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
Structure for Indirubin (DB12379)
- Weight
- Average: 262.268
Monoisotopic: 262.07422757 - Chemical Formula
- C16H10N2O2
- Synonyms
- Couroupitine B
- Indirubin
- External IDs
- C.I. 73200
Pharmacology
- Indication
Not Available
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Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareArticaine The risk or severity of methemoglobinemia can be increased when Indirubin is combined with Articaine. Benzocaine The risk or severity of methemoglobinemia can be increased when Indirubin is combined with Benzocaine. Benzyl alcohol The risk or severity of methemoglobinemia can be increased when Indirubin is combined with Benzyl alcohol. Bupivacaine The risk or severity of methemoglobinemia can be increased when Indirubin is combined with Bupivacaine. Butacaine The risk or severity of methemoglobinemia can be increased when Indirubin is combined with Butacaine. Butamben The risk or severity of methemoglobinemia can be increased when Indirubin is combined with Butamben. Capsaicin The risk or severity of methemoglobinemia can be increased when Indirubin is combined with Capsaicin. Chloroprocaine The risk or severity of methemoglobinemia can be increased when Indirubin is combined with Chloroprocaine. Cinchocaine The risk or severity of methemoglobinemia can be increased when Indirubin is combined with Cinchocaine. Cocaine The risk or severity of methemoglobinemia can be increased when Indirubin is combined with Cocaine. 
Identify potential medication risksEasily compare up to 40 drugs with our drug interaction checker.Get severity rating, description, and management advice.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
- 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
- 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. [Article]
- 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. [Article]
- 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