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

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 39 Target ID: CHEMBL1875 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28103616	Antagonist 2760
GABA-A receptor; anion channel 202 Target ID: CHEMBL2093872 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8587651	Agonist 2662

Conditions

Condition	Modality	Highest Phase	Product
Herpes simplex infection 27 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 94 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 97 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 266 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 8360	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

Title	Date	PubMed
Antibodies to SOX13 (ICA12) are associated with type 1 diabetes.	2001	11264788
Thermal and enzymatic recovering of proteins from untanned leather waste.	2001	11150136
Assays for mitogen-activated protein kinase (MAPK) subtypes and MAPK activating protein kinase-2 (MAPKAP K-2) using a common cell lysate.	2001	11100471
Identification of the alpha-aminoadipic semialdehyde dehydrogenase-phosphopantetheinyl transferase gene, the human ortholog of the yeast LYS5 gene.	2001 Apr	11286508
A systematic approach to the analysis of protein phosphorylation.	2001 Apr	11283598
Differences in sialic acid density in pathogenic and non-pathogenic Aspergillus species.	2001 Apr	11283283
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
Glycophorin as a receptor for Escherichia coli alpha-hemolysin in erythrocytes.	2001 Apr 20	11134007
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
Efficient preparation of natural and synthetic galactosides with a recombinant beta-1,4-galactosyltransferase-/UDP-4'-gal epimerase fusion protein.	2001 Apr 6	11281786
Biochemical and functional characterization of a molecule expressed by a subset of thymic medullary epithelial cells.	2001 Feb	11292258
In vivo distribution and speciation of [114mIn]InCl3 in the Wistar rat.	2001 Feb	11253025
How does endotoxin trigger inflammation in otitis media with effusion?	2001 Feb	11210878
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
Purification and structure elucidation of the N-acetylbacillosamine-containing polysaccharide from Bacillus licheniformis ATCC 9945.	2001 Feb	11168428
Rapid polyubiquitination and proteasomal degradation of a mutant form of NAD(P)H:quinone oxidoreductase 1.	2001 Feb	11160862
Increased L-arginine uptake and inducible nitric oxide synthase activity in aortas of rats with heart failure.	2001 Feb	11158987
Evidence that fragile X mental retardation protein is a negative regulator of translation.	2001 Feb 15	11157796
Identification of the main ubiquitination site in human erythroid alpha-spectrin.	2001 Feb 2	11165260
Purification and biophysical characterization of a minimal functional domain and of an N-terminal Zn2+-binding fragment from the human papillomavirus type 16 E6 protein.	2001 Feb 6	11170444
Uptake and accumulation of exogenous docosahexaenoic acid by Chlorella.	2001 Jan	11272831
Endotoxemia and acute-phase proteins in major abdominal surgery.	2001 Jan	11248174
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
Purification, characterization and developmental expression of chick (Gallus domesticus) liver PSP protein.	2001 Jan	11163312
Charge-dependent binding of polymeric IgA1 to human mesangial cells in IgA nephropathy.	2001 Jan	11135081
Increased stability of nucleophosmin/B23 in anti-apoptotic effect of ras during serum deprivation.	2001 Jan	11125022
Therapy of HPV 16-associated carcinoma with dendritic cell-based vaccines: in vitro priming of the effector cell responses by DC pulsed with tumour lysates and synthetic RAHYNIVTF peptide.	2001 Jan	11115616
RNA interference is mediated by 21- and 22-nucleotide RNAs.	2001 Jan 15	11157775
Identification of lysine 346 as a functionally important residue for pyridoxal 5'-phosphate binding and catalysis in lysine 2, 3-aminomutase from Bacillus subtilis.	2001 Jan 16	11148055
Panaxagin, a new protein from Chinese ginseng possesses anti-fungal, anti-viral, translation-inhibiting and ribonuclease activities.	2001 Jan 5	11205866
Bullous pemphigoid: interaction of interleukin 5, anti-basement membrane zone antibodies and eosinophils. A preliminary observation.	2001 Jan 7	11145840
Purification of recombinant green fluorescent protein using chromatofocusing with a pH gradient composed of multiple stepwise fronts.	2001 Jan-Feb	11170493
The function of interdomain interactions in controlling nucleotide exchange rates in transducin.	2001 Jun 29	11290746
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
Post-transcriptional effects of extracellular pH on tumour necrosis factor-alpha production in RAW 246.7 and J774 A.1 cells.	2001 Mar	11222111
Investigating the surface expression of the renal type IIa Na+/Pi-cotransporter in Xenopus laevis oocytes.	2001 Mar 1	11284206
Quantitative analysis of specific mRNA species in minute cell samples by RT-PCR and flow cytometry.	2001 Mar 1	11226479
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
A simple method for midkine purification by affinity chromatography with a heavy chain variable domain (VH) fragment of antibody.	2001 Mar 28	11282403
Influence of crystal shape on the tableting performance of L-lysine monohydrochloride dihydrate.	2001 May	11288101
Human corneal GlcNac 6-O-sulfotransferase and mouse intestinal GlcNac 6-O-sulfotransferase both produce keratan sulfate.	2001 May 11	11278593
Inhibition of cytosolic phospholipase A2 by annexin I. Specific interaction model and mapping of the interaction site.	2001 May 11	11278580
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.

Name

Type

Language

LYSINE

Official Name

English

LYSINE [MI]

Common Name

English

(+)-S-LYSINE

Common Name

English

Lysine [WHO-DD]

Common Name

English

L-LYSINE

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

LYSINE [II]

Common Name

English

LYSINE [INCI]

Common Name

English

TYROSINE IMPURITY B [EP IMPURITY]

Common Name

English

lysine [INN]

Common Name

English

Classification Tree Code System Code

LOINC

32256-0