LEUCINE

US Previously Marketed

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C6H13NO2
Molecular Weight	131.1729
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)C[C@H](N)C(O)=O

InChI

InChIKey=ROHFNLRQFUQHCH-YFKPBYRVSA-N

InChI=1S/C6H13NO2/c1-4(2)3-5(7)6(8)9/h4-5H,3,7H2,1-2H3,(H,8,9)/t5-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C6H13NO2
Molecular Weight	131.1729
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: description was created based on several sources, including https://www.drugbank.ca/drugs/DB00149 | https://clinicaltrials.gov/ct2/show/NCT01362595 | https://www.ncbi.nlm.nih.gov/pubmed/6883121

Leucine is an α-amino acid used in the biosynthesis of proteins. Leucine is an essential hydrophobic amino acid. It is used in the Leucine may be used some people as a supplement to build muscle. Leucine is also found in fish, meat, and poultry. In the pharmaceutical industry, L-leucine is used for parenteral and enteral nutrition and feeding, and is also used as a flavoring product and tablet lubricant in manufacturing. Leucine is an mTOR activator. It is a dietary amino acid with the capacity to directly stimulate muscle protein synthesis. As a dietary supplement, leucine has been found to slow the degradation of muscle tissue by increasing the synthesis of muscle proteins in aged rats. Long-term leucine supplementation does not increase muscle mass or strength in healthy elderly men. Leucine potently activates the mammalian target of rapamycin kinase that regulates cell growth. Infusion of leucine into the rat brain has been shown to decrease food intake and body weight via activation of the mTOR pathway.

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/28237591	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
Diamond-Blackfan anemia 3 Sources: https://clinicaltrials.gov/ct2/show/NCT01362595	Primary	Phase II 1132	Unknown Approved Use Unknown
Pure red cell aplasia 2 Sources: https://clinicaltrials.gov/ct2/show/NCT01362595	Primary	Phase II 1132	Unknown Approved Use Unknown
Non-alcoholic fatty liver disease 30 Sources: https://clinicaltrials.gov/ct2/show/NCT02546609	Primary	Phase II 1132	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
15.9 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26119505/	100 mg/kg single, oral dose: 100 mg/kg route of administration: Oral experiment type: SINGLE co-administered:		LEUCINE plasma	Canis lupus population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
48.63 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26119505/	100 mg/kg single, oral dose: 100 mg/kg route of administration: Oral experiment type: SINGLE co-administered:		LEUCINE plasma	Canis lupus population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
1.49 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26119505/	100 mg/kg single, oral dose: 100 mg/kg route of administration: Oral experiment type: SINGLE co-administered:		LEUCINE plasma	Canis lupus population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:25017	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:25017
ChemicalBook	CB4365169	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB4365169
MolPort	MolPort-001-780-225	https://www.molport.com/shop/molecule-link/MolPort-001-780-225
eMolecules	499483	https://www.emolecules.com/cgi-bin/more?vid=499483

PubMed

Title	Date	PubMed
Prevalence of mutations causing retinitis pigmentosa and other inherited retinopathies.	2001	11139241
Expression pattern and gene characterization of asporin. a newly discovered member of the leucine-rich repeat protein family.	2001 Apr 13	11152695
The biosynthetic incorporation of the intact leucine skeleton into sterol by the trypanosomatid Leishmania mexicana.	2001 Apr 13	11148203
Stem cell factor presentation to c-Kit. Identification of a basolateral targeting domain.	2001 Apr 20	11152680
Different usage of the glycosaminoglycan attachment sites of biglycan.	2001 Apr 20	11145959
Identification of a new Leu354Pro mutation responsible for factor XIII deficiency.	2001 Feb	11168522
Determination of binding constant of transcription factor AP-1 and DNA. Application of inhibitors.	2001 Feb	11168395
The Drosophila homolog of human AF10/AF17 leukemia fusion genes (Dalf) encodes a zinc finger/leucine zipper nuclear protein required in the nervous system for maintaining EVE expression and normal growth.	2001 Feb	11165485
Homeodomain leucine zipper proteins bind to the phosphate response domain of the soybean VspB tripartite promoter.	2001 Feb	11161037
Temperature dependence of the folding and unfolding kinetics of the GCN4 leucine zipper via 13C(alpha)-NMR.	2001 Feb	11159461
A compound heterozygous one amino-acid insertion/nonsense mutation in the plectin gene causes epidermolysis bullosa simplex with plectin deficiency.	2001 Feb	11159198
The digestion rate of protein is an independent regulating factor of postprandial protein retention.	2001 Feb	11158939
Amino acid interconversions in the fetal-placental unit: the animal model and human studies in vivo.	2001 Feb	11158506
Increased albumin and fibrinogen synthesis in hemodialysis patients with normal nutritional status.	2001 Feb	11158225
Differential insulin sensitivities of glucose, amino acid, and albumin metabolism in elderly men and women.	2001 Feb	11158022
A novel syndrome affecting multiple mitochondrial functions, located by microcell-mediated transfer to chromosome 2p14-2p13.	2001 Feb	11156534
Abnormal secretion and function of recombinant human factor VII as the result of modification to a calcium binding site caused by a 15-base pair insertion in the F7 gene.	2001 Feb 15	11159523
Multiple zonal projections of the basilar pontine nuclei to the cerebellar cortex of the rat.	2001 Feb 19	11169481
Identification of the main ubiquitination site in human erythroid alpha-spectrin.	2001 Feb 2	11165260
Fragmentary form of thermostable leucine dehydrogenase of Bacillus stearothermophilus: its construction and reconstitution of active fragmentary enzyme.	2001 Feb 2	11162651
The metabolic evidence of synergistic effect between ohmefentanyl and [D-Pen2, D-Pen5] enkephalin on differentiated SH-SY5Y cells in humans.	2001 Feb 9	11165441
Identification and characterization of a novel gene that is upregulated in leukaemia cells by nitric oxide.	2001 Jan	11167794
V89L polymorphism of type-2, 5-alpha reductase enzyme gene predicts prostate cancer presence and progression.	2001 Jan	11164181
Precursor supply for polyketide biosynthesis: the role of crotonyl-CoA reductase.	2001 Jan	11162231
Simvastatin inhibits noradrenaline-induced hypertrophy of cultured neonatal rat cardiomyocytes.	2001 Jan	11156573
Enhanced flavour formation by combination of selected lactococci from industrial and artisanal origin with focus on completion of a metabolic pathway.	2001 Jan	11155123
Net amino acid flux across the fetal liver and placenta during spontaneous ovine parturition.	2001 Jan	11150831
Proteoglycan synthesis is increased in cells with impaired clathrin-dependent endocytosis.	2001 Jan	11148135
Characterization of 3-[(123)I]iodo-L-alpha-methyl tyrosine transport in astrocytes of neonatal rats.	2001 Jan	11145982
Effect of elective abdominal surgery on human colon protein synthesis in situ.	2001 Jan	11141223
Structure of the human zinc finger protein HIVEP3: molecular cloning, expression, exon-intron structure, and comparison with paralogous genes HIVEP1 and HIVEP2.	2001 Jan 1	11161801
Central neurocytomas express photoreceptor differentiation.	2001 Jan 1	11148570
Chloramine-T in radiolabeling techniques. IV. Penta-O-acetyl-N-chloro-N-methylglucamine as an oxidizing agent in radiolabelling techniques.	2001 Jan 1	11141301
Nrf2-dependent activation of the antioxidant responsive element by tert-butylhydroquinone is independent of oxidative stress in IMR-32 human neuroblastoma cells.	2001 Jan 12	11162512
Spontaneous dimerization and leucine-zipper induced activation of the recombinant catalytic domain of a new adenylyl cyclase of Trypanosoma brucei, GRESAG4.4B.	2001 Jan 15	11166383
The basal turnover of yeast branched-chain amino acid permease Bap2p requires its C-terminal tail.	2001 Jan 15	11164310
Secondary structure and post-translational modifications of the leucine-rich repeat protein PGIP (polygalacturonase-inhibiting protein) from Phaseolus vulgaris.	2001 Jan 16	11148052
Amino acid residues in ribonuclease MC1 from bitter gourd seeds which are essential for uridine specificity.	2001 Jan 16	11148047
Peptide models of the helical hydrophobic transmembrane segments of membrane proteins: interactions of acetyl-K2-(LA)12-K2-amide with phosphatidylethanolamine bilayer membranes.	2001 Jan 16	11148042
Strain is more important than electrostatic interaction in controlling the pKa of the catalytic group in aspartate aminotransferase.	2001 Jan 16	11148029
Substituting leucine for alanine-86 in the tether region of the iron-sulfur protein of the cytochrome bc1 complex affects the mobility of the [2Fe2S] domain.	2001 Jan 16	11148026
Identification and characterization of functional domains in a mixed lineage kinase LZK.	2001 Jan 19	11163770
PIST: a novel PDZ/coiled-coil domain binding partner for the rho-family GTPase TC10.	2001 Jan 19	11162552
Overexpression of 12-lipoxygenase causes cardiac fibroblast cell growth.	2001 Jan 19	11139476
Hepatitis B virus X protein activates transcription by bypassing CREB phosphorylation, not by stabilizing bZIP-DNA complexes.	2001 Jan 23	11170386
MgATP-Bound and nucleotide-free structures of a nitrogenase protein complex between the Leu 127 Delta-Fe-protein and the MoFe-protein.	2001 Jan 23	11170380
The bZIP-like motif of hnRNP C directs the nuclear accumulation of pre-mRNA and lethality in yeast.	2001 Jan 26	11162095
An antiparallel four-helix bundle orients the high-affinity RNA binding sites in hnRNP C: a mechanism for RNA chaperonin activity.	2001 Jan 26	11162094
Contryphans from Conus textile venom ducts.	2001 Jun	11137539
Cohesin-dockerin interaction in cellulosome assembly: a single hydroxyl group of a dockerin domain distinguishes between nonrecognition and high affinity recognition.	2001 Mar 30	11148206

Patents

Sample Use Guides

In Vivo Use Guide

leucine 700 mg/m2/dose by mouth three times a day

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 `Sat Dec 16 15:50:08 GMT 2023` Edited by `admin` on `Sat Dec 16 15:50:08 GMT 2023`
Record UNII	GMW67QNF9C
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LEUCINE

Official Name

English

leucine [INN]

Common Name

English

L-LEUCINE [USP-RS]

Common Name

English

LEUCINE [HSDB]

Common Name

English

VALINE IMPURITY C [EP IMPURITY]

Common Name

English

L-LEUCINE [FCC]

Common Name

English

LEUCINE [VANDF]

Common Name

English

LEUCINE, L-

Systematic Name

English

LEU

Common Name

English

LYSINE HYDROCHLORIDE IMPURITY A [EP IMPURITY]

Common Name

English

L-LEUCINE [JAN]

Common Name

English

LEUCINE [INCI]

Common Name

English

FEMA NO. 3297

Code

English

LEUCINE [EP MONOGRAPH]

Common Name

English

Leucine [WHO-DD]

Common Name

English

LEUCINE [USP MONOGRAPH]

Common Name

English

LEUCINE, L

Common Name

English

LEUCINE [II]

Common Name

English

(S)-2-AMINO-4-METHYLPENTANOIC ACID

Systematic Name

English

LEUCINE [USAN]

Common Name

English

NSC-46709

Code

English

L-LEUCINE

Systematic Name

English

LEUCINE [MI]

Common Name

English

LEUCINE [MART.]

Common Name

English

L-LEUCINE [FHFI]

Common Name

English

Classification Tree Code System Code

LOINC

53154-1