Nandrolone hexyloxyphenylpropionate

Nandrolone hexyloxyphenylpropionate (NHPP; brand names Anador, Anadur, Anadurine), also known as 19-nortestosterone 17β-(3-(4-hexyloxy)phenyl)propionate, is a synthetic androgen and anabolic steroid and a nandrolone ester that is marketed in France, Denmark, Austria, Luxembourg, and Turkey.[3][4][5][6] It has been studied as a potential long-acting injectable male contraceptive, though it has not been marketed for this indication.[7] Approximately 70% of men became azoospermic, while the remaining men all became oligospermic.[7] 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.[1]

Relative affinities (%) of nandrolone and related steroids
CompoundPRARERGRMRSHBGCBG
Nandrolone20154–155<0.10.51.61–160.1
Testosterone1.0–1.2100<0.10.170.919–823–8
Estradiol2.67.91000.60.138.7–12<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.
Nandrolone hexyloxyphenylpropionate
Clinical data
Trade namesAnador, Anadur, Anadurine
Other namesNHPP; 19-Nortestosterone 17β-(3-(4-hexyloxy)phenyl)propionate
Routes of
administration
Intramuscular injection
Drug classAndrogen; Anabolic steroid; Androgen ester; Progestogen
Pharmacokinetic data
Elimination half-lifeIntramuscular: 20 days[1][2]
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.052.538
Chemical and physical data
FormulaC33H46O4
Molar mass506.727 g·mol−1
3D model (JSmol)

See also

References

  1. Eberhard Nieschlag; Hermann M. Behre (6 December 2012). Testosterone: Action - Deficiency - Substitution. Springer Science & Business Media. pp. 127–128. ISBN 978-3-662-00814-0.
  2. Geraline C. Lin; Lynda Erinoff (July 1996). Anabolic Steroid Abuse. DIANE Publishing. pp. 125–. ISBN 978-0-7881-2969-8.
  3. 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.
  4. Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 716–717. ISBN 978-3-88763-075-1.
  5. 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.
  6. Ashraf Mozayani; Lionel Raymon (15 October 2003). Handbook of Drug Interactions: A Clinical and Forensic Guide. Springer Science & Business Media. pp. 501–. ISBN 978-1-59259-654-6.
  7. Anita H. Payne; Matthew P. Hardy (28 October 2007). The Leydig Cell in Health and Disease. Springer Science & Business Media. pp. 423–. ISBN 978-1-59745-453-7.
  8. 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.
  9. 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.
  10. 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.
  11. 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.
  12. Kalicharan, Raween Wikesh (2017). New Insights into Drug Absorption from Oil Depots (Thesis). Utrecht University.



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