flumazenil   

GtoPdb Ligand ID: 4192

Synonyms: Anexate® | Ro15-1788
flumazenil is an approved drug (FDA (1991))
Compound class: Synthetic organic
Comment: Flumazenil reverses the effects of benzodiazepine sedatives.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 5
Hydrogen bond donors 0
Rotatable bonds 3
Topological polar surface area 63.91
Molecular weight 303.1
XLogP 2.92
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES CCOC(=O)c1ncn2c1CN(C)C(=O)c1c2ccc(c1)F
Isomeric SMILES CCOC(=O)c1ncn2c1CN(C)C(=O)c1c2ccc(c1)F
InChI InChI=1S/C15H14FN3O3/c1-3-22-15(21)13-12-7-18(2)14(20)10-6-9(16)4-5-11(10)19(12)8-17-13/h4-6,8H,3,7H2,1-2H3
InChI Key OFBIFZUFASYYRE-UHFFFAOYSA-N
References
1. Huang Q, Liu R, Zhang P, He X, McKernan R, Gan T, Bennett DW, Cook JM. (1998)
Predictive models for GABAA/benzodiazepine receptor subtypes: studies of quantitative structure-activity relationships for imidazobenzodiazepines at five recombinant GABAA/benzodiazepine receptor subtypes [alphaxbeta3gamma2 (x = 1-3, 5, and 6)] via comparative molecular field analysis.
J. Med. Chem., 41 (21): 4130-42. [PMID:9767648]
2. Wieland HA, Lüddens H. (1994)
Four amino acid exchanges convert a diazepam-insensitive, inverse agonist-preferring GABAA receptor into a diazepam-preferring GABAA receptor.
J. Med. Chem., 37 (26): 4576-80. [PMID:7799410]