Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C9H14N4O3.HNO3 |
| Molecular Weight | 289.2453 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O[N+]([O-])=O.NCCC(=O)N[C@@H](CC1=CN=CN1)C(O)=O
InChI
InChIKey=CPZFLUMGMDPGIE-FJXQXJEOSA-N
InChI=1S/C9H14N4O3.HNO3/c10-2-1-8(14)13-7(9(15)16)3-6-4-11-5-12-6;2-1(3)4/h4-5,7H,1-3,10H2,(H,11,12)(H,13,14)(H,15,16);(H,2,3,4)/t7-;/m0./s1
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
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Differential expression of carnosine, homocarnosine and N-acetyl-L-histidine hydrolytic activities in cultured rat macroglial cells. | 2001 Dec |
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| Monocarboxylate transporters and lactate metabolism in equine athletes: a review. | 2002 |
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| Efficacy of N-acetylcarnosine in the treatment of cataracts. | 2002 |
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| Electrospray mass spectrometric studies of L-carnosine (beta-alanyl-L-histidine) complexes with copper(II) or zinc ions in aqueous solution. | 2002 |
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| High level of skeletal muscle carnosine contributes to the latter half of exercise performance during 30-s maximal cycle ergometer sprinting. | 2002 Apr |
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| Olfactory neuroepithelioma in a dog: an immunohistochemical and electron microscopic study. | 2002 Apr |
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| 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 Apr |
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| Effects of carnosine on volatile generation from Maillard reaction of ribose and cysteine. | 2002 Apr 10 |
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| Protective effect of L-carnosine against 12-O-tetradecanoylphorbol-13-acetate- or hydrogen peroxide-induced apoptosis on v-myc transformed rat liver epithelial cells. | 2002 Apr 8 |
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| 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 Dec |
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| Polaprezinc attenuates Helicobacter pylori-associated gastritis in Mongolian gerbils. | 2002 Dec |
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| tan and ebony genes regulate a novel pathway for transmitter metabolism at fly photoreceptor terminals. | 2002 Dec 15 |
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| The botanical extracts of Achyrocline satureoides and Ilex paraguariensis prevent methylglyoxal-induced inhibition of plasminogen and antithrombin III. | 2002 Dec 6 |
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| Protective effect of Biolan during ischemic damages to cultured cerebellar granular cells. | 2002 Feb |
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| Effect of zinc-carnosine chelate compound on muscle function in mdx mouse. | 2002 Feb |
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| [Chaperon-induction therapy for peptic ulcers]. | 2002 Feb |
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| [New therapeutic approaches to peptic ulcer using mucosal protective agents]. | 2002 Feb |
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| Protection by carnosine-related dipeptides against hydrogen peroxide-mediated ceruloplasmin modification. | 2002 Feb 28 |
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| Effect of carnosine and related compounds on the inactivation of human Cu,Zn-superoxide dismutase by modification of fructose and glycolaldehyde. | 2002 Jan |
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| Carnosine modifies the incidence of genetically abnormal sex cells in the testes of senescence-accelerated mice. | 2002 Jul |
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| Carnosine prevents methamphetamine-induced gliosis but not dopamine terminal loss in rats. | 2002 Jul 19 |
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| Could carnosine be a naturally-occurring scavenger for acrolein and other reactive aldehydes in the brain? | 2002 Jul-Aug |
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| Effect of carnosine on Drosophila melanogaster lifespan. | 2002 Jun |
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| Role of PEPT2 in peptide/mimetic trafficking at the blood-cerebrospinal fluid barrier: studies in rat choroid plexus epithelial cells in primary culture. | 2002 Jun |
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| Enhanced delivery of drugs to the liver by adenovirus-mediated heterologous expression of the human oligopeptide transporter PEPT1. | 2002 Jun |
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| Carnosine and related dipeptides protect human ceruloplasmin against peroxyl radical-mediated modification. | 2002 Jun 30 |
|
| [Efficacy and safety of polaprezinc as a preventive drug for radiation-induced stomatitis]. | 2002 Mar |
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| l-carnosine and verapamil inhibit hypoxia-induced expression of hypoxia inducible factor (HIF-1 alpha) in H9c2 cardiomyoblasts. | 2002 Mar |
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| Effects of thermal denaturation on protein glycation. | 2002 Mar 1 |
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| Distribution of gamma-glutamyl-beta-alanylhistidine isopeptide in the macromolecular fractions of commercial meat extracts and correlation with the color of the macromolecular fractions. | 2002 Mar 27 |
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| Analysis of products of animal origin in feeds by determination of carnosine and related dipeptides by high-performance liquid chromatography. | 2002 Mar 27 |
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| Neuroprotective effects of carnosine and homocarnosine on pheochromocytoma PC12 cells exposed to ischemia. | 2002 May 15 |
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| Effects of L-carnosine on renal sympathetic nerve activity and DOCA-salt hypertension in rats. | 2002 May 31 |
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| Double-blind, placebo-controlled study of L-carnosine supplementation in children with autistic spectrum disorders. | 2002 Nov |
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| Inhibitory effect of polaprezinc on the inflammatory response to Helicobacter pylori. | 2002 Nov |
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| Carnosine is a quencher of 4-hydroxy-nonenal: through what mechanism of reaction? | 2002 Nov 15 |
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| Antioxidant properties of carnosine re-evaluated in a ferrylmyoglobin model system and in cooked pork patties. | 2002 Nov 20 |
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| Induction of the estrogen effect-switching phenomenon by ethanol and its correction. | 2002 Nov-Dec |
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| Effect of zinc-carnosine complex on muscular function in frail distrophin-deficient (mdx) mice. | 2002 Oct |
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| Plasma carnosine concentration: diurnal variation and effects of age, exercise and muscle damage. | 2002 Sep |
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| Transport characteristics of L-carnosine and the anticancer derivative 4-toluenesulfonylureido-carnosine in a human epithelial cell line. | 2002 Sep |
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| Development of a new assay for the screening of hypochlorous acid scavengers based on reversed-phase high-performance liquid chromatography. | 2002 Sep |
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| 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 Sep |
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| Involvement of reactive oxygen species in cardiac preconditioning in rats. | 2003 Feb |
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| RSD931, a novel anti-tussive agent acting on airway sensory nerves. | 2003 Feb |
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| The carnosine C-2 proton's chemical shift reports intracellular pH in oxidative and glycolytic muscle fibers. | 2003 Feb |
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| Sequence identification and characterization of human carnosinase and a closely related non-specific dipeptidase. | 2003 Feb 21 |
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| Carnosine promotes the heat denaturation of glycated protein. | 2003 Jan 3 |
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| A practical method to study functional impairment of proteins by glycation and effects of inhibitors using current coagulation/fibrinolysis reagent kits. | 2003 Mar |
|
| Antioxidant peptides with Angiotensin converting enzyme inhibitory activities and applications for Angiotensin converting enzyme purification. | 2003 Mar 12 |
Patents
Sample Use Guides
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
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).
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DBSALT002050
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m3121
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5852-98-2
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71586821
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1059P8M705
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DTXSID80207237
Created by
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ACTIVE MOIETY
SUBSTANCE RECORD
