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| Names | |
|---|---|
| IUPAC name (3Z)-3-(3-Oxo-1,3-dihydro-2H-indol-2-ylidene)-1,3-dihydro-2H-indol-2-one | |
| Other names Indigo red | |
| Identifiers | |
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3D model (JSmol) | |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| DrugBank | |
| ECHA InfoCard | 100.119.646 |
| EC Number |
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| UNII | |
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| Properties | |
| C16H10N2O2 | |
| Molar mass | 262.268 g·mol−1 |
| Hazards | |
| GHS labelling: | |
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| Warning | |
| H315,H319,H335 | |
| P261,P264,P271,P280,P302+P352,P304+P340,P305+P351+P338,P312,P321,P332+P313,P337+P313,P362,P403+P233,P405,P501 | |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Indirubin is achemical compound most often produced as a byproduct of bacterial metabolism. For instance, it is one of the compounds responsible for the generally benign conditionpurple urine bag syndrome, resulting from bacteria metabolizingindoxyl sulfate found naturally in urine.
Indirubin is a structural isomer (more precisely is position isomer) ofindigo dye.
Indirubin is a chemical constituent ofindigo naturalis (also known as qing dai青黛), which has been used since 627 AD intraditional Chinese medicine. It is essentially the indigo dye as traditionally extracted from plants by fermentation and lime treatment.[1] The dye mixture contains a variety of organic compounds, indirubin andtryptanthrin being possible sources of some pharmacological actions. It is used inrealgar/Indigo naturalis, a medication foracute promyelocytic leukemia.[1]
Indirubin exerts its effects on the human body by downregulating expression of genes. GenesPLK1 andPIN1, both oncogenic, have been shown to be affected by indirubin. Indirubin has,in vitro andin vivo, been shown to reduce expression of theCDC25B gene, which codes for production of CDC25B enzyme. CDC stands for cell-division-cycle, and is used in cellular reproduction. Studies suggest that mouse cells are viable after the CDC25B (andCDC25C) genes are "knocked out", but removal ofCDC25A results in non-viable cells.
Indirubin has not been shown to prevent or treat cancer in humans.[2] However, it is being studied for treatment ofsmall-cell lung cancer,glioblastoma,[3] andchronic myeloid leukemia, either alone or in conjunction with more typical cancer management treatments. It has also been studied for potential use in the treatment ofulcerative colitis, an immune-modulated disease process.[4]
Indirubin showsanti-inflammatory andanti-angiogenesis propertiesin vitro.[5]
