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

Details

Stereochemistry ABSOLUTE
Molecular Formula C9H11NO2
Molecular Weight 165.1891
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PHENYLALANINE

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

HIDE SMILES / InChI

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

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
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
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
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
In vitro expression of 34 naturally occurring mutant variants of phenylalanine hydroxylase: correlation with metabolic phenotypes and susceptibility toward protein aggregation.
2001 Feb
Whole body and skeletal muscle glutamine metabolism in healthy subjects.
2001 Feb
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
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
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
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

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)
Substance Class Chemical
Created
by admin
on Fri Dec 16 16:11:27 UTC 2022
Edited
by admin
on Fri Dec 16 16:11:27 UTC 2022
Record UNII
47E5O17Y3R
Record Status Validated (UNII)
Record Version
  • Download
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
LEUCINE IMPURITY C [EP IMPURITY]
Common Name English
NSC-79477
Code English
TYROSINE IMPURITY A [EP IMPURITY]
Common Name English
FEMA NO. 3585
Code English
NATEGLINIDE IMPURITY D [EP IMPURITY]
Common Name English
Phenylalanine [WHO-DD]
Common Name English
3-PHENYL-L-ALANINE
Systematic Name English
PHENYLALANINE [VANDF]
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
L-.ALPHA.-AMINO-.BETA.-PHENYLPROPIONIC ACID
Common Name English
PHENYLALANINE [HSDB]
Common Name English
LYSINE HYDROCHLORIDE IMPURITY B [EP IMPURITY]
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
PHENYLALANINE [USP MONOGRAPH]
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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DSLD 1580 (Number of products:829)
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NCI_THESAURUS C68442
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Code System Code Type Description
HSDB
1825
Created by admin on Fri Dec 16 16:11:27 UTC 2022 , Edited by admin on Fri Dec 16 16:11:27 UTC 2022
PRIMARY
DRUG CENTRAL
2144
Created by admin on Fri Dec 16 16:11:27 UTC 2022 , Edited by admin on Fri Dec 16 16:11:27 UTC 2022
PRIMARY
ECHA (EC/EINECS)
200-568-1
Created by admin on Fri Dec 16 16:11:27 UTC 2022 , Edited by admin on Fri Dec 16 16:11:27 UTC 2022
PRIMARY
NCI_THESAURUS
C29601
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PRIMARY
MESH
D010649
Created by admin on Fri Dec 16 16:11:27 UTC 2022 , Edited by admin on Fri Dec 16 16:11:27 UTC 2022
PRIMARY
PUBCHEM
6140
Created by admin on Fri Dec 16 16:11:27 UTC 2022 , Edited by admin on Fri Dec 16 16:11:27 UTC 2022
PRIMARY
INN
6168
Created by admin on Fri Dec 16 16:11:27 UTC 2022 , Edited by admin on Fri Dec 16 16:11:27 UTC 2022
PRIMARY
CHEBI
58095
Created by admin on Fri Dec 16 16:11:27 UTC 2022 , Edited by admin on Fri Dec 16 16:11:27 UTC 2022
PRIMARY
FDA UNII
47E5O17Y3R
Created by admin on Fri Dec 16 16:11:27 UTC 2022 , Edited by admin on Fri Dec 16 16:11:27 UTC 2022
PRIMARY
ChEMBL
CHEMBL301523
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PRIMARY
CAS
63-91-2
Created by admin on Fri Dec 16 16:11:27 UTC 2022 , Edited by admin on Fri Dec 16 16:11:27 UTC 2022
PRIMARY
CHEBI
29997
Created by admin on Fri Dec 16 16:11:27 UTC 2022 , Edited by admin on Fri Dec 16 16:11:27 UTC 2022
PRIMARY
DRUG BANK
DB00120
Created by admin on Fri Dec 16 16:11:27 UTC 2022 , Edited by admin on Fri Dec 16 16:11:27 UTC 2022
PRIMARY
RXCUI
8156
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PRIMARY RxNorm
EVMPD
SUB32327
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PRIMARY
EVMPD
SUB09786MIG
Created by admin on Fri Dec 16 16:11:27 UTC 2022 , Edited by admin on Fri Dec 16 16:11:27 UTC 2022
PRIMARY
NSC
79477
Created by admin on Fri Dec 16 16:11:27 UTC 2022 , Edited by admin on Fri Dec 16 16:11:27 UTC 2022
PRIMARY
WIKIPEDIA
PHENYLALANINE
Created by admin on Fri Dec 16 16:11:27 UTC 2022 , Edited by admin on Fri Dec 16 16:11:27 UTC 2022
PRIMARY
RS_ITEM_NUM
1530503
Created by admin on Fri Dec 16 16:11:27 UTC 2022 , Edited by admin on Fri Dec 16 16:11:27 UTC 2022
PRIMARY
CHEBI
17295
Created by admin on Fri Dec 16 16:11:27 UTC 2022 , Edited by admin on Fri Dec 16 16:11:27 UTC 2022
PRIMARY
DAILYMED
47E5O17Y3R
Created by admin on Fri Dec 16 16:11:27 UTC 2022 , Edited by admin on Fri Dec 16 16:11:27 UTC 2022
PRIMARY
MERCK INDEX
M8652
Created by admin on Fri Dec 16 16:11:27 UTC 2022 , Edited by admin on Fri Dec 16 16:11:27 UTC 2022
PRIMARY Merck Index
CHEBI
28044
Created by admin on Fri Dec 16 16:11:27 UTC 2022 , Edited by admin on Fri Dec 16 16:11:27 UTC 2022
PRIMARY
EPA CompTox
DTXSID4040763
Created by admin on Fri Dec 16 16:11:27 UTC 2022 , Edited by admin on Fri Dec 16 16:11:27 UTC 2022
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
ENZYME->SUBSTRATE
INHIBITOR -> TARGET
DEGRADENT -> PARENT
Precursor is Phenylalanine
SALT/SOLVATE -> PARENT
LABELED -> NON-LABELED
INHIBITOR -> TARGET
RECOMBINANT ORGANISM->SUBSTRATE
DERIVATIVE -> PARENT
Related Record Type Details
PARENT -> METABOLITE
METABOLITE -> PARENT
Related Record Type Details
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