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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=CC=CC=C12)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
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
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
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
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
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
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
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
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
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
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
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
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
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
Dietary indoles and isothiocyanates that are generated from cruciferous vegetables can both stimulate apoptosis and confer protection against DNA damage in human colon cell lines.
2001 Aug 15
3,3'-diindolylmethane, a major condensation product of indole-3-carbinol, is a potent estrogen in the rainbow trout.
2001 Feb 1
Methyl-substituted diindolylmethanes as inhibitors of estrogen-induced growth of T47D cells and mammary tumors in rats.
2001 Mar
Cytostatic effects of 3,3'-diindolylmethane in human endometrial cancer cells result from an estrogen receptor-mediated increase in transforming growth factor-alpha expression.
2001 Nov
Effects of treatment of rats with indole-3-carbinol on apoptosis in the mammary gland and mammary adenocarcinomas.
2003 May-Jun
Pharmacokinetics and tissue disposition of indole-3-carbinol and its acid condensation products after oral administration to mice.
2004 Aug 1
Potent ligand-independent estrogen receptor activation by 3,3'-diindolylmethane is mediated by cross talk between the protein kinase A and mitogen-activated protein kinase signaling pathways.
2004 Feb
Physiological modeling of formulated and crystalline 3,3'-diindolylmethane pharmacokinetics following oral administration in mice.
2004 Jun
A new class of peroxisome proliferator-activated receptor gamma (PPARgamma) agonists that inhibit growth of breast cancer cells: 1,1-Bis(3'-indolyl)-1-(p-substituted phenyl)methanes.
2004 Mar
Lack of antagonism of 2,3,7,8-tetrachlorodibenzo-p-dioxin's (TCDDs) induction of cytochrome P4501A1 (CYP1A1) by the putative selective aryl hydrocarbon receptor modulator 6-alkyl-1,3,8-trichlorodibenzofuran (6-MCDF) in the mouse hepatoma cell line Hepa-1c1c7.
2004 Nov 20
Multifocal angiostatic therapy: an update.
2005 Dec
Indole-3-carbinol (I3C) inhibits cyclin-dependent kinase-2 function in human breast cancer cells by regulating the size distribution, associated cyclin E forms, and subcellular localization of the CDK2 protein complex.
2005 Mar 11
Gateways to clinical trials.
2005 Oct
Molecular targets of dietary polyphenols with anti-inflammatory properties.
2005 Oct 31
3,3'-diindolylmethane (DIM) and its derivatives induce apoptosis in pancreatic cancer cells through endoplasmic reticulum stress-dependent upregulation of DR5.
2006 Apr
Synthetic dimer of indole-3-carbinol: second generation diet derived anti-cancer agent in hormone sensitive prostate cancer.
2006 Apr 1
Single-dose and multiple-dose administration of indole-3-carbinol to women: pharmacokinetics based on 3,3'-diindolylmethane.
2006 Dec
Oxidized bis(indolyl)methane: a simple and efficient chromogenic-sensing molecule based on the proton transfer signaling mode.
2006 Jan 19
Multiple, disparate roles for calcium signaling in apoptosis of human prostate and cervical cancer cells exposed to diindolylmethane.
2006 Mar
Fate of 3,3'-diindolylmethane in cultured MCF-7 human breast cancer cells.
2006 Mar
Using salmonid microarrays to understand the dietary modulation of carcinogenesis in rainbow trout.
2006 Mar
Inhibition of breast cancer cell growth and induction of cell death by 1,1-bis(3'-indolyl)methane (DIM) and 5,5'-dibromoDIM.
2006 May 18
Fas-mediated apoptosis in cholangiocarcinoma cells is enhanced by 3,3'-diindolylmethane through inhibition of AKT signaling and FLICE-like inhibitory protein.
2006 Nov
Estrogen receptor alpha as a target for indole-3-carbinol.
2006 Oct
Extended treatment with physiologic concentrations of dietary phytochemicals results in altered gene expression, reduced growth, and apoptosis of cancer cells.
2007 Nov
Curcumin enhances the apoptosis-inducing potential of TRAIL in prostate cancer cells: molecular mechanisms of apoptosis, migration and angiogenesis.
2007 Oct 4
1,1-bis(3'-indolyl)-1-(p-methoxyphenyl)methane activates Nur77-independent proapoptotic responses in colon cancer cells.
2008 Apr
Red clover isoflavones biochanin A and formononetin are potent ligands of the human aryl hydrocarbon receptor.
2008 Jan
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
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
Name Type Language
3,3'-DIINDOLYLMETHANE
WHO-DD  
Common Name English
DIINDOLYLMETHANE
VANDF  
Systematic 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 Fri Dec 15 19:02:37 GMT 2023 , Edited by admin on Fri Dec 15 19:02:37 GMT 2023
NCI_THESAURUS C54677
Created by admin on Fri Dec 15 19:02:37 GMT 2023 , Edited by admin on Fri Dec 15 19:02:37 GMT 2023
DSLD 1346 (Number of products:303)
Created by admin on Fri Dec 15 19:02:37 GMT 2023 , Edited by admin on Fri Dec 15 19:02:37 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID8037047
Created by admin on Fri Dec 15 19:02:37 GMT 2023 , Edited by admin on Fri Dec 15 19:02:37 GMT 2023
PRIMARY
WIKIPEDIA
3,3'-Diindolylmethane
Created by admin on Fri Dec 15 19:02:37 GMT 2023 , Edited by admin on Fri Dec 15 19:02:37 GMT 2023
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DRUG BANK
DB11875
Created by admin on Fri Dec 15 19:02:37 GMT 2023 , Edited by admin on Fri Dec 15 19:02:37 GMT 2023
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FDA UNII
SSZ9HQT61Z
Created by admin on Fri Dec 15 19:02:37 GMT 2023 , Edited by admin on Fri Dec 15 19:02:37 GMT 2023
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CAS
1968-05-4
Created by admin on Fri Dec 15 19:02:37 GMT 2023 , Edited by admin on Fri Dec 15 19:02:37 GMT 2023
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DAILYMED
SSZ9HQT61Z
Created by admin on Fri Dec 15 19:02:37 GMT 2023 , Edited by admin on Fri Dec 15 19:02:37 GMT 2023
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RXCUI
1603521
Created by admin on Fri Dec 15 19:02:37 GMT 2023 , Edited by admin on Fri Dec 15 19:02:37 GMT 2023
PRIMARY RxNorm
NCI_THESAURUS
C53434
Created by admin on Fri Dec 15 19:02:37 GMT 2023 , Edited by admin on Fri Dec 15 19:02:37 GMT 2023
PRIMARY NCIT
MESH
C016392
Created by admin on Fri Dec 15 19:02:37 GMT 2023 , Edited by admin on Fri Dec 15 19:02:37 GMT 2023
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PUBCHEM
3071
Created by admin on Fri Dec 15 19:02:37 GMT 2023 , Edited by admin on Fri Dec 15 19:02:37 GMT 2023
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SMS_ID
100000126223
Created by admin on Fri Dec 15 19:02:37 GMT 2023 , Edited by admin on Fri Dec 15 19:02:37 GMT 2023
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EVMPD
SUB32854
Created by admin on Fri Dec 15 19:02:37 GMT 2023 , Edited by admin on Fri Dec 15 19:02:37 GMT 2023
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