Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C9H11NO2.ClH |
Molecular Weight | 201.65 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.N[C@@H](CC1=CC=CC=C1)C(O)=O
InChI
InChIKey=ZAIZDXVMSSDZFA-QRPNPIFTSA-N
InChI=1S/C9H11NO2.ClH/c10-8(9(11)12)6-7-4-2-1-3-5-7;/h1-5,8H,6,10H2,(H,11,12);1H/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 |
Molecular Formula | ClH |
Molecular Weight | 36.461 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
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 |
|
Mutation analysis of phenylketonuria in Yamagata prefecture, Japan. | 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 |
|
In vivo protein synthetic rates of atrial, ventricular, and pulmonary tissue proteins in aortic constriction, goldblatt, and bromoethylamine models of hypertension. | 2001 Feb |
|
Implicit solvent model studies of the interactions of the influenza hemagglutinin fusion peptide with lipid bilayers. | 2001 Feb |
|
American Academy of Pediatrics: Maternal phenylketonuria. | 2001 Feb |
|
Effects of the potent analgesic enkephalin-catabolizing enzyme inhibitors RB101 and kelatorphan on respiration. | 2001 Feb 1 |
|
FDA approves nateglinide for treatment of type 2 diabetes. | 2001 Feb 15 |
|
Cloning of dopamine, norepinephrine and serotonin transporters from monkey brain: relevance to cocaine sensitivity. | 2001 Feb 19 |
|
Physical stability of the blue pigments formed from geniposide of gardenia fruits: effects of pH, temperature, and light. | 2001 Jan |
|
New analogues of bradykinin containing a conformationally restricted dipeptide fragment in their molecules. | 2001 Jan |
|
Beta-adrenoceptor stimulation attenuates the hypertrophic effect of alpha-adrenoceptor stimulation in adult rat ventricular cardiomyocytes. | 2001 Jan |
|
Net amino acid flux across the fetal liver and placenta during spontaneous ovine parturition. | 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 |
|
An in vivo study of ovine placental transport of essential amino acids. | 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 |
|
Analysis of the subsite specificity of rat insulysin using fluorogenic peptide substrates. | 2001 Jan 12 |
|
A single arginyl residue in plastocyanin and in cytochrome c(6) from the cyanobacterium Anabaena sp. PCC 7119 is required for efficient reduction of photosystem I. | 2001 Jan 5 |
|
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 |
|
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 |
|
Acute effects of peritoneal dialysis with dialysates containing dextrose or dextrose and amino acids on muscle protein turnover in patients with chronic renal failure. | 2001 Mar |
|
Selected Contribution: IGF-I antibody prevents increases in protein synthesis in epitrochlearis muscles from refed, diabetic rats. | 2001 Mar |
|
Activation of BMK1 via tyrosine 1062 in RET by GDNF and MEN2A mutation. | 2001 Mar 2 |
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
Fri Dec 15 18:09:36 UTC 2023
by
admin
on
Fri Dec 15 18:09:36 UTC 2023
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Record UNII |
L6O14A5L6Q
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Record Status |
Validated (UNII)
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Record Version |
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PARENT -> SALT/SOLVATE |