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Details

Stereochemistry ACHIRAL
Molecular Formula C17H14N2
Molecular Weight 246.3071
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 3,3'-DIINDOLYLMETHANE

SMILES

c1ccc2c(c1)c(Cc3c[nH]c4ccccc34)c[nH]2

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 246.3071
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
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
Concurrent flavin-containing monooxygenase down regulation and cytochrome P450 induction by dietary indoles in the rat: implication for drug-drug interactions.
2001
Methyl-substituted diindolylmethanes as inhibitors of estrogen-induced growth of T47D cells and mammary tumors in rats.
2001 Mar
Involvement of a post-transcriptional mechanism in the inhibition of CYP1A1 expression by resveratrol in breast cancer cells.
2001 Oct 15
Therapy for recurrent respiratory papillomatosis.
2002 Mar
Peroxisome proliferator-activated receptor gamma-dependent activation of p21 in Panc-28 pancreatic cancer cells involves Sp1 and Sp4 proteins.
2004 Dec
Phytochemical-induced changes in gene expression of carcinogen-metabolizing enzymes in cultured human primary hepatocytes.
2004 Jul
Endoplasmic reticulum stress as a correlate of cytotoxicity in human tumor cells exposed to diindolylmethane in vitro.
2004 Mar
Anticarcinogenic and antioxidant activity of diindolylmethane derivatives.
2004 May
Dietary agent indole-3-carbinol protects female rats against the hepatotoxicity of the antitumor drug ET-743 (trabectidin) without compromising efficacy in a rat mammary carcinoma.
2004 Oct 10
Induction of apoptosis in human prostate cancer cell line, PC3, by 3,3'-diindolylmethane through the mitochondrial pathway.
2004 Oct 4
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
A comparison of two methods to determine the solubility of compounds in aerosol propellants.
2005 Mar 23
Indole-3-carbinol and 3,3'-diindolylmethane induce expression of NAG-1 in a p53-independent manner.
2005 Mar 4
Molecular targets and anticancer potential of indole-3-carbinol and its derivatives.
2005 Sep
Synthetic dimer of indole-3-carbinol: second generation diet derived anti-cancer agent in hormone sensitive prostate cancer.
2006 Apr 1
Activation and potentiation of interferon-gamma signaling by 3,3'-diindolylmethane in MCF-7 breast cancer cells.
2006 Feb
BRCA1 and BRCA2 as molecular targets for phytochemicals indole-3-carbinol and genistein in breast and prostate cancer cells.
2006 Feb 13
Oxidized bis(indolyl)methane: a simple and efficient chromogenic-sensing molecule based on the proton transfer signaling mode.
2006 Jan 19
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
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
Toxicogenomic profiling of the hepatic tumor promoters indole-3-carbinol, 17beta-estradiol and beta-naphthoflavone in rainbow trout.
2006 Mar
3,3'-diindolylmethane and paclitaxel act synergistically to promote apoptosis in HER2/Neu human breast cancer cells.
2006 May 15
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
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
Quantitative combination effects between sulforaphane and 3,3'-diindolylmethane on proliferation of human colon cancer cells in vitro.
2007 Jul
Gene expression analysis during tumor enhancement by the dietary phytochemical, 3,3'-diindolylmethane, in rainbow trout.
2007 Jul
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
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
Cruciferous vegetables and human cancer risk: epidemiologic evidence and mechanistic basis.
2007 Mar
Extended treatment with physiologic concentrations of dietary phytochemicals results in altered gene expression, reduced growth, and apoptosis of cancer cells.
2007 Nov
Inactivation of NF-kappaB by 3,3'-diindolylmethane contributes to increased apoptosis induced by chemotherapeutic agent in breast cancer cells.
2007 Oct
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
Substance Class Chemical
Created
by admin
on Sat Jun 26 01:45:32 UTC 2021
Edited
by admin
on Sat Jun 26 01:45:32 UTC 2021
Record UNII
SSZ9HQT61Z
Record Status Validated (UNII)
Record Version
  • Download
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
Classification Tree Code System Code
NCI_THESAURUS C54630
Created by admin on Sat Jun 26 01:45:32 UTC 2021 , Edited by admin on Sat Jun 26 01:45:32 UTC 2021
NCI_THESAURUS C54677
Created by admin on Sat Jun 26 01:45:32 UTC 2021 , Edited by admin on Sat Jun 26 01:45:32 UTC 2021
DSLD 1346 (Number of products:303)
Created by admin on Sat Jun 26 01:45:32 UTC 2021 , Edited by admin on Sat Jun 26 01:45:32 UTC 2021
Code System Code Type Description
EPA CompTox
1968-05-4
Created by admin on Sat Jun 26 01:45:32 UTC 2021 , Edited by admin on Sat Jun 26 01:45:32 UTC 2021
PRIMARY
WIKIPEDIA
3,3'-Diindolylmethane
Created by admin on Sat Jun 26 01:45:32 UTC 2021 , Edited by admin on Sat Jun 26 01:45:32 UTC 2021
PRIMARY
DRUG BANK
DB11875
Created by admin on Sat Jun 26 01:45:32 UTC 2021 , Edited by admin on Sat Jun 26 01:45:32 UTC 2021
PRIMARY
FDA UNII
SSZ9HQT61Z
Created by admin on Sat Jun 26 01:45:32 UTC 2021 , Edited by admin on Sat Jun 26 01:45:32 UTC 2021
PRIMARY
CAS
1968-05-4
Created by admin on Sat Jun 26 01:45:32 UTC 2021 , Edited by admin on Sat Jun 26 01:45:32 UTC 2021
PRIMARY
RXCUI
1603521
Created by admin on Sat Jun 26 01:45:32 UTC 2021 , Edited by admin on Sat Jun 26 01:45:32 UTC 2021
PRIMARY RxNorm
NCI_THESAURUS
C53434
Created by admin on Sat Jun 26 01:45:32 UTC 2021 , Edited by admin on Sat Jun 26 01:45:32 UTC 2021
PRIMARY NCIT
MESH
C016392
Created by admin on Sat Jun 26 01:45:32 UTC 2021 , Edited by admin on Sat Jun 26 01:45:32 UTC 2021
PRIMARY
PUBCHEM
3071
Created by admin on Sat Jun 26 01:45:32 UTC 2021 , Edited by admin on Sat Jun 26 01:45:32 UTC 2021
PRIMARY
EVMPD
SUB32854
Created by admin on Sat Jun 26 01:45:32 UTC 2021 , Edited by admin on Sat Jun 26 01:45:32 UTC 2021
PRIMARY
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PARENT -> POSSIBLE ACTIVE CONSTITUENT ALWAYS PRESENT
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ACTIVE MOIETY