NAV

Indirubin

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

Identification

Generic Name
Indirubin
DrugBank Accession Number
DB12379
Background

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

Type
Small Molecule
Groups
Investigational
Structure
3D
Similar Structures
Weight
Average: 262.268
Monoisotopic: 262.07422757
Chemical Formula
C16H10N2O2
Synonyms
  • Couroupitine B
  • Indirubin
External IDs
  • C.I. 73200
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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
UCytochrome P450 1A1
substrate
Humans
UAryl hydrocarbon receptor
agonist
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.
DrugInteraction
Integrate drug-drug
interactions in your software
AmbroxolThe risk or severity of methemoglobinemia can be increased when Indirubin is combined with Ambroxol.
ArticaineThe risk or severity of methemoglobinemia can be increased when Indirubin is combined with Articaine.
BenzocaineThe risk or severity of methemoglobinemia can be increased when Indirubin is combined with Benzocaine.
Benzyl alcoholThe risk or severity of methemoglobinemia can be increased when Indirubin is combined with Benzyl alcohol.
BupivacaineThe risk or severity of methemoglobinemia can be increased when Indirubin is combined with Bupivacaine.
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
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
Aldehyde / Amine / Amino acid or derivatives / Aromatic heteropolycyclic compound / Aryl ketone / Azacycle / Benzenoid / Carbonyl group / Carboxamide group / Carboxylic acid derivative
show 14 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
1LXW6D3W2Z
CAS number
479-41-4
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
(E)-1',2'-dihydro-1H,3H-[2,3'-biindolylidene]-2',3-dione
SMILES
O=C1NC2=C(C=CC=C2)\C1=C1/NC2=C(C=CC=C2)C1=O

References

General References
Not Available
PubChem Compound
5359405
PubChem Substance
347828627
ChemSpider
4514277
BindingDB
50349806
ZINC
ZINC000100015416
Wikipedia
Indirubin

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
Not AvailableCompletedTreatmentPsoriasis Vulgaris (Plaque Psoriasis)1

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)10.87Chemaxon
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
Polarizability27.42 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-MSsplash10-001i-0390000000-410947f1c15dc9a5efb0
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-0090000000-8343c0088071238625da
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-0190000000-daf88c961a8c6ab18f6e
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-0090000000-247bad982530e03db76f
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-0090000000-b813cfcbe05e7b2fc353
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0uki-0690000000-246b754a15fbc04d9f08
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0940000000-b4d8594acdc84f1e7f14
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]-168.3032158
predicted
DarkChem Lite v0.1.0
[M-H]-155.26772
predicted
DeepCCS 1.0 (2019)
[M+H]+169.3992158
predicted
DarkChem Lite v0.1.0
[M+H]+157.64095
predicted
DeepCCS 1.0 (2019)
[M+Na]+168.7692158
predicted
DarkChem Lite v0.1.0
[M+Na]+163.71886
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Cytochrome P450 1A1
Kind
Protein
Organism
Humans
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. [Article]
Details2. Aryl hydrocarbon receptor
Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]

Drug created at October 20, 2016 22:09 / Updated at June 12, 2020 16:53