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
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
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
Cmax
AUC
T1/2
Sourcing
PubMed
Patents
Sample Use Guides
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