INDOLE-3-CARBINOL

Investigational

Details

Stereochemistry	ACHIRAL
Molecular Formula	C9H9NO
Molecular Weight	147.1739
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OCC1=CNC2=C1C=CC=C2

InChI

InChIKey=IVYPNXXAYMYVSP-UHFFFAOYSA-N

InChI=1S/C9H9NO/c11-6-7-5-10-9-4-2-1-3-8(7)9/h1-5,10-11H,6H2

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27671815 | https://www.webmd.com/vitamins-supplements/ingredientmono-1027-indole-3-carbinol.aspx?activeingredientid=1027& | https://www.cancer.gov/publications/dictionaries/cancer-drug/def/indole-3-carbinol | https://www.ncbi.nlm.nih.gov/pubmed/20370707

Indole-3-carbinol (I3C), a common phytochemical in cruciferous vegetables, and its condensation product, 3,3'-diindolylmethane (DIM) exert several biological activities on cellular and molecular levels, which contribute to their well-recognized chemoprevention potential. ndole-3-carbinol is used for prevention of breast cancer, colon cancer, and other types of cancer. The National Institutes of Health (NIH) has reviewed indole-3-carbinol as a possible cancer preventive agent and is now sponsoring clinical research for breast cancer prevention. Indole-3-carbinol is also used for fibromyalgia, tumors inside the voice box (laryngeal papillomatosis) caused by a virus, tumors inside the respiratory tract (respiratory papillomatosis) caused by a virus, abnormal cell growth in the cervix (cervical dysplasia), and systemic lupus erythematosus (SLE). Indole-3-carbinol scavenges free radicals and induces various hepatic cytochrome P450 monooxygenases. Specifically, this agent induces the hepatic monooxygenase cytochrome P4501A1 (CYP1A1), resulting in increased 2-hydroxylation of estrogens and increased production of the chemoprotective estrogen 2-hydroxyestrone. Accumulating evidence indicates that the antitumor activity of indole-3- carbinol is attributable to its ability to interfere with multiple oncogenic signaling pathways governing cell cycle progression, survival, invasion, and other aggressive phenotypes of cancer cells. Reported signaling targets of indole-3- carbinol in various cancer cell lines include EGFR/Src, Akt/NF-B, stress responses, elastase, and Rho kinase. Moreover, indole-3-carbinol functions as a negative regulator of estrogen action in hormonesensitive cancer cells through the inhibition of estrogen receptor (ER)-alpha signaling and/or induction of cytochrome P-450-mediated estrogen metabolism, suggesting its clinical use in hormone-sensitive cancers.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Potency
Estrogen receptor alpha 134 Target ID: CHEMBL206 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12840226 \| https://www.ncbi.nlm.nih.gov/pubmed/27312859 \| https://www.ncbi.nlm.nih.gov/pubmed/16488130	Antagonist 2849
E3 ubiquitin-protein ligase NEDD4 1 Target ID: P46934\|\|\|D6RF89 Gene ID: 4734.0 Gene Symbol: NEDD4 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/27979631	Inhibitor 8504	284.0 µM [IC50]
Aryl hydrocarbon receptor 27 Target ID: CHEMBL3201 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28812970 \| https://www.ncbi.nlm.nih.gov/pubmed/27527145	Agonist 2752
NAD-dependent deacetylase sirtuin 1 19 Target ID: CHEMBL4506 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22986685	Inhibitor 8504

Conditions

Condition	Modality	Highest Phase	Product
Breast cancer 432 Sources: https://clinicaltrials.gov/ct2/show/NCT00033345	Primary	Phase III 665	Unknown Approved Use Unknown
Obesity 206 Sources: https://clinicaltrials.gov/ct2/show/NCT00988845	Primary	Phase II 1147	Unknown Approved Use Unknown
Cancer 609 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20370707	Preventing	Phase I 438	Unknown Approved Use Unknown

C_max

Value	Dose	Analyte	Population
262 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17164373	800 mg single, oral dose: 800 mg route of administration: Oral experiment type: SINGLE co-administered:	3,3'-DIINDOLYLMETHANE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
510 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17164373	1200 mg single, oral dose: 1200 mg route of administration: Oral experiment type: SINGLE co-administered:	3,3'-DIINDOLYLMETHANE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
61 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17164373/	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:	3,3'-DIINDOLYLMETHANE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
69 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17164373/	400 mg 2 times / day multiple, oral dose: 400 mg route of administration: Oral experiment type: MULTIPLE co-administered:	3,3'-DIINDOLYLMETHANE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
607 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17164373/	1000 mg single, oral dose: 1000 mg route of administration: Oral experiment type: SINGLE co-administered:	3,3'-DIINDOLYLMETHANE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
93 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17164373/	600 mg single, oral dose: 600 mg route of administration: Oral experiment type: SINGLE co-administered:	3,3'-DIINDOLYLMETHANE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED

AUC

Value	Dose	Analyte	Population
1608 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17164373	800 mg single, oral dose: 800 mg route of administration: Oral experiment type: SINGLE co-administered:	3,3'-DIINDOLYLMETHANE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
3212 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17164373	1200 mg single, oral dose: 1200 mg route of administration: Oral experiment type: SINGLE co-administered:	3,3'-DIINDOLYLMETHANE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
329 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17164373/	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:	3,3'-DIINDOLYLMETHANE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
372 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17164373/	400 mg 2 times / day multiple, oral dose: 400 mg route of administration: Oral experiment type: MULTIPLE co-administered:	3,3'-DIINDOLYLMETHANE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
3376 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17164373/	1000 mg single, oral dose: 1000 mg route of administration: Oral experiment type: SINGLE co-administered:	3,3'-DIINDOLYLMETHANE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
364 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17164373/	600 mg single, oral dose: 600 mg route of administration: Oral experiment type: SINGLE co-administered:	3,3'-DIINDOLYLMETHANE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED

T_1/2

Value	Dose	Analyte	Population
4.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17164373	800 mg single, oral dose: 800 mg route of administration: Oral experiment type: SINGLE co-administered:	3,3'-DIINDOLYLMETHANE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17164373	1200 mg single, oral dose: 1200 mg route of administration: Oral experiment type: SINGLE co-administered:	3,3'-DIINDOLYLMETHANE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
3.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17164373/	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:	3,3'-DIINDOLYLMETHANE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17164373/	400 mg 2 times / day multiple, oral dose: 400 mg route of administration: Oral experiment type: MULTIPLE co-administered:	3,3'-DIINDOLYLMETHANE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
5.7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17164373/	1000 mg single, oral dose: 1000 mg route of administration: Oral experiment type: SINGLE co-administered:	3,3'-DIINDOLYLMETHANE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17164373/	600 mg single, oral dose: 600 mg route of administration: Oral experiment type: SINGLE co-administered:	3,3'-DIINDOLYLMETHANE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY20402	https://www.001chemical.com/chem/search?q=DY20402
1PlusChem LLC	1P003RGV	https://www.1pchem.com/search?query=1P003RGV
A2B Chem	AB74767	http://a2bchem.com/prod/AB74767
AA Blocks	AA003QXF	http://aablocks.com/goods/Goods/detail?id=AA003QXF
Accela ChemBio Inc	SY015976	http://accelachem.com/cn/search.html?keyword=SY015976&attname=0
Aceschem	ACS011024	https://www.aceschem.com/catalog/search.do?q=ACS011024
Achemo Scientific Limited	AC-10921	http://www.achemo.com/search/?Keyword=AC-10921
AK Scientific	2717AD	https://aksci.com/item_detail.php?cat=2717AD
AK Scientific	A227	https://aksci.com/item_detail.php?cat=A227
Alfa Chemistry	ACM700061	http://www.alfa-chemistry.com/search.aspx?q=ACM700061
Angene	AGN-PC-0HX726	http://www.angenechemical.com/productshow/AGN-PC-0HX726.html
Angene	AGN-PC-0PHCYF	http://www.angenechemical.com/productshow/AGN-PC-0PHCYF.html
ApexBio Technology	B3667	https://www.apexbt.com/catalogsearch/result/?q=B3667
Apollo Scientific	OR10179	http://www.apolloscientific.co.uk/chemical_results.php?qstext=OR10179&product_group=%25&search_fieldname=header_search
AsisChem	V65629	https://asischem.com/catalogsearch/result/?q=V65629
AstaTech	26014	http://astatechinc.com/CPSResult.php?CRNO=26014
BioSynth	I-2100	https://www.biosynth.com/en/products/life-science/other-biochemicals/products/I-2100
BOC Sciences	700-06-1	http://www.bocsci.com/description.asp?cas=700-06-1
BOC Sciences	800-06-1	http://www.bocsci.com/description.asp?cas=800-06-1
Cayman Chemical	11325	http://www.caymanchem.com/app/template/Product.vm/catalog/11325
Chem-Impex International	21896	http://www.chemimpex.com/category/search/21896/2?filter=&search=21896&type=q&keywordoption=ANY&cid=2&fltrdesc=
Chem Scene	CS-7780	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-7780
Chemik	CHH14008	http://www.chemik.com/cgi/search-en.cgi?f=product_en+product_en1+company_en_1_&t=product_en7&w=product_en&terms=CHH14008
eMolecules	3718504	https://orderbb.emolecules.com/search/#?query=3718504
eMolecules	539712	https://orderbb.emolecules.com/search/#?query=539712
Enamine	BBV-34551189	http://www.enaminestore.com/catalog/BBV-34551189
Enamine	EN300-18594	https://www.enaminestore.com/catalog/EN300-18594
Frontier Scientific Services	500007481	http://orders.frontierssi.com/fssionline32/public/product.aspx?cat=500007481&type=hts
Hairui	HR124661	http://www.hairuichem.com/en/product/search.do?q=HR124661
KeyOrganics	GS-0916	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=GS-0916
Lab Network	LN00173548	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00173548
Lab Seeker	SC-06380	http://www.labseeker.com/search.php?keywords=SC-06380&category=0
LabSeeker	SC-06380	http://www.labseeker.com/search.php?keywords=SC-06380&category=0
Matrix Scientific	70050	http://www.matrixscientific.com/070050.html
Matrix Scientific	85510	http://www.matrixscientific.com/085510.html
mcule	MCULE-6344603304	https://mcule.com/MCULE-6344603304/
MedChem Express	HY-N0170	https://www.medchemexpress.com/search.html?q=HY-N0170&ft=&fa=&fp=
Molcore	MC20402	http://www.molcore.com/CatMC20402.html
Molnova	M15686	https://www.molnova.com/en/serch-list.html?keywords=M15686
MolPort	MolPort-000-139-921	https://www.molport.com/shop/molecule-link/MolPort-000-139-921
MuseChem	M026418	https://www.musechem.com/product/M026418.html
Oakwood	45221	http://www.oakwoodchemical.com/ProductsList.aspx?txtSearch=045221
PI Chemicals	PI-16182	http://www.pipharm.com/catalog_products/PI-16182.html
Selleck Chemicals	S2313	http://www.selleckchem.com/search.html?searchDTO.searchParam=S2313
ShangHai Biochempartner	BCP00087	http://www.biochempartner.com/search_BCP00087
SynQuest	4H01-1-M5	http://www.synquestlabs.com/search-result.html?q=4H01-1-M5
Synthonix	4626	https://synthonix.com/catalogsearch/result/?q=4626
Synthonix	I4626	https://synthonix.com/catalogsearch/result/?q=I4626
Tetrahedron	TS09190	http://www.thsci.com/search.do?q=TS09190
Tetrahedron	TS42902	http://www.thsci.com/search.do?q=TS42902
TimTec	SBB004095	http://www.echemstore.com/catalogsearch/result/?q=SBB004095
TimTec	ST50308202	http://www.echemstore.com/catalogsearch/result/?q=ST50308202
Toronto Research Chemicals	I578000	https://www.trc-canada.com/product-detail/?CatNum=I578000
Toronto Research Chemicals	O521010	https://www.trc-canada.com/product-detail/?CatNum=O521010
Vesino Industrial Co Ltd	VI30396	http://www.vsnchem.com/search.do?a=s&psize=20&q=VI30396
W&J PharmaChem	50A354115	http://wjpharmachem.com/new/searcht.php?keyword=50A354115
Wonderchem	WD03ZHW	http://www.wonder-chem.com/search.html?text=WD03ZHW
WuXi AppTec	WX640278	https://www.labnetwork.com/frontend-app/p/#!/supplier/wuxi/product/WX640278

PubMed

Title	Date	PubMed
Indole-3-carbinol stimulates transcription of the interferon gamma receptor 1 gene and augments interferon responsiveness in human breast cancer cells.	2004-07	14988219
Indole-3-carbinol for recurrent respiratory papillomatosis: long-term results.	2004-06	15193659
Effects of cruciferous vegetable consumption on urinary metabolites of the tobacco-specific lung carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in singapore chinese.	2004-06	15184256
Effects of dietary anticarcinogens and nonsteroidal anti-inflammatory drugs on rat gastrointestinal UDP-glucuronosyltransferases.	2004-05-27	15161036
Inhibition of MUC1 expression by indole-3-carbinol.	2004-05-10	15027113
Modulation of the constitutive activated STAT3 transcription factor in pancreatic cancer prevention: effects of indole-3-carbinol (I3C) and genistein.	2004-03-16	15015587
Endogenous and dietary indoles: a class of antioxidants and radical scavengers in the ABTS assay.	2004-03	15129740
Lack of an inducible effect of dietary soy isoflavones on the mRNA abundance of hepatic cytochrome P-450 isozymes in rats.	2004-03	15056880
Cruciferous vegetables: cancer protective mechanisms of glucosinolate hydrolysis products and selenium.	2004-03	15035868
Established and potential strategies against papillomavirus infections.	2004-02	14711837
Differences in the hepatic P450-dependent metabolism of estrogen and tamoxifen in response to treatment of rats with 3,3'-diindolylmethane and its parent compound indole-3-carbinol.	2004	15041081
Indole-3-carbinol induces a G1 cell cycle arrest and inhibits prostate-specific antigen production in human LNCaP prostate carcinoma cells.	2003-12-01	14635088
Broccoli compound inhibits HSV.	2003-11	14748359
A selective irreversible inhibitor targeting a PDZ protein interaction domain.	2003-10-08	14518976
Ingestion of a dietary supplement containing dehydroepiandrosterone (DHEA) and androstenedione has minimal effect on immune function in middle-aged men.	2003-10	14559928
Chemoprevention of gastrointestinal malignancies.	2003-09	12956781
Effects of treatment of rats with indole-3-carbinol on apoptosis in the mammary gland and mammary adenocarcinomas.	2003-08-05	12894530
The disposition and metabolism of 2-amino-3-methylimidazo-[4,5-f]quinoline in the F344 rat at high versus low doses of indole-3-carbinol.	2003-08	12842187
Evaluation of chronic dietary exposure to indole-3-carbinol and absorption-enhanced 3,3'-diindolylmethane in sprague-dawley rats.	2003-07	12730619
Arsenate reduction in human erythrocytes and rats--testing the role of purine nucleoside phosphorylase.	2003-07	12730608
Plant-derived 3,3'-Diindolylmethane is a strong androgen antagonist in human prostate cancer cells.	2003-06-06	12665522
Pretreatment of indole-3-carbinol augments TRAIL-induced apoptosis in a prostate cancer cell line, LNCaP.	2003-06-05	12782325
Indole-3-carbinol and 3,3'-diindolylmethane induce apoptosis in human prostate cancer cells.	2003-06	12738179
Cervical dysplasia: early intervention.	2003-05	12777161
Phase II in vitro metabolism of 3-methylindole metabolites in porcine liver.	2003-05	12746105
Liquid chromatographic assay for the simultaneous determination of indole-3-carbinol and its acid condensation products in plasma.	2003-04-25	12650751
Mutational analysis of Ctnnb1 and Apc in tumors from rats given 1,2-dimethylhydrazine or 2-amino-3-methylimidazo[4,5-f]quinoline: mutational 'hotspots' and the relative expression of beta-catenin and c-jun.	2003-04	12669311
Beneficial and adverse effects of chemopreventive agents.	2003-03-12	12628524
Mechanism-based in vitro screening of potential cancer chemopreventive agents.	2003-03-12	12628514
Chemoprevention of colon cancer by Korean food plant components.	2003-03-12	12628507
A high-throughput cell-based reporter gene system for measurement of CYP1A1 induction.	2003-03-12	12628305
The effect of indole-3-carbinol and sulforaphane on a prostate cancer cell line.	2003-03	12608980
The rainbow trout (Oncorhynchus mykiss) tumor model: recent applications in low-dose exposures to tumor initiators and promoters.	2003-02-25	12597433
Anti-metastatic activities of all-trans retinoic acid, indole-3-carbinol and (+)-catechin in Dunning rat invasive prostate adenocarcinoma cells.	2003-01-30	12553043
Modulation of vinca-alkaloid induced P-glycoprotein expression by indole-3-carbinol.	2003-01-28	12490309
Growth-inhibitory effects of the chemopreventive agent indole-3-carbinol are increased in combination with the polyamine putrescine in the SW480 colon tumour cell line.	2003-01-14	12525265
Convenient synthesis of 5,6,11,12,17,18- hexahydrocyclononal[1,2-b:4,5-b':7,8-b'']triindole, a novel phytoestrogen.	2003-01-10	12515475
Role of salicylic acid in systemic resistance induced by Pseudomonas fluorescens against Fusarium oxysporum f. sp. ciceri in chickpea.	2003	14521230
Chapter 17: Genital human papillomavirus infections--current and prospective therapies.	2003	12807955
Indole-3-carbinol (I3C) induces apoptosis in tumorigenic but not in nontumorigenic breast epithelial cells.	2003	12791510
Antigenotoxic potential of certain dietary constituents.	2003	12616623
Differential effects of vegetable-derived indoles on the induction of quinone reductase in hepatoma cells.	2002-12	12775114
Plant-derived biomolecules in fermented cabbage.	2002-11-06	12405778
Indole-3-carbinol inhibits protein kinase B/Akt and induces apoptosis in the human breast tumor cell line MDA MB468 but not in the nontumorigenic HBL100 line.	2002-11	12479697
Why phase II trials in cervical chemoprevention are negative: what have we learned?	2002-11	12462551
Further investigation of the modifying effect of various chemopreventive agents on apoptosis and cell proliferation in human colon cancer cells.	2002-10	12384797
Development of a multi-organ rat model for evaluating chemopreventive agents: efficacy of indole-3-carbinol-. Certain health supplements may cause both carcinogenic and anticarcinogenic effects.	2002-10	12376488
Endocrine disruption by indole-3-carbinol and tamoxifen: blockage of ovulation.	2002-09-15	12383709
Multiple molecular targets of indole-3-carbinol, a chemopreventive anti-estrogen in breast cancer.	2002-08	12570340
Lack of chemoprevention of indole-3-carbinol in N-methyl-N-nitrosourea-induced mammary carcinogenesis in rats.	2002	12484220

Patents

Sample Use Guides

In Vivo Use Guide

For treating abnormal cells on the surface of the cervix (cervical dysplasia): 200-400 mg per day has been used. However, 200 mg seems to be as effective as the higher dose.

Route of Administration: Oral

In Vitro Use Guide

Using mouse liver microsomes in an NADPH-fortified reaction mixture, Indole-3-carbinol inhibited, in a concentration-dependent manner, CCl4-initiated lipid peroxidation, with 50% inhibition at 35-40 uM Indole-3-carbinol.

Name

Type

Language

NSC-525801

Preferred Name

English

INDOLE-3-CARBINOL

Common Name

English

3-HYDROXYMETHYLINDOLE

Systematic Name

English

1H-INDOLE-3-METHANOL

Systematic Name

English

INDOLE-3-CARBINOL [VANDF]

Common Name

English

INDOLE-3-METHANOL

Systematic Name

English

I3C

Common Name

English

Indole-3-Carbinol [WHO-DD]

Common Name

English

INDOLE 3-CARBINOL

Common Name

English

Classification Tree Code System Code

DSLD

473 (Number of products:104)