Nandrolone phenylpropionate

Absorption

The absorption after oral dosing is rapid for testosterone and probably for other anabolic steroids, but there is extensive first-pass hepatic metabolism for all anabolic steroids except those that are substituted at the 17-alpha position. The rate of absorption from subcutaneous or intramuscular depots depends on the product and its formulation. Absorption is slow for the lipid-soluble esters such as the cypionate or enanthate, and for oily suspensions.

Chemical properties

White to Off-White Solid

Originator

Durabolin,Organon,US,1959

The Uses of Nandrolone phenylpropionate

Anabolic steroid; androgen.

Background

C18 steroid with androgenic and anabolic properties. It is generally prepared from alkyl ethers of estradiol to resemble testosterone but less one carbon at the 19 position. It is a schedule III drug in the U.S.

Indications

For the treatment of refractory deficient red cell production anemias, breast carcinoma, hereditary angioedema, antithrombin III deficiency, fibrinogen excess, growth failure and Turner's syndrome. It is also indicated in the prophylaxis of hereditary angioedema.

Definition

ChEBI: Nandrolone phenpropionate is a 3-phenylpropionate ester. It has a role as an anabolic agent and an androgen. It is functionally related to a nandrolone.

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.

Pharmacokinetics

Nandrolone is an anabolic steroid occurring naturally in the human body, albeit in small quantities. Nandrolone increases production and urinary excretion of erythropoietin. It may also have a direct action on bone marrow. Nandrolone binds to the androgen receptor to a greater degree than testosterone, but due to its inability to act on the muscle in ways unmediated by the receptor, has less overall effect on muscle growth.

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) |? 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

Metabolism

Nandrolone is unusual in that unlike most anabolic steroids, it is not broken down into the more reactive DHT by the enzyme 5α-reductase, but rather into a less effective product known as Dihydronandrolone.