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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
Structure of INDIRUBIN

SMILES

O=C1NC2=C(C=CC=C2)\C1=C3\NC4=C(C=CC=C4)C3=O

InChI

InChIKey=CRDNMYFJWFXOCH-YPKPFQOOSA-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-

HIDE SMILES / InChI
Molecular Formula C16H10N2O2
Molecular Weight 262.2628
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
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

Wu, K.M.|Zhang, M.Y.|Fang, Z.|Huang, L.
2
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

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
 2.2 µM [IC50]
Inhibitor
8297
 5.5 µM [IC50]
Inhibitor
8297
 7.5 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase II
1132
Unknown

Approved Use

Unknown
Primary
Phase II
1132
Unknown

Approved Use

Unknown
Primary
Preclinical
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Indirubin inhibits inflammatory reactions in delayed-type hypersensitivity.
2000 Dec 20
Indirubin and indigo are potent aryl hydrocarbon receptor ligands present in human urine.
2001 Aug 24
Studies of early hepatocellular proliferation and peroxisomal proliferation in Wistar rats treated with herbicide diclofop.
2001 Feb 14
Transient induction of cytochromes P450 1A1 and 1B1 in MCF-7 human breast cancer cells by indirubin.
2003 Dec 15
Construction of reporter yeasts for mouse aryl hydrocarbon receptor ligand activity.
2003 Sep 9
Comparison of gene expression patterns between 2,3,7,8-tetrachlorodibenzo-p-dioxin and a natural arylhydrocarbon receptor ligand, indirubin.
2004 Jul
Aryl hydrocarbon receptor response to indigoids in vitro and in vivo.
2004 Mar 15
Indirubin, a Chinese anti-leukaemia drug, promotes neutrophilic differentiation of human myelocytic leukaemia HL-60 cells.
2005 Sep
Novel mammalian cell lines expressing reporter genes for the detection of environmental chemicals activating endogenous aryl hydrocarbon receptors (ArhR) or estrogen receptors (ER).
2008 Dec
Pharmacologic profiling of human and rat cytochrome P450 1A1 and 1A2 induction and competition.
2008 Dec
Dissection of mechanisms of Chinese medicinal formula Realgar-Indigo naturalis as an effective treatment for promyelocytic leukemia.
2008 Mar 25
D-amino acid oxidase generates agonists of the aryl hydrocarbon receptor from D-tryptophan.
2009 Dec
Ligand selectivity and gene regulation by the human aryl hydrocarbon receptor in transgenic mice.
2009 Jun
CH223191 is a ligand-selective antagonist of the Ah (Dioxin) receptor.
2010 Oct
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
Nucleotide specificity of DNA binding of the aryl hydrocarbon receptor:ARNT complex is unaffected by ligand structure.
2014 Jan
Patents

Patents

JP2002265445A
2
JP2002541244A
2
JP2003040774A
2
JP2003246734A
2
JP2005220328A
3
JP2005336632A
3
JP2007186478A
2
JP2011506455A
51
JP2011527708A
2
JP2011529873A
2
JP4791664B2
2
JPS57209271A
2
JPS57209272A
2
JPS617254A
2

Sample Use Guides

In Vivo Use Guide
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
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 Fri Dec 15 19:44:01 UTC 2023
Edited
by admin
on Fri Dec 15 19:44:01 UTC 2023
Record UNII
V86L8P74GI
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
INDIRUBIN
MI  
INCI  
Official Name English
NSC-105327
Code English
Indirubin [WHO-DD]
Common Name English
COUROUPITINE B
Common Name English
C.I. 75790
Code English
INDIRUBIN [MI]
Common Name English
(3Z)-3-(1,3-DIHYDRO-3-OXO-2H-INDOL-2-YLIDENE)-1,3-DIHYDRO-2H-INDOL-2-ONE
Systematic Name English
Code System Code Type Description
FDA UNII
V86L8P74GI
Created by admin on Fri Dec 15 19:44:02 UTC 2023 , Edited by admin on Fri Dec 15 19:44:02 UTC 2023
PRIMARY
PUBCHEM
5359405
Created by admin on Fri Dec 15 19:44:02 UTC 2023 , Edited by admin on Fri Dec 15 19:44:02 UTC 2023
PRIMARY
DRUG BANK
DB12379
Created by admin on Fri Dec 15 19:44:02 UTC 2023 , Edited by admin on Fri Dec 15 19:44:02 UTC 2023
PRIMARY
CAS
906748-38-7
Created by admin on Fri Dec 15 19:44:01 UTC 2023 , Edited by admin on Fri Dec 15 19:44:01 UTC 2023
PRIMARY
EPA CompTox
DTXSID201026053
Created by admin on Fri Dec 15 19:44:02 UTC 2023 , Edited by admin on Fri Dec 15 19:44:02 UTC 2023
PRIMARY
WIKIPEDIA
Indirubin
Created by admin on Fri Dec 15 19:44:02 UTC 2023 , Edited by admin on Fri Dec 15 19:44:02 UTC 2023
PRIMARY
NSC
105327
Created by admin on Fri Dec 15 19:44:02 UTC 2023 , Edited by admin on Fri Dec 15 19:44:02 UTC 2023
PRIMARY
MERCK INDEX
m6255
Created by admin on Fri Dec 15 19:44:02 UTC 2023 , Edited by admin on Fri Dec 15 19:44:02 UTC 2023
PRIMARY Merck Index
CAS
479-41-4
Created by admin on Fri Dec 15 19:44:01 UTC 2023 , Edited by admin on Fri Dec 15 19:44:01 UTC 2023
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