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Identification
NameDantron
Accession NumberDB04816
Typesmall molecule
Groupsinvestigational, withdrawn
Description

Withdrawn from the Canadian, US, and UK markets in 1998 due to genotoxicity.

Structure
Thumb
Synonyms
SynonymLanguageCode
1,8-dihydroxy-9,10-anthracenedioneNot AvailableNot Available
1,8-dihydroxy-9,10-anthraquinoneNot AvailableNot Available
1,8-dihydroxyanthra-9,10-quinoneNot AvailableNot Available
1,8-DihydroxyanthrachinonNot AvailableNot Available
1,8-DihydroxyanthraquinoneNot AvailableNot Available
ChrysazinNot AvailableNot Available
DanthronNot AvailableNot Available
SaltsNot Available
Brand names
NameCompany
AltanNot Available
AntrapurolNot Available
BanconNot Available
ChrysazinNot Available
ChrysazineNot Available
CriasazinNot Available
DanivacNot Available
DantronNot Available
DiaquoneNot Available
DiononeNot Available
DorbaneNot Available
DorbanexNot Available
DorbantylNot Available
DuolaxNot Available
IstanNot Available
IstinNot Available
IstizinNot Available
LaxanormNot Available
LaxanthreenNot Available
LaxipurNot Available
LaxipurinNot Available
LTANNot Available
Neokutin sNot Available
PastominNot Available
PrugolNot Available
RoydanNot Available
Scatron dNot Available
ZwitsalaxNot Available
Brand mixturesNot Available
Categories
CAS number117-10-2
WeightAverage: 240.2109
Monoisotopic: 240.042258744
Chemical FormulaC14H8O4
InChI KeyInChIKey=QBPFLULOKWLNNW-UHFFFAOYSA-N
InChI
InChI=1S/C14H8O4/c15-9-5-1-3-7-11(9)14(18)12-8(13(7)17)4-2-6-10(12)16/h1-6,15-16H
IUPAC Name
1,8-dihydroxy-9,10-dihydroanthracene-9,10-dione
SMILES
OC1=CC=CC2=C1C(=O)C1=C(C=CC=C1O)C2=O
Mass Specshow(8.11 KB)
Taxonomy
KingdomOrganic Compounds
SuperclassBenzenoids
ClassAcenes and Derivatives
SubclassAnthracenes
Direct parentAnthraquinones
Alternative parentsPhenols and Derivatives; Ketones; Polyamines; Enols
Substituentsphenol derivative; benzene; ketone; polyamine; enol; carbonyl group
Classification descriptionThis compound belongs to the anthraquinones. These are organic compounds containing anthracene-9,10-quinone, an anthracene derivative with two ketone groups attached to the central benzene ring.
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9899
Blood Brain Barrier + 0.7514
Caco-2 permeable + 0.6963
P-glycoprotein substrate Non-substrate 0.5556
P-glycoprotein inhibitor I Non-inhibitor 0.9605
P-glycoprotein inhibitor II Non-inhibitor 0.9419
Renal organic cation transporter Non-inhibitor 0.8913
CYP450 2C9 substrate Non-substrate 0.7982
CYP450 2D6 substrate Non-substrate 0.9168
CYP450 3A4 substrate Non-substrate 0.7151
CYP450 1A2 substrate Inhibitor 0.8918
CYP450 2C9 substrate Inhibitor 0.775
CYP450 2D6 substrate Non-inhibitor 0.7456
CYP450 2C19 substrate Non-inhibitor 0.6159
CYP450 3A4 substrate Non-inhibitor 0.8357
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7605
Ames test AMES toxic 0.9261
Carcinogenicity Non-carcinogens 0.893
Biodegradation Not ready biodegradable 0.7278
Rat acute toxicity 2.8601 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9505
hERG inhibition (predictor II) Non-inhibitor 0.9192
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point193 °CPhysProp
Predicted Properties
PropertyValueSource
water solubility3.05e-01 g/lALOGPS
logP2.98ALOGPS
logP3.61ChemAxon
logS-2.9ALOGPS
pKa (strongest acidic)9.09ChemAxon
pKa (strongest basic)-4.4ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count4ChemAxon
hydrogen donor count2ChemAxon
polar surface area74.6ChemAxon
rotatable bond count0ChemAxon
refractivity65.11ChemAxon
polarizability23.19ChemAxon
number of rings3ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ResourceLink
KEGG DrugD07107
KEGG CompoundC10312
PubChem Compound2950
PubChem Substance46509077
ChemSpider2845
BindingDB11316
ChEBI3682
ChEMBL
PharmGKBPA449206
WikipediaDanthron
ATC CodesA06AB03
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

1. Cytochrome P450 1A2

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inducer

Components

Name UniProt ID Details
Cytochrome P450 1A2 P05177 Details

References:

  1. Mikhailova ON, Filipenko ML, Timofeeva OA, Kaledin VI, Guliaeva LF, Liakhovich VV: [mRNA level and cytochrome P450 1A activity in the liver of C57BL mice induced by various xenobiotics]. Biomed Khim. 2003 Jul-Aug;49(4):388-93. Pubmed

Comments
Drug created on September 11, 2007 14:07 / Updated on September 16, 2013 17:25