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Pregnanolone

Note

the 3α,5β-reduced metabolite of progesterone

Pregnanolone, also known as eltanolone, is an endogenous inhibitory neurosteroid which is produced in the body from progesterone. It is closely related to allopregnanolone, which has similar properties.

Biological activity

Pregnanolone is a positive allosteric modulator of the GABAA receptor, as well as a negative allosteric modulator of the glycine receptor.

Biological function

Pregnanolone has sedative, anxiolytic, anesthetic, and anticonvulsant effects. During pregnancy, pregnanolone and allopregnanolone are involved in sedation and anesthesia of the fetus.

Biochemistry

Pregnanolone is synthesized from progesterone via the enzymes 5β-reductase and 3α-hydroxysteroid dehydrogenase, with 5β-dihydroprogesterone occurring as a metabolic intermediate. The elimination half-life of pregnanolone is between 0.9 and 3.5 hours.

Chemistry

Pregnanolone, also known as 3α,5β-tetrahydroprogesterone (3α,5β-THP) or as 5β-pregnan-3α-ol-20-one, is a naturally occurring pregnane steroid and a derivative of progesterone. Related compounds include allopregnanolone (3α,5α-THP; brexanolone), epipregnanolone (3β,5β-THP), hydroxydione, isopregnanolone (3β,5α-THP), and renanolone.

History

Pregnanolone was first isolated from the urine of pregnant women in 1937. Its anesthetic properties were first demonstrated in animals in 1957.

Research

Pregnanolone was investigated for clinical use as a general anesthetic under the name eltanolone (), but produced unwanted side effects such as convulsions on occasion, and for this reason, was never marketed.

References

References

  1. (March 1992). "Preliminary study of a pregnanolone emulsion (Kabi 2213) for i.v. induction of general anaesthesia". Br J Anaesth.
  2. (March 1990). "Pregnanolone emulsion. A preliminary pharmacokinetic and pharmacodynamic study of a new intravenous anaesthetic agent". Anaesthesia.
  3. Reddy DS. (2003). "Pharmacology of endogenous neuroactive steroids". Critical Reviews? In Neurobiology.
  4. (8 January 2008). "Modern Anesthetics". Springer Science & Business Media.
  5. (October 1994). "Pharmacokinetics and pharmacodynamics of eltanolone (pregnanolone), a new steroid intravenous anaesthetic, in humans". Acta Anaesthesiol Scand.
  6. (2005). "The importance of 'awareness' for understanding fetal pain". Brain Res. Brain Res. Rev..
  7. (2009). "The emergence of human consciousness: from fetal to neonatal life". Pediatr. Res..
  8. (21 January 2009). "Principles and Practice of Pharmacology for Anaesthetists". John Wiley & Sons.
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5β-pregnanes gabaa-receptor-positive-allosteric-modulators gabaa-rho-receptor-negative-allosteric-modulators general-anesthetics glycine-receptor-antagonists neurosteroids pregnane-x-receptor-agonists
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