3,3'-DIINDOLYLMETHANE

Possibly Marketed Outside US

First approved in 2023

Details

Stereochemistry	ACHIRAL
Molecular Formula	C17H14N2
Molecular Weight	246.3065
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C(C1=CNC2=C1C=CC=C2)C3=CNC4=C3C=CC=C4

InChI

InChIKey=VFTRKSBEFQDZKX-UHFFFAOYSA-N

InChI=1S/C17H14N2/c1-3-7-16-14(5-1)12(10-18-16)9-13-11-19-17-8-4-2-6-15(13)17/h1-8,10-11,18-19H,9H2

HIDE SMILES / InChI

Molecular Formula	C17H14N2
Molecular Weight	246.3065
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.bioresponse.com/BioResponse-DIM.asp | https://www.ncbi.nlm.nih.gov/pubmed/20068155 | https://www.ncbi.nlm.nih.gov/pubmed/16142445 | https://www.ncbi.nlm.nih.gov/pubmed/19939441

3,3′-diindolylmethane or diindolylmethane (DIM), a natural product from cruciferous vegetables, which possesses chemopreventive activity in all stages of breast cancer carcinogenesis and is under investigation for the different form of cancer. DIM selectively induced proteasome-mediated degradation of the class I histone deacetylases (HDAC1, HDAC2, HDAC3, and HDAC8) without affecting the class II HDAC proteins (HDAC4, 5, 6, 7, and 10). Histone deacetylases are components of high molecular weight multisubunit complexes of co-repressor proteins that are recruited by transcription factors to the promoters to regulate gene expression. In addition, was identified another mechanism of action: DIM suppressed cancer cells proliferation and miR-30e down-regulated during this effect. miR-30e targeted the 3'-UTR of ATG5 to inhibit its translation. Thus DIM may through the miR-30e-ATG5 modulating autophagy inhibit the proliferation of gastric cancer cells. DIM is also sold as absorption-enhanced formulation under the brand name Patented BioResponse DIM®. BioResponse DIM supports a more favorable metabolism of estrogen and supports the production of 2 hydroxyestrone and 2-methoxyestrone, key metabolites in men and women. DIM is used to treat recurrent respiratory papillomatosis and it has been studied for patients with cervical intraepithelial neoplasia.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Histone deacetylase 1 51 Target ID: Q13547 Gene ID: 3065.0 Gene Symbol: HDAC1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/20068155	Inhibitor 8504
Histone deacetylase 2 37 Target ID: Q92769 Gene ID: 3066.0 Gene Symbol: HDAC2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/20068155	Inhibitor 8504
Histone deacetylase 8 16 Target ID: Q9BY41\|\|\|Q86VC8 Gene ID: 55869.0 Gene Symbol: HDAC8 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/20068155	Inhibitor 8504
Histone deacetylase 3 35 Target ID: O15379 Gene ID: 8841.0 Gene Symbol: HDAC3 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/20068155	Inhibitor 8504
microRNA 30e 1 Target ID: 407034.0 Gene Symbol: MIR30E Sources: https://www.ncbi.nlm.nih.gov/pubmed/27372603	Inhibitor 8504

Conditions

Condition	Modality	Highest Phase	Product
Breast cancer 432 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27261275	Preventing	Phase III 665	Unknown Approved Use Unknown
Recurrent respiratory papillomatosis 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16142445	Primary	Not Provided 511	Unknown Approved Use Unknown
Cervical dysplasia 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19939441	Primary	Not Provided 511	Unknown Approved Use Unknown

C_max

Value	Dose	Analyte	Population
79 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18843002	150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered:	3,3'-DIINDOLYLMETHANE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
108 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18843002	300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered:	3,3'-DIINDOLYLMETHANE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
104 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20733950	150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered:	3,3'-DIINDOLYLMETHANE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN
134 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20733950	225 mg single, oral dose: 225 mg route of administration: Oral experiment type: SINGLE co-administered:	3,3'-DIINDOLYLMETHANE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN
42 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20733950	75 mg single, oral dose: 75 mg route of administration: Oral experiment type: SINGLE co-administered:	3,3'-DIINDOLYLMETHANE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN
236 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20733950	300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered:	3,3'-DIINDOLYLMETHANE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
314 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18843002	150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered:	3,3'-DIINDOLYLMETHANE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
532 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18843002	300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered:	3,3'-DIINDOLYLMETHANE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
450 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20733950	150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered:	3,3'-DIINDOLYLMETHANE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN
599 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20733950	225 mg single, oral dose: 225 mg route of administration: Oral experiment type: SINGLE co-administered:	3,3'-DIINDOLYLMETHANE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN
192 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20733950	75 mg single, oral dose: 75 mg route of administration: Oral experiment type: SINGLE co-administered:	3,3'-DIINDOLYLMETHANE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN
899 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20733950	300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered:	3,3'-DIINDOLYLMETHANE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18843002	150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered:		3,3'-DIINDOLYLMETHANE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
4.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18843002	300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered:		3,3'-DIINDOLYLMETHANE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P003BRA	https://www.1pchem.com/search?query=1P003BRA
A2B Chem	AB54406	http://a2bchem.com/prod/AB54406
AA Blocks	AA003B7U	http://aablocks.com/goods/Goods/detail?id=AA003B7U
Accela ChemBio Inc	SY038972	http://accelachem.com/cn/search.html?keyword=SY038972&attname=0
Achemo Scientific Limited	AC-13491	http://www.achemo.com/search/?Keyword=AC-13491
AK Scientific	D117	https://aksci.com/item_detail.php?cat=D117
Alinda	ALBB-016048	http://alinda.ru/finechem_en_.html?i=ALBB-016048
Ambeed	A155014	http://www.ambeed.com/search/Search.html?keyword=A155014
ApexBio Technology	A3118	https://www.apexbt.com/catalogsearch/result/?q=A3118
AstaTech	23183	http://astatechinc.com/CPSResult.php?CRNO=23183
BioSynth	D-3720	https://www.biosynth.com/en/products/life-science/other-biochemicals/products/D-3720
BOC Sciences	24962	http://www.bocsci.com/description.asp?cas=1968-05-4
Capot Chemical	8119	https://www.capotchem.com/search.do?q=8119
Cayman Chemical	15927	http://www.caymanchem.com/app/template/Product.vm/catalog/15927
Chem-Impex International	21231	http://www.chemimpex.com/category/search/21231/2?filter=&search=21231&type=q&keywordoption=ANY&cid=2&fltrdesc=
Chem Scene	CS-1652	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-1652
ChemBridge	5140807	http://www.hit2lead.com/screening-compounds/5140807
ChemDiv	BB55-8683	http://chemistryondemand.com:8080/eShop/search_results.jsp?idnumber=BB55-8683
Combi-Blocks	OR-0683	http://www.combi-blocks.com/cgi-bin/find.cgi?OR-0683
eMolecules	1060539	https://orderbb.emolecules.com/search/#?query=1060539
Enamine	EN300-1717487	https://www.enaminestore.com/catalog/EN300-1717487
Fluorochem	24220	http://www.fluorochem.co.uk/Products/Product?code=024220
Frontier Scientific Services	100087033	http://orders.frontierssi.com/fssionline32/public/product.aspx?cat=100087033&type=hts
KeyOrganics	KS-5266	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=KS-5266
Lab Network	LN00165990	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00165990
Lab Seeker	SC-19468	http://www.labseeker.com/search.php?keywords=SC-19468&category=0
LabSeeker	SC-19468	http://www.labseeker.com/search.php?keywords=SC-19468&category=0
Matrix Scientific	65339	http://www.matrixscientific.com/065339.html
mcule	MCULE-3718375492	https://mcule.com/MCULE-3718375492/
MedChem Express	HY-15758	https://www.medchemexpress.com/search.html?q=HY-15758&ft=&fa=&fp=
MolPort	MolPort-001-815-286	https://www.molport.com/shop/molecule-link/MolPort-001-815-286
PI Chemicals	PI-11090	http://www.pipharm.com/catalog_products/PI-11090.html
Princeton BioMolecular Research	OSSK_984284	http://www.princetonbio.com/order_online?common_id=OSSK_984284
Selleck Chemicals	S4728	http://www.selleckchem.com/search.html?searchDTO.searchParam=S4728
ShangHai Biochempartner	BCP00470	http://www.biochempartner.com/search_BCP00470
Tetrahedron	TS59557	http://www.thsci.com/search.do?q=TS59557
TimTec	ST104725	http://www.echemstore.com/catalogsearch/result/?q=ST104725
Toronto Research Chemicals	D455238	https://www.trc-canada.com/product-detail/?CatNum=D455238
Vitas-M Laboratory	STK263696	http://www.vitasmlab.biz/search/STK263696
W&J PharmaChem	50A486069	http://wjpharmachem.com/new/searcht.php?keyword=50A486069

PubMed

Title	Date	PubMed
Down-regulation of c-FLIP contributes to the sensitization effect of 3,3'-diindolylmethane on TRAIL-induced apoptosis in cancer cells.	2005 Dec	16373712
Multifocal angiostatic therapy: an update.	2005 Dec	16282507
[Current therapeutic options for recurrent respiratory papillomatosis].	2005 Nov	16142445
3,3'-Diindolylmethane, a cruciferous vegetable derived synthetic anti-proliferative compound in thyroid disease.	2005 Nov 25	16219298
Gateways to clinical trials.	2005 Oct	16273137
Molecular targets of dietary polyphenols with anti-inflammatory properties.	2005 Oct 31	16259055
Chemoprevention of cervical cancer.	2006 Apr	16386963
3,3'-diindolylmethane is a novel topoisomerase IIalpha catalytic inhibitor that induces S-phase retardation and mitotic delay in human hepatoma HepG2 cells.	2006 Apr	16385077
3,3'-diindolylmethane (DIM) and its derivatives induce apoptosis in pancreatic cancer cells through endoplasmic reticulum stress-dependent upregulation of DR5.	2006 Apr	16332727
Synthetic dimer of indole-3-carbinol: second generation diet derived anti-cancer agent in hormone sensitive prostate cancer.	2006 Apr 1	16353249
Single-dose and multiple-dose administration of indole-3-carbinol to women: pharmacokinetics based on 3,3'-diindolylmethane.	2006 Dec	17164373
Activation and potentiation of interferon-gamma signaling by 3,3'-diindolylmethane in MCF-7 breast cancer cells.	2006 Feb	16267208
3,3'-Diindolylmethane downregulates pro-survival pathway in hormone independent prostate cancer.	2006 Feb 10	16380095
BRCA1 and BRCA2 as molecular targets for phytochemicals indole-3-carbinol and genistein in breast and prostate cancer cells.	2006 Feb 13	16434996
Oxidized bis(indolyl)methane: a simple and efficient chromogenic-sensing molecule based on the proton transfer signaling mode.	2006 Jan 19	16408908
Comparison of growth inhibition profiles and mechanisms of apoptosis induction in human colon cancer cell lines by isothiocyanates and indoles from Brassicaceae.	2006 Jul 25	16500682
Multiple, disparate roles for calcium signaling in apoptosis of human prostate and cervical cancer cells exposed to diindolylmethane.	2006 Mar	16546969
Fate of 3,3'-diindolylmethane in cultured MCF-7 human breast cancer cells.	2006 Mar	16544949
Using salmonid microarrays to understand the dietary modulation of carcinogenesis in rainbow trout.	2006 Mar	16532552
Inhibition of growth factor-induced Ras signaling in vascular endothelial cells and angiogenesis by 3,3'-diindolylmethane.	2006 Mar	16199440
Toxicogenomic profiling of the hepatic tumor promoters indole-3-carbinol, 17beta-estradiol and beta-naphthoflavone in rainbow trout.	2006 Mar	16192472
The natural chemopreventive compound indole-3-carbinol: state of the science.	2006 Mar-Apr	16634522
Gene expression profiling revealed survivin as a target of 3,3'-diindolylmethane-induced cell growth inhibition and apoptosis in breast cancer cells.	2006 May 1	16651453
3,3'-Diindolylmethane is a novel mitochondrial H(+)-ATP synthase inhibitor that can induce p21(Cip1/Waf1) expression by induction of oxidative stress in human breast cancer cells.	2006 May 1	16651444
3,3'-diindolylmethane and paclitaxel act synergistically to promote apoptosis in HER2/Neu human breast cancer cells.	2006 May 15	16580691
Fas-mediated apoptosis in cholangiocarcinoma cells is enhanced by 3,3'-diindolylmethane through inhibition of AKT signaling and FLICE-like inhibitory protein.	2006 Nov	17071604
Estrogen receptor alpha as a target for indole-3-carbinol.	2006 Oct	16488130
Down-regulation of androgen receptor by 3,3'-diindolylmethane contributes to inhibition of cell proliferation and induction of apoptosis in both hormone-sensitive LNCaP and insensitive C4-2B prostate cancer cells.	2006 Oct 15	17047070
Aryl hydrocarbon receptor agonists directly activate estrogen receptor alpha in MCF-7 breast cancer cells.	2006 Sep	16972788
1,1-Bis(3'-indolyl)-1-(p-biphenyl)methane inhibits basal-like breast cancer growth in athymic nude mice.	2007	17764562
Inhibition of angiogenesis and invasion by 3,3'-diindolylmethane is mediated by the nuclear factor-kappaB downstream target genes MMP-9 and uPA that regulated bioavailability of vascular endothelial growth factor in prostate cancer.	2007 Apr 1	17409440
Combination of tunicamycin with anticancer drugs synergistically enhances their toxicity in multidrug-resistant human ovarian cystadenocarcinoma cells.	2007 Apr 18	17439664
Interplay of genes regulated by estrogen and diindolylmethane in breast cancer cell lines.	2007 Jan-Feb	17515958
Quantitative combination effects between sulforaphane and 3,3'-diindolylmethane on proliferation of human colon cancer cells in vitro.	2007 Jul	17331956
Gene expression analysis during tumor enhancement by the dietary phytochemical, 3,3'-diindolylmethane, in rainbow trout.	2007 Jul	17272308
Indole-3-carbinol inhibits 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone plus benzo(a)pyrene-induced lung tumorigenesis in A/J mice and modulates carcinogen-induced alterations in protein levels.	2007 Jul 1	17616712
Regulation of FOXO3a/beta-catenin/GSK-3beta signaling by 3,3'-diindolylmethane contributes to inhibition of cell proliferation and induction of apoptosis in prostate cancer cells.	2007 Jul 20	17522055
A review of the clinical efficacy and safety of cruciferous vegetable phytochemicals.	2007 Jun	17605302
Cruciferous vegetables and human cancer risk: epidemiologic evidence and mechanistic basis.	2007 Mar	17317210
Extended treatment with physiologic concentrations of dietary phytochemicals results in altered gene expression, reduced growth, and apoptosis of cancer cells.	2007 Nov	18025290
Inactivation of NF-kappaB by 3,3'-diindolylmethane contributes to increased apoptosis induced by chemotherapeutic agent in breast cancer cells.	2007 Oct	17913854
Curcumin enhances the apoptosis-inducing potential of TRAIL in prostate cancer cells: molecular mechanisms of apoptosis, migration and angiogenesis.	2007 Oct 4	17916240
Predicting the physiological relevance of in vitro cancer preventive activities of phytochemicals.	2007 Sep	17723163
Eco-friendly synthesis and study of new plant growth promoters: 3,3'-Diindolylmethane and its derivatives.	2007 Sep 1	17583501
Gene expression profiling reveals effects of Cimicifuga racemosa (L.) NUTT. (black cohosh) on the estrogen receptor positive human breast cancer cell line MCF-7.	2007 Sep 20	17880733
1,1-bis(3'-indolyl)-1-(p-methoxyphenyl)methane activates Nur77-independent proapoptotic responses in colon cancer cells.	2008 Apr	17957723
Red clover isoflavones biochanin A and formononetin are potent ligands of the human aryl hydrocarbon receptor.	2008 Jan	18060767
Comparative study of aryl hydrocarbon receptor ligand activities of six chemicals in vitro and in vivo.	2008 Jan	17899013
An insight into the mechanism of inhibition of unusual bi-subunit topoisomerase I from Leishmania donovani by 3,3'-di-indolylmethane, a novel DNA topoisomerase I poison with a strong binding affinity to the enzyme.	2008 Jan 15	17922678
3,3'-Diindolylmethane stimulates murine immune function in vitro and in vivo.	2008 May	17707631

Patents

Sample Use Guides

In Vivo Use Guide

75 mg of 3,3´-diindolylmethane (DIM) once a day for 30 days. Two pills of BioResponse DIM® 150 are equal to 75 mg of DIM pure.

Route of Administration: Oral

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:31:22 GMT 2025` Edited by `admin` on `Mon Mar 31 19:31:22 GMT 2025`
Record UNII	SSZ9HQT61Z
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DIINDOLYLMETHANE

Preferred Name

English

3,3'-DIINDOLYLMETHANE

Common Name

English

DIINDOLYLMETHANE, 3,3'-

Common Name

English

DIINDOLYLMETHANE [VANDF]

Common Name

English

3,3'-Diindolylmethane [WHO-DD]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C54630