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 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LEUCINE

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

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.

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
15.9 μg/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
48.63 μg × h/mL
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
1.49 h
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
PubMed

PubMed

TitleDatePubMed
Characterization of L-leucine transport system in brush border membranes from human and rabbit small intestine.
1999 Nov
Primary structure, functional characteristics and tissue expression pattern of human ATA2, a subtype of amino acid transport system A.
2000 Jul 31
Expression pattern and gene characterization of asporin. a newly discovered member of the leucine-rich repeat protein family.
2001 Apr 13
Consensus and variant cAMP-regulated enhancers have distinct CREB-binding properties.
2001 Apr 13
Stem cell factor presentation to c-Kit. Identification of a basolateral targeting domain.
2001 Apr 20
Different usage of the glycosaminoglycan attachment sites of biglycan.
2001 Apr 20
An intrahelical salt bridge within the trigger site stabilizes the GCN4 leucine zipper.
2001 Apr 27
Myomegalin is a novel protein of the golgi/centrosome that interacts with a cyclic nucleotide phosphodiesterase.
2001 Apr 6
Determination of binding constant of transcription factor AP-1 and DNA. Application of inhibitors.
2001 Feb
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
Increased albumin and fibrinogen synthesis in hemodialysis patients with normal nutritional status.
2001 Feb
A novel syndrome affecting multiple mitochondrial functions, located by microcell-mediated transfer to chromosome 2p14-2p13.
2001 Feb
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
Defective intracellular transport and processing of JAG1 missense mutations in Alagille syndrome.
2001 Feb 15
Tryptophan- and dileucine-based endocytosis signals in the neonatal Fc receptor.
2001 Feb 16
Fragmentary form of thermostable leucine dehydrogenase of Bacillus stearothermophilus: its construction and reconstitution of active fragmentary enzyme.
2001 Feb 2
Chloroplast RNA editing required for functional acetyl-CoA carboxylase in plants.
2001 Feb 9
V89L polymorphism of type-2, 5-alpha reductase enzyme gene predicts prostate cancer presence and progression.
2001 Jan
Simvastatin inhibits noradrenaline-induced hypertrophy of cultured neonatal rat cardiomyocytes.
2001 Jan
Proteoglycan synthesis is increased in cells with impaired clathrin-dependent endocytosis.
2001 Jan
Effect of elective abdominal surgery on human colon protein synthesis in situ.
2001 Jan
Quantifying nutrient production by the microbial symbionts in an aphid.
2001 Jan
Isolation, characterization, and expression analysis of zebrafish large Mafs.
2001 Jan
Activation of caspase-3 by lysosomal cysteine proteases and its role in 2,2'-azobis-(2-amidinopropane)dihydrochloride (AAPH)-induced apoptosis in HL-60 cells.
2001 Jan
High sensitivity of Nrf2 knockout mice to acetaminophen hepatotoxicity associated with decreased expression of ARE-regulated drug metabolizing enzymes and antioxidant genes.
2001 Jan
Selectively labeling the heterologous protein in Escherichia coli for NMR studies: a strategy to speed up NMR spectroscopy.
2001 Jan
Reactive oxygen species mediate alpha-adrenergic receptor-stimulated hypertrophy in adult rat ventricular myocytes.
2001 Jan
Intestinal aminooligopeptidase in diabetic BioBreed rat: altered posttranslational processing and trafficking.
2001 Jan
Double blind, randomised, placebo controlled study of a platelet activating factor antagonist, lexipafant, in the treatment and prevention of organ failure in predicted severe acute pancreatitis.
2001 Jan
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
Central neurocytomas express photoreceptor differentiation.
2001 Jan 1
The destabilization of human GCAP1 by a proline to leucine mutation might cause cone-rod dystrophy.
2001 Jan 1
Amino acid residues in ribonuclease MC1 from bitter gourd seeds which are essential for uridine specificity.
2001 Jan 16
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
Identification and characterization of functional domains in a mixed lineage kinase LZK.
2001 Jan 19
PIST: a novel PDZ/coiled-coil domain binding partner for the rho-family GTPase TC10.
2001 Jan 19
Hepatitis B virus X protein activates transcription by bypassing CREB phosphorylation, not by stabilizing bZIP-DNA complexes.
2001 Jan 23
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
An antiparallel four-helix bundle orients the high-affinity RNA binding sites in hnRNP C: a mechanism for RNA chaperonin activity.
2001 Jan 26
Contributions of Torpedo nicotinic acetylcholine receptor gamma Trp-55 and delta Trp-57 to agonist and competitive antagonist function.
2001 Jan 26
Structure-function analysis of TFII-I. Roles of the N-terminal end, basic region, and I-repeats.
2001 Mar 16
The DNA binding properties of the parsley bZIP transcription factor CPRF4a are regulated by light.
2001 Mar 2
Core LXXLL motif sequences in CREB-binding protein, SRC1, and RIP140 define affinity and selectivity for steroid and retinoid receptors.
2001 Mar 2
Role of two histidines in the (6-4) photolyase reaction.
2001 Mar 30
Prostaglandin endoperoxide H synthase-1: the functions of cyclooxygenase active site residues in the binding, positioning, and oxygenation of arachidonic acid.
2001 Mar 30
Mutational definition of RNA-binding and protein-protein interaction domains of heterogeneous nuclear RNP C1.
2001 Mar 9
Patents

Sample Use Guides

leucine 700 mg/m2/dose by mouth three times a day
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 Sat Dec 16 15:50:08 UTC 2023
Edited
by admin
on Sat Dec 16 15:50:08 UTC 2023
Record UNII
GMW67QNF9C
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LEUCINE
EP   HSDB   II   INCI   INN   MART.   MI   USAN   USP   VANDF   WHO-DD  
INN   INCI   USAN  
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
FCC   FHFI   USP-RS  
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
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LOINC 15131-6
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NCI_THESAURUS C68442
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LOINC 47683-8
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LOINC 75268-3
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LOINC 2562-7
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LOINC 53152-5
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LOINC 47680-4
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LOINC 29293-8
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LOINC 47681-2
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LOINC 22693-6
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LOINC 57994-6
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DSLD 2188 (Number of products:87)
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LOINC 57996-1
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LOINC 32783-3
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LOINC 2561-9
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LOINC 72899-8
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LOINC 47682-0
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LOINC 49834-5
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LOINC 2559-3
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LOINC 21056-7
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DSLD 173 (Number of products:424)
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LOINC 47685-3
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LOINC 20649-0
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LOINC 53393-5
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LOINC 21057-5
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LOINC 44334-1
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LOINC 30053-3
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LOINC 47679-6
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CFR 21 CFR 172.320
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LOINC 2560-1
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LOINC 13403-1
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LOINC 45214-4
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LOINC 29284-7
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LOINC 32253-7
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FDA ORPHAN DRUG 33588
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DSLD 2315 (Number of products:2347)
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LOINC 25942-4
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LOINC 56954-1
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LOINC 17074-6
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LOINC 25460-7
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LOINC 13768-7
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LOINC 22719-9
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LOINC 25941-6
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LOINC 2558-5
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JECFA EVALUATION 1423
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LOINC 53397-6
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LOINC 26710-4
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FDA ORPHAN DRUG 93095
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LOINC 27323-5
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LOINC 9412-8
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LOINC 32254-5
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LOINC 55933-6
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LOINC 57995-3
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LOINC 15138-1
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Code System Code Type Description
WIKIPEDIA
LEUCINE
Created by admin on Sat Dec 16 15:50:10 UTC 2023 , Edited by admin on Sat Dec 16 15:50:10 UTC 2023
PRIMARY
SMS_ID
100000092265
Created by admin on Sat Dec 16 15:50:10 UTC 2023 , Edited by admin on Sat Dec 16 15:50:10 UTC 2023
PRIMARY
RS_ITEM_NUM
1357001
Created by admin on Sat Dec 16 15:50:10 UTC 2023 , Edited by admin on Sat Dec 16 15:50:10 UTC 2023
PRIMARY
EVMPD
SUB21983
Created by admin on Sat Dec 16 15:50:10 UTC 2023 , Edited by admin on Sat Dec 16 15:50:10 UTC 2023
PRIMARY
CHEBI
25017
Created by admin on Sat Dec 16 15:50:10 UTC 2023 , Edited by admin on Sat Dec 16 15:50:10 UTC 2023
PRIMARY
EVMPD
SUB08446MIG
Created by admin on Sat Dec 16 15:50:10 UTC 2023 , Edited by admin on Sat Dec 16 15:50:10 UTC 2023
PRIMARY
MERCK INDEX
m6773
Created by admin on Sat Dec 16 15:50:10 UTC 2023 , Edited by admin on Sat Dec 16 15:50:10 UTC 2023
PRIMARY Merck Index
CHEBI
57427
Created by admin on Sat Dec 16 15:50:10 UTC 2023 , Edited by admin on Sat Dec 16 15:50:10 UTC 2023
PRIMARY
HSDB
7799
Created by admin on Sat Dec 16 15:50:10 UTC 2023 , Edited by admin on Sat Dec 16 15:50:10 UTC 2023
PRIMARY
ECHA (EC/EINECS)
200-522-0
Created by admin on Sat Dec 16 15:50:10 UTC 2023 , Edited by admin on Sat Dec 16 15:50:10 UTC 2023
PRIMARY
DRUG BANK
DB00149
Created by admin on Sat Dec 16 15:50:10 UTC 2023 , Edited by admin on Sat Dec 16 15:50:10 UTC 2023
PRIMARY
GRAS Notification (GRN No.)
523
Created by admin on Sat Dec 16 15:50:10 UTC 2023 , Edited by admin on Sat Dec 16 15:50:10 UTC 2023
PRIMARY
MESH
D007930
Created by admin on Sat Dec 16 15:50:10 UTC 2023 , Edited by admin on Sat Dec 16 15:50:10 UTC 2023
PRIMARY
CHEBI
15603
Created by admin on Sat Dec 16 15:50:10 UTC 2023 , Edited by admin on Sat Dec 16 15:50:10 UTC 2023
PRIMARY
EPA CompTox
DTXSID9023203
Created by admin on Sat Dec 16 15:50:10 UTC 2023 , Edited by admin on Sat Dec 16 15:50:10 UTC 2023
PRIMARY
INN
6165
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PRIMARY
DRUG CENTRAL
1557
Created by admin on Sat Dec 16 15:50:10 UTC 2023 , Edited by admin on Sat Dec 16 15:50:10 UTC 2023
PRIMARY
PUBCHEM
6106
Created by admin on Sat Dec 16 15:50:10 UTC 2023 , Edited by admin on Sat Dec 16 15:50:10 UTC 2023
PRIMARY
RXCUI
6308
Created by admin on Sat Dec 16 15:50:10 UTC 2023 , Edited by admin on Sat Dec 16 15:50:10 UTC 2023
PRIMARY RxNorm
ChEMBL
CHEMBL291962
Created by admin on Sat Dec 16 15:50:10 UTC 2023 , Edited by admin on Sat Dec 16 15:50:10 UTC 2023
PRIMARY
DAILYMED
GMW67QNF9C
Created by admin on Sat Dec 16 15:50:10 UTC 2023 , Edited by admin on Sat Dec 16 15:50:10 UTC 2023
PRIMARY
CHEBI
30006
Created by admin on Sat Dec 16 15:50:10 UTC 2023 , Edited by admin on Sat Dec 16 15:50:10 UTC 2023
PRIMARY
FDA UNII
GMW67QNF9C
Created by admin on Sat Dec 16 15:50:10 UTC 2023 , Edited by admin on Sat Dec 16 15:50:10 UTC 2023
PRIMARY
JECFA MONOGRAPH
1413
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PRIMARY
NSC
46709
Created by admin on Sat Dec 16 15:50:10 UTC 2023 , Edited by admin on Sat Dec 16 15:50:10 UTC 2023
PRIMARY
CAS
61-90-5
Created by admin on Sat Dec 16 15:50:10 UTC 2023 , Edited by admin on Sat Dec 16 15:50:10 UTC 2023
PRIMARY
GRAS Notification (GRN No.)
308
Created by admin on Sat Dec 16 15:50:10 UTC 2023 , Edited by admin on Sat Dec 16 15:50:10 UTC 2023
PRIMARY
NCI_THESAURUS
C29599
Created by admin on Sat Dec 16 15:50:10 UTC 2023 , Edited by admin on Sat Dec 16 15:50:10 UTC 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
Related Record Type Details
METABOLITE -> PARENT
METABOLITE -> PARENT
Related Record Type Details
IMPURITY -> PARENT
impurity A at 570 nm: maximum 0.8 per cent
CHROMATOGRAPHIC PURITY (TLC)
EP
PARENT -> IMPURITY
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (TLC)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (TLC)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (TLC)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (TLC)
EP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (TLC)
EP
Related Record Type Details
ACTIVE MOIETY