NAV

Hycanthone

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
3D
Similar Structures
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
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
AP-glycoprotein 1
inhibitor
Humans
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
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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

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Product Ingredients
IngredientUNIICASInChI Key
Hycanthone mesylate48830NW22A23255-93-8LOEQGPPJCCUXEJ-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
KEGG Drug
D00541
ChemSpider
3508
BindingDB
50066721
ChEBI
52768
ChEMBL
CHEMBL22077
ZINC
ZINC000003830916
PDBe Ligand
QHM
Wikipedia
Hycanthone
PDB Entries
6uux / 6uuy

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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
PropertyValueSource
Water Solubility0.0168 mg/mLALOGPS
logP3.87ALOGPS
logP3.74Chemaxon
logS-4.3ALOGPS
pKa (Strongest Acidic)14.79Chemaxon
pKa (Strongest Basic)8.67Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area52.57 Å2Chemaxon
Rotatable Bond Count7Chemaxon
Refractivity107.79 m3·mol-1Chemaxon
Polarizability40.57 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a59-0089000000-b3cf7d96966eb51f4c75
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-0009000000-85dd54b7eb19986a0a2b
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0f89-6942000000-0d14bb87b8df329c5b7b
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-0059000000-f3effe4f9e57a0d5c61b
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udv-0090000000-9ef41e51fb8d8c6f65c5
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-9120000000-7cae77081133f0e43c7a
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-184.84549
predicted
DeepCCS 1.0 (2019)
[M+H]+187.20349
predicted
DeepCCS 1.0 (2019)
[M+Na]+193.41425
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. P-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
  1. 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]
  2. 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]
  3. Miguel P. Rocha, Florentino Fernández Riverola, Hagit Shatkay, Juan Manuel Corchado Rodríguez (2010). Advances in Bioinformatics. Springer.

Transporters

Details1. P-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
  1. 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