N-acetyltyrosine

Identification

Name
N-acetyltyrosine
Accession Number
DB11102
Type
Small Molecule
Groups
Approved
Description

N-acetyltyrosine, also referred to as N-acetyl-L-tyrosine, is used in place of as a tyrosine precursor. L-Tyrosine is a non-essential amino acid with a polar side group. N-acetyltyrosine is administered as parenteral nutrition or intravenous infusion due to its enhanced solubility compared to tyrosine [2]. It is typically administered as a source of nutritional support where oral nutrition is inadequate or cannot be tolerated.

Structure
Thumb
Synonyms
  • (+)-(2s)-2-(acetylamino)-3-(4-hydroxyphenyl)propanoic acid
  • (2s)-2-acetylamino-3-(4-hydroxyphenyl)propanoic acid
  • Acetyl tyrosine
  • L-N-acetyltyrosine
  • Melanowhite-A
  • N-acetyl-L-tyrosine
  • N-acetyl-tyrosine
  • N-acetyltyrosin
External IDs
208-671-3 / NSC-10853
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Aminosyn IIN-acetyltyrosine (189 mg/100mL) + Glutamic Acid (517 mg/100mL) + Glycine (350 mg/100mL) + Histidine (210 mg/100mL) + L-Alanine (695 mg/100mL) + L-Arginine (713 mg/100mL) + L-Aspartic Acid (490 mg/100mL) + L-Isoleucine (462 mg/100mL) + L-Leucine (700 mg/100mL) + L-Lysine acetate (735 mg/100mL) + L-Phenylalanine (209 mg/100mL) + L-Proline (505 mg/100mL) + L-Threonine (280 mg/100mL) + L-Tryptophan (140 mg/100mL) + L-Valine (350 mg/100mL) + Methionine (120 mg/100mL) + Serine (371 mg/100mL)Injection, solutionIntravenousHospira, Inc.2005-11-012010-12-01Us
Aminosyn IIN-acetyltyrosine (405 mg) + Glutamic Acid (1107 mg) + Glycine (750 mg) + Histidine (450 mg) + L-Alanine (1490 mg) + L-Arginine (1527 mg) + L-Aspartic Acid (1050 mg) + L-Isoleucine (990 mg) + L-Leucine (1500 mg) + L-Lysine acetate (1575 mg) + L-Phenylalanine (447 mg) + L-Proline (1083 mg) + L-Threonine (600 mg) + L-Tryptophan (300 mg) + L-Valine (750 mg) + Methionine (258 mg) + Serine (795 mg)SolutionIntravenousIcu Medical Canada Inc1995-12-31Not applicableCanada
Aminosyn IIN-acetyltyrosine (270 mg/100mL) + Glutamic Acid (738 mg/100mL) + Glycine (500 mg/100mL) + Histidine (300 mg/100mL) + L-Alanine (993 mg/100mL) + L-Arginine (1018 mg/100mL) + L-Aspartic Acid (700 mg/100mL) + L-Isoleucine (660 mg/100mL) + L-Leucine (1000 mg/100mL) + L-Lysine acetate (1050 mg/100mL) + L-Phenylalanine (298 mg/100mL) + L-Proline (722 mg/100mL) + L-Threonine (400 mg/100mL) + L-Tryptophan (200 mg/100mL) + L-Valine (500 mg/100mL) + Methionine (172 mg/100mL) + Serine (530 mg/100mL)Injection, solutionIntravenousHospira, Inc.1991-12-19Not applicableUs
Aminosyn IIN-acetyltyrosine (270 mg/100mL) + Glutamic Acid (738 mg/100mL) + Glycine (500 mg/100mL) + Histidine (300 mg/100mL) + L-Alanine (993 mg/100mL) + L-Arginine (1018 mg/100mL) + L-Aspartic Acid (700 mg/100mL) + L-Isoleucine (660 mg/100mL) + L-Leucine (1000 mg/100mL) + L-Lysine acetate (1050 mg/100mL) + L-Phenylalanine (298 mg/100mL) + L-Proline (722 mg/100mL) + L-Threonine (400 mg/100mL) + L-Tryptophan (200 mg/100mL) + L-Valine (500 mg/100mL) + Methionine (172 mg/100mL) + Serine (530 mg/100mL)Injection, solutionIntravenousHospira, Inc.2005-09-01Not applicableUs
Aminosyn IIN-acetyltyrosine (405 mg/100mL) + Glutamic Acid (1107 mg/100mL) + Glycine (750 mg/100mL) + Histidine (450 mg/100mL) + L-Alanine (1490 mg/100mL) + L-Arginine (1527 mg/100mL) + L-Aspartic Acid (1050 mg/100mL) + L-Isoleucine (990 mg/100mL) + L-Leucine (1500 mg/100mL) + L-Lysine acetate (1575 mg/100mL) + L-Phenylalanine (447 mg/100mL) + L-Proline (1083 mg/100mL) + L-Threonine (600 mg/100mL) + L-Tryptophan (300 mg/100mL) + L-Valine (750 mg/100mL) + Methionine (258 mg/100mL) + Serine (795 mg/100mL)Injection, solutionIntravenousHospira, Inc.1991-12-19Not applicableUs
Aminosyn IIN-acetyltyrosine (230 mg/100mL) + Glutamic Acid (627 mg/100mL) + Glycine (425 mg/100mL) + Histidine (255 mg/100mL) + L-Alanine (844 mg/100mL) + L-Arginine (865 mg/100mL) + L-Aspartic Acid (595 mg/100mL) + L-Isoleucine (561 mg/100mL) + L-Leucine (850 mg/100mL) + L-Lysine acetate (893 mg/100mL) + L-Phenylalanine (253 mg/100mL) + L-Proline (614 mg/100mL) + L-Threonine (340 mg/100mL) + L-Tryptophan (170 mg/100mL) + L-Valine (425 mg/100mL) + Methionine (146 mg/100mL) + Serine (450 mg/100mL)Injection, solutionIntravenousHospira, Inc.2005-07-29Not applicableUs
Aminosyn IIN-acetyltyrosine (270 mg/100mL) + Glutamic Acid (738 mg/100mL) + Glycine (500 mg/100mL) + Histidine (300 mg/100mL) + L-Alanine (993 mg/100mL) + L-Arginine (1018 mg/100mL) + L-Aspartic Acid (700 mg/100mL) + L-Isoleucine (660 mg/100mL) + L-Leucine (1000 mg/100mL) + L-Lysine acetate (1050 mg/100mL) + L-Phenylalanine (298 mg/100mL) + L-Proline (722 mg/100mL) + L-Threonine (400 mg/100mL) + L-Tryptophan (200 mg/100mL) + L-Valine (500 mg/100mL) + Methionine (172 mg/100mL) + Serine (530 mg/100mL)Injection, solutionIntravenousHospira, Inc.1991-12-19Not applicableUs
Aminosyn IIN-acetyltyrosine (405 mg/100mL) + Glutamic Acid (1107 mg/100mL) + Glycine (750 mg/100mL) + Histidine (450 mg/100mL) + L-Alanine (1490 mg/100mL) + L-Arginine (1527 mg/100mL) + L-Aspartic Acid (1050 mg/100mL) + L-Isoleucine (990 mg/100mL) + L-Leucine (1500 mg/100mL) + L-Lysine acetate (1575 mg/100mL) + L-Phenylalanine (447 mg/100mL) + L-Proline (1083 mg/100mL) + L-Threonine (600 mg/100mL) + L-Tryptophan (300 mg/100mL) + L-Valine (750 mg/100mL) + Methionine (258 mg/100mL) + Serine (795 mg/100mL)Injection, solutionIntravenousHospira, Inc.1991-12-192011-10-01Us
Aminosyn IIN-acetyltyrosine (270 mg) + Glutamic Acid (738 mg) + Glycine (500 mg) + Histidine (300 mg) + L-Alanine (993 mg) + L-Arginine (1018 mg) + L-Aspartic Acid (700 mg) + L-Isoleucine (660 mg) + L-Leucine (1000 mg) + L-Lysine (1050 mg) + L-Phenylalanine (298 mg) + L-Proline (722 mg) + L-Threonine (400 mg) + L-Tryptophan (200 mg) + L-Valine (500 mg) + Methionine (172 mg) + Serine (530 mg)SolutionIntravenousIcu Medical Canada Inc1987-12-31Not applicableCanada
Aminosyn II 10% With ElectrolytesN-acetyltyrosine (270 mg) + Dipotassium phosphate (522 mg) + Glutamic Acid (738 mg) + Glycine (500 mg) + Histidine (300 mg) + L-Alanine (993 mg) + L-Arginine (1.018 g) + L-Aspartic Acid (700 mg) + L-Isoleucine (660 mg) + L-Leucine (1 g) + L-Lysine (1.05 g) + L-Phenylalanine (298 mg) + L-Proline (722 mg) + L-Threonine (400 mg) + L-Tryptophan (200 mg) + L-Valine (500 mg) + Magnesium chloride (102 mg) + Methionine (172 mg) + Potassium Chloride (45 mg) + Serine (530 mg) + Sodium Chloride (410 mg)SolutionIntravenousHospira, Inc.1991-12-312016-07-29Canada
Categories
UNII
DA8G610ZO5
CAS number
537-55-3
Weight
Average: 223.2252
Monoisotopic: 223.084457909
Chemical Formula
C11H13NO4
InChI Key
CAHKINHBCWCHCF-JTQLQIEISA-N
InChI
InChI=1S/C11H13NO4/c1-7(13)12-10(11(15)16)6-8-2-4-9(14)5-3-8/h2-5,10,14H,6H2,1H3,(H,12,13)(H,15,16)/t10-/m0/s1
IUPAC Name
(2S)-2-acetamido-3-(4-hydroxyphenyl)propanoic acid
SMILES
CC(=O)N[C@@H](CC1=CC=C(O)C=C1)C(O)=O

Pharmacology

Indication

N-acetyltyrosine is indicated, in combination with several other amino acids and dextrose, as a peripherally administered source of nitrogen for nutritional support in patients with adequate stores of body fat in whom, for short periods, oral administration cannot be tolerated, is undesirable, or inadequate [Label].

It is also indicated, with other amino acids, 5-10% dextrose, and fat emulsion, for parenteral nutrition to preserve protein and reduce catabolism in stress conditions where oral administration is inadequate [Label].

When administered with other amino acids and concentrated dextrose, it is indicated for central vein infusion to prevent or reverse negative nitrogen balance in patients where the alimentary tract by the oral, gastrostomy, or jejestomy routes cannot or should not be used or in patients in which gastrointestinal absorption of protein is impaired, metabolic requirements for protein are substantially increased, or morbidity and mortality may be reduced by replacing amino acids lost from tissue breakdown [Label]

Pharmacodynamics

N-acetyltyrosine is used as a high solubility precursor to L-Tyrosine used due to L-Tyrosine's poor solubility [2]. It is deacetylated to form L-Tyrosine.

Mechanism of action

Used as a source of L-Tyrosine. See L-Tyrosine for more information on its role and pharmacology.

Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination

N-acetyltyrosine is eliminated in the urine [1]. The extent of urinary elimination versus utilization in the tissues appears to be related to the rapidity of infusion. When infused slowly in standard doses as in the clinical setting, about 35% is excreted unchanged in the urine. When larger doses are infused rapidly, much higher amounts are excreted reaching values up to 56% [3]. In rat studies it was found that of the drug eliminated in the urine about 74% is present as unchanged N-acetyltyrosine and 23% is present as tyrosine [2].

Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
AbacavirAbacavir may decrease the excretion rate of N-acetyltyrosine which could result in a higher serum level.
AcarboseAcarbose may decrease the excretion rate of N-acetyltyrosine which could result in a higher serum level.
AceclofenacAceclofenac may decrease the excretion rate of N-acetyltyrosine which could result in a higher serum level.
AcemetacinAcemetacin may decrease the excretion rate of N-acetyltyrosine which could result in a higher serum level.
AcetaminophenAcetaminophen may decrease the excretion rate of N-acetyltyrosine which could result in a higher serum level.
Acetylsalicylic acidAcetylsalicylic acid may decrease the excretion rate of N-acetyltyrosine which could result in a higher serum level.
AclidiniumAclidinium may decrease the excretion rate of N-acetyltyrosine which could result in a higher serum level.
AcrivastineAcrivastine may decrease the excretion rate of N-acetyltyrosine which could result in a higher serum level.
AcyclovirAcyclovir may decrease the excretion rate of N-acetyltyrosine which could result in a higher serum level.
AdefovirAdefovir may decrease the excretion rate of N-acetyltyrosine which could result in a higher serum level.
Food Interactions
Not Available

References

General References
  1. Hoffer LJ, Sher K, Saboohi F, Bernier P, MacNamara EM, Rinzler D: N-acetyl-L-tyrosine as a tyrosine source in adult parenteral nutrition. JPEN J Parenter Enteral Nutr. 2003 Nov-Dec;27(6):419-22. [PubMed:14621123]
  2. Im HA, Meyer PD, Stegink LD: N-acetyl-L-tyrosine as a tyrosine source during total parenteral nutrition in adult rats. Pediatr Res. 1985 Jun;19(6):514-8. [PubMed:3925425]
  3. Magnusson I, Ekman L, Wangdahl M, Wahren J: N-acetyl-L-tyrosine and N-acetyl-L-cysteine as tyrosine and cysteine precursors during intravenous infusion in humans. Metabolism. 1989 Oct;38(10):957-61. [PubMed:2507878]
External Links
Human Metabolome Database
HMDB0000866
PubChem Compound
68310
PubChem Substance
347827896
ChemSpider
61606
BindingDB
50043802
ChEBI
21563
ChEMBL
CHEMBL65543
HET
3NF
PDB Entries
3nfz
FDA label
Download (1 MB)
MSDS
Download (35.9 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2Active Not RecruitingTreatmentCarcinoid Tumors / Medulloblastomas / Neuroblastomas / Neuroendocrine Tumors1
3CompletedTreatmentInfant, Low Birth Weight / Infant, Small for Gestational Age / Infants, Premature / Newborn Infants / Sepsis1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
LiquidIntravenous
SolutionIntravenous
Injection, solutionIntravenous
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)149-152MSDS
Predicted Properties
PropertyValueSource
Water Solubility2.51 mg/mLALOGPS
logP1.03ALOGPS
logP0.59ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)3.67ChemAxon
pKa (Strongest Basic)-2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.63 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity56.54 m3·mol-1ChemAxon
Polarizability22.25 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-MS (3 TMS)GC-MSsplash10-02t9-1790000000-9484167b29dc57768b67
GC-MS Spectrum - GC-MS (2 TMS)GC-MSsplash10-004i-1921000000-91d4d68bb345a8a8a747
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - GC-MSGC-MSsplash10-02t9-1790000000-9484167b29dc57768b67
GC-MS Spectrum - GC-MSGC-MSsplash10-004i-1921000000-91d4d68bb345a8a8a747
MS/MS Spectrum - Quattro_QQQ 10V, PositiveLC-MS/MSsplash10-0059-0900000000-1a298550f3c63022066c
MS/MS Spectrum - Quattro_QQQ 25V, PositiveLC-MS/MSsplash10-000i-1900000000-489314daf5773f9fa91e
MS/MS Spectrum - Quattro_QQQ 40V, PositiveLC-MS/MSsplash10-0006-9300000000-3a02844e3f23883a2818
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
1H NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as tyrosine and derivatives. These are compounds containing tyrosine or a derivative thereof resulting from reaction of tyrosine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Tyrosine and derivatives
Alternative Parents
Phenylalanine and derivatives / N-acyl-L-alpha-amino acids / Phenylpropanoic acids / Amphetamines and derivatives / 1-hydroxy-2-unsubstituted benzenoids / Acetamides / Secondary carboxylic acid amides / Monocarboxylic acids and derivatives / Carboxylic acids / Organopnictogen compounds
show 4 more
Substituents
Tyrosine or derivatives / Phenylalanine or derivatives / N-acyl-alpha-amino acid / N-acyl-alpha amino acid or derivatives / N-acyl-l-alpha-amino acid / 3-phenylpropanoic-acid / Amphetamine or derivatives / 1-hydroxy-2-unsubstituted benzenoid / Phenol / Monocyclic benzene moiety
show 15 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
L-tyrosine derivative, N-acetyl-L-amino acid (CHEBI:21563)

Drug created on December 03, 2015 09:51 / Updated on November 02, 2018 07:06