Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C6H13NO2 |
Molecular Weight | 131.1729 |
Optical Activity | UNSPECIFIED |
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 |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/25073372Curator'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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25073372
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 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22298573 |
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 Date5.4345601E10 |
|||
Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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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 |
---|---|---|
Lysine metabolism in higher plants. | 2001 |
|
Leucine and protein metabolism in rats with chronic renal insufficiency. | 2001 Apr |
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Activation of skeletal muscle protein breakdown following consumption of soyabean protein in pigs. | 2001 Apr |
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Involvement of branched-chain amino acid aminotransferases in the production of fusel alcohols during fermentation in yeast. | 2001 Apr |
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Trans-(DL-isoleucinato-N,O)[tris(2-aminoethyl)amine-kappa(4)N]cobalt(III)diperchlorate. | 2001 Apr |
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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 Apr |
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Analysis of amino acids in human serum by isocratic reversed-phase high-performance liquid chromatography with electrochemical detection. | 2001 Apr 13 |
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Vanilloid and isovanilloid analogues as inhibitors of methionyl-tRNA and isoleucyl-tRNA synthetases. | 2001 Apr 23 |
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Ester and hydroxamate analogues of methionyl and isoleucyl adenylates as inhibitors of methionyl-tRNA and isoleucyl-tRNA synthetases. | 2001 Apr 23 |
|
Superoxide reductase from Desulfoarculus baarsii: reaction mechanism and role of glutamate 47 and lysine 48 in catalysis. | 2001 Apr 24 |
|
Tyrosine 331 and phenylalanine 334 in Clostridium perfringens alpha-toxin are essential for cytotoxic activity. | 2001 Apr 27 |
|
Re: Population-based, case-control study of HER2 genetic polymorphism and breast cancer risk. | 2001 Apr 4 |
|
Recombinant tyrosine aminotransferase from Trypanosoma cruzi: structural characterization and site directed mutagenesis of a broad substrate specificity enzyme. | 2001 Apr 7 |
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Identification of human CYP2C19 residues that confer S-mephenytoin 4'-hydroxylation activity to CYP2C9. | 2001 Feb 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 Jan 12 |
|
Homoserine dehydrogenase from Saccharomyces cerevisiae: kinetic mechanism and stereochemistry of hydride transfer. | 2001 Jan 12 |
|
Characterization of yeast homoserine dehydrogenase, an antifungal target: the invariant histidine 309 is important for enzyme integrity. | 2001 Jan 12 |
|
Comparative in vitro studies on native and recombinant human cationic trypsins. Cathepsin B is a possible pathological activator of trypsinogen in pancreatitis. | 2001 Jul 6 |
|
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 Mar |
|
Sequence information, distinction and quantitation of C-terminal leucine and isoleucine in ternary complexes of tripeptides with Cu(II) and 2,2'-bipyridine. | 2001 Mar |
|
New auxiliaries for copper-catalyzed asymmetric Michael reactions: generation of quaternary stereocenters at room temperature. | 2001 Mar 2 |
|
[Significance of trypsinogen gene mutations in the etiology of hereditary pancreatitis]. | 2001 Mar 25 |
|
Energy utilization of low-protein diets in growing pigs. | 2001 May |
|
Why do female Aedes aegypti (Diptera: Culicidae) feed preferentially and frequently on human blood? | 2001 May |
|
Enzymology, structure, and dynamics of acetohydroxy acid isomeroreductase. | 2001 May |
|
The central enzymes of the aspartate family of amino acid biosynthesis. | 2001 May |
|
The internal propeptide of the ricin precursor carries a sequence-specific determinant for vacuolar sorting. | 2001 May |
|
Dissociation pathways of alkali-cationized peptides: opportunities for C-terminal peptide sequencing. | 2001 May |
|
Does glutamine act as a substrate for transamination reactions in the liver of fed and fasted sheep? | 2001 May |
|
Proton MR spectroscopy with metabolite-nulling reveals elevated macromolecules in acute multiple sclerosis. | 2001 May |
|
The amino acid residues affecting the activity and azole susceptibility of rat CYP51 (sterol 14-demethylase P450). | 2001 May |
|
A single residue differentiates between human cardiac and skeletal muscle Na+ channel slow inactivation. | 2001 May |
|
Structural and thermodynamic analysis of the binding of solvent at internal sites in T4 lysozyme. | 2001 May |
|
Inhibition of dipeptidyl peptidase IV (DP IV, CD26) activity abrogates stress-induced, cytokine-mediated murine abortions. | 2001 May |
|
The amino-terminal tail of glycogen phosphorylase is a switch for controlling phosphorylase conformation, activation, and response to ligands. | 2001 May 1 |
|
Characterization and manipulation of the acyl chain selectivity of fatty acid amide hydrolase. | 2001 May 22 |
|
Role of surface lysine residues of adipocyte fatty acid-binding protein in fatty acid transfer to phospholipid vesicles. | 2001 May 29 |
|
Acrodermatitis acidemica secondary to malnutrition in glutaric aciduria type I. | 2001 May-Jun |
|
Molecular epidemiology and mutations at gyrA and parC genes of ciprofloxacin-resistant Escherichia coli isolates from a Taiwan medical center. | 2001 Spring |
|
[Dynamics of infection of Fringilla coelebs chaffinch nestlings with feather mites (Acari: Analgoidea)]. | 2002 Sep-Oct |
|
Studies on the biosynthesis of asperparaline A: origin of the spirosuccinimde ring system. | 2003 Dec 3 |
|
Salmonella invasion gene regulation: a story of environmental awareness. | 2005 Feb |
|
Enantioselective and diastereoselective separation of synthetic pyrethroid insecticides on a novel chiral stationary phase by high-performance liquid chromatography. | 2007 Jul |
|
Rho-kinase-dependent F-actin rearrangement is involved in the inhibition of PI3-kinase/Akt during ischemia-reperfusion-induced endothelial cell apoptosis. | 2008 Mar |
|
Comparative genomic analysis uncovers 3 novel loci encoding type six secretion systems differentially distributed in Salmonella serotypes. | 2009 Aug 4 |
|
Imaging improves diagnosis of dementia with lewy bodies. | 2009 Dec |
|
Incidence of lower-limb amputation in the diabetic and nondiabetic general population: a 10-year population-based cohort study of initial unilateral and contralateral amputations and reamputations. | 2009 Feb |
|
[Surgical complications of renal transplantation from living donors: experience of the CHU Ibn Sina, Rabat]. | 2010 |
|
What is a microsatellite: a computational and experimental definition based upon repeat mutational behavior at A/T and GT/AC repeats. | 2010 |
|
The role of coupled positive feedback in the expression of the SPI1 type three secretion system in Salmonella. | 2010 Jul 29 |
Patents
Sample Use Guides
2.9g of L-isoleucine over 6 months
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28089725
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
Fri Dec 15 15:02:26 UTC 2023
by
admin
on
Fri Dec 15 15:02:26 UTC 2023
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Record UNII |
04Y7590D77
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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LOINC |
25938-2
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2510-6
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53397-6
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47673-9
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20648-2
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44329-1
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53393-5
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JECFA EVALUATION |
L-ISOLEUCINE
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LOINC |
56689-3
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57996-1
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FDA ORPHAN DRUG |
93095
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2509-8
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DSLD |
173 (Number of products:424)
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53152-5
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47672-1
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26965-4
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55929-4
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53154-1
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32251-1
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FDA ORPHAN DRUG |
33588
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32252-9
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47671-3
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2507-2
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32783-3
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15138-1
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13765-3
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25939-0
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2415 (Number of products:1910)
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22659-7
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NCI_THESAURUS |
C68442
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CFR |
21 CFR 172.320
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15131-6
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47677-0
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17191
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04Y7590D77
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100000091969
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C29598
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6306
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DB00167
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ISOLEUCINE
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6164
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200-798-2
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CHEMBL1233584
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D007532
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Related Record | Type | Details | ||
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PARENT -> IMPURITY |
impurity A at 570 nm: maximum 0.8 per cent
CHROMATOGRAPHIC PURITY (TLC)
EP
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PARENT -> IMPURITY |
impurity B at 570 nm
CHROMATOGRAPHIC PURITY (TLC)
EP
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Related Record | Type | Details | ||
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ACTIVE MOIETY |