ISOLEUCINE

US Previously Marketed

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 Search

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
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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Mammalian target of Rapamycin (mTORC1) 23 Target ID: CHEMBL2221341 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22298573	Activator 1430

Conditions

Condition	Modality	Highest Phase	Product
Burns 17 Sources: https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=overview.process&ApplNo=016822	Primary	Approved 8429	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 1971
Acute infectious diarrhoea 2 Sources: https://clinicaltrials.gov/ct2/show/NCT01034228	Primary	Phase II 1132	Unknown Approved Use Unknown
Hyperglycemia 4 Sources: https://clinicaltrials.gov/ct2/show/record/NCT02634164	Primary	Not Provided 504	Unknown Approved Use Unknown
Liver cirrhosis 15 Sources: https://clinicaltrials.gov/ct2/show/study/NCT02837302	Primary	Phase IV 63	Unknown Approved Use Unknown

C_max

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

T_1/2

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

Sourcing

Vendor/Aggregator	ID	URL
3B Scientific (Wuhan) Corp	3B1-01561	http://www.3bsc.com/index/pro_info.php?id=21773
3B Scientific (Wuhan) Corp	3B3-024437	http://www.3bsc.com/index/pro_info.php?id=45513
AA Blocks	AA003R7U	http://www.aablocks.com/goods/Goods/detail?id=AA003R7U
AHH Chemical co.,ltd	MT-00788	http://www.ahhchemical.com/product/MT-00788.html
AHH Chemical co.,ltd	MT-16045	http://www.ahhchemical.com/product/MT-16045.html
AHH Chemical co.,ltd	NP-1180	http://www.ahhchemical.com/product/NP-1180.html
AK Scientific, Inc. (AKSCI)	371141	http://www.aksci.com/item_detail.php?cat=371141
AK Scientific, Inc. (AKSCI)	67373	http://www.aksci.com/item_detail.php?cat=67373
Aaron Chemicals	AR003RZM	http://www.aaronchem.com/73-32-5
AbMole Bioscience	M9327	http://www.abmole.com/products/l-isoleucine.html
Acadechem	ACDS-063683	http://www.acadechemical.com/product/138382
Acadechem	ACDS-067977	http://www.acadechemical.com/product/142676
Achemo Scientific Limited	AC-74012	http://www.achemo.com/search/?Keyword= 73-32-5
Achemo Scientific Limited	AC-74021	http://www.achemo.com/search/?Keyword= 73-32-5
Achemtek	0101-001279	http://www.achemtek.com/73-32-5
Acorn PharmaTech	ACN-033303	http://www.acornpharmatech.com/
Acros Organics	AC166170050	https://www.fishersci.com/shop/products/l-isoleucine-99-acros-organics-1/AC166170050
Acros Organics	AC166170250	https://www.fishersci.com/shop/products/l-isoleucine-99-acros-organics-1/AC166170250
Acros Organics	AC166171000	https://www.fishersci.com/shop/products/l-isoleucine-99-acros-organics-1/AC166171000
Acros Organics	AC166175000	https://www.fishersci.com/shop/products/l-isoleucine-99-acros-organics/AC166175000
Alfa Aesar	A13699	https://www.alfa.com/en/catalog/A13699/
Alfa Chemistry	AP73325	https://reagents.alfa-chemistry.com/product/l-isoleucine-cas-73-32-5-15708.html
Alfa Chemistry	AP73325-A	https://reagents.alfa-chemistry.com/product/l-isoleucine-cas-73-32-5-15709.html
Alichem	471003772	http://www.alichem.com/en/products/73-32-5.html
Ambeed	A868688	https://www.ambeed.com/products/443-79-8.html
Angene	AGN-PC-0WA1X0	http://www.angenechemical.com/productshow/AGN-PC-0WA1X0.html
Anward	ANW-36330	http://www.anward.com/pro_result/24908
ApexBio Technology	A6806	http://www.apexbt.com/h-ile-2-chlorotrityl-resin.html
ApexBio Technology	A7207	http://www.apexbt.com/h-ile-oh.html
Aurora Fine Chemicals LLC	A02.556.670	http://online.aurorafinechemicals.com/info?ID=A02.556.670
Aurum Pharmatech LLC	Z-4689	http://www.Aurumpharmatech.com/Product/ProductDetails/Z_4689
Avantor Inc	BT129375-10G	https://us.vwr.com/store/product/16637361/l-isoleucine-99
Avantor Inc	BT129375-50G	https://us.vwr.com/store/product/16637361/l-isoleucine-99
Avantor Inc	200001-520	https://us.vwr.com/store/product/7516119/l-isoleucine-99
BLD Pharm	BD40390	http://www.bldpharm.com/products/443-79-8.html
BLD Pharm	BD34776	http://www.bldpharm.com/products/73-32-5.html
BioSynth	Q-201311	https://www.biosynth.com/en/products/life-science/other-biochemicals/products/Q-201311.html
BroadPharm	BP-20357	https://www.broadpharm.com/web/product.php?catalog=BP-20357
CSNpharm	CSN23582	https://www.csnpharm.com/products/l-isoleucine.html
Capot Chemical	12389	http://www.capotchem.com/en/12389.htm
Capot Chemical	PubChem12389	http://www.capotchem.com/en/12389.htm
Capot Chemical	21625	http://www.capotchem.com/en/21625.htm
Capot Chemical	PubChem21625	http://www.capotchem.com/en/21625.htm
Chem Scene	CS-W018502	http://www.chemscene.com/73-32-5.html
ChemMol	1201570	http://www.chemmol.com/chemmol/1201570.html
ChemMol	1202962	http://www.chemmol.com/chemmol/1202962.html
ChemMol	30202568	http://www.chemmol.com/chemmol/30202568.html
ChemMol	30202569	http://www.chemmol.com/chemmol/30202569.html
ChemMol	49402320	http://www.chemmol.com/chemmol/49402320.html
Chemenu	CM119424	http://www.chemenu.com/products/CM119424
Chemspace	CSSB00011417156	https://chem-space.com/CSSB00011417156
China MainChem Co., Ltd	MS73-32-5	https://www.mainchem.com/product/l-isoleucine/
Chiralblock Biosciences	CB10358	http://www.chiralblock.com/products/73-32-5.html
DC Chemicals	DCY-146	http://www.dcchemicals.com//product_show-L_Isoleucine.html
Enamine	Z1250208653	https://www.enaminestore.com/catalog/Z1250208653
Glentham Life Sciences	GM0912	http://www.glentham.com/products/product/GM0912/
Glentham Life Sciences	GM6591	http://www.glentham.com/products/product/GM6591/
Hairui	HR134488	http://www.hairuichem.com/en/product/73-32-5.html
LGC Standards	DRE-C14429000	https://www.lgcstandards.com/US/en/p/DRE-C14429000
LGC Standards	DRE-C14429100	https://www.lgcstandards.com/US/en/p/DRE-C14429100
LGC Standards	LGCFOR1564.00	https://www.lgcstandards.com/US/en/p/LGCFOR1564.00
LGC Standards	MM1564.00	https://www.lgcstandards.com/US/en/p/MM1564.00
Lab Network	LN00195374	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00195374
MedChem Express	HY-N0771	https://www.medchemexpress.com/L-Isoleucine.html
OChem	3795	http://www.ocheminc.com/index.php?act=psearch&pid=064l222
Oakwood	M03002	http://www.oakwoodchemical.com/ProductsList.aspx?CategoryID=-2&txtSearch=127805&ExtHyperLink=1
Parchem	396	http://www.parchem.com/chemical-supplier-distributor/L-Isoleucine-000976.aspx
Parchem	21554	http://www.parchem.com/chemical-supplier-distributor/laevo-isoleucine-011554.aspx
Renno Tech	RP17314	http://www.rennotech.com/product_show.asp?id=23215
Sigma-Aldrich	151718_ALDRICH	https://www.sigmaaldrich.com/catalog/product/aldrich/151718?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	15-2120_SAJ	https://www.sigmaaldrich.com/catalog/product/saj/152120?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	56241_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/56241?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	58879_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/58879?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	1349502_USP	https://www.sigmaaldrich.com/catalog/product/usp/1349502?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sinfoo Biotech	S048026	http://www.sinfoobiotech.com/product/1051424
Sinfoo Biotech	S052320	http://www.sinfoobiotech.com/product/1055718
TCI (Tokyo Chemical Industry)	I0181	http://www.tcichemicals.com/eshop/en/us/commodity/I0181/index.html
VladaChem	VL142921	https://www.vladachem.com/product.php?products=73-32-5
VladaChem	VL163433	https://www.vladachem.com/product.php?products=73-32-5
VladaChem	VL264784-100G	https://www.vladachem.com/product.php?products=73-32-5
Watanabe Chemical Ind.	G00022	https://www.watanabechem.co.jp/en/search/details.php?code=G00022
Yuhao Chemical	HL3430	http://www.chemyuhao.com/131598-62-4.html
abcr GmbH	AB117129	http://www.abcr.com/shop/en/AB117129
abcr GmbH	AB177057	http://www.abcr.com/shop/en/AB177057
abcr GmbH	AB354900	http://www.abcr.com/shop/en/AB354900
eNovation Chemicals	D380618	https://www.enovationchem.com/ProductDetails.asp?ProductID=D380618
eNovation Chemicals	K21854	https://www.enovationchem.com/ProductDetails.asp?ProductID=K21854
eNovation Chemicals	Y1045988	https://www.enovationchem.com/ProductDetails.asp?ProductID=Y1045988
iChemical	EBD2198111	http://www.ichemical.com/products/73-32-5.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
mcule	MCULE-2215911951	https://mcule.com/MCULE-2215911951/

PubMed

Title	Date	PubMed
A C-terminally elongated form of PHI from porcine intestine.	1999 Nov 15	11212317
Lysine metabolism in higher plants.	2001	11354603
An algorithm for mapping positively selected members of quasispecies-type viruses.	2001	11265061
Structural investigation of cyclic peptidolipids from Bacillus subtilis by high-energy tandem mass spectrometry.	2001	11180551
Leucine and protein metabolism in rats with chronic renal insufficiency.	2001 Apr	11370737
Regulation of a Rho-associated kinase expression during the corneal epithelial cell cycle.	2001 Apr	11274069
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	11254699
Coordinate changes in drug resistance and drug-induced conformational transitions in altered-function mutants of the multidrug transporter P-glycoprotein.	2001 Apr 10	11284689
Dependence of the bi-functional nature of a sialyltransferase from Neisseria meningitidis on a single amino acid substitution.	2001 Apr 20	11278878
Ester and hydroxamate analogues of methionyl and isoleucyl adenylates as inhibitors of methionyl-tRNA and isoleucyl-tRNA synthetases.	2001 Apr 23	11327600
Recombinant tyrosine aminotransferase from Trypanosoma cruzi: structural characterization and site directed mutagenesis of a broad substrate specificity enzyme.	2001 Apr 7	11295433
Metabolic regulation by leucine of translation initiation through the mTOR-signaling pathway by pancreatic beta-cells.	2001 Feb	11272147
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	11245253
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	11245252
Comparison of in vitro systems of protein digestion using either mammal or fish proteolytic enzymes.	2001 Feb	11223397
Reduction of nonpolar amino acids to amino alcohols to enhance volatility for high-precision isotopic analysis.	2001 Feb 15	11248895
Fragmentary form of thermostable leucine dehydrogenase of Bacillus stearothermophilus: its construction and reconstitution of active fragmentary enzyme.	2001 Feb 2	11162651
Cloning and characterization of Chinese hamster homologue of yeast DBF4 (ChDBF4).	2001 Feb 21	11250080
Extracellular amino acid profiles in the paraventricular nucleus of the rat hypothalamus are influenced by diet composition.	2001 Feb 23	11172779
Blunted cardiac responses to receptor activation in subjects with Thr164Ile beta(2)-adrenoceptors.	2001 Feb 27	11222464
Incidence of the endothelin receptor B mutation that causes lethal white foal syndrome in white-patterned horses.	2001 Jan	11197568
Precursor supply for polyketide biosynthesis: the role of crotonyl-CoA reductase.	2001 Jan	11162231
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	11341933
Homoserine dehydrogenase from Saccharomyces cerevisiae: kinetic mechanism and stereochemistry of hydride transfer.	2001 Jan 12	11341915
The basal turnover of yeast branched-chain amino acid permease Bap2p requires its C-terminal tail.	2001 Jan 15	11164310
Protein control of the redox potential of the primary quinone acceptor in reactioncCenters from Rhodobacter sphaeroides.	2001 Jan 30	11170424
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	11312265
Identification of a novel single-nucleotide polymorphism (Val554Ile) and definition of eight common alleles for human IL4RA exon 11.	2001 Mar	11285129
Regression of human mammary adenocarcinoma by systemic administration of a recombinant gene encoding the hFlex-TRAIL fusion protein.	2001 Mar	11273779
Role of the Bacillus subtilis fatty acid desaturase in membrane adaptation during cold shock.	2001 Mar	11251847
Ligand migration in human myoglobin: steric effects of isoleucine 107(G8) on O(2) and CO binding.	2001 Mar	11222311
Mechanism of pH-dependent photolysis of aliphatic amino acids and enantiomeric enrichment of racemic leucine by circularly polarized light.	2001 Mar 22	11263916
Thermodynamics of trimer-of-hairpins formation by the SIV gp41 envelope protein.	2001 Mar 23	11254387
Structural and functional analysis of the HIV gp41 core containing an Ile573 to Thr substitution: implications for membrane fusion.	2001 Mar 6	11258890
Direct comparison of experimental and calculated folding free energies for hydrophobic deletion mutants of chymotrypsin inhibitor 2: free energy perturbation calculations using transition and denatured states from molecular dynamics simulations of unfolding.	2001 Mar 6	11258883
Why do female Aedes aegypti (Diptera: Culicidae) feed preferentially and frequently on human blood?	2001 May	11372967
Enzymology, structure, and dynamics of acetohydroxy acid isomeroreductase.	2001 May	11352718
The internal propeptide of the ricin precursor carries a sequence-specific determinant for vacuolar sorting.	2001 May	11351080
Dissociation pathways of alkali-cationized peptides: opportunities for C-terminal peptide sequencing.	2001 May	11349947
Does glutamine act as a substrate for transamination reactions in the liver of fed and fasted sheep?	2001 May	11348574
Reduction of large neutral amino acid levels in plasma and brain of hyperleucinemic rats.	2001 May	11248401
Role of surface lysine residues of adipocyte fatty acid-binding protein in fatty acid transfer to phospholipid vesicles.	2001 May 29	11371211
Salmonella invasion gene regulation: a story of environmental awareness.	2005 Feb	15765064
Enantioselective and diastereoselective separation of synthetic pyrethroid insecticides on a novel chiral stationary phase by high-performance liquid chromatography.	2007 Jul	17508398
Rho-kinase-dependent F-actin rearrangement is involved in the inhibition of PI3-kinase/Akt during ischemia-reperfusion-induced endothelial cell apoptosis.	2008 Mar	18165899
Comparative genomic analysis uncovers 3 novel loci encoding type six secretion systems differentially distributed in Salmonella serotypes.	2009 Aug 4	19653904
Imaging improves diagnosis of dementia with lewy bodies.	2009 Dec	20140120
[Surgical complications of renal transplantation from living donors: experience of the CHU Ibn Sina, Rabat].	2010	22087350
What is a microsatellite: a computational and experimental definition based upon repeat mutational behavior at A/T and GT/AC repeats.	2010	20668018
The role of coupled positive feedback in the expression of the SPI1 type three secretion system in Salmonella.	2010 Jul 29	20686667

Patents

Sample Use Guides

In Vivo Use Guide

2.9g of L-isoleucine over 6 months

Route of Administration: Oral

In Vitro Use Guide

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 GMT 2023` Edited by `admin` on `Fri Dec 15 15:02:26 GMT 2023`
Record UNII	04Y7590D77
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ISOLEUCINE

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

Systematic Name

English

Classification Tree Code System Code

LOINC

25938-2