Allopregnanolone

From DrugPedia: A Wikipedia for Drug discovery

[edit] Description

Show 3-D Structure

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.

[edit] 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

[edit] PhysioChemical Properties

*Melting Point

*LogP

*Water Solubility

[edit] External Links

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