This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.
Identification
- Generic Name
- Bicuculline
- DrugBank Accession Number
- DB11562
- Background
Bicuculline is a light-sensitive competitive antagonist of GABAA receptors. It was originally identified in 1932 in plant alkaloid extracts and has been isolated from Dicentra cucullaria, Adlumia fungosa, Fumariaceae, and several Corydalis species.
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for Bicuculline (DB11562)
- Weight
- Average: 367.3521
Monoisotopic: 367.105587281 - Chemical Formula
- C20H17NO6
- Synonyms
- Bicculine
- Bicucullin
- d-Bicuculline
Pharmacology
- Indication
Not Available
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Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
- Not Available
- Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as phthalide isoquinolines. These are organic compounds with a structure characterized by an isoquinoline moiety linked to phthalide.
- Kingdom
- Organic compounds
- Super Class
- Alkaloids and derivatives
- Class
- Phthalide isoquinolines
- Sub Class
- Not Available
- Direct Parent
- Phthalide isoquinolines
- Alternative Parents
- Tetrahydroisoquinolines / Phthalides / Benzofuranones / Benzodioxoles / Aralkylamines / Benzenoids / Trialkylamines / Amino acids and derivatives / Lactones / Carboxylic acid esters show 7 more
- Substituents
- Acetal / Amine / Amino acid or derivatives / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Benzodioxole / Benzofuranone / Carboxylic acid derivative show 19 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- isoquinoline alkaloid, isoquinolines (CHEBI:3092) / Isoquinoline alkaloids (C09364)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- Y37615DVKC
- CAS number
- 485-49-4
- InChI Key
- IYGYMKDQCDOMRE-ZWKOTPCHSA-N
- InChI
- InChI=1S/C20H17NO6/c1-21-5-4-10-6-14-15(25-8-24-14)7-12(10)17(21)18-11-2-3-13-19(26-9-23-13)16(11)20(22)27-18/h2-3,6-7,17-18H,4-5,8-9H2,1H3/t17-,18+/m0/s1
- IUPAC Name
- (10R)-10-[(5S)-6-methyl-2H,5H,6H,7H,8H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-3,5,11-trioxatricyclo[7.3.0.0^{2,6}]dodeca-1(9),2(6),7-trien-12-one
- SMILES
- [H][C@]1(OC(=O)C2=C1C=CC1=C2OCO1)[C@@]1([H])N(C)CCC2=CC3=C(OCO3)C=C12
References
- General References
- Khawaled R, Bruening-Wright A, Adelman JP, Maylie J: Bicuculline block of small-conductance calcium-activated potassium channels. Pflugers Arch. 1999 Aug;438(3):314-21. [Article]
- External Links
- KEGG Compound
- C09364
- PubChem Compound
- 10237
- PubChem Substance
- 347827985
- ChemSpider
- 9820
- BindingDB
- 50000693
- ChEBI
- 3092
- ChEMBL
- CHEMBL417990
- ZINC
- ZINC000019899011
- PDBe Ligand
- H0Z
- Wikipedia
- Bicuculline
- PDB Entries
- 6huk
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.361 mg/mL ALOGPS logP 1.76 ALOGPS logP 2.68 Chemaxon logS -3 ALOGPS pKa (Strongest Acidic) 13.1 Chemaxon pKa (Strongest Basic) 6.67 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 6 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 66.46 Å2 Chemaxon Rotatable Bond Count 1 Chemaxon Refractivity 93.45 m3·mol-1 Chemaxon Polarizability 37.3 Å3 Chemaxon Number of Rings 6 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Drug created at March 29, 2016 16:20 / Updated at June 12, 2020 16:53