Description
Methyltestosterone is a synthetic analog of testosterone that possesses all of the properties of
testosterone, exhibiting stimulatory action on the development of male sex organs and secondary sex characteristics, although it is not degraded by enzymes in the gastrointestinal
tract, and therefore it can only be taken orally
Chemical Properties
white to slightly yellowish-white crystalline
Originator
Metandren ,Ciba,US,1941
Uses
It is used for the same indications as testosterone for sexual underdevelopment, functional problems of the reproductive system, and the
vascular nerve disorders associated with climacteric problems in men. It is also used for dysfunctional uterine bleeding in premenopausal and menopausal women as well as for breast
and ovarian cancer.
Uses
Androgen. It has been used as an androgenic agent.
Controlled substance (anabolic steroid).
Definition
ChEBI: A 17beta-hydroxy steroid that is testosterone bearing a methyl group at the 17alpha position.
Manufacturing Process
0.6 g of 17-Methyl-?5,6-androstenediol-(3,17) is heated under reflux cooling during 20 hours in 50 cm3 of benzene and 12 cm3 of acetone with 3 g of tertiary chloromagnesium butylate, which may be prepared by conversion of acetone with methyl magnesium chloride. The magnesium is then removed by shaking out with dilute H2SO4; the benzene layer is washed with water, dried with sodium sulfate and then evaporated to dryness. Methyltestosterone (MP 160° to 162°C) is obtained in a yield of more than 75% of the theory, according to US Patent 2,384,335.
Brand name
Android (Valeant);Metandren (Novartis); Oreton (Schering); Testred (Valeant); Virilon (Star).
Therapeutic Function
Androgen
Pharmacokinetics
The synthesis of 17α-methyltestosterone made available a compound that was orally active in
daily doses between 10 and 50 mg, which is equivalent to a 400 mg oral dose of testosterone. The
presence of a 17α alkyl group reduces susceptibility to hepatic oxidative metabolism, thereby
increasing oral bioavailability by slowing metabolism. Following oral administration,
methyltestosterone is well absorbed from the gastrointestinal tract, with a half-life of approximately 3
hours. This drug has the androgenic and anabolic activities of testosterone. Although orally active, it
is more effective when administered sublingually. The alkylated oral androgens should be viewed as
potentially hepatotoxic and should not be used.
Synthesis
Methyltestosterone, 17|?-hydroxy-17|á-methylandrost-4-en-3-one
(29.1.7), is also synthesized from androstenolone by reacting it with methylmagnesiumiodide, forming the corresponding tertiary alcohol (29.1.6), and subsequent oxidation of the
hydroxyl group at C3 to a ketone using chromium (VI) oxide. Simultaneous isomerization
of the double bond takes place under the reaction conditions, giving the desired methyltestosterone (29.1.7).
Purification Methods
This anabolic steroid is crystallised from hexane or hexane/*benzene. It has E1cm 1% 495-530 at 241nm (EtOH). The colour reaction with 2,4-dinitrophenyl hydrazine is used for assaying it. [Gornall & Macdonald J Biol Chem 201 279 1953.] In another colour reaction the sterone (1mg) in acetic acid (0.2ml) + 88% H3PO4 (2mL) is allowed to stand for 1hour when it becames fluorescent. After 1hour it is diluted with acetic acid (~3mL) and provides a strong yellow fluorescence with the intensity of 50-100 times that of estrone. [Stuart & Stuckey J Pharm Pharmacol 1 130 1949, Openauer Rec Trav Chim Pays-Bas 56 137 137, Beilstein 8 IV 1010.]
