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

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
Structure of ISOLEUCINE

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

HIDE SMILES / InChI

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

Description
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

Originator

Sources: Biokhim. Chain. Proizv., Akad. Nauk SSSR, Inst. Biokhim., Issue No. 9, Pages 182-4

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

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
Primary
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
7.87 μg/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
21.72 μg × h/mL
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

T1/2

ValueDoseCo-administeredAnalytePopulation
1.45 h
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
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
A C-terminally elongated form of PHI from porcine intestine.
1999 Nov 15
Structural investigation of cyclic peptidolipids from Bacillus subtilis by high-energy tandem mass spectrometry.
2001
Activation of skeletal muscle protein breakdown following consumption of soyabean protein in pigs.
2001 Apr
Involvement of branched-chain amino acid aminotransferases in the production of fusel alcohols during fermentation in yeast.
2001 Apr
Trans-(DL-isoleucinato-N,O)[tris(2-aminoethyl)amine-kappa(4)N]cobalt(III)diperchlorate.
2001 Apr
Distinguishing self from nonself: immunogenicity of the murine H47 locus is determined by a single amino acid substitution in an unusual peptide.
2001 Apr 1
Dependence of the bi-functional nature of a sialyltransferase from Neisseria meningitidis on a single amino acid substitution.
2001 Apr 20
Mechanism of dihydropyridine interaction with critical binding residues of L-type Ca2+ channel alpha 1 subunits.
2001 Apr 20
Recombinant tyrosine aminotransferase from Trypanosoma cruzi: structural characterization and site directed mutagenesis of a broad substrate specificity enzyme.
2001 Apr 7
Conformational preferences of heterochiral peptides. Crystal structures of heterochiral peptides Boc-(D) Val-(D) Ala-Leu-Ala-OMe and Boc-Val-Ala-Leu-(D) Ala-OMe--enhanced stability of beta-sheet through C-H...O hydrogen bonds.
2001 Feb
Recognition and stabilization of a unique CPRI--structural motif in cucurbitaceae family trypsin inhibitor peptides: molecular dynamics based homology modeling using the X-ray structure of MCTI-II.
2001 Feb
Comparison of in vitro systems of protein digestion using either mammal or fish proteolytic enzymes.
2001 Feb
Fragmentary form of thermostable leucine dehydrogenase of Bacillus stearothermophilus: its construction and reconstitution of active fragmentary enzyme.
2001 Feb 2
Extracellular amino acid profiles in the paraventricular nucleus of the rat hypothalamus are influenced by diet composition.
2001 Feb 23
Blunted cardiac responses to receptor activation in subjects with Thr164Ile beta(2)-adrenoceptors.
2001 Feb 27
Enhancement, relaxation, and reversal of the stereoselectivity for phosphotriesterase by rational evolution of active site residues.
2001 Feb 6
Incidence of the endothelin receptor B mutation that causes lethal white foal syndrome in white-patterned horses.
2001 Jan
Precursor supply for polyketide biosynthesis: the role of crotonyl-CoA reductase.
2001 Jan
Homoserine dehydrogenase from Saccharomyces cerevisiae: kinetic mechanism and stereochemistry of hydride transfer.
2001 Jan 12
The basal turnover of yeast branched-chain amino acid permease Bap2p requires its C-terminal tail.
2001 Jan 15
Structural basis for oligosaccharide recognition by Pyrococcus furiosus maltodextrin-binding protein.
2001 Jan 26
Protein control of the redox potential of the primary quinone acceptor in reactioncCenters from Rhodobacter sphaeroides.
2001 Jan 30
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
The conserved active site motif A of Escherichia coli DNA polymerase I is highly mutable.
2001 Jun 1
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
Identification of a novel single-nucleotide polymorphism (Val554Ile) and definition of eight common alleles for human IL4RA exon 11.
2001 Mar
Role of the Bacillus subtilis fatty acid desaturase in membrane adaptation during cold shock.
2001 Mar
Early alteration in glomerular reserve in humans at genetic risk of essential hypertension: mechanisms and consequences.
2001 Mar
Molecular anatomy and pathophysiologic implications of drug resistance in hepatitis B virus infection.
2001 Mar
Ligand migration in human myoglobin: steric effects of isoleucine 107(G8) on O(2) and CO binding.
2001 Mar
Helix packing in the lactose permease of Escherichia coli: distances between site-directed nitroxides and a lanthanide.
2001 Mar 13
New auxiliaries for copper-catalyzed asymmetric Michael reactions: generation of quaternary stereocenters at room temperature.
2001 Mar 2
Hydrophobic analogues of the winter flounder 'antifreeze' protein.
2001 Mar 2
Mechanism of pH-dependent photolysis of aliphatic amino acids and enantiomeric enrichment of racemic leucine by circularly polarized light.
2001 Mar 22
Structural and functional analysis of the HIV gp41 core containing an Ile573 to Thr substitution: implications for membrane fusion.
2001 Mar 6
Why do female Aedes aegypti (Diptera: Culicidae) feed preferentially and frequently on human blood?
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
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
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
Reduction of large neutral amino acid levels in plasma and brain of hyperleucinemic rats.
2001 May
The amino-terminal tail of glycogen phosphorylase is a switch for controlling phosphorylase conformation, activation, and response to ligands.
2001 May 1
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
[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

In Vivo Use Guide
Curator's Comment: in combination with L-valine and L-leucine
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 Fri Dec 15 15:02:26 UTC 2023
Edited
by admin
on Fri Dec 15 15:02:26 UTC 2023
Record UNII
04Y7590D77
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ISOLEUCINE
EP   HSDB   II   INCI   INN   MART.   MI   USAN   USP   VANDF   WHO-DD  
USAN   INCI   INN  
Official Name English
ISOLEUCINE [II]
Common Name English
(S-(R*,R*))-2-AMINO-3-METHYLPENTANOIC ACID
Systematic Name English
L-ISOLEUCINE [USP-RS]
Common Name English
Isoleucine [WHO-DD]
Common Name English
ISOLEUCINE, L-
Systematic Name English
ISOLEUCINE [USP MONOGRAPH]
Common Name English
NSC-46708
Code English
(2S,3S)-2-AMINO-3-METHYLPENTANOIC ACID
Systematic Name English
ISOLEUCINE [INCI]
Common Name English
ISOLEUCINE [MI]
Common Name English
ISOLEUCINE [MART.]
Common Name English
L-ISOLEUCINE [FCC]
Common Name English
VALINE IMPURITY B [EP IMPURITY]
Common Name English
ISOLEUCINE [VANDF]
Common Name English
FEMA NO. 4675
Code English
ISOLEUCINE [USAN]
Common Name English
ISOLEUCINE [EP MONOGRAPH]
Common Name English
ISOLEUCINE [HSDB]
Common Name English
LEUCINE IMPURITY A [EP IMPURITY]
Common Name English
isoleucine [INN]
Common Name English
ILE
Code English
L-ISOLEUCINE [JAN]
Common Name English
L-ISOLEUCINE
FCC   USP-RS  
Systematic Name English
Classification Tree Code System Code
LOINC 25938-2
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LOINC 2510-6
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LOINC 53397-6
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LOINC 47673-9
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LOINC 20648-2
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LOINC 44329-1
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LOINC 53393-5
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JECFA EVALUATION L-ISOLEUCINE
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LOINC 56689-3
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LOINC 57996-1
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FDA ORPHAN DRUG 93095
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LOINC 2509-8
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DSLD 173 (Number of products:424)
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LOINC 53152-5
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LOINC 47672-1
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LOINC 26965-4
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LOINC 55929-4
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LOINC 53154-1
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LOINC 32251-1
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FDA ORPHAN DRUG 33588
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LOINC 32252-9
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LOINC 17029-0
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LOINC 30052-5
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LOINC 47671-3
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LOINC 2507-2
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LOINC 32783-3
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LOINC 22714-0
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LOINC 53153-3
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LOINC 47676-2
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LOINC 47674-7
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LOINC 15138-1
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LOINC 13765-3
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LOINC 25939-0
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DSLD 2415 (Number of products:1910)
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LOINC 22659-7
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LOINC 26730-2
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LOINC 45214-4
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LOINC 2508-0
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LOINC 25450-8
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NCI_THESAURUS C68442
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CFR 21 CFR 172.320
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LOINC 15131-6
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LOINC 9743-6
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LOINC 47675-4
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LOINC 72899-8
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LOINC 22706-6
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LOINC 13402-3
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LOINC 47677-0
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Code System Code Type Description
DAILYMED
04Y7590D77
Created by admin on Fri Dec 15 15:02:26 UTC 2023 , Edited by admin on Fri Dec 15 15:02:26 UTC 2023
PRIMARY
CHEBI
17191
Created by admin on Fri Dec 15 15:02:26 UTC 2023 , Edited by admin on Fri Dec 15 15:02:26 UTC 2023
PRIMARY
FDA UNII
04Y7590D77
Created by admin on Fri Dec 15 15:02:26 UTC 2023 , Edited by admin on Fri Dec 15 15:02:26 UTC 2023
PRIMARY
SMS_ID
100000091969
Created by admin on Fri Dec 15 15:02:26 UTC 2023 , Edited by admin on Fri Dec 15 15:02:26 UTC 2023
PRIMARY
NCI_THESAURUS
C29598
Created by admin on Fri Dec 15 15:02:26 UTC 2023 , Edited by admin on Fri Dec 15 15:02:26 UTC 2023
PRIMARY
RS_ITEM_NUM
1349502
Created by admin on Fri Dec 15 15:02:26 UTC 2023 , Edited by admin on Fri Dec 15 15:02:26 UTC 2023
PRIMARY
PUBCHEM
6306
Created by admin on Fri Dec 15 15:02:26 UTC 2023 , Edited by admin on Fri Dec 15 15:02:26 UTC 2023
PRIMARY
DRUG BANK
DB00167
Created by admin on Fri Dec 15 15:02:26 UTC 2023 , Edited by admin on Fri Dec 15 15:02:26 UTC 2023
PRIMARY
WIKIPEDIA
ISOLEUCINE
Created by admin on Fri Dec 15 15:02:26 UTC 2023 , Edited by admin on Fri Dec 15 15:02:26 UTC 2023
PRIMARY
INN
6164
Created by admin on Fri Dec 15 15:02:26 UTC 2023 , Edited by admin on Fri Dec 15 15:02:26 UTC 2023
PRIMARY
HSDB
7798
Created by admin on Fri Dec 15 15:02:26 UTC 2023 , Edited by admin on Fri Dec 15 15:02:26 UTC 2023
PRIMARY
EVMPD
SUB08320MIG
Created by admin on Fri Dec 15 15:02:26 UTC 2023 , Edited by admin on Fri Dec 15 15:02:26 UTC 2023
PRIMARY
RXCUI
6033
Created by admin on Fri Dec 15 15:02:26 UTC 2023 , Edited by admin on Fri Dec 15 15:02:26 UTC 2023
PRIMARY RxNorm
EPA CompTox
DTXSID1047441
Created by admin on Fri Dec 15 15:02:26 UTC 2023 , Edited by admin on Fri Dec 15 15:02:26 UTC 2023
PRIMARY
CHEBI
24898
Created by admin on Fri Dec 15 15:02:26 UTC 2023 , Edited by admin on Fri Dec 15 15:02:26 UTC 2023
PRIMARY
EVMPD
SUB21979
Created by admin on Fri Dec 15 15:02:26 UTC 2023 , Edited by admin on Fri Dec 15 15:02:26 UTC 2023
PRIMARY
DRUG CENTRAL
4129
Created by admin on Fri Dec 15 15:02:26 UTC 2023 , Edited by admin on Fri Dec 15 15:02:26 UTC 2023
PRIMARY
CHEBI
30009
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PRIMARY
CHEBI
58045
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PRIMARY
MERCK INDEX
m6495
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PRIMARY Merck Index
JECFA MONOGRAPH
2095
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PRIMARY
CAS
73-32-5
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PRIMARY
NSC
46708
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PRIMARY
ECHA (EC/EINECS)
200-798-2
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PRIMARY
ChEMBL
CHEMBL1233584
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PRIMARY
MESH
D007532
Created by admin on Fri Dec 15 15:02:26 UTC 2023 , Edited by admin on Fri Dec 15 15:02:26 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> IMPURITY
impurity A at 570 nm: maximum 0.8 per cent
CHROMATOGRAPHIC PURITY (TLC)
EP
PARENT -> IMPURITY
impurity B at 570 nm
CHROMATOGRAPHIC PURITY (TLC)
EP
Related Record Type Details
ACTIVE MOIETY