5α-Dihydrolevonorgestrel

A metabolite of the progestin levonorgestrel

Chemical structure of 5α-Dihydrolevonorgestrel

5α-Dihydrolevonorgestrel is a steroidal compound that is a metabolite of the synthetic progestin levonorgestrel. It is formed in the body through the action of the enzyme 5α-reductase, which reduces the double bond in the A-ring of levonorgestrel, resulting in the 5α-dihydro form.

Biochemistry

5α-Dihydrolevonorgestrel is produced from levonorgestrel, a widely used progestin in hormonal contraception. The conversion is catalyzed by the enzyme 5α-reductase, which is also responsible for the conversion of testosterone to dihydrotestosterone (DHT) in the body. This reduction process is a common metabolic pathway for many steroid hormones.

Pharmacology

The pharmacological properties of 5α-dihydrolevonorgestrel are not as well-studied as those of its parent compound, levonorgestrel. However, it is known that the reduction of the A-ring can alter the binding affinity and activity of steroid hormones at their respective receptors. In the case of 5α-dihydrolevonorgestrel, it is likely to have a different profile of activity at the progesterone receptor compared to levonorgestrel.

Clinical Significance

While 5α-dihydrolevonorgestrel itself is not used as a drug, understanding its formation and activity is important in the context of the pharmacokinetics and pharmacodynamics of levonorgestrel. The presence of this metabolite can influence the overall hormonal activity and side effect profile of levonorgestrel-containing contraceptives.

Related Compounds

• Levonorgestrel
• 5α-Reductase
• Dihydrotestosterone

Related Pages

• Hormonal contraception
• Progestin
• Steroid metabolism