Nandrolone hexyloxyphenylpropionate

Nandrolone hexyloxyphenylpropionate
Clinical data
Trade names	Anador, Anadur, Anadurine
Other names	NHPP; 19-Nortestosterone 17β-(3-(4-hexyloxy)phenyl)propionate
Routes of; administration	Intramuscular injection
Drug class	Androgen; Anabolic steroid; Androgen ester; Progestogen
Pharmacokinetic data
Elimination half-life	Intramuscular: 20 days[1][2]
Identifiers
	IUPAC name [(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	52279-57-9 ;
PubChem CID	92341;
ChemSpider	83364;
UNII	602JJC2862;
CompTox Dashboard (EPA)	DTXSID20966654 ;
ECHA InfoCard	100.052.538
Chemical and physical data
Formula	C33H46O4
Molar mass	506.727 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES 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 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	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.

Hormone levels with nandrolone esters by intramuscular injection

Nandrolone levels after a single 50, 100, or 150 mg intramuscular injection of nandrolone decanoate in oil solution in men.[8]
Nandrolone levels after a single 100 mg intramuscular injection of nandrolone decanoate or nandrolone phenylpropionate in 4 mL or 1 mL arachis oil solution into gluteal or deltoid muscle in men.[9]
Nandrolone levels with a single 50 mg intramuscular injection of nandrolone decanoate or nandrolone hexyloxyphenylpropionate in oil solution in men.[10]
Dose-normalized nandrolone exposure (serum level divided by dose administered) with nandrolone decanoate in oil solution by intramuscular or subcutaneous injection in men.[11][12]

References

Nieschlag E, Behre HM (6 December 2012). Testosterone: Action - Deficiency - Substitution. Springer Science & Business Media. pp. 127–128. ISBN 978-3-662-00814-0.
Lin GC, Erinoff L (July 1996). Anabolic Steroid Abuse. DIANE Publishing. pp. 125–. ISBN 978-0-7881-2969-8.
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.
Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 716–717. ISBN 978-3-88763-075-1.
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.
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.
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.
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.
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.
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.
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.
Kalicharan, Raween Wikesh (2017). New Insights into Drug Absorption from Oil Depots (Thesis). Utrecht University.

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[NieschlagBehre2012-1] Nieschlag E, Behre HM (6 December 2012). Testosterone: Action - Deficiency - Substitution. Springer Science & Business Media. pp. 127–128. ISBN 978-3-662-00814-0.

[LinErinoff1996-2] Lin GC, Erinoff L (July 1996). Anabolic Steroid Abuse. DIANE Publishing. pp. 125–. ISBN 978-0-7881-2969-8.

[Elks2014-3] 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.

[IndexNominum2000-4] Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 716–717. ISBN 978-3-88763-075-1.

[MortonHall2012-5] 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.

[MozayaniRaymon2003-6] 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.

[PayneHardy2007-7] 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.

[pmid4010287-10] 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.

[pmid26690043-11] 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.

[Kalicharan2017-12] Kalicharan, Raween Wikesh (2017). New Insights into Drug Absorption from Oil Depots (Thesis). Utrecht University.

Nandrolone hexyloxyphenylpropionate

See also

References