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

Details

Stereochemistry ABSOLUTE
Molecular Formula C6H14N2O2
Molecular Weight 146.1878
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LYSINE

SMILES

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

InChI

InChIKey=KDXKERNSBIXSRK-YFKPBYRVSA-N
InChI=1S/C6H14N2O2/c7-4-2-1-3-5(8)6(9)10/h5H,1-4,7-8H2,(H,9,10)/t5-/m0/s1

HIDE SMILES / InChI

Description
Curator's Comment:: description was created based on several sources, including https://www.drugs.com/npp/lysine.html | https://www.ncbi.nlm.nih.gov/pubmed/26252373

Lysing is an essential basic amino-acid encoded by codone AAA and AAG, and used in the biosynthesis of proteins. The daily requirement for lysine is 38 mg/kg body weight. The most rich source of lysine is fish, beef, chicken. In a clinical study lysine supplements was found to be an effective for reduction of occurrence, severity and healing time for recurrent HSV infection, however Cochrane Review concluded that the evidence is insufficient. Lysine was investigated for improving anxiety, ameliorating angina prectoris. Lysine acetylsalicylate has been used to treat pain and to detoxify the body after heroin use. Lysine clonixinate has been used for its analgesic properties for the treatment of migraine headaches and other painful conditions. However, limited clinical trials exist for these conditions.

Originator

Curator's Comment:: Lysine was first isolated from casein (a milk phosphoprotein) in 1889 by the German dentist Heinrich Drechsel

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
L-LYSINE MONOHYDRATE

Approved Use

Lysine has been studied for the prevention and treatment of herpes infections and cold sores.
Primary
L-LYSINE MONOHYDRATE

Approved Use

Lysine supplements may relieve effort-related angina pectoris.
Primary
L-LYSINE MONOHYDRATE

Approved Use

Lysine increases the intestinal absorption and reduces the renal elimination of calcium.
Primary
L-LYSINE MONOHYDRATE

Approved Use

Lysine is believed to exert anxiolytic effects by acting as a partial serotonin receptor 4 antagonist and as a partial benzodiazepine agonist
Palliative
L-LYSINE MONOHYDRATE

Approved Use

Lysine acetylsalicylate has been used to detoxify the body after heroin use.
Primary
NEOPROFEN

Approved Use

NeoProfen is indicated to close a clinically significant patent ductus arteriosus (PDA) in premature infants weighing between 500 and 1500 g, who are no more than 32 weeks gestational age when usual medical management (e.g., fluid restriction, diuretics, respiratory support, etc.) is ineffective. The clinical trial was conducted among infants with an asymptomatic PDA. However, the consequences beyond 8 weeks after treatment have not been evaluated; therefore, treatment should be reserved for infants with clear evidence of a clinically significant PDA.

Launch Date

1.14488639E12
PubMed

PubMed

TitleDatePubMed
Antibodies to SOX13 (ICA12) are associated with type 1 diabetes.
2001
The antioxidant system beta-D(+) glucose-glucose oxidase-catalase: tests for pyrogenicity and antigenicity.
2001
Identification of the alpha-aminoadipic semialdehyde dehydrogenase-phosphopantetheinyl transferase gene, the human ortholog of the yeast LYS5 gene.
2001 Apr
A systematic approach to the analysis of protein phosphorylation.
2001 Apr
Differences in sialic acid density in pathogenic and non-pathogenic Aspergillus species.
2001 Apr
Formation of 1,1'-iminodicarboxylic acid derivatives, 2,6-diketo-piperazine and dibenzodiazocine-2,6-dione by variations of multicomponent reactions.
2001 Apr
The fermentative production of L-lysine as an animal feed additive.
2001 Apr
Translational extracts active biologically in vitro obtained from eukaryotic monolayer cells: a versatile method for viral RNA studies.
2001 Apr
Effect of the degree of fatty acid unsaturation of rat heart mitochondria on their rates of H2O2 production and lipid and protein oxidative damage.
2001 Apr 15
The number of morphological synapses between neurons does not predict the strength of their physiological synaptic interactions: a study of dendrites in the nematode Ascaris suum.
2001 Apr 16
Properties of microtubules assembled from mammalian tubulin synthesized in Escherichia coli.
2001 Apr 17
Peflin and ALG-2, members of the penta-EF-hand protein family, form a heterodimer that dissociates in a Ca2+-dependent manner.
2001 Apr 27
Ethanol production from wheat straw hemicellulose hydrolysate by Pichia stipitis.
2001 Apr 27
Efficient preparation of natural and synthetic galactosides with a recombinant beta-1,4-galactosyltransferase-/UDP-4'-gal epimerase fusion protein.
2001 Apr 6
Biochemical and functional characterization of a molecule expressed by a subset of thymic medullary epithelial cells.
2001 Feb
Isolation of the Escherichia coli nucleoid.
2001 Feb
Detection of early gene expression changes during activation of human primary lymphocytes by in vitro synthesis of proteins from polysome-associated mRNAs.
2001 Feb
The effect of protease inhibitors on the two-dimensional electrophoresis pattern of red blood cell membranes.
2001 Feb
In vivo distribution and speciation of [114mIn]InCl3 in the Wistar rat.
2001 Feb
L-lysine reduces nonenzymatic glycation of glomerular basement membrane collagen and albuminuria in diabetic rats.
2001 Feb
Endotoxin, endotoxin-neutralizing-capacity, sCD14, sICAM-1, and cytokines in patients with various degrees of alcoholic liver disease.
2001 Feb
Hydrolysed protein accelerates the gastrointestinal transport of formula in preterm infants.
2001 Feb
Uptake and accumulation of exogenous docosahexaenoic acid by Chlorella.
2001 Jan
Endotoxemia and acute-phase proteins in major abdominal surgery.
2001 Jan
Influence of lysates of the salivary glands of Lutzomyia longipalpis on the development of a Leishmania-major-like parasite in the skin of the golden hamster.
2001 Jan
ESR detection of intraphagosomal superoxide in polymorphonuclear leukocytes using 5-(diethoxyphosphoryl)-5-methyl-l-pyrroline-N-oxide.
2001 Jan
The function of interdomain interactions in controlling nucleotide exchange rates in transducin.
2001 Jun 29
Endogenous formation of protein adducts with carcinogenic aldehydes: implications for oxidative stress.
2001 Jun 29
Chemical and biological evaluation of endotoxin contamination on natural rubber latex products.
2001 Jun 5
Enhancement of antitumor immune response in glioma models in mice by genetically modified dendritic cells pulsed with Semliki forest virus-mediated complementary DNA.
2001 Mar
Mechanisms of photoreceptor cell death in cancer-associated retinopathy.
2001 Mar
Investigating the surface expression of the renal type IIa Na+/Pi-cotransporter in Xenopus laevis oocytes.
2001 Mar 1
T cell-dependent antitumor immunity mediated by secondary lymphoid tissue chemokine: augmentation of dendritic cell-based immunotherapy.
2001 Mar 1
XIAP regulates Akt activity and caspase-3-dependent cleavage during cisplatin-induced apoptosis in human ovarian epithelial cancer cells.
2001 Mar 1
Characterisation of L-tryptophan transporters in human placenta: a comparison of brush border and basal membrane vesicles.
2001 Mar 1
Quantitative analysis of specific mRNA species in minute cell samples by RT-PCR and flow cytometry.
2001 Mar 1
Effects of initial particle size on the tableting properties of L-lysine monohydrochloride dihydrate powder.
2001 Mar 14
Enhancement of tumor lysate- and peptide-pulsed dendritic cell-based vaccines by the addition of foreign helper protein.
2001 Mar 15
Induction and clonal expansion of tumor-specific cytotoxic T lymphocytes from renal cell carcinoma patients after stimulation with autologous dendritic cells loaded with tumor cells.
2001 Mar 15
High pressure increases bactericidal activity and spectrum of lactoferrin, lactoferricin and nisin.
2001 Mar 20
Clinical studies of human papilloma vaccines in pre-invasive and invasive cancer.
2001 Mar 21
A simple method for midkine purification by affinity chromatography with a heavy chain variable domain (VH) fragment of antibody.
2001 Mar 28
Characterization of mouse brain-specific angiogenesis inhibitor 1 (BAI1) and phytanoyl-CoA alpha-hydroxylase-associated protein 1, a novel BAI1-binding protein.
2001 Mar 5
Influence of crystal shape on the tableting performance of L-lysine monohydrochloride dihydrate.
2001 May
Human corneal GlcNac 6-O-sulfotransferase and mouse intestinal GlcNac 6-O-sulfotransferase both produce keratan sulfate.
2001 May 11
Inhibition of cytosolic phospholipase A2 by annexin I. Specific interaction model and mapping of the interaction site.
2001 May 11
Isolation and characterization of senescence-induced cDNAs encoding deoxyhypusine synthase and eucaryotic translation initiation factor 5A from tomato.
2001 May 18
CYP2A6*6, a novel polymorphism in cytochrome p450 2A6, has a single amino acid substitution (R128Q) that inactivates enzymatic activity.
2001 May 25
The heme-regulated eukaryotic initiation factor 2alpha kinase. A potential regulatory target for control of protein synthesis by diffusible gases.
2001 May 4
Evidence that the peptidylprolyl isomerase domain of the hsp90-binding immunophilin FKBP52 is involved in both dynein interaction and glucocorticoid receptor movement to the nucleus.
2001 May 4
Patents

Sample Use Guides

In Vivo Use Guide
Lysin is an essential amino-acid. The daily requirement for lysine is 38 mg/kg body weight. The most rich source of lysine is fish, beef, chicken.
Route of Administration: Oral
In the in vitro study of herpes simplex virus (HSV) growth in tissue culture, arginine deficiency suppressed HSV growth. Maximum herpes growth (as measured by plaques counting) was observed in flasks, containing 10-20 ug/ml of arginine. The addition of 50 ug/ml of lysine to the flasks containing 2.5 and 5.0 ug/ml of arginine reduced the number of viable plaque-forming units (PFU) from 3300 and 48800 to less than 10.
Name Type Language
LYSINE
HSDB   II   INCI   INN   MART.   MI   USAN   VANDF   WHO-DD  
INN   USAN   INCI  
Official Name English
LYSINE [MI]
Common Name English
(+)-S-LYSINE
Common Name English
L-LYSINE
FHFI  
Systematic Name English
LYSINE [HSDB]
Common Name English
LYSINE [MART.]
Common Name English
LYSINE [USAN]
Common Name English
L-LYSINE [FHFI]
Common Name English
LYSINE [VANDF]
Common Name English
TYROSINE IMPURITY B [EP]
Common Name English
LYSINE [WHO-DD]
Common Name English
LYSINE [II]
Common Name English
LYSINE [INCI]
Common Name English
LYSINE [INN]
Common Name English
Classification Tree Code System Code
LOINC 32256-0
Created by admin on Sat Jun 26 09:50:30 UTC 2021 , Edited by admin on Sat Jun 26 09:50:30 UTC 2021
LOINC 56955-8
Created by admin on Sat Jun 26 09:50:30 UTC 2021 , Edited by admin on Sat Jun 26 09:50:30 UTC 2021
LOINC 22651-4
Created by admin on Sat Jun 26 09:50:30 UTC 2021 , Edited by admin on Sat Jun 26 09:50:30 UTC 2021
LOINC 15140-7
Created by admin on Sat Jun 26 09:50:30 UTC 2021 , Edited by admin on Sat Jun 26 09:50:30 UTC 2021
WHO-VATC QB05XB03
Created by admin on Sat Jun 26 09:50:31 UTC 2021 , Edited by admin on Sat Jun 26 09:50:31 UTC 2021
LOINC 13375-1
Created by admin on Sat Jun 26 09:50:30 UTC 2021 , Edited by admin on Sat Jun 26 09:50:30 UTC 2021
LOINC 2587-4
Created by admin on Sat Jun 26 09:50:30 UTC 2021 , Edited by admin on Sat Jun 26 09:50:30 UTC 2021
LOINC 13769-5
Created by admin on Sat Jun 26 09:50:30 UTC 2021 , Edited by admin on Sat Jun 26 09:50:30 UTC 2021
LOINC 2586-6
Created by admin on Sat Jun 26 09:50:30 UTC 2021 , Edited by admin on Sat Jun 26 09:50:30 UTC 2021
LOINC 47689-5
Created by admin on Sat Jun 26 09:50:30 UTC 2021 , Edited by admin on Sat Jun 26 09:50:30 UTC 2021
LOINC 20650-8
Created by admin on Sat Jun 26 09:50:30 UTC 2021 , Edited by admin on Sat Jun 26 09:50:30 UTC 2021
LOINC 47693-7
Created by admin on Sat Jun 26 09:50:30 UTC 2021 , Edited by admin on Sat Jun 26 09:50:30 UTC 2021
LOINC 47694-5
Created by admin on Sat Jun 26 09:50:30 UTC 2021 , Edited by admin on Sat Jun 26 09:50:30 UTC 2021
CFR 21 CFR 172.320
Created by admin on Sat Jun 26 09:50:30 UTC 2021 , Edited by admin on Sat Jun 26 09:50:30 UTC 2021
LOINC 22713-2
Created by admin on Sat Jun 26 09:50:30 UTC 2021 , Edited by admin on Sat Jun 26 09:50:30 UTC 2021
LOINC 47692-9
Created by admin on Sat Jun 26 09:50:30 UTC 2021 , Edited by admin on Sat Jun 26 09:50:30 UTC 2021
LOINC 25952-3
Created by admin on Sat Jun 26 09:50:30 UTC 2021 , Edited by admin on Sat Jun 26 09:50:30 UTC 2021
LOINC 47695-2
Created by admin on Sat Jun 26 09:50:30 UTC 2021 , Edited by admin on Sat Jun 26 09:50:30 UTC 2021
WHO-ATC B05XB03
Created by admin on Sat Jun 26 09:50:30 UTC 2021 , Edited by admin on Sat Jun 26 09:50:30 UTC 2021
LOINC 44335-8
Created by admin on Sat Jun 26 09:50:30 UTC 2021 , Edited by admin on Sat Jun 26 09:50:30 UTC 2021
LOINC 2585-8
Created by admin on Sat Jun 26 09:50:30 UTC 2021 , Edited by admin on Sat Jun 26 09:50:30 UTC 2021
LOINC 30048-3
Created by admin on Sat Jun 26 09:50:30 UTC 2021 , Edited by admin on Sat Jun 26 09:50:30 UTC 2021
LOINC 13404-9
Created by admin on Sat Jun 26 09:50:30 UTC 2021 , Edited by admin on Sat Jun 26 09:50:30 UTC 2021
LOINC 15136-5
Created by admin on Sat Jun 26 09:50:30 UTC 2021 , Edited by admin on Sat Jun 26 09:50:30 UTC 2021
LOINC 55935-1
Created by admin on Sat Jun 26 09:50:30 UTC 2021 , Edited by admin on Sat Jun 26 09:50:30 UTC 2021
LOINC 88018-7
Created by admin on Sat Jun 26 09:50:30 UTC 2021 , Edited by admin on Sat Jun 26 09:50:30 UTC 2021
DSLD 172 (Number of products:1388)
Created by admin on Sat Jun 26 09:50:30 UTC 2021 , Edited by admin on Sat Jun 26 09:50:30 UTC 2021
LOINC 27333-4
Created by admin on Sat Jun 26 09:50:30 UTC 2021 , Edited by admin on Sat Jun 26 09:50:30 UTC 2021
WHO-VATC QA12AA09
Created by admin on Sat Jun 26 09:50:31 UTC 2021 , Edited by admin on Sat Jun 26 09:50:31 UTC 2021
LOINC 17230-4
Created by admin on Sat Jun 26 09:50:30 UTC 2021 , Edited by admin on Sat Jun 26 09:50:30 UTC 2021
LOINC 27107-2
Created by admin on Sat Jun 26 09:50:30 UTC 2021 , Edited by admin on Sat Jun 26 09:50:30 UTC 2021
LOINC 25464-9
Created by admin on Sat Jun 26 09:50:30 UTC 2021 , Edited by admin on Sat Jun 26 09:50:30 UTC 2021
JECFA EVALUATION L-LYSINE
Created by admin on Sat Jun 26 09:50:30 UTC 2021 , Edited by admin on Sat Jun 26 09:50:30 UTC 2021
LOINC 32255-2
Created by admin on Sat Jun 26 09:50:30 UTC 2021 , Edited by admin on Sat Jun 26 09:50:30 UTC 2021
LOINC 2584-1
Created by admin on Sat Jun 26 09:50:30 UTC 2021 , Edited by admin on Sat Jun 26 09:50:30 UTC 2021
LOINC 22679-5
Created by admin on Sat Jun 26 09:50:30 UTC 2021 , Edited by admin on Sat Jun 26 09:50:30 UTC 2021
CFR 21 CFR 310.537
Created by admin on Sat Jun 26 09:50:30 UTC 2021 , Edited by admin on Sat Jun 26 09:50:30 UTC 2021
LOINC 27304-5
Created by admin on Sat Jun 26 09:50:30 UTC 2021 , Edited by admin on Sat Jun 26 09:50:30 UTC 2021
LOINC 25953-1
Created by admin on Sat Jun 26 09:50:30 UTC 2021 , Edited by admin on Sat Jun 26 09:50:30 UTC 2021
LOINC 47690-3
Created by admin on Sat Jun 26 09:50:30 UTC 2021 , Edited by admin on Sat Jun 26 09:50:30 UTC 2021
LOINC 47691-1
Created by admin on Sat Jun 26 09:50:30 UTC 2021 , Edited by admin on Sat Jun 26 09:50:30 UTC 2021
NCI_THESAURUS C68442
Created by admin on Sat Jun 26 09:50:31 UTC 2021 , Edited by admin on Sat Jun 26 09:50:31 UTC 2021
Code System Code Type Description
HSDB
2108
Created by admin on Sat Jun 26 09:50:30 UTC 2021 , Edited by admin on Sat Jun 26 09:50:30 UTC 2021
PRIMARY
INN
6166
Created by admin on Sat Jun 26 09:50:30 UTC 2021 , Edited by admin on Sat Jun 26 09:50:30 UTC 2021
PRIMARY
DRUG BANK
DB00123
Created by admin on Sat Jun 26 09:50:30 UTC 2021 , Edited by admin on Sat Jun 26 09:50:30 UTC 2021
PRIMARY
MERCK INDEX
M6967
Created by admin on Sat Jun 26 09:50:30 UTC 2021 , Edited by admin on Sat Jun 26 09:50:30 UTC 2021
PRIMARY Merck Index
EVMPD
SUB36688
Created by admin on Sat Jun 26 09:50:30 UTC 2021 , Edited by admin on Sat Jun 26 09:50:30 UTC 2021
PRIMARY
ECHA (EC/EINECS)
200-294-2
Created by admin on Sat Jun 26 09:50:30 UTC 2021 , Edited by admin on Sat Jun 26 09:50:30 UTC 2021
PRIMARY
EVMPD
SUB08629MIG
Created by admin on Sat Jun 26 09:50:30 UTC 2021 , Edited by admin on Sat Jun 26 09:50:30 UTC 2021
PRIMARY
PUBCHEM
5962
Created by admin on Sat Jun 26 09:50:31 UTC 2021 , Edited by admin on Sat Jun 26 09:50:31 UTC 2021
PRIMARY
EPA CompTox
56-87-1
Created by admin on Sat Jun 26 09:50:30 UTC 2021 , Edited by admin on Sat Jun 26 09:50:30 UTC 2021
PRIMARY
CAS
56-87-1
Created by admin on Sat Jun 26 09:50:30 UTC 2021 , Edited by admin on Sat Jun 26 09:50:30 UTC 2021
PRIMARY
FDA UNII
K3Z4F929H6
Created by admin on Sat Jun 26 09:50:30 UTC 2021 , Edited by admin on Sat Jun 26 09:50:30 UTC 2021
PRIMARY
ChEMBL
CHEMBL8085
Created by admin on Sat Jun 26 09:50:30 UTC 2021 , Edited by admin on Sat Jun 26 09:50:30 UTC 2021
PRIMARY
NCI_THESAURUS
C1505
Created by admin on Sat Jun 26 09:50:30 UTC 2021 , Edited by admin on Sat Jun 26 09:50:30 UTC 2021
CONCEPT Dietary Supplement
DRUG CENTRAL
1622
Created by admin on Sat Jun 26 09:50:30 UTC 2021 , Edited by admin on Sat Jun 26 09:50:30 UTC 2021
PRIMARY
NCI_THESAURUS
C29171
Created by admin on Sat Jun 26 09:50:30 UTC 2021 , Edited by admin on Sat Jun 26 09:50:30 UTC 2021
PRIMARY
WIKIPEDIA
LYSINE
Created by admin on Sat Jun 26 09:50:31 UTC 2021 , Edited by admin on Sat Jun 26 09:50:31 UTC 2021
PRIMARY
RXCUI
6536
Created by admin on Sat Jun 26 09:50:31 UTC 2021 , Edited by admin on Sat Jun 26 09:50:31 UTC 2021
PRIMARY RxNorm
MESH
D008239
Created by admin on Sat Jun 26 09:50:30 UTC 2021 , Edited by admin on Sat Jun 26 09:50:30 UTC 2021
PRIMARY