Identification
- Summary
N-acetyltyrosine is an amino acid used in total parenteral nutrition.
- Brand Names
- Aminosyn II 7 %, Sulfite-free, Trophamine 10 %
- Generic Name
- N-acetyltyrosine
- DrugBank Accession Number
- DB11102
- Background
N-acetyltyrosine, also referred to as N-acetyl-L-tyrosine, is used in place of as a tyrosine precursor. 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.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for N-acetyltyrosine (DB11102)
- Weight
- Average: 223.2252
Monoisotopic: 223.084457909 - Chemical Formula
- C11H13NO4
- 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
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
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Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
N-acetyltyrosine is used as a high solubility precursor to Tyrosine used due to Tyrosine's poor solubility 2. It is deacetylated to form Tyrosine.
- Mechanism of action
Used as a source of Tyrosine. See 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
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir Abacavir may decrease the excretion rate of N-acetyltyrosine which could result in a higher serum level. Aceclofenac Aceclofenac may decrease the excretion rate of N-acetyltyrosine which could result in a higher serum level. Acemetacin Acemetacin may decrease the excretion rate of N-acetyltyrosine which could result in a higher serum level. Acetaminophen Acetaminophen may decrease the excretion rate of N-acetyltyrosine which could result in a higher serum level. Acetazolamide Acetazolamide may increase the excretion rate of N-acetyltyrosine which could result in a lower serum level and potentially a reduction in efficacy. - Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Aminoplasmal Paed 10% Infusionslösung N-acetyltyrosine (1.3 g) + Acetylcysteine (0.7 g) + Alanine (15.9 g) + Arginine (9.1 g) + Aspartic acid (6.6 g) + Glutamic acid (9.3 g) + Glycine (2 g) + Histidine (4.6 g) + Isoleucine (5.1 g) + Leucine (7.6 g) + Lysine (8.8 g) + Methionine (2 g) + Phenylalanine (3.1 g) + Proline (6.1 g) + Serine (2 g) + Taurine (0.3 g) + Threonine (5.1 g) + Tryptophan (4 g) + Valine (6.1 g) Solution Parenteral B. Braun Melsungen Ag 2013-09-04 Not applicable Austria 
AMINOPLASMAL-10% E INFUSION N-acetyltyrosine (1 g/l) + Acetylcysteine (0.5 g/l) + Alanine (13.7 g/l) + Arginine (9.2 g/l) + Asparagine (3.27 g/l) + Aspartic acid (1.3 g/l) + Glutamic acid (4.6 g/l) + Glycine (7.9 g/l) + Histidine (5.2 g/l) + Isoleucine (5.1 g/l) + Leucine (8.9 g/l) + Lysine hydrochloride (5.6 g/l) + Magnesium acetate (0.56 g/l) + Malic acid (1.01 g/l) + Methionine (3.8 g/l) + Ornithine hydrochloride (2.51 g/l) + Phenylalanine (5.1 g/l) + Potassium acetate (2.45 g/l) + Proline (8.9 g/l) + Serine (2.4 g/l) + Sodium acetate (3.95 g/l) + Sodium hydroxide (0.2 g/l) + Sodium phosphate, monobasic (1.4 g/l) + Threonine (4.1 g/l) + Tryptophan (1.8 g/l) + Tyrosine (0.3 g/l) + Valine (4.8 g/l) Injection Intravenous B. BRAUN SINGAPORE PTE LTD 1991-05-13 Not applicable Singapore 
AMINOPLASMAL-5% E INFUSION N-acetyltyrosine (0.35 g/1000ml) + Acetylcysteine (0.25 g/1000ml) + Alanine (6.85 g/1000ml) + Arginine (4.6 g/1000ml) + Asparagine (1.64 g/1000ml) + Aspartic acid (0.65 g/1000ml) + Glutamic acid (2.3 g/1000ml) + Glycine (3.95 g/1000ml) + Histidine (2.6 g/1000ml) + Isoleucine (2.55 g/1000ml) + Leucine (4.45 g/1000ml) + Lysine hydrochloride (2.8 g/1000ml) + Magnesium acetate (0.56 g/1000ml) + Malic acid (1.01 g/1000ml) + Methionine (1.9 g/1000ml) + Ornithine hydrochloride (1.25 g/1000ml) + Phenylalanine (2.55 g/1000ml) + Potassium acetate (2.45 g/1000ml) + Proline (4.45 g/1000ml) + Serine (1.2 g/1000ml) + Sodium acetate (3.95 g/1000ml) + Sodium hydroxide (0.2 g/1000ml) + Sodium phosphate, monobasic (1.4 g/1000ml) + Threonine (2.05 g/1000ml) + Tryptophan (0.9 g/1000ml) + Tyrosine (0.3 g/1000ml) + Valine (2.4 g/1000ml) Injection Intravenous B. BRAUN SINGAPORE PTE LTD 1991-05-13 Not applicable Singapore Aminosyn II N-acetyltyrosine (189 mg/100mL) + Alanine (695 mg/100mL) + Arginine (713 mg/100mL) + Aspartic acid (490 mg/100mL) + Glutamic acid (517 mg/100mL) + Glycine (350 mg/100mL) + Histidine (210 mg/100mL) + Isoleucine (462 mg/100mL) + Leucine (700 mg/100mL) + Lysine acetate (735 mg/100mL) + Methionine (120 mg/100mL) + Phenylalanine (209 mg/100mL) + Proline (505 mg/100mL) + Serine (371 mg/100mL) + Threonine (280 mg/100mL) + Tryptophan (140 mg/100mL) + Valine (350 mg/100mL) Injection, solution Intravenous Hospira, Inc. 2005-11-01 2010-12-01 US 
Aminosyn II N-acetyltyrosine (405 mg / 100 mL) + Alanine (1490 mg / 100 mL) + Arginine (1527 mg / 100 mL) + Aspartic acid (1050 mg / 100 mL) + Glutamic acid (1107 mg / 100 mL) + Glycine (750 mg / 100 mL) + Histidine (450 mg / 100 mL) + Isoleucine (990 mg / 100 mL) + Leucine (1500 mg / 100 mL) + Lysine acetate (1575 mg / 100 mL) + Methionine (258 mg / 100 mL) + Phenylalanine (447 mg / 100 mL) + Proline (1083 mg / 100 mL) + Serine (795 mg / 100 mL) + Threonine (600 mg / 100 mL) + Tryptophan (300 mg / 100 mL) + Valine (750 mg / 100 mL) Solution Intravenous Icu Medical Canada Inc 1995-12-31 Not applicable Canada 
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- 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
- 1-hydroxy-2-unsubstituted benzenoid / 3-phenylpropanoic-acid / Acetamide / Amphetamine or derivatives / Aromatic homomonocyclic compound / Benzenoid / Carbonyl group / Carboxamide group / Carboxylic acid / Hydrocarbon derivative show 15 more
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- L-tyrosine derivative, N-acetyl-L-amino acid (CHEBI:21563)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- DA8G610ZO5
- CAS number
- 537-55-3
- 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
References
- General References
- 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. [Article]
- 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. [Article]
- 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. [Article]
- External Links
- Human Metabolome Database
- HMDB0000866
- PubChem Compound
- 68310
- PubChem Substance
- 347827896
- ChemSpider
- 61606
- BindingDB
- 50043802
- 31005
- ChEBI
- 21563
- ChEMBL
- CHEMBL65543
- ZINC
- ZINC000000156395
- PDBe Ligand
- 3NF
- PDB Entries
- 3nfz
- FDA label
- Download (1 MB)
- MSDS
- Download (35.9 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 3 Completed Treatment Infants, Premature / Low Birth Weight Infants / Newborn Infants / Sepsis / Small for Gestational Age Infants 1 2 Active Not Recruiting Treatment Carcinoid Tumors / Medulloblastomas / Neuroblastoma (NB) / Neuroendocrine Tumors 1 Not Available Completed Treatment Hematological Malignancy 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Solution Parenteral Injection Intravenous 0.5 g/l Injection Intravenous 0.25 g/1000ml Liquid Intravenous Injection, solution Intravenous Solution Intravenous - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 149-152 MSDS - Predicted Properties
Property Value Source Water Solubility 2.51 mg/mL ALOGPS logP 1.03 ALOGPS logP 0.59 Chemaxon logS -2 ALOGPS pKa (Strongest Acidic) 3.67 Chemaxon pKa (Strongest Basic) -2 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 86.63 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 56.54 m3·mol-1 Chemaxon Polarizability 22.25 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 154.5189951 predictedDarkChem Lite v0.1.0 [M-H]- 149.7313197 predictedDarkChem Standard v0.1.0 [M-H]- 153.0748951 predictedDarkChem Lite v0.1.0 [M-H]- 147.65102 predictedDeepCCS 1.0 (2019) [M+H]+ 154.3277951 predictedDarkChem Lite v0.1.0 [M+H]+ 152.2503951 predictedDarkChem Lite v0.1.0 [M+H]+ 152.4546951 predictedDarkChem Lite v0.1.0 [M+H]+ 150.04655 predictedDeepCCS 1.0 (2019) [M+Na]+ 153.8390951 predictedDarkChem Lite v0.1.0 [M+Na]+ 162.8612187 predictedDarkChem Standard v0.1.0 [M+Na]+ 156.01462 predictedDeepCCS 1.0 (2019)
Drug created at December 03, 2015 16:51 / Updated at June 12, 2020 16:53