LYSINE

US Previously Marketed

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C6H14N2O2
Molecular Weight	146.1876
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

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

Molecular Formula	C6H14N2O2
Molecular Weight	146.1876
Charge	0
Count

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

Description
Sources: https://www.nap.edu/read/10490/chapter/12
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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Serotonin 4 (5-HT4) receptor 38 Target ID: CHEMBL1875 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28103616	Antagonist 2849
GABA-A receptor; anion channel 203 Target ID: CHEMBL2093872 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8587651	Agonist 2752

Conditions

Condition	Modality	Highest Phase	Product
Herpes simplex infection 28 Sources: https://www.drugs.com/npp/lysine.html	Primary	Natural Metabolite	L-LYSINE MONOHYDRATE Approved Use Lysine has been studied for the prevention and treatment of herpes infections and cold sores.
Angina pectoris 110 Sources: https://www.drugs.com/npp/lysine.html	Primary	Natural Metabolite	L-LYSINE MONOHYDRATE Approved Use Lysine supplements may relieve effort-related angina pectoris.
Osteoporosis 101 Sources: https://www.drugs.com/npp/lysine.html	Primary	Natural Metabolite	L-LYSINE MONOHYDRATE Approved Use Lysine increases the intestinal absorption and reduces the renal elimination of calcium.
Anxiety 275 Sources: https://www.drugs.com/npp/lysine.html	Primary	Natural Metabolite	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
Heroin dependence 10 Sources: https://www.drugs.com/npp/lysine.html	Palliative	Natural Metabolite	L-LYSINE MONOHYDRATE Approved Use Lysine acetylsalicylate has been used to detoxify the body after heroin use.
Patent ductus arteriosus 8 Sources: https://www.drugs.com/pro/neoprofen.html	Primary	Approved 8583	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 2006

PubMed

Title	Date	PubMed
Antibodies to SOX13 (ICA12) are associated with type 1 diabetes.	2001	11264788
The antioxidant system beta-D(+) glucose-glucose oxidase-catalase: tests for pyrogenicity and antigenicity.	2001	11247273
Protein profiling comes of age.	2001	11182890
Identification of the alpha-aminoadipic semialdehyde dehydrogenase-phosphopantetheinyl transferase gene, the human ortholog of the yeast LYS5 gene.	2001 Apr	11286508
Differences in sialic acid density in pathogenic and non-pathogenic Aspergillus species.	2001 Apr	11283283
Formation of 1,1'-iminodicarboxylic acid derivatives, 2,6-diketo-piperazine and dibenzodiazocine-2,6-dione by variations of multicomponent reactions.	2001 Apr	11233828
The fermentative production of L-lysine as an animal feed additive.	2001 Apr	11233822
Translational extracts active biologically in vitro obtained from eukaryotic monolayer cells: a versatile method for viral RNA studies.	2001 Apr	11226564
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	11240164
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	11268011
Properties of microtubules assembled from mammalian tubulin synthesized in Escherichia coli.	2001 Apr 17	11294652
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	11278427
Ethanol production from wheat straw hemicellulose hydrolysate by Pichia stipitis.	2001 Apr 27	11267696
Biochemical and functional characterization of a molecule expressed by a subset of thymic medullary epithelial cells.	2001 Feb	11292258
Isolation of the Escherichia coli nucleoid.	2001 Feb	11278063
Detection of early gene expression changes during activation of human primary lymphocytes by in vitro synthesis of proteins from polysome-associated mRNAs.	2001 Feb	11266628
The effect of protease inhibitors on the two-dimensional electrophoresis pattern of red blood cell membranes.	2001 Feb	11258769
In vivo distribution and speciation of [114mIn]InCl3 in the Wistar rat.	2001 Feb	11253025
L-lysine reduces nonenzymatic glycation of glomerular basement membrane collagen and albuminuria in diabetic rats.	2001 Feb	11244310
Endotoxin, endotoxin-neutralizing-capacity, sCD14, sICAM-1, and cytokines in patients with various degrees of alcoholic liver disease.	2001 Feb	11236841
Hydrolysed protein accelerates the gastrointestinal transport of formula in preterm infants.	2001 Feb	11236051
Combination of HPLC and solid-phase binding assay for isolation and purification of MHC class I and associated peptides using a bladder tumour cell line.	2001 Feb	11180296
Identification of novel hypocholesterolemic peptides derived from bovine milk beta-lactoglobulin.	2001 Feb 16	11178953
Identification of a candidate integrin-fraction associated with the activated form of the PDGF-receptor.	2001 Feb 23	11181089
Uptake and accumulation of exogenous docosahexaenoic acid by Chlorella.	2001 Jan	11272831
Endotoxemia and acute-phase proteins in major abdominal surgery.	2001 Jan	11248174
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	11235554
ESR detection of intraphagosomal superoxide in polymorphonuclear leukocytes using 5-(diethoxyphosphoryl)-5-methyl-l-pyrroline-N-oxide.	2001 Jan	11234998
A novel protein-RNA binding assay: functional interactions of the foot-and-mouth disease virus internal ribosome entry site with cellular proteins.	2001 Jan	11214173
Inhibition of the nitrosothiol production of cultured osteoarthritic chondrocytes by rhein, cortisol and diclofenac.	2001 Jan	11178941
Continuous cell introduction for the analysis of individual cells by capillary electrophoresis.	2001 Jan 1	11195493
A single-chain variable region immunoglobulin library from the abomasal lymph node of sheep infected with the gastrointestinal nematode parasite Haemonchus contortus.	2001 Jan 26	11182152
Purification of recombinant green fluorescent protein using chromatofocusing with a pH gradient composed of multiple stepwise fronts.	2001 Jan-Feb	11170493
Endogenous formation of protein adducts with carcinogenic aldehydes: implications for oxidative stress.	2001 Jun 29	11283024
Chemical and biological evaluation of endotoxin contamination on natural rubber latex products.	2001 Jun 5	11255197
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	11235953
Mechanisms of photoreceptor cell death in cancer-associated retinopathy.	2001 Mar	11222531
Post-transcriptional effects of extracellular pH on tumour necrosis factor-alpha production in RAW 246.7 and J774 A.1 cells.	2001 Mar	11222111
Characterisation of L-tryptophan transporters in human placenta: a comparison of brush border and basal membrane vesicles.	2001 Mar 1	11230513
Quantitative analysis of specific mRNA species in minute cell samples by RT-PCR and flow cytometry.	2001 Mar 1	11226479
Effects of initial particle size on the tableting properties of L-lysine monohydrochloride dihydrate powder.	2001 Mar 14	11250107
Enhancement of tumor lysate- and peptide-pulsed dendritic cell-based vaccines by the addition of foreign helper protein.	2001 Mar 15	11289139
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	11275975
High pressure increases bactericidal activity and spectrum of lactoferrin, lactoferricin and nisin.	2001 Mar 20	11294354
Clinical studies of human papilloma vaccines in pre-invasive and invasive cancer.	2001 Mar 21	11257391
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	11245925
Western blotting as a method for studying cell-biomaterial interactions: the role of protein collection.	2001 Mar 5	11189044
Influence of crystal shape on the tableting performance of L-lysine monohydrochloride dihydrate.	2001 May	11288101
Isolation and characterization of senescence-induced cDNAs encoding deoxyhypusine synthase and eucaryotic translation initiation factor 5A from tomato.	2001 May 18	11278418
The heme-regulated eukaryotic initiation factor 2alpha kinase. A potential regulatory target for control of protein synthesis by diffusible gases.	2001 May 4	11278914

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 Vitro Use Guide

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.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:35:16 GMT 2025` Edited by `admin` on `Mon Mar 31 17:35:16 GMT 2025`
Record UNII	K3Z4F929H6
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

L-LYSINE

Preferred Name

English

LYSINE

Official Name

English

LYSINE [MI]

Common Name

English

(+)-S-LYSINE

Common Name

English

Lysine [WHO-DD]

Common 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

LYSINE [II]

Common Name

English

TYROSINE IMPURITY B [EP IMPURITY]

Common Name

English

lysine [INN]

Common Name

English

Classification Tree Code System Code

LOINC

32256-0