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 2778
GABA-A receptor; anion channel 202 Target ID: CHEMBL2093872 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8587651	Agonist 2678

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 106 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 267 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 8429	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
The antioxidant system beta-D(+) glucose-glucose oxidase-catalase: tests for pyrogenicity and antigenicity.	2001	11247273
The fermentative production of L-lysine as an animal feed additive.	2001 Apr	11233822
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
Biochemical and functional characterization of a molecule expressed by a subset of thymic medullary epithelial cells.	2001 Feb	11292258
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
Affinity purification of Csk protein tyrosine kinase based on its catalytic requirement for divalent metal cations.	2001 Feb	11162381
Characterization of the lipopolysaccharide of Yersinia pestis.	2001 Feb	11162185
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
The role of small intestinal bacterial overgrowth, intestinal permeability, endotoxaemia, and tumour necrosis factor alpha in the pathogenesis of non-alcoholic steatohepatitis.	2001 Feb	11156641
Identification of a candidate integrin-fraction associated with the activated form of the PDGF-receptor.	2001 Feb 23	11181089
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
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
Increased stability of nucleophosmin/B23 in anti-apoptotic effect of ras during serum deprivation.	2001 Jan	11125022
A Mycobacterium smegmatis gyrase B specific monoclonal antibody reveals association of gyrase A and B subunits in the cell.	2001 Jan 1	11150671
Mechanism of release of urinary Tamm-Horsfall glycoprotein from the kidney GPI-anchored counterpart.	2001 Jan 12	11162486
Acceleration of thrombomodulin gene transcription by retinoic acid: retinoic acid receptors and Sp1 regulate the promoter activity through interactions with two different sequences in the 5'-flanking region of human gene.	2001 Jan 26	11036068
Hsp90 regulates p50(cdc37) function during the biogenesis of the activeconformation of the heme-regulated eIF2 alpha kinase.	2001 Jan 5	11036079
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
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
Inositol phosphates from barley low-phytate grain mutants analysed by metal-dye detection HPLC and NMR.	2001 Mar 1	11171128
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
Inhibition of cytosolic phospholipase A2 by annexin I. Specific interaction model and mapping of the interaction site.	2001 May 11	11278580
CYP2A6*6, a novel polymorphism in cytochrome p450 2A6, has a single amino acid substitution (R128Q) that inactivates enzymatic activity.	2001 May 25	11278503
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