secobarbital   Click here for help

GtoPdb Ligand ID: 7615

Synonyms: Seconal®
Approved drug
secobarbital is an approved drug (FDA (1950))
Compound class: Synthetic organic
Comment: The approved drug is a racemic mixture of enantiomers; R-secobarbital and S-secobarbital. We show the non-stereo structure to represent the mixture.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 2
Rotatable bonds 5
Topological polar surface area 75.27
Molecular weight 238.13
XLogP 2.28
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES CCCC(C1(CC=C)C(=O)NC(=O)NC1=O)C
Isomeric SMILES CCCC(C1(CC=C)C(=O)NC(=O)NC1=O)C
InChI InChI=1S/C12H18N2O3/c1-4-6-8(3)12(7-5-2)9(15)13-11(17)14-10(12)16/h5,8H,2,4,6-7H2,1,3H3,(H2,13,14,15,16,17)
InChI Key KQPKPCNLIDLUMF-UHFFFAOYSA-N
No information available.
Summary of Clinical Use Click here for help
Secobarbital is used short-term to treat insomnia, as a pre-operative sedative, or as an anaesthetic for short surgical, diagnostic, or therapeutic procedures.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Secobarbital is a positive allosteric modulator of GABAA channels, enhancing the inhibitory effects of GABA in the CNS. The drug binds to a barbituate allosteric site [1], which is distinct from the benzodiazepine allosteric site, and from the GABA binding site. Barbiturate modulation prolongs the duration of bursts of chloride channel opening [1] and this is responsible for the anxiolytic, anticonvulsant, amnesic, sedative, hypnotic, euphoriant, and muscle relaxant properties of the drug.
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