Hycanthone
Star0
This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.
Identification
- Generic Name
- Hycanthone
- DrugBank Accession Number
- DB14061
- Background
Potentially toxic, but effective antischistosomal agent, it is a metabolite of LUCANTHONE. Hycanthone was approved by the FDA in 1975 but is no longer used.
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 356.48
Monoisotopic: 356.155849195 - Chemical Formula
- C20H24N2O2S
- Synonyms
- 1-((2-(Diethylamino)ethyl)amino)-4-(hydroxymethyl)-9H-thioxanthen-9-one
- 1-((2-(Diethylamino)ethyl)amino)-4-(hydroxymethyl)thioxanthen-9-one
- Hicantona
- Hycanthon
- Hycanthone
- Hycanthonum
- Lucanthone metabolite
- External IDs
- Win 24,933
- WIN 24933
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism AP-glycoprotein 1 inhibitorHumans - 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
Products
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- Product Ingredients
Ingredient UNII CAS InChI Key Hycanthone mesylate 48830NW22A 23255-93-8 LOEQGPPJCCUXEJ-UHFFFAOYSA-N
Categories
- Drug Categories
- Classification
- Not classified
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 2BXX5EVN2A
- CAS number
- 3105-97-3
- InChI Key
- MFZWMTSUNYWVBU-UHFFFAOYSA-N
- InChI
- InChI=1S/C20H24N2O2S/c1-3-22(4-2)12-11-21-16-10-9-14(13-23)20-18(16)19(24)15-7-5-6-8-17(15)25-20/h5-10,21,23H,3-4,11-13H2,1-2H3
- IUPAC Name
- 1-{[2-(diethylamino)ethyl]amino}-4-(hydroxymethyl)-9H-thioxanthen-9-one
- SMILES
- CCN(CC)CCNC1=C2C(=O)C3=CC=CC=C3SC2=C(CO)C=C1
References
- General References
- Not Available
- External Links
- KEGG Drug
- D00541
- ChemSpider
- 3508
- BindingDB
- 50066721
- ChEBI
- 52768
- ChEMBL
- CHEMBL22077
- ZINC
- ZINC000003830916
- PDBe Ligand
- QHM
- Wikipedia
- Hycanthone
- PDB Entries
- 6uux / 6uuy
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 0.0168 mg/mL ALOGPS logP 3.87 ALOGPS logP 3.74 Chemaxon logS -4.3 ALOGPS pKa (Strongest Acidic) 14.79 Chemaxon pKa (Strongest Basic) 8.67 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 52.57 Å2 Chemaxon Rotatable Bond Count 7 Chemaxon Refractivity 107.79 m3·mol-1 Chemaxon Polarizability 40.57 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0a59-0089000000-b3cf7d96966eb51f4c75 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0a4i-0009000000-85dd54b7eb19986a0a2b Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0f89-6942000000-0d14bb87b8df329c5b7b Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0a4i-0059000000-f3effe4f9e57a0d5c61b Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0udv-0090000000-9ef41e51fb8d8c6f65c5 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-00di-9120000000-7cae77081133f0e43c7a Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 184.84549 predictedDeepCCS 1.0 (2019) [M+H]+ 187.20349 predictedDeepCCS 1.0 (2019) [M+Na]+ 193.41425 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsP-glycoprotein 1
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Xenobiotic-transporting atpase activity
- Specific Function
- Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
- Gene Name
- ABCB1
- Uniprot ID
- P08183
- Uniprot Name
- Multidrug resistance protein 1
- Molecular Weight
- 141477.255 Da
References
- Palmeira A, Rodrigues F, Sousa E, Pinto M, Vasconcelos MH, Fernandes MX: New uses for old drugs: pharmacophore-based screening for the discovery of P-glycoprotein inhibitors. Chem Biol Drug Des. 2011 Jul;78(1):57-72. doi: 10.1111/j.1747-0285.2011.01089.x. Epub 2011 Mar 29. [Article]
- Genovese I, Ilari A, Assaraf YG, Fazi F, Colotti G: Not only P-glycoprotein: Amplification of the ABCB1-containing chromosome region 7q21 confers multidrug resistance upon cancer cells by coordinated overexpression of an assortment of resistance-related proteins. Drug Resist Updat. 2017 May;32:23-46. doi: 10.1016/j.drup.2017.10.003. Epub 2017 Oct 16. [Article]
- Miguel P. Rocha, Florentino Fernández Riverola, Hagit Shatkay, Juan Manuel Corchado Rodríguez (2010). Advances in Bioinformatics. Springer.
Transporters
1. DetailsP-glycoprotein 1
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Xenobiotic-transporting atpase activity
- Specific Function
- Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
- Gene Name
- ABCB1
- Uniprot ID
- P08183
- Uniprot Name
- Multidrug resistance protein 1
- Molecular Weight
- 141477.255 Da
References
- Genovese I, Ilari A, Assaraf YG, Fazi F, Colotti G: Not only P-glycoprotein: Amplification of the ABCB1-containing chromosome region 7q21 confers multidrug resistance upon cancer cells by coordinated overexpression of an assortment of resistance-related proteins. Drug Resist Updat. 2017 May;32:23-46. doi: 10.1016/j.drup.2017.10.003. Epub 2017 Oct 16. [Article]
Drug created at June 14, 2018 19:40 / Updated at February 21, 2021 18:54