Nandrolone hexyloxyphenylpropionate

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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
  • [(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-(4-hexoxyphenyl)propanoate
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.052.538 Edit this at Wikidata
Chemical and physical data
FormulaC33H46O4
Molar mass506.727 g·mol−1
3D model (JSmol)
  • CCCCCCOC1=CC=C(C=C1)CCC(=O)O[C@H]2CC[C@@H]3[C@@]2(CC[C@H]4[C@H]3CCC5=CC(=O)CC[C@H]45)C
  • InChI=1S/C33H46O4/c1-3-4-5-6-21-36-26-12-7-23(8-13-26)9-18-32(35)37-31-17-16-30-29-14-10-24-22-25(34)11-15-27(24)28(29)19-20-33(30,31)2/h7-8,12-13,22,27-31H,3-6,9-11,14-21H2,1-2H3/t27-,28+,29+,30-,31-,33-/m0/s1
  • Key:PQKRYXHYWWQULJ-JMKYFRMNSA-N

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
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.
Hormone levels with nandrolone esters by intramuscular injection

See also

References

  1. ^ a b Nieschlag E, Behre HM (6 December 2012). Testosterone: Action - Deficiency - Substitution. Springer Science & Business Media. pp. 127–128. ISBN 978-3-662-00814-0.
  2. ^ Lin GC, Erinoff L (July 1996). Anabolic Steroid Abuse. DIANE Publishing. pp. 125–. ISBN 978-0-7881-2969-8.
  3. ^ 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.
  4. ^ Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 716–717. ISBN 978-3-88763-075-1.
  5. ^ 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.
  6. ^ Mozayani A, Raymon L (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. ^ a b Payne AH, Hardy MP (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 (PhD). Utrecht University.



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