Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C9H11NO2 |
Molecular Weight | 165.1891 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
N[C@@H](CC1=CC=CC=C1)C(O)=O
InChI
InChIKey=COLNVLDHVKWLRT-QMMMGPOBSA-N
InChI=1S/C9H11NO2/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5,8H,6,10H2,(H,11,12)/t8-/m0/s1
Molecular Formula | C9H11NO2 |
Molecular Weight | 165.1891 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Phenylalanine is a biologically essential amino acid that acts as a precursor to tyrosine and the catecholamines (epinephrine, norepinephrine, dopamine, and tyramine), and is a constituent
of many central nervous system neuropeptides. Normal dietary levels of phenylalanine are approximately 1-2 grams daily. Phenylalanine appears in two forms which are identical mirror images of each other: L-phenylalanine, a nutritional supplement, and D-phenylalanine, an effective painkiller and antidepressant due to its ability to inhibit the breakdown of enkephalins, the brain’s natural pain killers.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL3076 |
|||
Target ID: CHEMBL1907608 |
1.71 mM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | FREAMINE III 10% Approved UseParenteral nutrition with 8.5% FreAmine® III (Amino Acid Injection) with Electrolytes is
indicated to prevent nitrogen loss or treat negative nitrogen balance in adults and pediatric
patients, where (1) the alimentary tract, by the oral, gastrostomy, or jejunostomy route, cannot or
should not be used, or adequate protein intake is not feasible by these routes; (2) gastrointestinal
absorption of protein is impaired; or (3) protein requirements are substantially increased as with
extensive burns. Dosage, route of administration, and concomitant infusion of non-protein
calories are dependent on various factors, such as nutritional metabolic status of the patient, anticipated duration of parenteral nutritional support, and vein tolerance Launch Date1971 |
|||
Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1389 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11244252/ |
20 mg/kg single, intravenous dose: 20 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
PHENYLALANINE plasma | Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
35.7 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11244252/ |
20 mg/kg single, intravenous dose: 20 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
PHENYLALANINE plasma | Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
3 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11244252/ |
20 mg/kg single, intravenous dose: 20 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
PHENYLALANINE plasma | Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: FASTED |
PubMed
Title | Date | PubMed |
---|---|---|
Cloning and functional expression of a human Na(+) and Cl(-)-dependent neutral and cationic amino acid transporter B(0+). | 1999 Aug 20 |
|
L-amino acid sensing by the extracellular Ca2+-sensing receptor. | 2000 Apr 25 |
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Ten novel mutations in the phenylalanine hydroxylase gene (PAH) observed in Brazilian patients with phenylketonuria. | 2001 |
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Association between minihaplotypes and mutations at the PAH locus in Polish hyperphenylalaninemic patients. | 2001 |
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Self-association of the H3 region of syntaxin 1A. Implications for intermediates in SNARE complex assembly. | 2001 Apr 20 |
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Disruption of an active site hydrogen bond converts human heme oxygenase-1 into a peroxidase. | 2001 Apr 6 |
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Development of procedures for determining the amino acid requirements of chickens by the indicator amino acid oxidation method. | 2001 Feb |
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Detection and typing of human papillomavirus in anal epidermoid carcinomas: sequence variation in the E7 gene of human papillomavirus Type 16. | 2001 Feb |
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Comparison of in vitro systems of protein digestion using either mammal or fish proteolytic enzymes. | 2001 Feb |
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Whole body and skeletal muscle glutamine metabolism in healthy subjects. | 2001 Feb |
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American Academy of Pediatrics: Maternal phenylketonuria. | 2001 Feb |
|
Conserved transmembrane tyrosine residues of the TCR beta chain are required for TCR expression and function in primary T cells and hybridomas. | 2001 Feb |
|
Site-directed mutagenesis of human immunodeficiency virus type 1 reverse transcriptase at amino acid position 138. | 2001 Feb 1 |
|
FDA approves nateglinide for treatment of type 2 diabetes. | 2001 Feb 15 |
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Antioxidant alpha-lipoic acid and protein turnover in insulin-resistant rat muscle. | 2001 Feb 15 |
|
Cloning of dopamine, norepinephrine and serotonin transporters from monkey brain: relevance to cocaine sensitivity. | 2001 Feb 19 |
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Enhancement, relaxation, and reversal of the stereoselectivity for phosphotriesterase by rational evolution of active site residues. | 2001 Feb 6 |
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Development of matrix metalloproteinase inhibitors in cancer therapy. | 2001 Feb 7 |
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Critical role of the residue size at position 87 in H2O2- dependent substrate hydroxylation activity and H2O2 inactivation of cytochrome P450BM-3. | 2001 Feb 9 |
|
Kynurenine aminotransferase I activity in human placenta. | 2001 Feb-Mar |
|
The suppressive effect of dietary restriction and weight loss in the obese on the generation of reactive oxygen species by leukocytes, lipid peroxidation, and protein carbonylation. | 2001 Jan |
|
Three new mutations in the gene for the growth hormone (gh)-releasing hormone receptor in familial isolated gh deficiency type ib. | 2001 Jan |
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A silent mutation induces exon skipping in the phenylalanine hydroxylase gene in phenylketonuria. | 2001 Jan |
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Physical stability of the blue pigments formed from geniposide of gardenia fruits: effects of pH, temperature, and light. | 2001 Jan |
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New analogues of bradykinin containing a conformationally restricted dipeptide fragment in their molecules. | 2001 Jan |
|
Epidermal H(2)O(2) accumulation alters tetrahydrobiopterin (6BH4) recycling in vitiligo: identification of a general mechanism in regulation of all 6BH4-dependent processes? | 2001 Jan |
|
Tryptophan fluorescence of yeast actin resolved via conserved mutations. | 2001 Jan |
|
Beta-adrenoceptor stimulation attenuates the hypertrophic effect of alpha-adrenoceptor stimulation in adult rat ventricular cardiomyocytes. | 2001 Jan |
|
Chronic maternal smoking and cord blood amino acid and enzyme levels at term. | 2001 Jan |
|
The unique tryptophan residue of the vitamin D receptor is critical for ligand binding and transcriptional activation. | 2001 Jan |
|
A study of peptide--peptide interaction by matrix-assisted laser desorption/ionization. | 2001 Jan |
|
Single-stranded DNA intermediates in IS91 rolling-circle transposition. | 2001 Jan |
|
Increasing the thermal stability of euphauserase. A cold-active and multifunctional serine protease from Antarctic krill. | 2001 Jan |
|
Ligand binding to integrin alpha(v)beta(3) requires tyrosine 178 in the alpha(v) subunit. | 2001 Jan 1 |
|
[Fasting blood glucose has little value. Postprandial glucose indicates risk]. | 2001 Jan 11 |
|
Biological properties of Phe(o)-opioid peptide analogues. | 2001 Jan 12 |
|
Tyrosine phosphorylation of the beta 4 integrin cytoplasmic domain mediates Shc signaling to extracellular signal-regulated kinase and antagonizes formation of hemidesmosomes. | 2001 Jan 12 |
|
Development and de novo protein synthetic activity of bovine embryos produced in vitro in different culture systems. | 2001 Jan 15 |
|
Haem-linked interactions in horseradish peroxidase revealed by spectroscopic analysis of the Phe-221-->Met mutant. | 2001 Jan 15 |
|
Molecular engineering of myoglobin: the improvement of oxidation activity by replacing Phe-43 with tryptophan. | 2001 Jan 30 |
|
Role of the conserved acidic residue Asp21 in the structure of phosphatidylinositol 3-kinase Src homology 3 domain: circular dichroism and nuclear magnetic resonance studies. | 2001 Jan 9 |
|
Plasma free amino acid concentrations in healthy Guatemalan adults and in patients with classic dengue. | 2001 Mar |
|
Binding diversity of a noncovalent-type low-molecular-weight serine protease inhibitor and function of a catalytic water molecule: X-ray crystal structure of PKSI-527--inhibited trypsin. | 2001 Mar |
|
Combined pituitary hormone deficiency due to the F135C human Pit-1 (pituitary-specific factor 1) gene mutation: functional and structural correlates. | 2001 Mar |
|
Ligand migration in human myoglobin: steric effects of isoleucine 107(G8) on O(2) and CO binding. | 2001 Mar |
|
Detection of hydroxyl radicals by D-phenylalanine hydroxylation: a specific assay for hydroxyl radical generation in biological systems. | 2001 Mar 1 |
|
Activation of BMK1 via tyrosine 1062 in RET by GDNF and MEN2A mutation. | 2001 Mar 2 |
|
Tight control of exogenous SERCA expression is required to obtain acceleration of calcium transients with minimal cytotoxic effects in cardiac myocytes. | 2001 Mar 2 |
|
Crystallographic and solution studies of an activation loop mutant of the insulin receptor tyrosine kinase: insights into kinase mechanism. | 2001 Mar 30 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: http://www.cpmedical.net/pdf/Phenylalanine.pdf
L-Phenylalanine Capsules (400 mg/cap): one to two capsules per day on an empty stomach.
L-Phenylalanine Powder: 480 mg one to two times per day on an empty stomach.
DL-Phenylalanine Capsules (500 mg/cap): one capsule daily on an empty stomach.
DL-Phenylalanine Powder: 1/8 level teaspoon two to three times daily on an empty stomach.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11986979
In cultured hippocampal neurons from newborn rats L-phenylalanine specifically and reversibly attenuated NMDA-activated currents in a concentration-dependent manner (IC50=1.71 mM)
Substance Class |
Chemical
Created
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Record UNII |
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m8652
Created by
admin on Mon Mar 31 17:46:29 GMT 2025 , Edited by admin on Mon Mar 31 17:46:29 GMT 2025
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PRIMARY | Merck Index | ||
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28044
Created by
admin on Mon Mar 31 17:46:29 GMT 2025 , Edited by admin on Mon Mar 31 17:46:29 GMT 2025
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PRIMARY | |||
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DTXSID4040763
Created by
admin on Mon Mar 31 17:46:29 GMT 2025 , Edited by admin on Mon Mar 31 17:46:29 GMT 2025
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PRIMARY |
Related Record | Type | Details | ||
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METABOLIC ENZYME -> SUBSTRATE |
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SALT/SOLVATE -> PARENT |
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ENZYME->SUBSTRATE |
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METABOLIC ENZYME -> SUBSTRATE |
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SALT/SOLVATE -> PARENT |
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LABELED -> NON-LABELED |
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INHIBITOR -> TARGET |
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DEGRADENT -> PARENT | |||
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METABOLIC ENZYME -> SUBSTRATE |
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RECOMBINANT ORGANISM->SUBSTRATE | |||
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INHIBITOR -> TARGET | |||
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DERIVATIVE -> PARENT |
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Related Record | Type | Details | ||
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METABOLITE -> PARENT |
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METABOLITE -> PARENT |
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PARENT -> METABOLITE |
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METABOLITE -> PARENT |
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METABOLITE -> PARENT |
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Related Record | Type | Details | ||
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (TLC)
EP
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PARENT -> IMPURITY |
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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PARENT -> IMPURITY |
EP
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (TLC)
EP
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PARENT -> IMPURITY |
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
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