This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Name
Indirubin
Accession Number
DB12379
Type
Small Molecule
Groups
Investigational
Description

Indirubin is under investigation in clinical trial NCT01735864 (Dosage Determination Trial for Indigo Naturalis Extract in Oil Ointment).

Structure
Thumb
Synonyms
Not Available
External IDs
C.I. 75790
Categories
UNII
V86L8P74GI
CAS number
479-41-4
Weight
Average: 262.268
Monoisotopic: 262.07422757
Chemical Formula
C16H10N2O2
InChI Key
CRDNMYFJWFXOCH-BUHFOSPRSA-N
InChI
InChI=1S/C16H10N2O2/c19-15-10-6-2-4-8-12(10)17-14(15)13-9-5-1-3-7-11(9)18-16(13)20/h1-8,17H,(H,18,20)/b14-13+
IUPAC Name
3-[(2E)-3-oxo-2,3-dihydro-1H-indol-2-ylidene]-2,3-dihydro-1H-indol-2-one
SMILES
O=C1NC2=CC=CC=C2\C1=C1/NC2=CC=CC=C2C1=O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UCytochrome P450 1A1
substrate
Human
UAryl hydrocarbon receptor
agonist
Human
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Indirubin.Approved
AcetyldigoxinAcetyldigoxin may decrease the cardiotoxic activities of Indirubin.Experimental
BevacizumabBevacizumab may increase the cardiotoxic activities of Indirubin.Approved, Investigational
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Indirubin.Approved
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of Indirubin.Approved, Investigational
CymarinCymarin may decrease the cardiotoxic activities of Indirubin.Experimental
DeslanosideDeslanoside may decrease the cardiotoxic activities of Indirubin.Approved
DigitoxinDigitoxin may decrease the cardiotoxic activities of Indirubin.Approved, Investigational
DigoxinDigoxin may decrease the cardiotoxic activities of Indirubin.Approved
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with Indirubin.Approved, Investigational
GitoformateGitoformate may decrease the cardiotoxic activities of Indirubin.Experimental
Lanatoside CLanatoside C may decrease the cardiotoxic activities of Indirubin.Experimental
MetildigoxinMetildigoxin may decrease the cardiotoxic activities of Indirubin.Experimental
OleandrinOleandrin may decrease the cardiotoxic activities of Indirubin.Experimental, Investigational
OuabainOuabain may decrease the cardiotoxic activities of Indirubin.Approved
PaclitaxelThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Indirubin.Approved, Vet Approved
PeruvosidePeruvoside may decrease the cardiotoxic activities of Indirubin.Experimental
ProscillaridinProscillaridin may decrease the cardiotoxic activities of Indirubin.Experimental
TrastuzumabTrastuzumab may increase the cardiotoxic activities of Indirubin.Approved, Investigational
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
5359405
PubChem Substance
347828627
ChemSpider
4514277
BindingDB
50349806

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
Not AvailableUnknown StatusTreatmentPsoriasis Vulgaris1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0347 mg/mLALOGPS
logP3.05ALOGPS
logP2.43ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)7.42ChemAxon
pKa (Strongest Basic)-2.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area58.2 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity79 m3·mol-1ChemAxon
Polarizability27.41 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as indolines. These are compounds containing an indole moiety, which consists of pyrrolidine ring fused to benzene to form 2,3-dihydroindole.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Indoles and derivatives
Sub Class
Indolines
Direct Parent
Indolines
Alternative Parents
Aryl ketones / Benzenoids / Vinylogous amides / Secondary carboxylic acid amides / Lactams / Amino acids and derivatives / Secondary amines / Enamines / Azacyclic compounds / Organopnictogen compounds
show 3 more
Substituents
Dihydroindole / Aryl ketone / Benzenoid / Vinylogous amide / Amino acid or derivatives / Carboxamide group / Ketone / Lactam / Secondary carboxylic acid amide / Carboxylic acid derivative
show 14 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d 24-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A1
Uniprot ID
P04798
Uniprot Name
Cytochrome P450 1A1
Molecular Weight
58164.815 Da
References
  1. Adachi J, Mori Y, Matsui S, Matsuda T: Comparison of gene expression patterns between 2,3,7,8-tetrachlorodibenzo-p-dioxin and a natural arylhydrocarbon receptor ligand, indirubin. Toxicol Sci. 2004 Jul;80(1):161-9. Epub 2004 Mar 31. [PubMed:15056799]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Agonist
General Function
Transcription regulatory region dna binding
Specific Function
Ligand-activated transcriptional activator. Binds to the XRE promoter region of genes it activates. Activates the expression of multiple phase I and II xenobiotic chemical metabolizing enzyme genes...
Gene Name
AHR
Uniprot ID
P35869
Uniprot Name
Aryl hydrocarbon receptor
Molecular Weight
96146.705 Da
References
  1. Adachi J, Mori Y, Matsui S, Matsuda T: Comparison of gene expression patterns between 2,3,7,8-tetrachlorodibenzo-p-dioxin and a natural arylhydrocarbon receptor ligand, indirubin. Toxicol Sci. 2004 Jul;80(1):161-9. Epub 2004 Mar 31. [PubMed:15056799]
  2. Perkins A, Phillips JL, Kerkvliet NI, Tanguay RL, Perdew GH, Kolluri SK, Bisson WH: A Structural Switch between Agonist and Antagonist Bound Conformations for a Ligand-Optimized Model of the Human Aryl Hydrocarbon Receptor Ligand Binding Domain. Biology (Basel). 2014 Oct 17;3(4):645-69. doi: 10.3390/biology3040645. [PubMed:25329374]

Drug created on October 20, 2016 16:09 / Updated on November 09, 2017 05:06