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Details

Stereochemistry ABSOLUTE
Molecular Formula C9H14N4O3
Molecular Weight 226.2325
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CARNOSINE

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 226.2325
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Palliative
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
On the "struggle between chemistry and biology during aging"--implications for DNA repair, apoptosis and proteolysis, and a novel route of intervention.
2001
Low taurine, gamma-aminobutyric acid and carnosine levels in plasma of diabetic pregnant rats: consequences for the offspring.
2001
[Induction by ethanol of 'phenomenon of switching estrogen effect' and its correction].
2001 Apr
Topiramate rapidly raises brain GABA in epilepsy patients.
2001 Apr
Dipolar coupling and ordering effects observed in magnetic resonance spectra of skeletal muscle.
2001 Apr
Expression of the intermediate filament protein nestin by sustentacular cells in mature olfactory neuroepithelium.
2001 Aug 20
Hepatic uptake of solutes from the preservation solution during hypothermic storage: a (1)H NMR study in rat liver.
2001 Jun
PEPT2-mediated uptake of neuropeptides in rat choroid plexus.
2001 Jun
N-Acetylcarnosine, a natural histidine-containing dipeptide, as a potent ophthalmic drug in treatment of human cataracts.
2001 Jun
Reductions in occipital cortex GABA levels in panic disorder detected with 1h-magnetic resonance spectroscopy.
2001 Jun
Carnosine as a modulator of endogenous Zn(2+) effects.
2001 Mar
Homocarnosine elevations: a cause or a sign of seizure control?
2001 Mar 27
Effect of carnosine administration on metabolic parameters in bilharzia-infected hamsters.
2001 May
Carnosine, the anti-ageing, anti-oxidant dipeptide, may react with protein carbonyl groups.
2001 Sep 15
Monocarboxylate transporters and lactate metabolism in equine athletes: a review.
2002
Zinc suppresses IL-6 synthesis by prostaglandin F2alpha in osteoblasts: inhibition of phospholipase C and phospholipase D.
2002
Characterization of dioxygenated cobalt(II)-carnosine complexes by Raman and IR spectroscopy.
2002
Polaprezinc attenuates Helicobacter pylori-associated gastritis in Mongolian gerbils.
2002 Dec
Interaction of copper(II) with imidazole pyridine nitrogen-containing ligands in aqueous medium: a spectroscopic study.
2002 Jan 1
Carbonic anhydrase activators: high affinity isozymes I, II, and IV activators, incorporating a beta-alanyl-histidine scaffold.
2002 Jan 17
Carnosine prevents methamphetamine-induced gliosis but not dopamine terminal loss in rats.
2002 Jul 19
Carnosine and related dipeptides protect human ceruloplasmin against peroxyl radical-mediated modification.
2002 Jun 30
Effects of carnosine on bilharzial infestation in hamsters: biochemical and histochemical studies.
2002 Mar
Effects of thermal denaturation on protein glycation.
2002 Mar 1
Inhibitory effect of polaprezinc on the inflammatory response to Helicobacter pylori.
2002 Nov
Carnosine is a quencher of 4-hydroxy-nonenal: through what mechanism of reaction?
2002 Nov 15
Plasma carnosine concentration: diurnal variation and effects of age, exercise and muscle damage.
2002 Sep
Transport characteristics of L-carnosine and the anticancer derivative 4-toluenesulfonylureido-carnosine in a human epithelial cell line.
2002 Sep
Development of a new assay for the screening of hypochlorous acid scavengers based on reversed-phase high-performance liquid chromatography.
2002 Sep
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
The carnosine C-2 proton's chemical shift reports intracellular pH in oxidative and glycolytic muscle fibers.
2003 Feb
Ultraviolet spectrophotometric characterization of copper(II) complexes with imidazole N-methyl derivatives of L-histidine in aqueous solution.
2003 Jan 1
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).
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:14:59 UTC 2023
Edited
by admin
on Fri Dec 15 15:14:59 UTC 2023
Record UNII
8HO6PVN24W
Record Status Validated (UNII)
Record Version
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Name Type Language
CARNOSINE
INCI   MI   VANDF   WHO-DD  
INCI  
Official Name English
NSC-524045
Code English
CARNOSINE [INCI]
Common 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
Created by admin on Fri Dec 15 15:14:59 UTC 2023 , Edited by admin on Fri Dec 15 15:14:59 UTC 2023
LOINC 16557-1
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WIKIPEDIA Designer-drugs-Carnosine
Created by admin on Fri Dec 15 15:14:59 UTC 2023 , Edited by admin on Fri Dec 15 15:14:59 UTC 2023
LOINC 26606-4
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LOINC 15133-2
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LOINC 2049-5
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LOINC 26591-8
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LOINC 27294-8
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LOINC 2051-1
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LOINC 26580-1
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LOINC 25875-6
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LOINC 25365-8
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LOINC 25874-9
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LOINC 56675-2
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LOINC 13391-8
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LOINC 13720-8
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DSLD 673 (Number of products:141)
Created by admin on Fri Dec 15 15:14:59 UTC 2023 , Edited by admin on Fri Dec 15 15:14:59 UTC 2023
LOINC 12474-3
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LOINC 28597-3
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LOINC 15139-9
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NCI_THESAURUS C73539
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LOINC 44304-4
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LOINC 2050-3
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LOINC 53817-3
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LOINC 13369-4
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NCI_THESAURUS C275
Created by admin on Fri Dec 15 15:14:59 UTC 2023 , Edited by admin on Fri Dec 15 15:14:59 UTC 2023
Code System Code Type Description
EPA CompTox
DTXSID80879594
Created by admin on Fri Dec 15 15:14:59 UTC 2023 , Edited by admin on Fri Dec 15 15:14:59 UTC 2023
PRIMARY
NSC
524045
Created by admin on Fri Dec 15 15:14:59 UTC 2023 , Edited by admin on Fri Dec 15 15:14:59 UTC 2023
PRIMARY
EVMPD
SUB13248MIG
Created by admin on Fri Dec 15 15:14:59 UTC 2023 , Edited by admin on Fri Dec 15 15:14:59 UTC 2023
PRIMARY
RXCUI
1362697
Created by admin on Fri Dec 15 15:14:59 UTC 2023 , Edited by admin on Fri Dec 15 15:14:59 UTC 2023
PRIMARY RxNorm
CAS
305-84-0
Created by admin on Fri Dec 15 15:14:59 UTC 2023 , Edited by admin on Fri Dec 15 15:14:59 UTC 2023
PRIMARY
MERCK INDEX
m3121
Created by admin on Fri Dec 15 15:14:59 UTC 2023 , Edited by admin on Fri Dec 15 15:14:59 UTC 2023
PRIMARY Merck Index
CHEBI
57485
Created by admin on Fri Dec 15 15:14:59 UTC 2023 , Edited by admin on Fri Dec 15 15:14:59 UTC 2023
PRIMARY
WIKIPEDIA
CARNOSINE
Created by admin on Fri Dec 15 15:14:59 UTC 2023 , Edited by admin on Fri Dec 15 15:14:59 UTC 2023
PRIMARY
DRUG BANK
DB11695
Created by admin on Fri Dec 15 15:14:59 UTC 2023 , Edited by admin on Fri Dec 15 15:14:59 UTC 2023
PRIMARY
FDA UNII
8HO6PVN24W
Created by admin on Fri Dec 15 15:14:59 UTC 2023 , Edited by admin on Fri Dec 15 15:14:59 UTC 2023
PRIMARY
PUBCHEM
439224
Created by admin on Fri Dec 15 15:14:59 UTC 2023 , Edited by admin on Fri Dec 15 15:14:59 UTC 2023
PRIMARY
ECHA (EC/EINECS)
206-169-9
Created by admin on Fri Dec 15 15:14:59 UTC 2023 , Edited by admin on Fri Dec 15 15:14:59 UTC 2023
PRIMARY
CHEBI
15727
Created by admin on Fri Dec 15 15:14:59 UTC 2023 , Edited by admin on Fri Dec 15 15:14:59 UTC 2023
PRIMARY
SMS_ID
100000076300
Created by admin on Fri Dec 15 15:14:59 UTC 2023 , Edited by admin on Fri Dec 15 15:14:59 UTC 2023
PRIMARY
DAILYMED
8HO6PVN24W
Created by admin on Fri Dec 15 15:14:59 UTC 2023 , Edited by admin on Fri Dec 15 15:14:59 UTC 2023
PRIMARY
NCI_THESAURUS
C118880
Created by admin on Fri Dec 15 15:14:59 UTC 2023 , Edited by admin on Fri Dec 15 15:14:59 UTC 2023
PRIMARY
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