Allopregnanolone

From DrugPedia: A Wikipedia for Drug discovery

Contents 1 Description 2 General Properties 3 PhysioChemical Properties 4 External Links

Description

A pregnane found in the urine of pregnant women and sows. It has anesthetic, hypnotic, and sedative properties. Allopregnanolone, also known as 3α,5α-tetrahydroprogesterone or THP, is an important neurosteroid in the human brain. It is a metabolite of progesterone and a barbiturate-like modulator of central gamma-aminobutyric acid (GABA) receptors that modify a range of behaviors, including the stress response.

Allopregnanolone targets the GABA A receptor to reduce anxiety and create calm at times of stress. The hormone allopregnanolone normally released in response to stress, actually reverses its effect at puberty and instead increases anxiety.<ref>"Scientists find hormone activity explains adolescent mood swings" (Template:Dead link – ^{Scholar search}) . SUNY Downstate Medical Center. </ref>

The 3β enantiomer of this compound is known as pregnanolone, and has very similar properties to allopregnanolone. Both compounds are found endogenously and have similar hypnotic and anxiolytic effects.

General Properties

*Molecular Weight

318.49

*Molecular Formula

C₂₁H₃₄O₂

*IUPAC NAME

1-[(3R,5S,8R,9S,10S,13S,14S,17S)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanone

*Canonical Smiles

CC(=O)C1CCC2C1(CCC3C2CCC4C3(CCC(C4)O)C)C

*Isomeric Smiles

CC(=O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC[C@@H]4[C@@]3(CC[C@H](C4)O)C)C

PhysioChemical Properties

*Melting Point

*LogP

*Water Solubility

External Links

• [1]Pubchem
• [2]KEGG Compound
• [3]Human Metabolome DataBase