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
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
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
Primary Target | Pharmacology | Condition | Potency |
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Target ID: Q13547 Gene ID: 3065.0 Gene Symbol: HDAC1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/20068155 |
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Target ID: Q92769 Gene ID: 3066.0 Gene Symbol: HDAC2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/20068155 |
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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 |
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Target ID: O15379 Gene ID: 8841.0 Gene Symbol: HDAC3 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/20068155 |
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Target ID: 407034.0 Gene Symbol: MIR30E Sources: https://www.ncbi.nlm.nih.gov/pubmed/27372603 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Preventing | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 |
|
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 |
|
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 |
|
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 |
|
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 |
|
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 | Co-administered | Analyte | Population |
---|---|---|---|---|
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 |
|
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 |
|
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 |
|
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 |
|
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 |
|
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 |
T1/2
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 |
PubMed
Title | Date | PubMed |
---|---|---|
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 |
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Therapy for recurrent respiratory papillomatosis. | 2002 Mar |
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Peroxisome proliferator-activated receptor gamma-dependent activation of p21 in Panc-28 pancreatic cancer cells involves Sp1 and Sp4 proteins. | 2004 Dec |
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Phytochemical-induced changes in gene expression of carcinogen-metabolizing enzymes in cultured human primary hepatocytes. | 2004 Jul |
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Endoplasmic reticulum stress as a correlate of cytotoxicity in human tumor cells exposed to diindolylmethane in vitro. | 2004 Mar |
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Anticarcinogenic and antioxidant activity of diindolylmethane derivatives. | 2004 May |
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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 |
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Induction of apoptosis in human prostate cancer cell line, PC3, by 3,3'-diindolylmethane through the mitochondrial pathway. | 2004 Oct 4 |
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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 |
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A comparison of two methods to determine the solubility of compounds in aerosol propellants. | 2005 Mar 23 |
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Indole-3-carbinol and 3,3'-diindolylmethane induce expression of NAG-1 in a p53-independent manner. | 2005 Mar 4 |
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Molecular targets and anticancer potential of indole-3-carbinol and its derivatives. | 2005 Sep |
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Synthetic dimer of indole-3-carbinol: second generation diet derived anti-cancer agent in hormone sensitive prostate cancer. | 2006 Apr 1 |
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Activation and potentiation of interferon-gamma signaling by 3,3'-diindolylmethane in MCF-7 breast cancer cells. | 2006 Feb |
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BRCA1 and BRCA2 as molecular targets for phytochemicals indole-3-carbinol and genistein in breast and prostate cancer cells. | 2006 Feb 13 |
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Oxidized bis(indolyl)methane: a simple and efficient chromogenic-sensing molecule based on the proton transfer signaling mode. | 2006 Jan 19 |
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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 |
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Fate of 3,3'-diindolylmethane in cultured MCF-7 human breast cancer cells. | 2006 Mar |
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Using salmonid microarrays to understand the dietary modulation of carcinogenesis in rainbow trout. | 2006 Mar |
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Toxicogenomic profiling of the hepatic tumor promoters indole-3-carbinol, 17beta-estradiol and beta-naphthoflavone in rainbow trout. | 2006 Mar |
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3,3'-diindolylmethane and paclitaxel act synergistically to promote apoptosis in HER2/Neu human breast cancer cells. | 2006 May 15 |
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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 |
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Fas-mediated apoptosis in cholangiocarcinoma cells is enhanced by 3,3'-diindolylmethane through inhibition of AKT signaling and FLICE-like inhibitory protein. | 2006 Nov |
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Estrogen receptor alpha as a target for indole-3-carbinol. | 2006 Oct |
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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 |
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Quantitative combination effects between sulforaphane and 3,3'-diindolylmethane on proliferation of human colon cancer cells in vitro. | 2007 Jul |
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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 |
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Extended treatment with physiologic concentrations of dietary phytochemicals results in altered gene expression, reduced growth, and apoptosis of cancer cells. | 2007 Nov |
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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 |
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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
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27372603
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
Edited
Sat Jun 26 01:45:32 UTC 2021
by
admin
on
Sat Jun 26 01:45:32 UTC 2021
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Record UNII |
SSZ9HQT61Z
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Record Status |
Validated (UNII)
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Record Version |
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Name | Type | Language | ||
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Common Name | English | ||
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Systematic Name | English | ||
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Common Name | English | ||
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Common Name | English |
Classification Tree | Code System | Code | ||
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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
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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
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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
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Code System | Code | Type | Description | ||
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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
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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
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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
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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
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PRIMARY | |||
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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
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PRIMARY | |||
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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
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PRIMARY | RxNorm | ||
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C53434
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PRIMARY | NCIT | ||
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C016392
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3071
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PRIMARY | |||
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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
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PRIMARY |
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PARENT -> POSSIBLE ACTIVE CONSTITUENT ALWAYS PRESENT |
Related Record | Type | Details | ||
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ACTIVE MOIETY |