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.
Click here for help
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: secobarbital

2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
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
Click here for help
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
References
1. Twyman RE, Rogers CJ, Macdonald RL. (1989)
Differential regulation of gamma-aminobutyric acid receptor channels by diazepam and phenobarbital.
Ann Neurol, 25 (3): 213-20. [PMID:2471436]