Racemetyrosine
DRACPC ID DRACPC0084
Active Ingredients Racemetyrosine
Description 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.
Synonyms SM 88; SM-88; SM88; (+-)-alpha-Methyl-DL-tyrosine; alpha-Methylparatyrosine, DL-; alpha-Methyltyrosine; D,L-alpha-metyrosine; Racemetirosine; Racemetyrosine
Type Small Molecule
Disease Pancreatic Cancer
Classification
Amino acid and derivative
Structure Information
Molecular Formula C10H13NO3
Molecular Weight 195.21
Active Sequence Not available
Sequence Length Not available
Modification Not available
IUPAC Name 2-amino-3-(4-hydroxyphenyl)-2-methylpropanoic acid
InChI InChI=1S/C10H13NO3/c1-10(11,9(13)14)6-7-2-4-8(12)5-3-7/h2-5,12H,6,11H2,1H3,(H,13,14)
InChI_Key NHTGHBARYWONDQ-UHFFFAOYSA-N
SMILES O=C(O)C(C)(N)CC1=CC=C(O)C=C1
External Codes
PubChem CID 3125
DrugBank Accession Number DB16306
NCI Thesaurus Code C74152
UNII X88TTO174Z GSRS
CAS 658-48-0
Drug approval
Drug indication
Investigated for use/treatment in Pancreatic Cancer.
The drug is not approved.
| ClinicalTrials.gov Identifier | Title | Condition or disease | Phase | Purpose |
|---|---|---|---|---|
| NCT03512756 | A Randomized Phase 2/3 Multi-Center Study of SM-88 in Subjects With Pancreatic Cancer Whose Disease Has Progressed or Recurred | Pancreatic Cancer | Phase 2/3 | Treatment |
| NCT03778996 | A Phase 2 Clinical Trial to Evaluate the Efficacy and Safety of SM-88 Used With Methoxsalen, Phenytoin, and Sirolimus (MPS) as Response Maintenance Therapy Following Standard Treatments for Patients With Ewing's Sarcoma or as Salvage Therapy for Patients With Clinically Advanced Sarcomas | Sarcoma, EwingSarcoma | Phase 2 | Treatment |
More clinical information is obtained from ClinicalTrials.gov.
