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 Date5.4345601E10 |
|||
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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Association between minihaplotypes and mutations at the PAH locus in Polish hyperphenylalaninemic patients. | 2001 |
|
Further definition of the substance P (SP)/neurokinin-1 receptor complex. MET-174 is the site of photoinsertion p-benzoylphenylalanine4 SP. | 2001 Apr 6 |
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Reaction of oxidized dopamine with endogenous cysteine residues in the human dopamine transporter. | 2001 Feb |
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Auto-inhibition of Ca(2+)/calmodulin-dependent protein kinase II by its ATP-binding domain. | 2001 Feb |
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Mutations of the phenylalanine hydroxylase (PAH) gene in Brazilian patients with phenylketonuria. | 2001 Feb |
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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 |
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In vitro expression of 34 naturally occurring mutant variants of phenylalanine hydroxylase: correlation with metabolic phenotypes and susceptibility toward protein aggregation. | 2001 Feb |
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Whole body and skeletal muscle glutamine metabolism in healthy subjects. | 2001 Feb |
|
American Academy of Pediatrics: Maternal phenylketonuria. | 2001 Feb |
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Conserved transmembrane tyrosine residues of the TCR beta chain are required for TCR expression and function in primary T cells and hybridomas. | 2001 Feb |
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Effects of the potent analgesic enkephalin-catabolizing enzyme inhibitors RB101 and kelatorphan on respiration. | 2001 Feb 1 |
|
Site-directed mutagenesis of human immunodeficiency virus type 1 reverse transcriptase at amino acid position 138. | 2001 Feb 1 |
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Antioxidant alpha-lipoic acid and protein turnover in insulin-resistant rat muscle. | 2001 Feb 15 |
|
C-terminal elements control location, activation threshold, and p38 docking of ribosomal S6 kinase B (RSKB). | 2001 Feb 23 |
|
Development of matrix metalloproteinase inhibitors in cancer therapy. | 2001 Feb 7 |
|
Kynurenine aminotransferase I activity in human placenta. | 2001 Feb-Mar |
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Altered mitochondrial gene expression in human gestational trophoblastic diseases. | 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 |
|
A matrix metalloproteinase inhibitor, batimastat, retards the development of osteolytic bone metastases by MDA-MB-231 human breast cancer cells in Balb C nu/nu mice. | 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 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 |
|
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 |
|
Plasma free amino acid concentrations in healthy Guatemalan adults and in patients with classic dengue. | 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 |
|
A possible role for metalloproteinases in renal cyst development. | 2001 Mar |
|
Detection of hydroxyl radicals by D-phenylalanine hydroxylation: a specific assay for hydroxyl radical generation in biological systems. | 2001 Mar 1 |
|
Spectral and metal-binding properties of three single-point tryptophan mutants of the human transferrin N-lobe. | 2001 Mar 1 |
|
Essential tyrosine residues for interaction of the non-receptor protein-tyrosine phosphatase PTP1B with N-cadherin. | 2001 Mar 2 |
|
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
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
by
admin
on
Edited
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by
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Record UNII |
47E5O17Y3R
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Record Status |
Validated (UNII)
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Record Version |
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JECFA EVALUATION |
L-PHENYLALANINE
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Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT | |||
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ENZYME->SUBSTRATE |
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INHIBITOR -> TARGET | |||
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DEGRADENT -> PARENT |
Precursor is Phenylalanine
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LABELED -> NON-LABELED | |||
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|
RECOMBINANT ORGANISM->SUBSTRATE | |||
|
DERIVATIVE -> PARENT |
Related Record | Type | Details | ||
---|---|---|---|---|
|
PARENT -> METABOLITE | |||
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METABOLITE -> PARENT |
Related Record | Type | Details | ||
---|---|---|---|---|
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (TLC)
EP
|
||
|
PARENT -> IMPURITY | |||
|
PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
PARENT -> IMPURITY |
EP
|
||
|
PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (TLC)
EP
|
||
|
PARENT -> IMPURITY | |||
|
PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |