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Details

Stereochemistry ACHIRAL
Molecular Formula C9H9NO
Molecular Weight 147.1739
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of INDOLE-3-CARBINOL

SMILES

OCC1=CNC2=CC=CC=C12

InChI

InChIKey=IVYPNXXAYMYVSP-UHFFFAOYSA-N
InChI=1S/C9H9NO/c11-6-7-5-10-9-4-2-1-3-8(7)9/h1-5,10-11H,6H2

HIDE SMILES / InChI

Description

Indole-3-carbinol (I3C), a common phytochemical in cruciferous vegetables, and its condensation product, 3,3'-diindolylmethane (DIM) exert several biological activities on cellular and molecular levels, which contribute to their well-recognized chemoprevention potential. ndole-3-carbinol is used for prevention of breast cancer, colon cancer, and other types of cancer. The National Institutes of Health (NIH) has reviewed indole-3-carbinol as a possible cancer preventive agent and is now sponsoring clinical research for breast cancer prevention. Indole-3-carbinol is also used for fibromyalgia, tumors inside the voice box (laryngeal papillomatosis) caused by a virus, tumors inside the respiratory tract (respiratory papillomatosis) caused by a virus, abnormal cell growth in the cervix (cervical dysplasia), and systemic lupus erythematosus (SLE). Indole-3-carbinol scavenges free radicals and induces various hepatic cytochrome P450 monooxygenases. Specifically, this agent induces the hepatic monooxygenase cytochrome P4501A1 (CYP1A1), resulting in increased 2-hydroxylation of estrogens and increased production of the chemoprotective estrogen 2-hydroxyestrone. Accumulating evidence indicates that the antitumor activity of indole-3- carbinol is attributable to its ability to interfere with multiple oncogenic signaling pathways governing cell cycle progression, survival, invasion, and other aggressive phenotypes of cancer cells. Reported signaling targets of indole-3- carbinol in various cancer cell lines include EGFR/Src, Akt/NF-B, stress responses, elastase, and Rho kinase. Moreover, indole-3-carbinol functions as a negative regulator of estrogen action in hormonesensitive cancer cells through the inhibition of estrogen receptor (ER)-alpha signaling and/or induction of cytochrome P-450-mediated estrogen metabolism, suggesting its clinical use in hormone-sensitive cancers.

CNS Activity

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
284.0 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown
Preventing
Unknown

Cmax

ValueDoseCo-administeredAnalytePopulation
607 ng/mL
1000 mg single, oral
3,3'-DIINDOLYLMETHANE plasma
Homo sapiens
93 ng/mL
600 mg single, oral
3,3'-DIINDOLYLMETHANE plasma
Homo sapiens
69 ng/mL
400 mg 2 times / day multiple, oral
3,3'-DIINDOLYLMETHANE plasma
Homo sapiens
262 ng/mL
800 mg single, oral
3,3'-DIINDOLYLMETHANE plasma
Homo sapiens
510 ng/mL
1200 mg single, oral
3,3'-DIINDOLYLMETHANE plasma
Homo sapiens
61 ng/mL
400 mg single, oral
3,3'-DIINDOLYLMETHANE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
3376 ng × h/mL
1000 mg single, oral
3,3'-DIINDOLYLMETHANE plasma
Homo sapiens
364 ng × h/mL
600 mg single, oral
3,3'-DIINDOLYLMETHANE plasma
Homo sapiens
372 ng × h/mL
400 mg 2 times / day multiple, oral
3,3'-DIINDOLYLMETHANE plasma
Homo sapiens
1608 ng × h/mL
800 mg single, oral
3,3'-DIINDOLYLMETHANE plasma
Homo sapiens
3212 ng × h/mL
1200 mg single, oral
3,3'-DIINDOLYLMETHANE plasma
Homo sapiens
329 ng × h/mL
400 mg single, oral
3,3'-DIINDOLYLMETHANE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
5.7 h
1000 mg single, oral
3,3'-DIINDOLYLMETHANE plasma
Homo sapiens
2 h
600 mg single, oral
3,3'-DIINDOLYLMETHANE plasma
Homo sapiens
6 h
400 mg 2 times / day multiple, oral
3,3'-DIINDOLYLMETHANE plasma
Homo sapiens
4.2 h
800 mg single, oral
3,3'-DIINDOLYLMETHANE plasma
Homo sapiens
5 h
1200 mg single, oral
3,3'-DIINDOLYLMETHANE plasma
Homo sapiens
3.8 h
400 mg single, oral
3,3'-DIINDOLYLMETHANE plasma
Homo sapiens

PubMed

Sample Use Guides

In Vivo Use Guide
For treating abnormal cells on the surface of the cervix (cervical dysplasia): 200-400 mg per day has been used. However, 200 mg seems to be as effective as the higher dose.
Route of Administration: Oral
In Vitro Use Guide
Using mouse liver microsomes in an NADPH-fortified reaction mixture, Indole-3-carbinol inhibited, in a concentration-dependent manner, CCl4-initiated lipid peroxidation, with 50% inhibition at 35-40 uM Indole-3-carbinol.