Description
Drostanolone, also known as Dromostanolone[58-19-5], is an anabolic hormone and a derivative of methyltestosterone. Its action is similar to that of Conviron. Its anabolic effect is 4 times that of methyltestosterone and its androgenic activity is 0.39 times that of the latter. It is clinically used in the treatment of chronic wasting disease, pediatric underdevelopment, old age and frailty, serious illness and postoperative weakness, osteoporosis, aplastic anemia, leukopenia, thrombocytopenia, and hyperlipidemia.
Chemical Properties
White or off-white crystalline powder, odorless. Insoluble in water, slightly soluble in ethanol, slightly soluble in ether, soluble in chloroform.
Originator
Drolban,Lilly,US,1961
Uses
Drostanolone is a synthetic estrogen antagonist and is classified as an anabolic androgenic steroid. It has been used in sports to improve athletic performance and can be detected in urine. In the United States, Drostanolone is classified as a Schedule III substance, indicating it is regulated and controlled. This product is intended for research and forensic applications.
Definition
ChEBI: Metholone is a 17beta-hydroxy steroid, an anabolic androgenic steroid and a 3-oxo-5alpha-steroid. It has a role as an anabolic agent and an antineoplastic agent.
Manufacturing Process
A mixture of 1 gram of 2-hydroxymethylene-dihydrotestosterone, 10 cc of pyridine and 2 cc of propionic anhydride was allowed to react at room temperature for 16 hours and then poured into water. The resulting suspension was heated for 1 hour on the steam bath to hydrolyze the excess of propionic anhydride, cooled and extracted with methylene dichloride. The extract was consecutively washed with dilute hydrochloric acid, sodium bicarbonate solution and water, dried over anhydrous sodium sulfate and evaporated to dryness under vacuum. There was thus obtained the dipropionate of 2-hydroxymethylenedihydrotestosterone which was treated with hydrogen, in methanol solution.
When the uptake of hydrogen ceased, the catalyst was filtered and the solution was evaporated to dryness under vacuum. The residue was dissolved in a mixture of benzene-hexane, transferred to a chromatographic column with neutral alumina and the product was eluted with mixtures of benzenehexane, gradually increasing the proportion of benzene in the mixture. Crystallization of the eluates from acetone-hexane yielded the propionate of 2α-methyldihydrotestosterone(Dromostanolone).
brand name
Drolban (Lilly).
Therapeutic Function
Cancer chemotherapy
Synthesis
Drostanolone is prepared by this “one-pot-reaction”-step the conversion to the 1α-methyl-group is performed simultaneously with the cleavage of the protective group at the 17β-alcohol: 10.60 g Hydroxymethylene-precusor 2-Hydroxymethylene-androstan-17β-((tetrahydro-2H-pyran-2-yl)oxy)-3-one was nearly dissolved in 800 ml ethanol at 55°C. This
solution was hydrogenated in a pressure vessel (Parr reactor) with 6.00 g palladium on charcoal
(5%) at 4 bar and room temperature for 24 h. The mixture was filtered twice through paper and
the corresponding ethanol solution was evaporated, to yield 9.50 g colorless oil, still contains
traces of charcoal and ethanol. The crude product was purified by column chromatography on
silica gel by using hexane-ethyl acetate (8:2) as an eluent, to afford 5.45 g purified Drostanolone as
a colorless solid (69%) . MS (ESI+):
m/z = 304.96 (calculated MW: 304.47 g/mol)
Rf: 0.35, hexane/ethyl acetate 7:3, visualized by Seebach derivatization reagent.
1
H NMR(300 MHz, DMSO-d6) : δ 4.42 (d, 1 H, OH), 3.42 (m, 1H, HCHOH), 3.32 (s, 1H, CH),
2.37 (t, 1 H, CH), 1.99 (dd, 1 H, ), 1.84 (dd, 1H), 1.78 – 1.84 (m, 1H), 1.72 (m, 1H), 1.61 (m,
1H), 1.22-1.58 (m, 8H), 1.08 – 1.22 (m, 1H), 1.03 (s, 3H, CH3), 0.76-1.01 (m + d, 7H, 2α-CH3
+X), 0.65 – 0.72 (m, 1H), 0.64 (s, 3H, CH3).
Mode of action
It can promote protein synthesis and inhibit protein xenobiosis, reduce calcium and phosphorus excretion and alleviate bone marrow suppression, promote growth and development, promote tissue renewal and granulation, and reduce blood cholesterol, and have preventive and antagonistic effects on adrenocorticotropic hormone long-term use of adrenocorticotropic hypoplasia and protein anisotropy.
References
[1] SCH?NZER W, DONIKE M. Metabolism of anabolic steroids in man: synthesis and use of reference substances for identification of anabolic steroid metabolites[J]. Analytica Chimica Acta, 1993, 275: 23-48. DOI:10.1016/0003-2670(93)80274-O.
[2] KINTZ P, GHEDDAR L. Evidence of use of drostanolone, an anabolic steroid, at the time the subject committed a murder: Place of hair analysis[J]. Toxicologie Analytique et Clinique, 2021. DOI:10.1016/J.TOXAC.2021.05.002.
[3] LIU Y, LU J, YANG S, et al. New drostanolone metabolites in human urine by liquid chromatography time-of-flight tandem mass spectrometry and their application for doping control[J]. Steroids, 2016, 108: 61-67. DOI:
10.1016/j.steroids.2016.01.013.
