INDIRUBIN

Possibly Marketed Outside US

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 Search

SMILES

O=C1NC2=CC=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
Sources: https://www.mskcc.org/cancer-care/integrative-medicine/herbs/indirubin
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

Approval Year

Targets

Primary Target	Pharmacology	Potency
CDK2/Cyclin A 7 Target ID: CHEMBL3038469 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10559866	Inhibitor 8504	2.2 µM [IC50]
Cyclin-dependent kinase 5/CDK5 activator 1 8 Target ID: CHEMBL1907600 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10559866	Inhibitor 8504	5.5 µM [IC50]
Cyclin-dependent kinase 2/cyclin E 10 Target ID: CHEMBL2094126 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10559866	Inhibitor 8504	7.5 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Psoriasis 87 Sources: https://www.mskcc.org/cancer-care/integrative-medicine/herbs/indirubin https://www.ncbi.nlm.nih.gov/pubmed/3109707	Primary	Phase II 1147	Unknown Approved Use Unknown
Chronic myelocytic leukemia 4 Sources: https://www.mskcc.org/cancer-care/integrative-medicine/herbs/indirubin https://www.ncbi.nlm.nih.gov/pubmed/6355667 https://www.ncbi.nlm.nih.gov/pubmed/12685829	Primary	Phase II 1147	Unknown Approved Use Unknown
Ulcerative colitis 125 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27396532	Primary	Preclinical	Unknown Approved Use Unknown

Doses

Dose	Population	Adverse events
200 mg/kg 2 times / week multiple, topical Highest studied dose Dose: 200 mg/kg, 2 times / week Route: topical Route: multiple Dose: 200 mg/kg, 2 times / week Sources: https://pubmed.ncbi.nlm.nih.gov/28815560/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/28815560/	Sources: https://pubmed.ncbi.nlm.nih.gov/28815560/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inducer 1087			inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
BCRP 910 CYP1A1 132 CYP1A2 2153	CYP1A2 1197 P-gp 2052 CYP1A1 389	UGT1A6 34 UGT1A9 9 UGT1A1 78 UGT2B7 14

Drug as perpetrator

Target	Modality	Activity
BCRP 985	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/10177#section=BioAssay-Results Page: 58.0	no
CYP1A1 272	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/14637189/	yes
CYP1A2 2333	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/14637189/	yes
CYP3A4 2633	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/26987505/	yes
UGT1A1 303	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/20145913/	yes
UGT1A6 171	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/20145913/	yes
UGT1A9 155	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/20145913/	yes
UGT2B7 210	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/20145913/	yes

Drug as victim

Target	Modality	Activity
P-gp 2052	substrate 4014 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/10177#section=BioAssay-Results Page: 209.0	no
CYP1A1 389	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/14637189/	yes
CYP1A2 1197	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/14637189/	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/10177#section=BioAssay-Results Page: 193.0

PubMed

Title	Date	PubMed
Nucleotide specificity of DNA binding of the aryl hydrocarbon receptor:ARNT complex is unaffected by ligand structure.	2014-01	24136190
Differential effects of indirubin and 2,3,7,8-tetrachlorodibenzo-p-dioxin on the aryl hydrocarbon receptor (AhR) signalling in liver progenitor cells.	2011-01-11	20951181
CH223191 is a ligand-selective antagonist of the Ah (Dioxin) receptor.	2010-10	20634293
D-amino acid oxidase generates agonists of the aryl hydrocarbon receptor from D-tryptophan.	2009-12	19860415
Ligand selectivity and gene regulation by the human aryl hydrocarbon receptor in transgenic mice.	2009-06	19299563
Novel mammalian cell lines expressing reporter genes for the detection of environmental chemicals activating endogenous aryl hydrocarbon receptors (ArhR) or estrogen receptors (ER).	2008-12	18835349
Pharmacologic profiling of human and rat cytochrome P450 1A1 and 1A2 induction and competition.	2008-12	18493746
Dissection of mechanisms of Chinese medicinal formula Realgar-Indigo naturalis as an effective treatment for promyelocytic leukemia.	2008-03-25	18344322
Indirubin, a Chinese anti-leukaemia drug, promotes neutrophilic differentiation of human myelocytic leukaemia HL-60 cells.	2005-09	16115123
Comparison of gene expression patterns between 2,3,7,8-tetrachlorodibenzo-p-dioxin and a natural arylhydrocarbon receptor ligand, indirubin.	2004-07	15056799
Aryl hydrocarbon receptor response to indigoids in vitro and in vivo.	2004-03-15	15001395
Transient induction of cytochromes P450 1A1 and 1B1 in MCF-7 human breast cancer cells by indirubin.	2003-12-15	14637189
Construction of reporter yeasts for mouse aryl hydrocarbon receptor ligand activity.	2003-09-09	12972062
Indirubin and indigo are potent aryl hydrocarbon receptor ligands present in human urine.	2001-08-24	11425848
Studies of early hepatocellular proliferation and peroxisomal proliferation in Wistar rats treated with herbicide diclofop.	2001-02-14	11275354
Indirubin inhibits inflammatory reactions in delayed-type hypersensitivity.	2000-12-20	11134660

Patents

Sample Use Guides

In Vivo Use Guide

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 `Mon Mar 31 19:55:18 GMT 2025` Edited by `admin` on `Mon Mar 31 19:55:18 GMT 2025`
Record UNII	V86L8P74GI
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

C.I. 75790

Preferred Name

English

INDIRUBIN

Official Name

English

NSC-105327

Code

English

Indirubin [WHO-DD]

Common Name

English

COUROUPITINE B

Common Name

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