa
Testosterone ~1:1
Androstanolone (DHT) ~1:1
Methyltestosterone ~1:1
Methandriol ~1:1
Fluoxymesterone 1:1–1:15
Metandienone 1:1–1:8
Drostanolone 1:3–1:4
Metenolone 1:2–1:30
Oxymetholone 1:2–1:9
Oxandrolone 1:3–1:13
Stanozolol 1:1–1:30
Nandrolone 1:3–1:16
Ethylestrenol 1:2–1:19
Norethandrolone 1:1–1:20
Notes: In rodents. Footnotes: a = Ratio of androgenic to anabolic activity. Sources: See template.

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 metabolite estradiol) and moderate progestogenic activity.[3] Like other AAS, NPP has antigonadotropic effects, which are due to both its androgenic and progestogenic activity.[3]

Relative affinities (%) of nandrolone and related steroids
Compound PRTooltip Progesterone receptor ARTooltip Androgen receptor ERTooltip Estrogen receptor GRTooltip Glucocorticoid receptor MRTooltip Mineralocorticoid receptor SHBGTooltip Sex hormone-binding globulin CBGTooltip Corticosteroid-binding globulin
Nandrolone 20 154–155 <0.1 0.5 1.6 1–16 0.1
Testosterone 1.0–1.2 100 <0.1 0.17 0.9 19–82 3–8
Estradiol 2.6 7.9 100 0.6 0.13 8.7–12 <0.1
Notes: Values are percentages (%). Reference ligands (100%) were progesterone for the PRTooltip progesterone receptor, testosterone for the ARTooltip androgen receptor, estradiol for the ERTooltip estrogen receptor, dexamethasone for the GRTooltip glucocorticoid receptor, aldosterone for the MRTooltip mineralocorticoid receptor, dihydrotestosterone for SHBGTooltip sex hormone-binding globulin, and cortisol for CBGTooltip corticosteroid-binding globulin. 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.

Pharmacokinetics

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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]

Parenteral durations of androgens/anabolic steroids
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.
Hormone levels with nandrolone esters by intramuscular injection

Chemistry

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See also: Nandrolone § Chemistry, Androgen ester, and List of androgen esters § Nandrolone esters

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.

History

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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

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Generic names

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Nandrolone phenylpropionate is the generic name of the drug and its BANTooltip British Approved Name while nandrolone phenpropionate is its USANTooltip 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

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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

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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

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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]

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

References

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  1. ^ McEvoy JD, McVeigh CE, McCaughey WJ (December 1998). "Residues of nortestosterone esters at injection sites. Part 1. Oral bioavailability". The Analyst. 123 (12): 2475–2478. doi:10.1039/a804919j. PMID 10435281.
  2. ^ a b Matsumoto AM (2001). "Clinical Use and Abuse of Androgens and Antiandrogens". In Becker KL (ed.). Principles and Practice of Endocrinology and Metabolism. Lippincott Williams & Wilkins. pp. 1185–. ISBN 978-0-7817-1750-2.
  3. ^ 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.
  4. ^ a b Rogozkin VA (14 June 1991). "Enzymic Systems Participating in AAS Metabolism". Metabolism of Anabolic-Androgenic Steroids. CRC Press. pp. 108–. ISBN 978-0-8493-6415-0.
  5. ^ a b Colby HD, Longhurst PA (6 December 2012). "Fate of Anabolic Steroids in the Body". In Thomas JA (ed.). Drugs, Athletes, and Physical Performance. Springer Science & Business Media. pp. 27–29. ISBN 978-1-4684-5499-4.
  6. ^ a b 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.
  7. ^ a b c "Decadurabolin injection Data Sheet" (PDF). Merck Sharp & Dohme (NZ) Ltd. Archived from the original (PDF) on 21 January 2015. Retrieved 2017-12-13.
  8. ^ a b c d e f Elks J (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 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.
  11. ^ a b c d e f g "Nandrolone - FDA prescribing information, side effects and uses".
  12. ^ a b Kicman AT (June 2008). "Pharmacology of anabolic steroids". British Journal of Pharmacology. 154 (3): 502–521. doi:10.1038/bjp.2008.165. PMC 2439524. PMID 18500378.
  13. ^ Potts GO, Arnold A, Beyler AL (6 December 2012). "Dissociation of the Androgenic and Other Hormonal Activities from the Protein Anabolic Effects of Steroids". In Kochakian CD (ed.). Anabolic-Androgenic Steroids. Springer Science & Business Media. pp. 401–. ISBN 978-3-642-66353-6.
  14. ^ Sneader W (23 June 2005). "Drugs from Naturally Occurring Prototypes: Biochemicals". Drug Discovery: A History. John Wiley & Sons. pp. 206–. ISBN 978-0-471-89979-2.
  15. ^ Meikle AW (1 June 1999). "Androgen Replacement Therapy of Male Hypogonadism". In Meikle AW (ed.). Hormone Replacement Therapy. Springer Science & Business Media. pp. 271–. ISBN 978-1-59259-700-0.
  16. ^ Wu C, Kovac JR (October 2016). "Novel Uses for the Anabolic Androgenic Steroids Nandrolone and Oxandrolone in the Management of Male Health". Current Urology Reports. 17 (10): 72. doi:10.1007/s11934-016-0629-8. PMID 27535042. S2CID 43199715.
  17. ^ 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): 213–219. doi:10.21037/tau.2016.03.03. PMC 4837307. PMID 27141449.
  18. ^ Handelsman DJ (25 February 2015). "Androgen Physiology, Pharmacology, and Abuse". In Jameson JL, De Groot LJ (eds.). Endocrinology: Adult and Pediatric E-Book. Elsevier Health Sciences. pp. 2388–. ISBN 978-0-323-32195-2.
  19. ^ Brown TR (27 May 2003). "Androgen Action". In Bagatell C, Bremner WJ (eds.). 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 (September 2005). "Chemistry and structural biology of androgen receptor". Chemical Reviews. 105 (9): 3352–3370. doi:10.1021/cr020456u. PMC 2096617. PMID 16159155.
  21. ^ Lemke TL, Williams DA (24 January 2012). Foye's Principles of Medicinal Chemistry. Lippincott Williams & Wilkins. pp. 1362–. ISBN 978-1-60913-345-0.
  22. ^ 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.
  23. ^ 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.
  24. ^ 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.
  25. ^ 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.
  26. ^ Kalicharan, Raween Wikesh (2017). New Insights into Drug Absorption from Oil Depots (PhD). Utrecht University.
  27. ^ 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.[permanent dead link‍]
  28. ^ a b "Drugs@FDA: FDA Approved Drug Products". United States Food and Drug Administration. Retrieved 17 December 2016.
  29. ^ Bono JP (21 December 2006). "Criminalistics: Introduction to Controlled Substances". In Karch SB (ed.). Drug Abuse Handbook, Second Edition. CRC Press. pp. 30–. ISBN 978-1-4200-0346-8.

Further reading

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