Preferred Label : Racemetyrosine;
NCIt synonyms : ( -)-alpha-Methyl-DL-tyrosine; Racemetirosine; alpha-Methylparatyrosine, DL-; alpha-Methyltyrosine; D,L-alpha-metyrosine;
NCIt definition : A dysfunctional and modified form of the non-essential amino acid tyrosine and an
inhibitor of tyrosine hydroxylase (TH; tyrosine 3-monooxygenase), with potential antineoplastic
activity. Upon administration, racemetyrosine is specifically taken up by cancer cells
through the transporter L-amino acid transferase-1 (LAT1; CD98). As a tyrosine derivative
and faulty amino acid protein building block, racemetyrosine prevents protein synthesis
in cancer cells. Specifically, this prevents mucin-1 (MUC1) protein synthesis. MUC1
is highly overexpressed by most cancer cells and regulates the increased reactive
oxygen species (ROS) in cancer cells created from the altered metabolism that cancer
cells utilize, by upregulating key antioxidant defenses and preventing ROS-mediated
apoptosis. In the absence of MUC1, ROS levels are increased, leading to an increase
in oxidative stress, and induction of apoptosis. Also, being a protective transmembrane
protein, MUC1 is part of the protective layer on the outside of cancer cells and plays
a key role in shielding the cancer cell from the immune system. The loss of MUC1 compromises
the cell membrane, thereby making the cancer cell more vulnerable to be recognized
and attacked by the immune system. Normal cells do not regularly take up certain non-essential
amino acids, such as tyrosine, but readily convert phenylalanine to tyrosine, so normal
healthy cells are not expected to consume racemetyrosine. In addition, racemetyrosine
competes with tyrosine at the tyrosine-binding site of TH, thereby inhibiting TH,
an enzyme that activates molecular oxygen to catalyze the hydroxylation of tyrosine
to dihydroxyphenylalanine (Dopa), which is an intermediate to catecholamine (dopamine,
norepinephrine, and epinephrine) production. This inhibits the synthesis of catecholamines.;
UNII : X88TTO174Z;
InChIKey : NHTGHBARYWONDQ-UHFFFAOYSA-N;
CAS number : 620-30-4; 658-48-0;
Molecule name : SM 88; SM-88;
Chemical formula : C10H13NO3;
Origin ID : C74152;
UMLS CUI : C0949561;
Automatic exact mappings (from CISMeF team)
- Currated CISMeF NLP mapping
- Semantic type(s)
- UMLS correspondences (same concept)
- concept_is_in_subset
- has_target
