62-90-8/Nandrolone Phenylpropionate

Common hormone

Nandrolone Phenylpropionate is a commonly used hormone for promoting the synthesis metabolism of protein. It is produced by the esterification reaction between 19-nor-testosterone and phenylpropionyl chloride. Its dosage type is oily injection through intramuscular injection for administration. It can promote the protein synthesis as well as the savings of calcium, phosphorus, and potassium for treating severe osteoporosis, premature children, growth retardation, dwarfism, and severe malnutrition; it can also be used for inoperable breast cancer, dysfunctional uterine bleeding, and uterine muscle aneurysm. However, this product has a slightly masculine role which is not suitable for not long-term use; patients of prostate cancer, hypertension and pregnant women is disabled; patients of heart, liver and kidney dysfunction should take with caution.

Properties

It is white or white crystalline powder with special smell. Its melting point is 95~99 °C and relative density is 1.14g/cm3, [α] D20 + 48~+ 51 °C (dioxane). It is soluble in alcohol, tea oil, slightly soluble in vegetable oil but almost insoluble in water.

Pharmacological effects

This anabolic effect of this product is 12 times as high as testosterone propionate but has a relative small androgenic which is only 1.5 times as high as the latter one. It can promote protein synthesis and inhibit protein gluconeogenesis, and can also promote the deposition of calcium and phosphorus and the growth of bone tissue growth. Its effect of intramuscular injection can be maintained for 1 to 2 weeks.

Pharmacokinetics

Metabolism: hormone is mainly excreted in the urine with most part existing in the form of conjugate. However, the hormones in feces are mainly excreted in its free from while the major metabolized product of Nandrolone Phenylpropionate and nor-androstenediol in the urine is mainly 19-nor-androsterone (19-NA).

Indications

In the field of dermatology, it is mainly applied as a adjuvant treatment method for treating the negative nitrogen balance caused by high dose of corticosteroids, while increasing the protein in food; it is also used for treating exfoliative dermatitis, pemphigus, dermatomyositis, scleroderma, and senile pruritus. In addition, it can also used for treating severe burns, malignant tumor before and after surgery, refractory fractures and severe osteoporosis, premature children, significant growth retardation, dwarfism, severe malnutrition, loss of appetite, diarrhea and other serious chronic wasting diseases. In the mean time of other treatments, the product can be administrated. It can also alleviate the symptoms of inoperable breast cancer. It is also suitable to be applied to functional uterine bleeding, and uterine fibroids.

Function and Application

It is kind of anabolic hormones whose major effects include promoting protein synthesis, inhibiting protein degradation, promoting muscle growth, promoting weight increase, further retaining water, sodium, calcium, and phosphorus. It is clinical mainly used for treating the cases of lack of enough protein synthesis and increased protein decomposition such as malnutrition, stunted children, severe burns, post-operative recovery period, refractory fractures, osteoporosis in the elderly and chronic wasting disease (such as chronic kidney disease, malignant tumor, hyperthyroidism and anemia); also used for treating the negative nitrogen balance caused by long-term frequent use of glucocorticoids. However, at the mean time of administration, it is also necessary to increase the protein content contained in the food. This product has a unique foul smell; it is almost insoluble in water but soluble in ethanol and fatty oil.

Side effects

It has slightly masculine effect. After women’s administration of it, some cases such as hirsutism, acne, thicker sound, clitoral hypertrophy, amenorrhea, or menstrual disorders can occur. In these cases, the administration of this drug should be discontinued immediately. Long-term use can cause jaundice and liver dysfunction, and may also cause edema due to sodium retention.

Drug Interactions

1. Using it in combination with oral anticoagulant drug can improve the efficacy of the latter one and increase the tendency of increased bleeding. 2. Anabolic steroids can reduce glucose tolerance; diabetic patients should pay attention to adjust the dose insulin or orally administrated amount of hypoglycemic medicine during the treatment. 3. Others are the same as methyltestosterone.

Precautions

1. Patients of liver disease, kidney disease, hypertension, prostate cancer, breast cancer and pregnant women should be disabled. 2. It should not be used in healthy children. 3. Patient of benign prostatic hypertrophy, myocardial infarction or with history of coronary artery disease should take with caution. 4. This product is prohibited as long-term nutritional products used in healthy people. 5. During the medication period, patients should increase the uptake of nutrition, especially protein. 6. It demands deep intramuscular injection.

Chemical Properties

White to Off-White Solid

Originator

Durabolin,Organon,US,1959

Uses

Anabolic steroid; androgen.

Manufacturing Process

An ice-cold solution of 1.5 grams of 19-nortestosterone and 1.5 ml of dry pyridine in 10 ml of dry benzene is prepared and a solution of 1.5 ml of β- phenylpropionyl chloride in 5 ml of dry benzene is added dropwise over a period of about 2 minutes with stirring. The resulting mixture is allowed to stand overnight under an atmosphere of nitrogen and then washed successively with cold 5% aqueous hydrochloric acid solution, cold 2.5% aqueous sodium hydroxide solution, and water. After drying over anhydrous sodium sulfate, the solvent is evaporated to give an almost colorless oil. Recrystallization from methanol gives white crystals of 19-nortestosterone 17- β-phenylpropionate, MP 91° to 92.5°C.

Brand name

Durabolin (Organon);Anabolicas;Anabolicus;Anabolin depot;Anabolin la-100;Androline;Androlone-d;Anticatabolin;Bexobolic;Deca-durabolin;Docabolin;Durabolin phenpropionate;Dynabalon;Energital;Fherbolico;Hepa-obaton;Hybolin decabiate;Hybolin improved;Kabolin;Keratyl;Kompleteron;Methybol-depot;Neo-durabolic;Nerobolin;Norabol;Noralone;Norandrol;Norandros;Noromon;Norstenol;Nortesto;Sintabolin;Stenabolin;Superbolin;Suprabolin.

Therapeutic Function

Anabolic

World Health Organization (WHO)

Nandrolone phenylpropionate, an anabolic steroid, was introduced in 1959. In 1982, low dosage preparations were prohibited in Bangladesh due to inadmissible promotion of products containing anabolic steroids for malnourished children. Higher dosage preparations of nandrolone phenylpropionate remain available in many countries, including Bangladesh, for several highly specific but limited indications that apply to patients with chronic debilitating and emaciating diseases, particularly associated with neoplasia and some types of aplastic anaemia.

Synthesis

Nandrolone phenylpropionate is prepared by reacting anhydrous MeCN with a mixture of 3-phenylpropanoic acid, aryneprecursor, nandrolone CsF, K2CO3, and 18-crown-6 in 70 ℃ in an oil bath.Add anhydrous MeCN (0.5 mL) to a mixture of 3-phenylpropanoic acid (30.0 mg, 0.2 mmol, 1.0 equiv), aryneprecursor (119.2 mg, 0.4 mmol, 2.0 equiv), nandrolone (82.3 mg, 0.3 mmol, 1.5 equiv), CsF (182.3 mg, 1.2 mmol, 6.0 equiv), K2CO3 (82.9 mg, 0.6 mmol, 3.0 equiv), and 18-crown-6 (158.6 mg, 0.6 mmol, 3.0 equiv). Warm the mixture to 70 ℃ in an oil bath and stir at this temperature for8 hours. Remove all the volatiles directly on rotary evaporator. Purify by flash column chromatography with pet ether:EtOAc = 20:1. 1H NMR (400 MHz, CDCl3) δ 7.31-7.26(m,2H), 7.23-7.17(m,3H), 5.83 (s, lH), 4.65-4.58(m, lH), 2.95(t, J= 8.0 Hz,2H), 2.64(t, J= 8.0 Hz,2H), 2.51-2.36(m, 2H), 2.31-2.04(m, 5H), 1.86-1.79(m, 2H), 1.72-1.61 (m, 2H), 1.57-1.00(m, 8H),0.90-0.81(m, 1H), 0.79 (s, 3H)ppm.Fig The synthetic method 1 of Nandrolone phenylpropionate