Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C9H10NO2.Na |
| Molecular Weight | 187.171 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[Na+].N[C@@H](CC1=CC=CC=C1)C([O-])=O
InChI
InChIKey=ZRVUAXXSASAVFG-QRPNPIFTSA-M
InChI=1S/C9H11NO2.Na/c10-8(9(11)12)6-7-4-2-1-3-5-7;/h1-5,8H,6,10H2,(H,11,12);/q;+1/p-1/t8-;/m0./s1
| Molecular Formula | Na |
| Molecular Weight | 22.9898 |
| Charge | 1 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | C9H10NO2 |
| Molecular Weight | 164.1812 |
| Charge | -1 |
| 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 Date5.4345601E10 |
|||
| Primary | Unknown Approved UseUnknown |
|||
| 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 |
|---|---|---|
| Signal-binding specificity of the mu4 subunit of the adaptor protein complex AP-4. | 2001 Apr 20 |
|
| Development of procedures for determining the amino acid requirements of chickens by the indicator amino acid oxidation method. | 2001 Feb |
|
| Mutation analysis of phenylketonuria in Yamagata prefecture, Japan. | 2001 Feb |
|
| Auto-inhibition of Ca(2+)/calmodulin-dependent protein kinase II by its ATP-binding domain. | 2001 Feb |
|
| Mutations of the phenylalanine hydroxylase (PAH) gene in Brazilian patients with phenylketonuria. | 2001 Feb |
|
| A comparison of kinetic and regulatory properties of the tetrameric and dimeric forms of wild-type and Thr427-->Pro mutant human phenylalanine hydroxylase: contribution of the flexible hinge region Asp425-Gln429 to the tetramerization and cooperative substrate binding. | 2001 Feb |
|
| Pumping capacity of bacterial reaction centers and backpressure regulation of energy transduction. | 2001 Feb |
|
| In vivo protein synthetic rates of atrial, ventricular, and pulmonary tissue proteins in aortic constriction, goldblatt, and bromoethylamine models of hypertension. | 2001 Feb |
|
| Aldehyde dehydrogenase. Maintaining critical active site geometry at motif 8 in the class 3 enzyme. | 2001 Feb |
|
| Whole body and skeletal muscle glutamine metabolism in healthy subjects. | 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 |
|
| Enkephalin analogues with 2',6'-dimethylphenylalanine replacing phenylalanine in position 4. | 2001 Feb 12 |
|
| Antioxidant alpha-lipoic acid and protein turnover in insulin-resistant rat muscle. | 2001 Feb 15 |
|
| Occurrence of D-Amino Acids and a pyridoxal 5'-phosphate-dependent aspartate racemase in the acidothermophilic archaeon, Thermoplasma acidophilum. | 2001 Feb 23 |
|
| Kynurenine aminotransferase I activity in human placenta. | 2001 Feb-Mar |
|
| A silent mutation induces exon skipping in the phenylalanine hydroxylase gene in phenylketonuria. | 2001 Jan |
|
| Mealtime glucose regulation with nateglinide in healthy volunteers: comparison with repaglinide and placebo. | 2001 Jan |
|
| 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 |
|
| Characterization of the mouse phenylalanine hydroxylase mutation Pah(enu3). | 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 |
|
| Net amino acid flux across the fetal liver and placenta during spontaneous ovine parturition. | 2001 Jan |
|
| The unique tryptophan residue of the vitamin D receptor is critical for ligand binding and transcriptional activation. | 2001 Jan |
|
| The protein-retaining effects of growth hormone during fasting involve inhibition of muscle-protein breakdown. | 2001 Jan |
|
| Preparative HPLC resolution of the CIS cyclohexane analogs of phenylalanine. | 2001 Jan |
|
| The effect of graded intake of glycyl-L-tyrosine on phenylalanine and tyrosine metabolism in parenterally fed neonates with an estimation of tyrosine requirement. | 2001 Jan |
|
| Serine 187 is a crucial residue for allosteric regulation of Corynebacterium glutamicum 3-deoxy-D-arabino-heptulosonate-7-phosphate synthase. | 2001 Jan 1 |
|
| Ligand binding to integrin alpha(v)beta(3) requires tyrosine 178 in the alpha(v) subunit. | 2001 Jan 1 |
|
| Biological properties of Phe(o)-opioid peptide analogues. | 2001 Jan 12 |
|
| Development and de novo protein synthetic activity of bovine embryos produced in vitro in different culture systems. | 2001 Jan 15 |
|
| Amino acid phosphoramidate monoesters of 3'-azido-3'-deoxythymidine: relationship between antiviral potency and intracellular metabolism. | 2001 Jan 18 |
|
| Essential role of the N-terminal autoregulatory sequence in the regulation of phenylalanine hydroxylase. | 2001 Jan 19 |
|
| Crystal structure of aphrodisin, a sex pheromone from female hamster. | 2001 Jan 19 |
|
| Molecular engineering of myoglobin: the improvement of oxidation activity by replacing Phe-43 with tryptophan. | 2001 Jan 30 |
|
| Imide and lactam derivatives of N-benzylpyroglutamyl-L-phenylalanine as VCAM/VLA-4 antagonists. | 2001 Jan 8 |
|
| 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 |
|
| Outer sphere mutations perturb metal reactivity in manganese superoxide dismutase. | 2001 Jan 9 |
|
| 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 |
|
| A possible role for metalloproteinases in renal cyst development. | 2001 Mar |
|
| Complete loss of P/Q calcium channel activity caused by a CACNA1A missense mutation carried by patients with episodic ataxia type 2. | 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 |
|
| Conformational and temperature-sensitive stability defects of the delta F508 cystic fibrosis transmembrane conductance regulator in post-endoplasmic reticulum compartments. | 2001 Mar 23 |
|
| Evidence that phenylalanine 69 in Escherichia coli RuvC resolvase forms a stacking interaction during binding and destabilization of a Holliday junction DNA substrate. | 2001 Mar 30 |
|
| A novel adapter protein employs a phosphotyrosine binding domain and exceptionally basic N-terminal domains to capture and localize an atypical protein kinase C: characterization of Caenorhabditis elegans C kinase adapter 1, a protein that avidly binds protein kinase C3. | 2001 Mar 30 |
|
| Crystallographic and solution studies of an activation loop mutant of the insulin receptor tyrosine kinase: insights into kinase mechanism. | 2001 Mar 30 |
|
| Renal matrix metalloproteinase activity is unaffected by experimental ischemia-reperfusion injury and matrix metalloproteinase inhibition does not alter outcome of renal function. | 2001 Mar-Apr |
Patents
Sample Use Guides
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
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 16 23:26:52 UTC 2022
by
admin
on
Fri Dec 16 23:26:52 UTC 2022
|
| Record UNII |
M67R83MDEE
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
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|---|---|---|---|---|
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PARENT -> SALT/SOLVATE |
