Racemetyrosine is being investigated in the clinical trial NCT03512756 (a randomized phase II/III multicenter SM-88 study in patients with metastatic pancreatic cancer). Racemetyrosine is an aberrantly modified form of tyrosine (a non-essential amino acid) and an inhibitor of tyrosine hydroxylase (TH; tyrosine 3-monooxygenase), possessing potential antitumor activity. After administration, Racemetyrosine is specifically taken up by cancer cells via the L-amino acid transferase-1 (LAT1; CD98) transporter. As a tyrosine derivative and aberrant amino acid protein building block, Racemetyrosine inhibits protein synthesis in cancer cells, particularly mucin-1 (MUC1). MUC1 is highly overexpressed in most cancer cells and regulates reactive oxygen species (ROS) generated abnormally by cancer cell metabolism by upregulating key antioxidant defense mechanisms and inhibiting ROS-mediated apoptosis. MUC1 deficiency leads to elevated ROS levels, thereby increasing oxidative stress and inducing apoptosis. Furthermore, MUC1, as a protective transmembrane protein, is a crucial component of the outer protective layer of cancer cells, playing a key role in protecting them from the immune system. The absence of MUC1 disrupts the cell membrane, making cancer cells more vulnerable to recognition and attack by the immune system. Normal cells typically do not take up certain non-essential amino acids, such as tyrosine, but they can readily convert phenylalanine to tyrosine; therefore, normal healthy cells generally do not consume Racemetyrosine. Moreover, Racemetyrosine competes with tyrosine for the tyrosine binding site of tyrosine hydroxylase (TH), thereby inhibiting TH activity. TH is an enzyme that activates molecular oxygen to catalyze the hydroxylation of tyrosine to dihydroxyphenylalanine (DOPA), and DOPA is an intermediate in the synthesis of catecholamines (dopamine, norepinephrine, and epinephrine). Therefore, Racemetyrosine inhibits catecholamine synthesis. Tyrosine hydroxylase is a tyrosine 3-monooxygenase inhibitor, thus also inhibiting catecholamine synthesis. It is used to control symptoms caused by excessive sympathetic nerve excitation in patients with pheochromocytoma. (Martindale, Pharmacopoeia, 30th edition)

195.089

658-48-0

DL-Metirosine-13C,d3 hydrochloride

3125

White to off-white solid powder

1.3±0.1 g/cm3

383.7±32.0 °C at 760 mmHg

>300ºC(lit.)

185.9±25.1 °C

0.0±0.9 mmHg at 25°C

1.600

0.73

3

4

3

14

211

0

NHTGHBARYWONDQ-UHFFFAOYSA-N

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)

2-amino-3-(4-hydroxyphenyl)-2-methylpropanoic acid

2934.99.9001

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

H2O : ~2 mg/mL (~10.24 mM)

Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.

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Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)
*Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution.
Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline)
Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil)
Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals).

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Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)]
*Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline)

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Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium)
Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose
Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals).

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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders

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Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

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 (Please use freshly prepared in vivo formulations for optimal results.)