Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C6H13NO2 |
| Molecular Weight | 131.1729 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC[C@H](C)[C@H](N)C(O)=O
InChI
InChIKey=AGPKZVBTJJNPAG-WHFBIAKZSA-N
InChI=1S/C6H13NO2/c1-3-4(2)5(7)6(8)9/h4-5H,3,7H2,1-2H3,(H,8,9)/t4-,5-/m0/s1
| Molecular Formula | C6H13NO2 |
| Molecular Weight | 131.1729 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
DescriptionCurator's Comment: description was created based on several sources, including
https://www.drugbank.ca/drugs/DB00167 | https://www.ncbi.nlm.nih.gov/pubmed/22298573 | https://www.ncbi.nlm.nih.gov/pubmed/4698813 | https://www.ncbi.nlm.nih.gov/pubmed/28089725
Curator's Comment: description was created based on several sources, including
https://www.drugbank.ca/drugs/DB00167 | https://www.ncbi.nlm.nih.gov/pubmed/22298573 | https://www.ncbi.nlm.nih.gov/pubmed/4698813 | https://www.ncbi.nlm.nih.gov/pubmed/28089725
Isoleucine is an essential α-amino acid that is used in the biosynthesis of proteins. L-isoleucine is commonly used in parenteral and enteral nutrition. It is used in combination with the other branched chain amino acids to improve the nutritional status of patients with hepatic diseases. BCAAs serve as important fuel sources for skeletal muscle during periods of metabolic stress
CNS Activity
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2221341 |
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 Date1971 |
|||
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
7.87 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26119505/ |
50 mg/kg single, oral dose: 50 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
ISOLEUCINE plasma | Canis lupus population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
21.72 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26119505/ |
50 mg/kg single, oral dose: 50 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
ISOLEUCINE plasma | Canis lupus population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1.45 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26119505/ |
50 mg/kg single, oral dose: 50 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
ISOLEUCINE plasma | Canis lupus population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Comparative in vitro studies on native and recombinant human cationic trypsins. Cathepsin B is a possible pathological activator of trypsinogen in pancreatitis. | 2001-07-06 |
|
| A family of yeast proteins mediating bidirectional vacuolar amino acid transport. | 2001-06-29 |
|
| The conserved active site motif A of Escherichia coli DNA polymerase I is highly mutable. | 2001-06-01 |
|
| Role of surface lysine residues of adipocyte fatty acid-binding protein in fatty acid transfer to phospholipid vesicles. | 2001-05-29 |
|
| Characterization and manipulation of the acyl chain selectivity of fatty acid amide hydrolase. | 2001-05-22 |
|
| Acrodermatitis acidemica secondary to malnutrition in glutaric aciduria type I. | 2001-05-19 |
|
| The amino-terminal tail of glycogen phosphorylase is a switch for controlling phosphorylase conformation, activation, and response to ligands. | 2001-05-01 |
|
| Energy utilization of low-protein diets in growing pigs. | 2001-05 |
|
| Why do female Aedes aegypti (Diptera: Culicidae) feed preferentially and frequently on human blood? | 2001-05 |
|
| Enzymology, structure, and dynamics of acetohydroxy acid isomeroreductase. | 2001-05 |
|
| The central enzymes of the aspartate family of amino acid biosynthesis. | 2001-05 |
|
| The internal propeptide of the ricin precursor carries a sequence-specific determinant for vacuolar sorting. | 2001-05 |
|
| Dissociation pathways of alkali-cationized peptides: opportunities for C-terminal peptide sequencing. | 2001-05 |
|
| Does glutamine act as a substrate for transamination reactions in the liver of fed and fasted sheep? | 2001-05 |
|
| Proton MR spectroscopy with metabolite-nulling reveals elevated macromolecules in acute multiple sclerosis. | 2001-05 |
|
| The amino acid residues affecting the activity and azole susceptibility of rat CYP51 (sterol 14-demethylase P450). | 2001-05 |
|
| A single residue differentiates between human cardiac and skeletal muscle Na+ channel slow inactivation. | 2001-05 |
|
| Structural and thermodynamic analysis of the binding of solvent at internal sites in T4 lysozyme. | 2001-05 |
|
| Inhibition of dipeptidyl peptidase IV (DP IV, CD26) activity abrogates stress-induced, cytokine-mediated murine abortions. | 2001-05 |
|
| Tyrosine 331 and phenylalanine 334 in Clostridium perfringens alpha-toxin are essential for cytotoxic activity. | 2001-04-27 |
|
| Superoxide reductase from Desulfoarculus baarsii: reaction mechanism and role of glutamate 47 and lysine 48 in catalysis. | 2001-04-24 |
|
| Vanilloid and isovanilloid analogues as inhibitors of methionyl-tRNA and isoleucyl-tRNA synthetases. | 2001-04-23 |
|
| Ester and hydroxamate analogues of methionyl and isoleucyl adenylates as inhibitors of methionyl-tRNA and isoleucyl-tRNA synthetases. | 2001-04-23 |
|
| Roles of histidine residues in tobacco acetolactate synthase. | 2001-04-20 |
|
| Dependence of the bi-functional nature of a sialyltransferase from Neisseria meningitidis on a single amino acid substitution. | 2001-04-20 |
|
| Mechanism of dihydropyridine interaction with critical binding residues of L-type Ca2+ channel alpha 1 subunits. | 2001-04-20 |
|
| Analysis of amino acids in human serum by isocratic reversed-phase high-performance liquid chromatography with electrochemical detection. | 2001-04-13 |
|
| Coordinate changes in drug resistance and drug-induced conformational transitions in altered-function mutants of the multidrug transporter P-glycoprotein. | 2001-04-10 |
|
| Recombinant tyrosine aminotransferase from Trypanosoma cruzi: structural characterization and site directed mutagenesis of a broad substrate specificity enzyme. | 2001-04-07 |
|
| Re: Population-based, case-control study of HER2 genetic polymorphism and breast cancer risk. | 2001-04-04 |
|
| Leucine and protein metabolism in rats with chronic renal insufficiency. | 2001-04 |
|
| Activation of skeletal muscle protein breakdown following consumption of soyabean protein in pigs. | 2001-04 |
|
| Involvement of branched-chain amino acid aminotransferases in the production of fusel alcohols during fermentation in yeast. | 2001-04 |
|
| Trans-(DL-isoleucinato-N,O)[tris(2-aminoethyl)amine-kappa(4)N]cobalt(III)diperchlorate.. | 2001-04 |
|
| Aspartate kinase 2. A candidate gene of a quantitative trait locus influencing free amino acid content in maize endosperm. | 2001-04 |
|
| Identification of amino acid residues responsible for the alpha5 subunit binding selectivity of L-655,708, a benzodiazepine binding site ligand at the GABA(A) receptor. | 2001-04 |
|
| Identification of a novel COCH mutation, I109N, highlights the similar clinical features observed in DFNA9 families. | 2001-04 |
|
| Regulation of a Rho-associated kinase expression during the corneal epithelial cell cycle. | 2001-04 |
|
| [Significance of trypsinogen gene mutations in the etiology of hereditary pancreatitis]. | 2001-03-25 |
|
| New auxiliaries for copper-catalyzed asymmetric Michael reactions: generation of quaternary stereocenters at room temperature. | 2001-03-02 |
|
| Dethiosulfovibrio russensis sp. nov., Dethosulfovibrio marinus sp. nov. and Dethosulfovibrio acidaminovorans sp. nov., novel anaerobic, thiosulfate- and sulfur-reducing bacteria isolated from 'Thiodendron' sulfur mats in different saline environments. | 2001-03 |
|
| Sequence information, distinction and quantitation of C-terminal leucine and isoleucine in ternary complexes of tripeptides with Cu(II) and 2,2'-bipyridine. | 2001-03 |
|
| Identification of a novel single-nucleotide polymorphism (Val554Ile) and definition of eight common alleles for human IL4RA exon 11. | 2001-03 |
|
| Identification of human CYP2C19 residues that confer S-mephenytoin 4'-hydroxylation activity to CYP2C9. | 2001-02-20 |
|
| The Val-210-Ile pathogenic Creutzfeldt-Jakob disease mutation increases both the helical and aggregation propensities of a sequence corresponding to helix-3 of PrP(C). | 2001-01-12 |
|
| Homoserine dehydrogenase from Saccharomyces cerevisiae: kinetic mechanism and stereochemistry of hydride transfer. | 2001-01-12 |
|
| Characterization of yeast homoserine dehydrogenase, an antifungal target: the invariant histidine 309 is important for enzyme integrity. | 2001-01-12 |
|
| Lysine metabolism in higher plants. | 2001 |
|
| Molecular epidemiology and mutations at gyrA and parC genes of ciprofloxacin-resistant Escherichia coli isolates from a Taiwan medical center. | 2001 |
|
| Metabolism of branched-chain amino acids in starved rats: the role of hepatic tissue. | 2001 |
Patents
Sample Use Guides
2.9g of L-isoleucine over 6 months
Route of Administration:
Oral
Primary cultures of peripheral blood mononuclear cells were rinsed with PBS and harvested in phosphate buffer pH 7.4 (50 mmol/L KH2PO4, 1 mmol/L EGTA, 150 mmol/L sucrose). The reaction was started by the addition of a lucigenin mixture 5 μmol/L) and NADPH (100 μmol/L) (Sigma-Aldrich) to the protein sample in a final volume of 250 μL. Branched-chain amino acids were prepared as a mixture of leucine, isoleucine and valine at 0.2–12 mmol/L Cells were exposed to increasing concentrations of BCAA (4–12 mmol/L) for 1 h Chemiluminescence was determined every 2.4 s for 3 min in a microtiter plate luminometer (Enspire Perkin Elmer). Basal activity in the absence of NADPH was subtracted from each reading and normalized to protein concentration.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 17:48:44 GMT 2025
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| Record UNII |
5HX0BYT4E3
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| Record Status |
Validated (UNII)
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| Record Version |
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JECFA EVALUATION |
DL-ISOLEUCINE
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PRIMARY | Merck Index |