U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of 3,3'-DIINDOLYLMETHANE

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

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

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Q13547
Gene ID: 3065.0
Gene Symbol: HDAC1
Target Organism: Homo sapiens (Human)
Target ID: Q92769
Gene ID: 3066.0
Gene Symbol: HDAC2
Target Organism: Homo sapiens (Human)
Target ID: Q9BY41|||Q86VC8
Gene ID: 55869.0
Gene Symbol: HDAC8
Target Organism: Homo sapiens (Human)
Target ID: O15379
Gene ID: 8841.0
Gene Symbol: HDAC3
Target Organism: Homo sapiens (Human)
Target ID: 407034.0
Gene Symbol: MIR30E
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
79 ng/mL
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
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
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
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
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
314 ng × h/mL
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
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
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
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
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
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
3 h
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
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

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
3,3'-Diindolylmethane stimulates murine immune function in vitro and in vivo.
2008-05
1,1-bis(3'-indolyl)-1-(p-methoxyphenyl)methane activates Nur77-independent proapoptotic responses in colon cancer cells.
2008-04
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.
2008-01-15
Red clover isoflavones biochanin A and formononetin are potent ligands of the human aryl hydrocarbon receptor.
2008-01
Comparative study of aryl hydrocarbon receptor ligand activities of six chemicals in vitro and in vivo.
2008-01
Extended treatment with physiologic concentrations of dietary phytochemicals results in altered gene expression, reduced growth, and apoptosis of cancer cells.
2007-11
Curcumin enhances the apoptosis-inducing potential of TRAIL in prostate cancer cells: molecular mechanisms of apoptosis, migration and angiogenesis.
2007-10-04
Inactivation of NF-kappaB by 3,3'-diindolylmethane contributes to increased apoptosis induced by chemotherapeutic agent in breast cancer cells.
2007-10
Gene expression profiling reveals effects of Cimicifuga racemosa (L.) NUTT. (black cohosh) on the estrogen receptor positive human breast cancer cell line MCF-7.
2007-09-20
Eco-friendly synthesis and study of new plant growth promoters: 3,3'-Diindolylmethane and its derivatives.
2007-09-01
Predicting the physiological relevance of in vitro cancer preventive activities of phytochemicals.
2007-09
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.
2007-07-20
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.
2007-07-01
Quantitative combination effects between sulforaphane and 3,3'-diindolylmethane on proliferation of human colon cancer cells in vitro.
2007-07
Gene expression analysis during tumor enhancement by the dietary phytochemical, 3,3'-diindolylmethane, in rainbow trout.
2007-07
A review of the clinical efficacy and safety of cruciferous vegetable phytochemicals.
2007-06
Combination of tunicamycin with anticancer drugs synergistically enhances their toxicity in multidrug-resistant human ovarian cystadenocarcinoma cells.
2007-04-18
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.
2007-04-01
Cruciferous vegetables and human cancer risk: epidemiologic evidence and mechanistic basis.
2007-03
1,1-Bis(3'-indolyl)-1-(p-biphenyl)methane inhibits basal-like breast cancer growth in athymic nude mice.
2007
Single-dose and multiple-dose administration of indole-3-carbinol to women: pharmacokinetics based on 3,3'-diindolylmethane.
2006-12
Fas-mediated apoptosis in cholangiocarcinoma cells is enhanced by 3,3'-diindolylmethane through inhibition of AKT signaling and FLICE-like inhibitory protein.
2006-11
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.
2006-10-15
Estrogen receptor alpha as a target for indole-3-carbinol.
2006-10
Aryl hydrocarbon receptor agonists directly activate estrogen receptor alpha in MCF-7 breast cancer cells.
2006-09
Comparison of growth inhibition profiles and mechanisms of apoptosis induction in human colon cancer cell lines by isothiocyanates and indoles from Brassicaceae.
2006-07-25
Interplay of genes regulated by estrogen and diindolylmethane in breast cancer cell lines.
2006-05-22
3,3'-diindolylmethane and paclitaxel act synergistically to promote apoptosis in HER2/Neu human breast cancer cells.
2006-05-15
Gene expression profiling revealed survivin as a target of 3,3'-diindolylmethane-induced cell growth inhibition and apoptosis in breast cancer cells.
2006-05-01
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.
2006-05-01
The natural chemopreventive compound indole-3-carbinol: state of the science.
2006-04-26
Synthetic dimer of indole-3-carbinol: second generation diet derived anti-cancer agent in hormone sensitive prostate cancer.
2006-04-01
Chemoprevention of cervical cancer.
2006-04
3,3'-diindolylmethane is a novel topoisomerase IIalpha catalytic inhibitor that induces S-phase retardation and mitotic delay in human hepatoma HepG2 cells.
2006-04
3,3'-diindolylmethane (DIM) and its derivatives induce apoptosis in pancreatic cancer cells through endoplasmic reticulum stress-dependent upregulation of DR5.
2006-04
Multiple, disparate roles for calcium signaling in apoptosis of human prostate and cervical cancer cells exposed to diindolylmethane.
2006-03
Fate of 3,3'-diindolylmethane in cultured MCF-7 human breast cancer cells.
2006-03
Using salmonid microarrays to understand the dietary modulation of carcinogenesis in rainbow trout.
2006-03
Inhibition of growth factor-induced Ras signaling in vascular endothelial cells and angiogenesis by 3,3'-diindolylmethane.
2006-03
Toxicogenomic profiling of the hepatic tumor promoters indole-3-carbinol, 17beta-estradiol and beta-naphthoflavone in rainbow trout.
2006-03
BRCA1 and BRCA2 as molecular targets for phytochemicals indole-3-carbinol and genistein in breast and prostate cancer cells.
2006-02-13
3,3'-Diindolylmethane downregulates pro-survival pathway in hormone independent prostate cancer.
2006-02-10
Activation and potentiation of interferon-gamma signaling by 3,3'-diindolylmethane in MCF-7 breast cancer cells.
2006-02
Oxidized bis(indolyl)methane: a simple and efficient chromogenic-sensing molecule based on the proton transfer signaling mode.
2006-01-19
Down-regulation of c-FLIP contributes to the sensitization effect of 3,3'-diindolylmethane on TRAIL-induced apoptosis in cancer cells.
2005-12
Multifocal angiostatic therapy: an update.
2005-12
3,3'-Diindolylmethane, a cruciferous vegetable derived synthetic anti-proliferative compound in thyroid disease.
2005-11-25
[Current therapeutic options for recurrent respiratory papillomatosis].
2005-11
Molecular targets of dietary polyphenols with anti-inflammatory properties.
2005-10-31
Gateways to clinical trials.
2005-10
Patents

Patents

Sample Use Guides

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
Curator's Comment: 3,3′-diindolylmethane (DIM) dose-dependently inhibited the growth of gastric cancer cells in vitro. ATG5 and LC3 were activated by DIM in gastric cancer cells. Furthermore, miR-30e was down-regulated by DIM and miR-30e targeted the 3'-UTR of ATG5 to inhibit its translation.
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
VANDF  
Preferred Name English
3,3'-DIINDOLYLMETHANE
WHO-DD  
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
Created by admin on Mon Mar 31 19:31:22 GMT 2025 , Edited by admin on Mon Mar 31 19:31:22 GMT 2025
NCI_THESAURUS C54677
Created by admin on Mon Mar 31 19:31:22 GMT 2025 , Edited by admin on Mon Mar 31 19:31:22 GMT 2025
DSLD 1346 (Number of products:303)
Created by admin on Mon Mar 31 19:31:22 GMT 2025 , Edited by admin on Mon Mar 31 19:31:22 GMT 2025
Code System Code Type Description
EPA CompTox
DTXSID8037047
Created by admin on Mon Mar 31 19:31:22 GMT 2025 , Edited by admin on Mon Mar 31 19:31:22 GMT 2025
PRIMARY
WIKIPEDIA
3,3'-Diindolylmethane
Created by admin on Mon Mar 31 19:31:22 GMT 2025 , Edited by admin on Mon Mar 31 19:31:22 GMT 2025
PRIMARY
DRUG BANK
DB11875
Created by admin on Mon Mar 31 19:31:22 GMT 2025 , Edited by admin on Mon Mar 31 19:31:22 GMT 2025
PRIMARY
FDA UNII
SSZ9HQT61Z
Created by admin on Mon Mar 31 19:31:22 GMT 2025 , Edited by admin on Mon Mar 31 19:31:22 GMT 2025
PRIMARY
CAS
1968-05-4
Created by admin on Mon Mar 31 19:31:22 GMT 2025 , Edited by admin on Mon Mar 31 19:31:22 GMT 2025
PRIMARY
DAILYMED
SSZ9HQT61Z
Created by admin on Mon Mar 31 19:31:22 GMT 2025 , Edited by admin on Mon Mar 31 19:31:22 GMT 2025
PRIMARY
RXCUI
1603521
Created by admin on Mon Mar 31 19:31:22 GMT 2025 , Edited by admin on Mon Mar 31 19:31:22 GMT 2025
PRIMARY RxNorm
NCI_THESAURUS
C53434
Created by admin on Mon Mar 31 19:31:22 GMT 2025 , Edited by admin on Mon Mar 31 19:31:22 GMT 2025
PRIMARY NCIT
MESH
C016392
Created by admin on Mon Mar 31 19:31:22 GMT 2025 , Edited by admin on Mon Mar 31 19:31:22 GMT 2025
PRIMARY
PUBCHEM
3071
Created by admin on Mon Mar 31 19:31:22 GMT 2025 , Edited by admin on Mon Mar 31 19:31:22 GMT 2025
PRIMARY
SMS_ID
100000126223
Created by admin on Mon Mar 31 19:31:22 GMT 2025 , Edited by admin on Mon Mar 31 19:31:22 GMT 2025
PRIMARY
EVMPD
SUB32854
Created by admin on Mon Mar 31 19:31:22 GMT 2025 , Edited by admin on Mon Mar 31 19:31:22 GMT 2025
PRIMARY
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PARENT -> POSSIBLE ACTIVE CONSTITUENT ALWAYS PRESENT
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ACTIVE MOIETY