Chemistry:Nandrolone phenylpropionate

From HandWiki
Short description: Anabolic steroid
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
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
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
Chemical and physical data
FormulaC27H34O3
Molar mass406.566 g·mol−1
3D model (JSmol)

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]


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.[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]

v · d · e 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 (IM or SC) 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

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

Non-medical uses

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

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.
v · d · e Androgenic vs. anabolic activity
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]

v · d · e 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.
v · d · e 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

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]

v · d · e 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 14–20 days
Testosterone cypionate Oil solution Depovirin 14–20 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 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.


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]


History

NPP was first described in 1957 and was introduced for medical use in 1959.[3][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.[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.[22]

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, 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.[23] Nandrolone decanoate, conversely, is one of the few AAS that remains available for medical use in this country.[23]

Legal status

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

References

  1. ↑ "Residues of nortestosterone esters at injection sites. Part 1. Oral bioavailability". The Analyst 123 (12): 2475–2478. December 1998. doi:10.1039/a804919j. PMID 10435281. 
  2. ↑ 2.0 2.1 "Clinical Use and Abuse of Androgens and Antiandrogens". Principles and Practice of Endocrinology and Metabolism. Lippincott Williams & Wilkins. 2001. pp. 1185–. ISBN 978-0-7817-1750-2. https://books.google.com/books?id=FVfzRvaucq8C&pg=PA1185. 
  3. ↑ 3.00 3.01 3.02 3.03 3.04 3.05 3.06 3.07 3.08 3.09 3.10 3.11 3.12 3.13 3.14 3.15 3.16 3.17 3.18 3.19 3.20 3.21 3.22 3.23 3.24 3.25 3.26 3.27 3.28 3.29 3.30 3.31 3.32 3.33 3.34 3.35 3.36 3.37 3.38 William Llewellyn (2011). Anabolics. Molecular Nutrition Llc. pp. 460–467, 193–194. ISBN 978-0-9828280-1-4. https://books.google.com/books?id=afKLA-6wW0oC&pg=PT460. 
  4. ↑ 4.0 4.1 "Enzymic Systems Participating in AAS Metabolism". Metabolism of Anabolic-Androgenic Steroids. CRC Press. 14 June 1991. pp. 108–. ISBN 978-0-8493-6415-0. https://books.google.com/books?id=hRsnmJRF1WgC&pg=PA108. 
  5. ↑ 5.0 5.1 "Fate of Anabolic Steroids in the Body". Drugs, Athletes, and Physical Performance. Springer Science & Business Media. 6 December 2012. pp. 27–29. ISBN 978-1-4684-5499-4. https://books.google.com/books?id=9u0pBgAAQBAJ&pg=PA27. 
  6. ↑ 6.0 6.1 "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. April 1997. PMID 9103484. 
  7. ↑ 7.0 7.1 7.2 "Decadurabolin injection Data Sheet". Merck Sharp & Dohme (NZ) Ltd. http://www.medsafe.govt.nz/profs/Datasheet/d/Decadurabolininj.pdf. 
  8. ↑ 8.0 8.1 8.2 8.3 8.4 8.5 The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. 14 November 2014. pp. 660–. ISBN 978-1-4757-2085-3. https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA660. 
  9. ↑ 9.0 9.1 9.2 9.3 9.4 9.5 9.6 Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 716–717. ISBN 978-3-88763-075-1. https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA716. 
  10. ↑ 10.0 10.1 10.2 10.3 Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. 6 December 2012. ISBN 978-94-011-4439-1. https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA189. 
  11. ↑ 11.0 11.1 11.2 11.3 11.4 11.5 11.6 "Nandrolone - FDA prescribing information, side effects and uses". https://www.drugs.com/international/nandrolone.html. 
  12. ↑ 12.0 12.1 "Pharmacology of anabolic steroids". British Journal of Pharmacology 154 (3): 502–521. June 2008. doi:10.1038/bjp.2008.165. PMID 18500378. 
  13. ↑ "Dissociation of the Androgenic and Other Hormonal Activities from the Protein Anabolic Effects of Steroids". Anabolic-Androgenic Steroids. Springer Science & Business Media. 6 December 2012. pp. 401–. ISBN 978-3-642-66353-6. https://books.google.com/books?id=3-LrCAAAQBAJ&pg=PA401. 
  14. ↑ "Drugs from Naturally Occurring Prototypes: Biochemicals". Drug Discovery: A History. John Wiley & Sons. 23 June 2005. pp. 206–. ISBN 978-0-471-89979-2. https://books.google.com/books?id=Cb6BOkj9fK4C&pg=PA206. 
  15. ↑ "Androgen Replacement Therapy of Male Hypogonadism". Hormone Replacement Therapy. Springer Science & Business Media. 1 June 1999. pp. 271–. ISBN 978-1-59259-700-0. https://books.google.com/books?id=ja2nBgAAQBAJ&pg=PA271. 
  16. ↑ "Novel Uses for the Anabolic Androgenic Steroids Nandrolone and Oxandrolone in the Management of Male Health". Current Urology Reports 17 (10): 72. October 2016. doi:10.1007/s11934-016-0629-8. PMID 27535042. 
  17. ↑ "Beyond testosterone cypionate: evidence behind the use of nandrolone in male health and wellness". Translational Andrology and Urology 5 (2): 213–219. April 2016. doi:10.21037/tau.2016.03.03. PMID 27141449. 
  18. ↑ "Androgen Physiology, Pharmacology, and Abuse". Endocrinology: Adult and Pediatric E-Book. Elsevier Health Sciences. 25 February 2015. pp. 2388–. ISBN 978-0-323-32195-2. https://books.google.com/books?id=xmLeBgAAQBAJ&pg=PA2388. 
  19. ↑ "Androgen Action". Androgens in Health and Disease. Springer Science & Business Media. 27 May 2003. pp. 25–. ISBN 978-1-59259-388-0. https://books.google.com/books?id=vDcBCAAAQBAJ&pg=PA25. 
  20. ↑ 20.0 20.1 20.2 20.3 "Chemistry and structural biology of androgen receptor". Chemical Reviews 105 (9): 3352–3370. September 2005. doi:10.1021/cr020456u. PMID 16159155. 
  21. ↑ Foye's Principles of Medicinal Chemistry. Lippincott Williams & Wilkins. 24 January 2012. pp. 1362–. ISBN 978-1-60913-345-0. https://books.google.com/books?id=Sd6ot9ul-bUC&pg=PA1362. 
  22. ↑ 22.0 22.1 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. https://books.google.com/books?id=leVCukUgNlsC&pg=PA153. 
  23. ↑ 23.0 23.1 "Drugs@FDA: FDA Approved Drug Products". United States Food and Drug Administration. http://www.accessdata.fda.gov/scripts/cder/daf/. 
  24. ↑ "Criminalistics: Introduction to Controlled Substances". Drug Abuse Handbook, Second Edition. CRC Press. 21 December 2006. pp. 30–. ISBN 978-1-4200-0346-8. https://books.google.com/books?id=ZjrMBQAAQBAJ&pg=PA30. 

Further reading

External links



Retrieved from "https://handwiki.org/wiki/index.php?title=Chemistry:Nandrolone_phenylpropionate&oldid=3332020"