Details
Stereochemistry | ACHIRAL |
Molecular Formula | C16H10N2O2 |
Molecular Weight | 262.2628 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
O=C1NC2=C(C=CC=C2)\C1=C3/NC4=C(C=CC=C4)C3=O
InChI
InChIKey=CRDNMYFJWFXOCH-BUHFOSPRSA-N
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+
Molecular Formula | C16H10N2O2 |
Molecular Weight | 262.2628 |
Charge | 0 |
Count |
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Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionCurator's Comment: description was created based on several sources, including:
https://en.wikipedia.org/wiki/Indirubin | https://www.ncbi.nlm.nih.gov/pubmed/10559866
Curator's Comment: description was created based on several sources, including:
https://en.wikipedia.org/wiki/Indirubin | https://www.ncbi.nlm.nih.gov/pubmed/10559866
Indirubin is derived from the Indigo Plant (Isatis Root, Isatis Leaf). It is used as part of a traditional Chinese herbal prescription called Dang Gui Long Hui Wan, to treat chronic myelogenous leukemia (CML). Indirubin inhibits DNA synthesis in several cell lines, in a cell-free assay and in vivo in rats with Walker-256 sarcoma. A weak binding of indirubin to DNA in vitro has been described. Indirubin inhibited all cyclin-dependent kinases (1,2,4,5) almost equally. Indirubin has been approved for clinical trials against chronic myelocytic and chronic granulocytic leukaemia. A few studies show that Indirubin is effective against psoriasis. Mild to severe nausea, vomiting, abdominal pain, diarrhea, headache, and edema are reported adverse events of Indirubin. Long-term oral ingestion has also occasionally been associated with hepatitis, pulmonary arterial hypertension and cardiac insufficiency.
CNS Activity
Originator
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3869774
Curator's Comment: In 1966, the Institute of Haematology of the Chinese Academy of Medical Sciences embarked on the identification of the active factor of a mixture of 11 herbal medicines Danggui Longhui Wan. The activity was traced to one ingredient, Qing Dai (indigo naturalis), a dark blue powder prepared from the leaves of Baphicacanthus cusia (Acanthaceae), Polygonum tinctorium (Polygonaceae), Isatis indigotica (Brassicaceae), Indigofera suffrutticosa (Fabaceae) and Indigofera tinctoria (Fabaceae). This powder contained a high level of the blue dye indigo, but the antileukaemic activity was attributed to the redcoloured isomer of indigo, indirubin, a minor constituent of the mixture.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL3038469 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10559866 |
2.2 µM [IC50] | ||
Target ID: CHEMBL1907600 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10559866 |
5.5 µM [IC50] | ||
Target ID: CHEMBL2094126 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10559866 |
7.5 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
---|---|---|
Transient induction of cytochromes P450 1A1 and 1B1 in MCF-7 human breast cancer cells by indirubin. | 2003 Dec 15 |
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Construction of reporter yeasts for mouse aryl hydrocarbon receptor ligand activity. | 2003 Sep 9 |
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Comparison of gene expression patterns between 2,3,7,8-tetrachlorodibenzo-p-dioxin and a natural arylhydrocarbon receptor ligand, indirubin. | 2004 Jul |
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Aryl hydrocarbon receptor response to indigoids in vitro and in vivo. | 2004 Mar 15 |
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D-amino acid oxidase generates agonists of the aryl hydrocarbon receptor from D-tryptophan. | 2009 Dec |
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Differential effects of indirubin and 2,3,7,8-tetrachlorodibenzo-p-dioxin on the aryl hydrocarbon receptor (AhR) signalling in liver progenitor cells. | 2011 Jan 11 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12685829
Curator's Comment: https://clinicaltrials.gov/ct2/show/NCT01735864
Oral: 150–200 mg per day
Topical: apply 0.5 g of ointment per 10 x 10 cm psoriatic lesion twice daily (Indirubin 10 or 50 or 100 or 200 ug/g of oinment)
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20691774
Indirubin exhibited activity against dermatophytes such as Epidermophyton floccosum (MIC=6.25 ug/ml); Trichophyton rubrum and Trichophyton tonsurans (MIC=25 ug/ml); Trichophyton mentagrophytes and Trichophyton simii (MIC=50 ug/ml). It was also active against non-dermatophytes (Aspergillus niger, Candida albicans and Cryptococcus sp.) within a MIC range of 0.75-25 ug/ml.
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 14:57:56 GMT 2023
by
admin
on
Sat Dec 16 14:57:56 GMT 2023
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Record UNII |
1LXW6D3W2Z
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Record Status |
Validated (UNII)
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Record Version |
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1LXW6D3W2Z
Created by
admin on Sat Dec 16 14:57:56 GMT 2023 , Edited by admin on Sat Dec 16 14:57:56 GMT 2023
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