CARNOSINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C9H14N4O3
Molecular Weight	226.2328
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NCCC(=O)N[C@@H](CC1=CN=CN1)C(O)=O

InChI

InChIKey=CQOVPNPJLQNMDC-ZETCQYMHSA-N

InChI=1S/C9H14N4O3/c10-2-1-8(14)13-7(9(15)16)3-6-4-11-5-12-6/h4-5,7H,1-3,10H2,(H,11,12)(H,13,14)(H,15,16)/t7-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C9H14N4O3
Molecular Weight	226.2328
Charge	0
Count

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28672983 | https://www.ncbi.nlm.nih.gov/pubmed/28863318 | https://www.ncbi.nlm.nih.gov/pubmed/28848223

Carnosine is a dipeptide composed of the amino acids beta-histidine and l-alanine. It is widely present in muscle and brain tissues. It possesses strong and specific antioxidant properties, protects against radiation damage, and promotes wound healing. The antioxidant mechanism of carnosine is attributed to its chelating effect against metal ions, superoxide dismutase (SOD)-like activity, ROS and free radicals scavenging ability. In addition, was shown, that carnosine significantly protects against TCA-induced liver carcinogenesis in rats, through its antioxidant, antinutritive, and anti-inflammatory effects, and induction of apoptosis. It also may be a therapeutic agent against Parkinson's disease. Experiments on animal have shown the sepsis healing therapeutic potential of carnosine.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
transition-metal ion 3 Target ID: transition-metal ion Sources: https://www.ncbi.nlm.nih.gov/pubmed/15872311	Binding Agent 1076

Conditions

Condition	Modality	Highest Phase	Product
Parkinson's disease 232 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28672983	Primary	Preclinical	Unknown Approved Use Unknown
Hepatocellular carcinoma 83 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28863318	Palliative	Preclinical	Unknown Approved Use Unknown
Acute lung injury 20 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28848223	Primary	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Antioxidant peptides with Angiotensin converting enzyme inhibitory activities and applications for Angiotensin converting enzyme purification.	2003-03-12	12617609
A practical method to study functional impairment of proteins by glycation and effects of inhibitors using current coagulation/fibrinolysis reagent kits.	2003-03	12633766
Sequence identification and characterization of human carnosinase and a closely related non-specific dipeptidase.	2003-02-21	12473676
Involvement of reactive oxygen species in cardiac preconditioning in rats.	2003-02	12626123
RSD931, a novel anti-tussive agent acting on airway sensory nerves.	2003-02	12569065
The carnosine C-2 proton's chemical shift reports intracellular pH in oxidative and glycolytic muscle fibers.	2003-02	12541242
Carnosine promotes the heat denaturation of glycated protein.	2003-01-03	12480523
Ultraviolet spectrophotometric characterization of copper(II) complexes with imidazole N-methyl derivatives of L-histidine in aqueous solution.	2003-01-01	12509160
Aldehyde-sequestering drugs: tools for studying protein damage by lipid peroxidation products.	2002-12-27	12505316
tan and ebony genes regulate a novel pathway for transmitter metabolism at fly photoreceptor terminals.	2002-12-15	12486147
Induction of the estrogen effect-switching phenomenon by ethanol and its correction.	2002-12-10	12469887
The botanical extracts of Achyrocline satureoides and Ilex paraguariensis prevent methylglyoxal-induced inhibition of plasminogen and antithrombin III.	2002-12-06	12427487
Induction of a 72-kDa heat-shock protein in cultured rat gastric mucosal cells and rat gastric mucosa by zinc L-carnosine.	2002-12	12498304
Detoxification of cytotoxic alpha,beta-unsaturated aldehydes by carnosine: characterization of conjugated adducts by electrospray ionization tandem mass spectrometry and detection by liquid chromatography/mass spectrometry in rat skeletal muscle.	2002-12	12489081
Polaprezinc attenuates Helicobacter pylori-associated gastritis in Mongolian gerbils.	2002-12	12485126
Antioxidant properties of carnosine re-evaluated in a ferrylmyoglobin model system and in cooked pork patties.	2002-11-20	12428977
Carnosine is a quencher of 4-hydroxy-nonenal: through what mechanism of reaction?	2002-11-15	12419310
Double-blind, placebo-controlled study of L-carnosine supplementation in children with autistic spectrum disorders.	2002-11	12585724
Inhibitory effect of polaprezinc on the inflammatory response to Helicobacter pylori.	2002-11	12464972
Effect of zinc-carnosine complex on muscular function in frail distrophin-deficient (mdx) mice.	2002-10	12533250
Plasma carnosine concentration: diurnal variation and effects of age, exercise and muscle damage.	2002-09	12405702
Transport characteristics of L-carnosine and the anticancer derivative 4-toluenesulfonylureido-carnosine in a human epithelial cell line.	2002-09	12403071
Development of a new assay for the screening of hypochlorous acid scavengers based on reversed-phase high-performance liquid chromatography.	2002-09	12228898
Two broad-specificity dipeptide hydrolysing activities from cytoplasm of guinea pig brain, both of which contain prolinase but neither of which contain carnosinase activity.	2002-09	12204299
Carnosine prevents methamphetamine-induced gliosis but not dopamine terminal loss in rats.	2002-07-19	12144937
Carnosine modifies the incidence of genetically abnormal sex cells in the testes of senescence-accelerated mice.	2002-07	12459876
The ceruloplasmin and hydrogen peroxide system induces alpha-synuclein aggregation in vitro.	2002-07	12453634
Carnosine and related dipeptides protect human ceruloplasmin against peroxyl radical-mediated modification.	2002-06-30	12132593
Effect of carnosine on Drosophila melanogaster lifespan.	2002-06	12447464
Role of PEPT2 in peptide/mimetic trafficking at the blood-cerebrospinal fluid barrier: studies in rat choroid plexus epithelial cells in primary culture.	2002-06	12023509
Enhanced delivery of drugs to the liver by adenovirus-mediated heterologous expression of the human oligopeptide transporter PEPT1.	2002-06	12023508
Effects of L-carnosine on renal sympathetic nerve activity and DOCA-salt hypertension in rats.	2002-05-31	12132650
Could carnosine be a naturally-occurring scavenger for acrolein and other reactive aldehydes in the brain?	2002-05-16	12009514
Neuroprotective effects of carnosine and homocarnosine on pheochromocytoma PC12 cells exposed to ischemia.	2002-05-15	11992473
[Do the glutamate excitotoxicity theory and potential free radicals implication in schizophrenia aetiopathogenesis provide a new enlightenment to links between: genome, environment and biology in the determinism of that disorder?].	2002-04-25	11972141
High level of skeletal muscle carnosine contributes to the latter half of exercise performance during 30-s maximal cycle ergometer sprinting.	2002-04	12139778
Olfactory neuroepithelioma in a dog: an immunohistochemical and electron microscopic study.	2002-04	12014590
Increase of gamma-glutamyl-beta-alanyl-histidine isopeptide in the macromolecular fraction of model chicken extract during heating and distribution in commercial chicken extracts.	2002-04	11989761
Reaction of carnosine with aged proteins: another protective process?	2002-04	11976203
Protective effects of carnosine, homocarnosine and anserine against peroxyl radical-mediated Cu,Zn-superoxide dismutase modification.	2002-03-15	11985892
Effects of thermal denaturation on protein glycation.	2002-03-01	12002523
[Efficacy and safety of polaprezinc as a preventive drug for radiation-induced stomatitis].	2002-03	12043217
Protective effect of Biolan during ischemic damages to cultured cerebellar granular cells.	2002-02	12428281
Effect of zinc-carnosine chelate compound on muscle function in mdx mouse.	2002-02	12047809
[Polaprezinc].	2002-02	11979877
[Chaperon-induction therapy for peptic ulcers].	2002-02	11979849
[New therapeutic approaches to peptic ulcer using mucosal protective agents].	2002-02	11979810
Monocarboxylate transporters and lactate metabolism in equine athletes: a review.	2002	12173504
Efficacy of N-acetylcarnosine in the treatment of cataracts.	2002	12001824
Zinc suppresses IL-6 synthesis by prostaglandin F2alpha in osteoblasts: inhibition of phospholipase C and phospholipase D.	2002	11968002

Patents

Sample Use Guides

In Vivo Use Guide

in rat liver carcinogenesis: carnosine (10mg/kg/day, i.p.) for 2 weeks. protective effect of carnosine on acute lung injury in sepsis rats: 25 mg/kg and 50 mg/kg, were administered for 30 consecutive days

Route of Administration: Other

In Vitro Use Guide

It was studied the anti-carcinogenic effect of L-carnosine in human carcinoma cells (SNU-423). The SNU-423 cancer cells were cultured at a density of 2 × 104 cells/well in Dulbecco modified Eagle medium. After 24 h of adherence, the cells were treated with L-carnosine (0.2 and 1 mg/mL) for 48 h. L-Carnosine significantly inhibited the growth of the SNU-423 cells (p < 0.05). The relative fluorescent unit was increased in a dose-dependent manner by L-carnosine, with values of 79.43, 186.87 and 400.89 for 0.6, 0.8 and 1 mg/mL of L-carnosine, respectively (p < 0.05).

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:51:37 GMT 2025` Edited by `admin` on `Mon Mar 31 17:51:37 GMT 2025`
Record UNII	8HO6PVN24W
Record Status	`FAILED`
Record Version

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Name

Type

Language

NSC-524045

Preferred Name

English

CARNOSINE

Official Name

English

CARNOSINE [MI]

Common Name

English

.BETA.-ALANYL-L-HISTIDINE

Systematic Name

English

Carnosine [WHO-DD]

Common Name

English

IGNOTINE

Common Name

English

L-CARNOSINE

Common Name

English

CARNOSINE [VANDF]

Common Name

English

Classification Tree Code System Code

LOINC

26750-0