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| Clinical data | |
|---|---|
| Trade names | Durabolin, others |
| Other names | • NPP • Nandrolone phenpropionate • 19-Nortestosterone phenylpropionate • Nandrolone hydrocinnamate • 19-Nortestosterone 17β-phenylpropionate • NSC-23162 |
| Pregnancy category |
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| Routes of administration | Intramuscular injection |
| Drug class | Androgen;Anabolic steroid;Androgen ester;Progestogen |
| Legal status | |
| Legal status |
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| Pharmacokinetic data | |
| Bioavailability | •Oral: 0.3–2.9% (pigs)[1] •Intramuscular: high[2] |
| Metabolism | Blood (hydrolysis),liver (reduction)[7][5] |
| Metabolites | •Nandrolone[3] •5α-Dihydronandrolone[3] •19-Norandrosterone[4] •19-Noretiocholanolone[4] •Conjugates[5] |
| Eliminationhalf-life | • Intramuscular: 2.7 days[6] • Nandrolone: <4.3 hours[7] |
| Duration of action | • Intramuscular: 5–7 days[3][6] |
| Excretion | Urine[7] |
| Identifiers | |
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| CAS Number | |
| PubChemCID | |
| DrugBank | |
| ChemSpider | |
| UNII |
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| CompTox Dashboard(EPA) | |
| ECHA InfoCard | 100.000.502 |
| Chemical and physical data | |
| Formula | C27H34O3 |
| Molar mass | 406.566 g·mol−1 |
| 3D model (JSmol) | |
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Nandrolone phenylpropionate (NPP), ornandrolone phenpropionate, sold under the brand nameDurabolin among others, is anandrogen andanabolic steroid (AAS) medication which has been used primarily in the treatment ofbreast cancer andosteoporosis in women.[8][9][10][11][3] It is given byinjection 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 includesymptoms ofmasculinization likeacne,increased hair growth,voice changes, and increasedsexual desire.[3] The drug is asynthetic androgen and anabolic steroid and hence is anagonist of theandrogen receptor (AR), thebiological target of androgens liketestosterone anddihydrotestosterone (DHT).[3][12] It has stronganabolic effects and weakandrogenic 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 anandrolone ester and a long-lastingprodrug ofnandrolone 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 bynandrolone 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 toimprove physique and performance.[3] The drug is acontrolled substance in many countries and so non-medical use is generally illicit.[3]
NPP has been used mainly in the treatment of advancedbreast cancer in women and as anadjunct therapy for the treatment ofsenile orpostmenopausalosteoporosis 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 inandrogen replacement therapy forandrogen 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 ofprostate enlargement,prostate cancer, andscalp hair loss relative to testosterone.[16][17]
| 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 (IMTooltip intramuscular injection orSCTooltip subcutaneous injection) | 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. | ||||
NPP is or has been available 25 mg/mL and 50 mg/mL formulations inoil solution forintramuscular injection.[3]
NPP is used forphysique- and performance-enhancing purposes bycompetitiveathletes,bodybuilders, andpowerlifters.[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 forandrogenic andestrogenicside effects.[3]
The most common side effects of NPP consist ofvirilization (masculinization) in women, including symptoms such asacne,hirsutism (increasedbody/facial hair growth),hoarseness of the voice, andvoice 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]
Antiestrogens likearomatase inhibitors (e.g.,anastrozole) andselective estrogen receptor modulators (e.g.,tamoxifen,raloxifene) can interfere with and prevent theestrogenic effects of NPP.[3]5α-Reductase inhibitors likefinasteride anddutasteride can prevent the inactivation of nandrolone in so-called "androgenic"tissues like theskin,hair follicles, andprostate 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 by5α-reductase in such tissues or are notmetabolized by 5α-reductase.[3]Antiandrogens likecyproterone acetate,spironolactone, andbicalutamide can block both the anabolic and androgenic effects of NPP.[19]
| 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 | 1:2–1:3 |
| Oxymetholone | 1:2–1:9 |
| Oxandrolone | 1:13–1:3 |
| Stanozolol | 1:1–1:3 |
| Nandrolone | 1:3–1:16 |
| Ethylestrenol | 1:2–1:19 |
| Norethandrolone | 1:1–1:2 |
| Notes: In rodents.Footnotes:a = Ratio of androgenic to anabolic activity.Sources: See template. | |
NPP is anandrolone ester, or aprodrug ofnandrolone.[20][3] As such, it is anandrogen andanabolic steroid, or anagonist of theandrogen receptor, thebiological target of androgens liketestosterone.[3][20] Relative to testosterone, NPP has enhancedanabolic effects and reducedandrogenic effects.[20][3] In addition to its anabolic and androgenic activity, NPP has lowestrogenic activity (via itsmetaboliteestradiol) and moderateprogestogenic activity.[3] Like other AAS, NPP hasantigonadotropic effects, which are due to both its androgenic and progestogenic activity.[3]
| 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 (%). Referenceligands (100%) wereprogesterone for thePRTooltip progesterone receptor,testosterone for theARTooltip androgen receptor,estradiol for theERTooltip estrogen receptor,dexamethasone for theGRTooltip glucocorticoid receptor,aldosterone for theMRTooltip mineralocorticoid receptor,dihydrotestosterone forSHBGTooltip sex hormone-binding globulin, andcortisol forCBGTooltip corticosteroid-binding globulin.Sources: See template. | |||||||
| 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. | ||||||||
NPP is converted intonandrolone in the body, which is the active form of the drug.[3] It has an extendedelimination half-life in the body when administered viaintramuscular injection.[20] Itsduration 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 ofnandrolone decanoate.[3][21]
| 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 | 14–28 days |
| Testosterone cypionate | Oil solution | Depovirin | 14–28 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 | 21–28 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 viai.m. injection.Footnotes:a =TP,TV, andTUe.b =TP andTKL.c =TP,TPP,TiCa, andTD.d = Studied but never marketed.e = Developmental code names.Sources: See template. | |||
Nandrolone phenylpropionate, or nandrolone 17β-phenylpropionate, is asyntheticestranesteroid and aderivative oftestosterone.[8][9] It is anandrogen ester; specifically, it is the C17βphenylpropionateester ofnandrolone (19-nortestosterone), which itself is the 19-demethylatedanalogue of testosterone.[8][9]
| Anabolic steroid | Structure | Ester | Relative mol. weight | Relative AAS contentb | Durationc | ||||
|---|---|---|---|---|---|---|---|---|---|
| Position | Moiety | Type | Lengtha | ||||||
| Boldenone undecylenate |  | C17β | Undecylenic acid | Straight-chain fatty acid | 11 | 1.58 | 0.63 | Long | |
| Drostanolone propionate |  | C17β | Propanoic acid | Straight-chain fatty acid | 3 | 1.18 | 0.84 | Short | |
| Metenolone acetate |  | C17β | Ethanoic acid | Straight-chain fatty acid | 2 | 1.14 | 0.88 | Short | |
| Metenolone enanthate |  | C17β | Heptanoic acid | Straight-chain fatty acid | 7 | 1.37 | 0.73 | Long | |
| Nandrolone decanoate |  | C17β | Decanoic acid | Straight-chain fatty acid | 10 | 1.56 | 0.64 | Long | |
| Nandrolone phenylpropionate | | C17β | Phenylpropanoic acid | Aromatic fatty acid | – (~6–7) | 1.48 | 0.67 | Long | |
| Trenbolone acetate |  | C17β | Ethanoic acid | Straight-chain fatty acid | 2 | 1.16 | 0.87 | Short | |
| Trenbolone enanthated |  | C17β | Heptanoic acid | Straight-chain fatty acid | 7 | 1.41 | 0.71 | Long | |
| Footnotes:a = Length ofester incarbonatoms forstraight-chain fatty acids or approximate length of ester in carbon atoms foraromatic fatty acids.b = Relative androgen/anabolic steroid content by weight (i.e., relativeandrogenic/anabolicpotency).c =Duration byintramuscular orsubcutaneous injection inoil solution.d = Never marketed.Sources: See individual articles. | |||||||||
NPP was first described in 1957 and was introduced for medical use in 1959.[3][27] 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.[27]
Nandrolone phenylpropionate is thegeneric name of the drug and itsBANTooltip British Approved Name whilenandrolone phenpropionate is itsUSANTooltip United States Adopted Name.[8][9][10][11] It has also been referred to asnandrolone phenylpropanoate or asnandrolone hydrocinnamate.[8][9][10][11]
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]
NPP is or has been marketed in many countries throughout the world, including in theUnited States, theUnited Kingdom, andCanada.[9][11]
NPP was marketed previously in the United States but is no longer available in this country.[28] Nandrolone decanoate, conversely, is one of the few AAS that remains available for medical use in this country.[28]
NPP, along with other AAS, is aschedule IIIcontrolled substance in theUnited States under theControlled Substances Act.[29]
