Indirubin
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
- Description
Indirubin is under investigation in clinical trial NCT01735864 (Dosage Determination Trial for Indigo Naturalis Extract in Oil Ointment).
- Type
- Small Molecule
- Groups
- Investigational
- Structure
- Weight
- Average: 262.268
Monoisotopic: 262.07422757 - Chemical Formula
- C16H10N2O2
- Synonyms
- Couroupitine B
- Indirubin
- External IDs
- C.I. 73200
Pharmacology
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- Indication
- Not Available
- Contraindications & Blackbox Warnings
- Contraindications & Blackbox WarningsWith our commercial data, access important information on dangerous risks, contraindications, and adverse effects.Our Blackbox Warnings cover Risks, Contraindications, and Adverse Effects
- Pharmacodynamics
- Not Available
- Mechanism of action
Target Actions Organism UCytochrome P450 1A1 substrateHumans UAryl hydrocarbon receptor agonistHumans - 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
- Reduce medical errorsand improve treatment outcomes with our comprehensive & structured data on drug adverse effects.Reduce medical errors & improve treatment outcomes with our adverse effects data
- Toxicity
- Not Available
- Affected organisms
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareDarbepoetin alfa The risk or severity of Thrombosis can be increased when Darbepoetin alfa is combined with Indirubin. Erythropoietin The risk or severity of Thrombosis can be increased when Erythropoietin is combined with Indirubin. Methoxy polyethylene glycol-epoetin beta The risk or severity of Thrombosis can be increased when Methoxy polyethylene glycol-epoetin beta is combined with Indirubin. Peginesatide The risk or severity of Thrombosis can be increased when Peginesatide is combined with Indirubin. Improve patient outcomesBuild effective decision support tools with the industry’s most comprehensive drug-drug interaction checker.Learn more - 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
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
- External Links
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count Not Available Completed Treatment Psoriasis 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
Property Value Source Water Solubility 0.0347 mg/mL ALOGPS logP 3.05 ALOGPS logP 2.43 ChemAxon logS -3.9 ALOGPS pKa (Strongest Acidic) 10.87 ChemAxon pKa (Strongest Basic) -2.6 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 3 ChemAxon Hydrogen Donor Count 2 ChemAxon Polar Surface Area 58.2 Å2 ChemAxon Rotatable Bond Count 0 ChemAxon Refractivity 79 m3·mol-1 ChemAxon Polarizability 27.42 Å3 ChemAxon Number of Rings 4 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets

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- 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
- 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
- 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
- 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]
- 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 22:09 / Updated on June 12, 2020 16:53