nandrolone phenylpropionate

{{Short description|Anabolic steroid}}

{{Drugbox

| Verifiedfields =

| Watchedfields =

| verifiedrevid =

| 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-phenylpropanoate

| image = Nandrolone phenylpropionate.svg

| image_class = skin-invert-image

| width = 250px

| image2 = Nandrolone phenylpropionate molecule ball.png

| width2 = 250px

| tradename = Durabolin, others

| pregnancy_AU = D

| pregnancy_US = X

| pregnancy_category =

| legal_AU = S4

| legal_CA = Schedule IV

| legal_UK = Class C

| legal_US = Schedule III

| legal_status =

| routes_of_administration = Intramuscular injection

| class = Androgen; Anabolic steroid; Androgen ester; Progestogen

| bioavailability = • Oral: 0.3–2.9% (pigs){{cite journal | vauthors = McEvoy JD, McVeigh CE, McCaughey WJ | title = Residues of nortestosterone esters at injection sites. Part 1. Oral bioavailability | journal = The Analyst | volume = 123 | issue = 12 | pages = 2475–2478 | date = December 1998 | pmid = 10435281 | doi = 10.1039/a804919j }}
Intramuscular: high{{cite book | vauthors = Matsumoto AM | chapter = Clinical Use and Abuse of Androgens and Antiandrogens | veditors = Becker KL |title=Principles and Practice of Endocrinology and Metabolism| chapter-url = https://books.google.com/books?id=FVfzRvaucq8C&pg=PA1185|year=2001|publisher=Lippincott Williams & Wilkins|isbn=978-0-7817-1750-2|pages=1185–}}

| protein_bound =

| metabolism = Blood (hydrolysis), liver (reduction){{cite book| vauthors = Colby HD, Longhurst PA | chapter = Fate of Anabolic Steroids in the Body| veditors = Thomas JA |title=Drugs, Athletes, and Physical Performance| chapter-url = https://books.google.com/books?id=9u0pBgAAQBAJ&pg=PA27|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-1-4684-5499-4|pages=27–29}}

| metabolites = • Nandrolone
5α-Dihydronandrolone
19-Norandrosterone{{cite book| vauthors = Rogozkin VA | chapter = Enzymic Systems Participating in AAS Metabolism |title=Metabolism of Anabolic-Androgenic Steroids| chapter-url = https://books.google.com/books?id=hRsnmJRF1WgC&pg=PA108|date=14 June 1991|publisher=CRC Press|isbn=978-0-8493-6415-0|pages=108–}}
19-Noretiocholanolone
Conjugates

| elimination_half-life = • Intramuscular: 2.7 days{{cite journal | vauthors = Minto CF, Howe C, Wishart S, Conway AJ, Handelsman DJ | title = Pharmacokinetics and pharmacodynamics of nandrolone esters in oil vehicle: effects of ester, injection site and injection volume | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 281 | issue = 1 | pages = 93–102 | date = April 1997 | doi = 10.1016/S0022-3565(24)36598-X | pmid = 9103484 }}
• Nandrolone: <4.3 hours{{Cite web |url=http://www.medsafe.govt.nz/profs/Datasheet/d/Decadurabolininj.pdf |title=Decadurabolin injection Data Sheet |access-date=2017-12-13 |archive-date=21 January 2015 |archive-url=https://web.archive.org/web/20150121112319/http://medsafe.govt.nz/profs/datasheet/d/Decadurabolininj.pdf |url-status=dead | work = Merck Sharp & Dohme (NZ) Ltd | publisher = }}

| duration_of_action = • Intramuscular: 5–7 days

| excretion = Urine

| CAS_number_Ref = {{cascite|correct|CAS}}

| CAS_number2_Ref = {{cascite|correct|CAS}}

| index2_label = nandrolone

| CAS_number = 62-90-8

| CAS_number2 = 434-22-0

| CAS_supplemental =

| ATC_prefix =

| ATC_suffix =

| PubChem = 229455

| DrugBank_Ref =

| DrugBank = DB00984

| ChemSpiderID_Ref =

| ChemSpiderID = 199761

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = KF7Z9K2T3W

| UNII2_Ref = {{fdacite|correct|FDA}}

| UNII2 = 6PG9VR430D

| synonyms = • NPP
• Nandrolone phenpropionate
• 19-Nortestosterone phenylpropionate
• Nandrolone hydrocinnamate
• 19-Nortestosterone 17β-phenylpropionate
• NSC-23162

| C=27 | H=34 | O=3

| SMILES = 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

| StdInChI_Ref =

| StdInChI = 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

| StdInChIKey_Ref =

| StdInChIKey = UBWXUGDQUBIEIZ-QNTYDACNSA-N

}}

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.{{cite book| vauthors = Elks J |title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA660|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=660–}}{{cite book|title=Index Nominum 2000: International Drug Directory|url=https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA716|date=January 2000|publisher=Taylor & Francis|isbn=978-3-88763-075-1|pages=716–717}}{{cite book| vauthors = Morton IK, Hall JM |title=Concise Dictionary of Pharmacological Agents: Properties and Synonyms|url=https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA189|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-94-011-4439-1}}{{Cite web|url=https://www.drugs.com/international/nandrolone.html|title=Nandrolone - FDA prescribing information, side effects and uses}}{{cite book|author=William Llewellyn|title=Anabolics|url=https://books.google.com/books?id=afKLA-6wW0oC&pg=PT460|year=2011|publisher=Molecular Nutrition Llc|isbn=978-0-9828280-1-4|pages=460–467, 193–194}} It is given by injection into muscle once every week. Although it was widely used in the past, the drug has mostly been discontinued and hence is now mostly no longer available.

Side effects of NPP include symptoms of masculinization like acne, increased hair growth, voice changes, and increased sexual desire. 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).{{cite journal | vauthors = Kicman AT | title = Pharmacology of anabolic steroids | journal = British Journal of Pharmacology | volume = 154 | issue = 3 | pages = 502–521 | date = June 2008 | pmid = 18500378 | pmc = 2439524 | doi = 10.1038/bjp.2008.165 }} 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.{{cite book| vauthors = Potts GO, Arnold A, Beyler AL | chapter = Dissociation of the Androgenic and Other Hormonal Activities from the Protein Anabolic Effects of Steroids | veditors = Kochakian CD |title=Anabolic-Androgenic Steroids|chapter-url=https://books.google.com/books?id=3-LrCAAAQBAJ&pg=PA401|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-3-642-66353-6|pages=401–}} NPP is a nandrolone ester and a long-lasting prodrug of nandrolone in the body.

NPP was first described in 1957 and was introduced for medical use in 1959. 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.{{cite book| vauthors = Sneader W | chapter = Drugs from Naturally Occurring Prototypes: Biochemicals |title=Drug Discovery: A History| chapter-url = https://books.google.com/books?id=Cb6BOkj9fK4C&pg=PA206|date=23 June 2005|publisher=John Wiley & Sons|isbn=978-0-471-89979-2|pages=206–}} However, in more recent times, the drug has been largely superseded by nandrolone decanoate, which is longer-acting and more convenient to use. In addition to its medical use, NPP is used to improve physique and performance. The drug is a controlled substance in many countries and so non-medical use is generally illicit.

{{TOC limit|3}}

Medical uses

{{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. Historically, it has also had a variety of other uses. 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.{{cite book| vauthors = Meikle AW | chapter = Androgen Replacement Therapy of Male Hypogonadism| veditors = Meikle AW |title=Hormone Replacement Therapy | chapter-url= https://books.google.com/books?id=ja2nBgAAQBAJ&pg=PA271|date=1 June 1999|publisher=Springer Science & Business Media|isbn=978-1-59259-700-0|pages=271–}} 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.{{cite journal | vauthors = Wu C, Kovac JR | title = Novel Uses for the Anabolic Androgenic Steroids Nandrolone and Oxandrolone in the Management of Male Health | journal = Current Urology Reports | volume = 17 | issue = 10 | pages = 72 | date = October 2016 | pmid = 27535042 | doi = 10.1007/s11934-016-0629-8 | s2cid = 43199715 }}{{cite journal | vauthors = Pan MM, Kovac JR | title = Beyond testosterone cypionate: evidence behind the use of nandrolone in male health and wellness | journal = Translational Andrology and Urology | volume = 5 | issue = 2 | pages = 213–219 | date = April 2016 | pmid = 27141449 | pmc = 4837307 | doi = 10.21037/tau.2016.03.03 | doi-access = free }}

{{Androgen/anabolic steroid dosages for breast cancer}}

=Available forms=

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

Non-medical uses

{{See also|Anabolic steroid#Enhancing performance}}

NPP is used for physique- and performance-enhancing purposes by competitive athletes, bodybuilders, and powerlifters. Nandrolone esters have been said to be the most popular AAS used by bodybuilders and in sports.{{cite book| vauthors = Handelsman DJ | chapter = Androgen Physiology, Pharmacology, and Abuse| veditors = Jameson JL, De Groot LJ |title=Endocrinology: Adult and Pediatric E-Book| chapter-url = https://books.google.com/books?id=xmLeBgAAQBAJ&pg=PA2388|date=25 February 2015|publisher=Elsevier Health Sciences|isbn=978-0-323-32195-2|pages=2388–}} 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.

Side effects

{{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. However, relative to most other AAS, NPP has a greatly reduced propensity for virilization and such side effects are relatively uncommon at recommended dosages. At higher dosages and/or with long-term treatment they make increase in incidence and magnitude however. A variety of uncommon and rare side effects may also occur.

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. 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. 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. Antiandrogens like cyproterone acetate, spironolactone, and bicalutamide can block both the anabolic and androgenic effects of NPP.{{cite book| vauthors = Brown TR | chapter = Androgen Action | veditors = Bagatell C, Bremner WJ |title=Androgens in Health and Disease| chapter-url = https://books.google.com/books?id=vDcBCAAAQBAJ&pg=PA25 |date=27 May 2003|publisher=Springer Science & Business Media|isbn=978-1-59259-388-0|pages=25–}}

Pharmacology

=Pharmacodynamics=

File:Nandrolone.svg, the active form of NPP.]]

{{Relative androgenic to anabolic activity in animals}}

NPP is a nandrolone ester, or a prodrug of nandrolone. As such, it is an androgen and anabolic steroid, or an agonist of the androgen receptor, the biological target of androgens like testosterone.{{cite journal | vauthors = Gao W, Bohl CE, Dalton JT | title = Chemistry and structural biology of androgen receptor | journal = Chemical Reviews | volume = 105 | issue = 9 | pages = 3352–3370 | date = September 2005 | pmid = 16159155 | pmc = 2096617 | doi = 10.1021/cr020456u }} Relative to testosterone, NPP has enhanced anabolic effects and reduced androgenic effects. In addition to its anabolic and androgenic activity, NPP has low estrogenic activity (via its metabolite estradiol) and moderate progestogenic activity. Like other AAS, NPP has antigonadotropic effects, which are due to both its androgenic and progestogenic activity.

{{Relative affinities of nandrolone and related steroids}}

{{Relative affinities of nandrolone and related steroids at the androgen receptor}}

=Pharmacokinetics=

NPP is converted into nandrolone in the body, which is the active form of the drug. It has an extended elimination half-life in the body when administered via intramuscular injection. Its duration of action is approximately one week and it is administered once every few days to once per week. The elimination half-life and duration of action of NPP are much shorter than those of nandrolone decanoate.{{cite book| vauthors = Lemke TL, Williams DA |title=Foye's Principles of Medicinal Chemistry|url=https://books.google.com/books?id=Sd6ot9ul-bUC&pg=PA1362|date=24 January 2012|publisher=Lippincott Williams & Wilkins|isbn=978-1-60913-345-0|pages=1362–}}

{{Parenteral durations of androgens/anabolic steroids}}

{{Hormone levels with nandrolone esters by intramuscular injection}}

Chemistry

{{See also|Nandrolone#Chemistry|Androgen ester|List of androgen esters#Nandrolone esters}}

Nandrolone phenylpropionate, or nandrolone 17β-phenylpropionate, is a synthetic estrane steroid and a derivative of testosterone. 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.

{{Structural properties of major anabolic steroid esters}}

History

NPP was first described in 1957 and was introduced for medical use in 1959.{{cite book|title=Consolidated List of Products Whose Consumption And/or Sale Have Been Banned, Withdrawn, Severely Restricted Or Not Approved by Governments|url=https://books.google.com/books?id=leVCukUgNlsC&pg=PA153|year=1983|publisher=United Nations Publications|isbn=978-92-1-130230-1|pages=153–154}}{{Dead link|date=September 2024 |bot=InternetArchiveBot |fix-attempted=yes }} 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. Today, NPP is scarcely available. 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.

Society and culture

=Generic names=

Nandrolone phenylpropionate is the generic name of the drug and its {{abbrlink|BAN|British Approved Name}} while nandrolone phenpropionate is its {{abbrlink|USAN|United States Adopted Name}}. It has also been referred to as nandrolone phenylpropanoate or as nandrolone hydrocinnamate.

=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.

=Availability=

NPP is or has been marketed in many countries throughout the world, including in the United States, the United Kingdom, and Canada.

==United States==

{{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.{{cite web | title = Drugs@FDA: FDA Approved Drug Products | publisher = United States Food and Drug Administration | access-date = 17 December 2016 | url = http://www.accessdata.fda.gov/scripts/cder/daf/}} Nandrolone decanoate, conversely, is one of the few AAS that remains available for medical use in this country.

=Legal status=

NPP, along with other AAS, is a schedule III controlled substance in the United States under the Controlled Substances Act.{{cite book| vauthors = Bono JP | chapter = Criminalistics: Introduction to Controlled Substances| veditors = Karch SB |title=Drug Abuse Handbook, Second Edition| chapter-url = https://books.google.com/books?id=ZjrMBQAAQBAJ&pg=PA30|date=21 December 2006|publisher=CRC Press|isbn=978-1-4200-0346-8|pages=30–}}

References

{{Reflist}}

Further reading

{{refbegin}}

  • {{cite journal | vauthors = Kicman AT | title = Pharmacology of anabolic steroids | journal = British Journal of Pharmacology | volume = 154 | issue = 3 | pages = 502–521 | date = June 2008 | pmid = 18500378 | pmc = 2439524 | doi = 10.1038/bjp.2008.165 }}
  • {{cite journal | vauthors = Wu C, Kovac JR | title = Novel Uses for the Anabolic Androgenic Steroids Nandrolone and Oxandrolone in the Management of Male Health | journal = Current Urology Reports | volume = 17 | issue = 10 | pages = 72 | date = October 2016 | pmid = 27535042 | doi = 10.1007/s11934-016-0629-8 | s2cid = 43199715 }}
  • {{cite journal | vauthors = Pan MM, Kovac JR | title = Beyond testosterone cypionate: evidence behind the use of nandrolone in male health and wellness | journal = Translational Andrology and Urology | volume = 5 | issue = 2 | pages = 213–219 | date = April 2016 | pmid = 27141449 | pmc = 4837307 | doi = 10.21037/tau.2016.03.03 | doi-access = free }}

{{refend}}