U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C9H11NO2
Molecular Weight 165.1895
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PHENYLALANINE

SMILES

c1ccc(cc1)C[C@@]([H])(C(=O)O)N

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

HIDE SMILES / InChI
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

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
FREAMINE III 10%

Approved Use

Parenteral 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 Date

5.4345601E10
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1389 μM
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

AUC

ValueDoseCo-administeredAnalytePopulation
35.7 μM × h
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

T1/2

ValueDoseCo-administeredAnalytePopulation
3 min
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
Doses

Doses

DosePopulationAdverse events​
1.5 g single, oral
Dose: 1.5 g
Route: oral
Route: single
Dose: 1.5 g
Sources:
healthy, 36 years
Health Status: healthy
Age Group: 36 years
Sex: M
Sources:
8.2 g single, intravenous (total)
Highest studied dose
Dose: 8.2 g
Route: intravenous
Route: single
Dose: 8.2 g
Sources:
healthy, adult
n = 1
Health Status: healthy
Age Group: adult
Sex: M
Population Size: 1
Sources:
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Development of procedures for determining the amino acid requirements of chickens by the indicator amino acid oxidation method.
2001 Feb
Detection and typing of human papillomavirus in anal epidermoid carcinomas: sequence variation in the E7 gene of human papillomavirus Type 16.
2001 Feb
Comparison of in vitro systems of protein digestion using either mammal or fish proteolytic enzymes.
2001 Feb
Mutation analysis of phenylketonuria in Yamagata prefecture, Japan.
2001 Feb
Reaction of oxidized dopamine with endogenous cysteine residues in the human dopamine transporter.
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
Design, X-ray crystallography, molecular modelling and thermal stability studies of mutant enzymes at site 172 of 3-isopropylmalate dehydrogenase from Thermus thermophilus.
2001 Feb
[A study of phenylketonuria heterozygotes screening in married population of Tianjin area].
2001 Feb
Tyrosine phosphorylation of p120(ctn) in v-Src transfected L cells depends on its association with E-cadherin and reduces adhesion activity.
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
Effects of the potent analgesic enkephalin-catabolizing enzyme inhibitors RB101 and kelatorphan on respiration.
2001 Feb 1
Enkephalin analogues with 2',6'-dimethylphenylalanine replacing phenylalanine in position 4.
2001 Feb 12
FDA approves nateglinide for treatment of type 2 diabetes.
2001 Feb 15
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
Occurrence of D-Amino Acids and a pyridoxal 5'-phosphate-dependent aspartate racemase in the acidothermophilic archaeon, Thermoplasma acidophilum.
2001 Feb 23
Enhancement, relaxation, and reversal of the stereoselectivity for phosphotriesterase by rational evolution of active site residues.
2001 Feb 6
Kynurenine aminotransferase I activity in human placenta.
2001 Feb-Mar
Altered mitochondrial gene expression in human gestational trophoblastic diseases.
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
A silent mutation induces exon skipping in the phenylalanine hydroxylase gene in phenylketonuria.
2001 Jan
N-(Hydroxyaminocarbonyl)phenylalanine: a novel class of inhibitor for carboxypeptidase A.
2001 Jan
Mealtime glucose regulation with nateglinide in healthy volunteers: comparison with repaglinide and placebo.
2001 Jan
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
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
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
[Fasting blood glucose has little value. Postprandial glucose indicates risk].
2001 Jan 11
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
Molecular engineering of myoglobin: the improvement of oxidation activity by replacing Phe-43 with tryptophan.
2001 Jan 30
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
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
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
Spectral and metal-binding properties of three single-point tryptophan mutants of the human transferrin N-lobe.
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
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
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)
Name Type Language
PHENYLALANINE
EP   HSDB   II   INCI   INN   MART.   MI   USAN   USP   VANDF   WHO-DD  
INCI   USAN   INN  
Official Name English
L-PHENYLALANINE [USP-RS]
Common Name English
NSC-79477
Code English
PHENYLALANINE [USP]
Common Name English
FEMA NO. 3585
Code English
PHENYLALANINE [WHO-DD]
Common Name English
3-PHENYL-L-ALANINE
Systematic Name English
PHENYLALANINE [VANDF]
Common Name English
TYROSINE IMPURITY A [EP]
Common Name English
LEUCINE IMPURITY C [EP]
Common Name English
PHENYLALANINE [INCI]
Common Name English
PHENYLALANINE [INN]
Common Name English
PHENYLALANINE [MI]
Common Name English
L-PHENYLALANINE
FCC   FHFI   USP-RS  
Systematic Name English
LYSINE HYDROCHLORIDE IMPURITY B [EP]
Common Name English
L-.ALPHA.-AMINO-.BETA.-PHENYLPROPIONIC ACID
Common Name English
NATEGLINIDE IMPURITY D [EP]
Common Name English
PHENYLALANINE [HSDB]
Common Name English
PHENYLALANINE [MART.]
Common Name English
L-PHENYLALANINE [FHFI]
Common Name English
LAEVO-PHENYL ALANINE
Common Name English
(2S)-2-AMINO-3-PHENYLPROPANOIC ACID
Systematic Name English
PHENYLALANINE [USAN]
Common Name English
L-PHENYLALANINE [JAN]
Common Name English
PHENYLALANINE [EP MONOGRAPH]
Common Name English
PHENYLALANINE [II]
Common Name English
L-PHENYLALANINE [FCC]
Common Name English
Classification Tree Code System Code
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JECFA EVALUATION L-PHENYLALANINE
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Code System Code Type Description
HSDB
1825
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PRIMARY
DRUG CENTRAL
2144
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PRIMARY
ECHA (EC/EINECS)
200-568-1
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PRIMARY
USP_CATALOG
1530503
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PRIMARY USP-RS
NCI_THESAURUS
C29601
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PRIMARY
MESH
D010649
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PRIMARY
PUBCHEM
6140
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PRIMARY
INN
6168
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PRIMARY
FDA UNII
47E5O17Y3R
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PRIMARY
ChEMBL
CHEMBL301523
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PRIMARY
CAS
63-91-2
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PRIMARY
DRUG BANK
DB00120
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PRIMARY
RXCUI
8156
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PRIMARY RxNorm
EVMPD
SUB32327
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PRIMARY
EVMPD
SUB09786MIG
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PRIMARY
WIKIPEDIA
PHENYLALANINE
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PRIMARY
MERCK INDEX
M8652
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PRIMARY Merck Index
EPA CompTox
63-91-2
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PRIMARY