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N-Acetylcarnosine

Cat No.:V40493 Purity: ≥98%
N-Acetylcarnosine is a natural, histidine-containing dipeptide and the main pharmacological source of L-carnosine.
N-Acetylcarnosine
N-Acetylcarnosine Chemical Structure CAS No.: 56353-15-2
Product category: New2
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
500mg
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Product Description
N-Acetylcarnosine is a natural, histidine-containing dipeptide and the main pharmacological source of L-carnosine. N-Acetylcarnosine is a potent ophthalmologically active molecule with potential for human cataract treatment.
N-Acetylcarnosine (NAC) is a naturally occurring dipeptide derivative of L-carnosine, consisting of the amino acids beta-alanine and histidine with an acetyl group attached to the amino terminus. It is used in the treatment of cataracts and UV-induced immunosuppression. It is widely studied in ophthalmology, particularly in eye drop formulations for the prevention and treatment of cataracts, oxidative stress-related eye disorders, and age-related vision decline.
Biological Activity I Assay Protocols (From Reference)
Targets
N-Acetylcarnosine acts as an antioxidant, scavenging free radicals and protecting cells from oxidative damage. It targets oxidative stress pathways and protein glycation, which are implicated in cataract formation and other age-related conditions. As a derivative of carnosine, it has similar antioxidant and anti-glycation properties but with improved stability and bioavailability. The compound protects proteins, lipids, and DNA from oxidative damage. Its primary mechanism involves neutralizing reactive oxygen species (ROS) and preventing protein cross-linking and glycation.
ln Vitro
In vitro studies have demonstrated that N-Acetylcarnosine has potent antioxidant activity, scavenging free radicals and protecting cells from oxidative damage. The compound protects proteins, lipids, and DNA from oxidative damage. It prevents protein glycation and cross-linking, which are key processes in cataract formation. In cell culture models, NAC has been shown to reduce oxidative stress-induced damage and protect lens epithelial cells from apoptosis. The compound's antioxidant properties are attributed to its ability to chelate metal ions and scavenge reactive oxygen species (ROS).
ln Vivo
The formulation in 80 μL A 1% N-acetyl carnosine injection was made into the right eye of a gray rat rabbit that was 2-3 k in weight and 4–5 months old. The therapeutic outcomes of treating ocular conditions, such as preventing and treating cataracts in animal eyes, are enhanced by N-Acetyl Carnosine Prodrug Eye Drops [1].
N-Acetylcarnosine has demonstrated in vivo efficacy in the treatment of cataracts and UV-induced immunosuppression. In ophthalmology, the compound is used in eye drop formulations for the prevention and treatment of cataracts and age-related vision decline. Clinical studies have shown that N-acetylcarnosine eye drops can improve lens transparency and visual function in patients with cataracts. The compound has also been studied for its effects on UV-induced immunosuppression, showing protective effects against UV radiation damage.
Enzyme Assay
N-Acetylcarnosine is evaluated in vitro for its antioxidant and anti-glycation activities using biochemical assays. For antioxidant activity, DPPH radical scavenging, ABTS, FRAP, and ORAC assays are performed. The compound is incubated with the radical-generating system and the decrease in absorbance is measured spectrophotometrically. For anti-glycation activity, bovine serum albumin (BSA) is incubated with glucose or fructose in the presence of various concentrations of N-Acetylcarnosine (1-100 μM) for 1-4 weeks at 37°C. The formation of advanced glycation end products (AGEs) is measured by fluorescence spectroscopy (excitation 370 nm, emission 440 nm). Metal chelation activity is assessed using ferrozine-based assays. IC₅₀ values are determined from dose-response curves.
Cell Assay
For in vitro cell-based assays, lens epithelial cells or other relevant cell types are cultured in appropriate media. Cells are treated with N-Acetylcarnosine at concentrations ranging from 1-100 μM for 24-72 hours. Oxidative stress is induced by exposure to H₂O₂, UV radiation, or other oxidants. Cell viability is assessed by MTT or CCK-8 assays. Intracellular ROS levels are measured using DCFH-DA fluorescent probe. Apoptosis is evaluated by Annexin V-FITC/PI staining and caspase activity assays. Mitochondrial membrane potential is assessed using JC-1 staining. Protein carbonylation and lipid peroxidation are measured as markers of oxidative damage. Gene expression changes related to antioxidant defense (e.g., Nrf2, HO-1, SOD) are analyzed by qRT-PCR and Western blot.
Animal Protocol
In vivo animal studies with N-Acetylcarnosine typically use rodent models of cataract formation or UV-induced skin damage. For cataract studies, rats or mice are treated with agents that induce cataract formation (e.g., galactose, selenite, or streptozotocin for diabetic cataracts). N-Acetylcarnosine is administered as eye drops at concentrations of 1-10% (w/v) or orally at doses of 10-100 mg/kg daily for 4-12 weeks. Lens opacity is assessed using slit-lamp biomicroscopy. At study endpoint, lenses are excised and examined for opacity, and biochemical markers of oxidative stress (MDA, GSH, SOD) are measured in lens homogenates. For UV-induced immunosuppression studies, mice are exposed to UV radiation with or without NAC treatment, and immune responses are assessed by contact hypersensitivity assays.
ADME/Pharmacokinetics
Tissue distribution and elimination half-life data are limited for N-Acetylcarnosine. The compound has a molecular weight of 268.27 g/mol and molecular formula C₁₁H₁₆N₄O₄. As a dipeptide derivative, the compound is expected to be hydrolyzed to its constituent amino acids (beta-alanine and histidine) in the gastrointestinal tract if administered orally. In eye drop formulations, the compound is absorbed through the cornea and reaches therapeutic concentrations in the lens. The acetyl group improves stability compared to carnosine, protecting it from enzymatic degradation by carnosinase. The compound is primarily excreted via urine.
Toxicity/Toxicokinetics
N-Acetylcarnosine is considered to have a favorable safety profile. As a naturally occurring dipeptide derivative found in the human body, it is generally well-tolerated. In eye drop formulations, N-acetylcarnosine has been used clinically without significant adverse effects. The compound has been studied for the treatment of cataracts with a good safety record. Oral administration is also considered safe at recommended doses. No significant toxicity has been reported in preclinical studies. The compound is not associated with major organ toxicity or genotoxicity.
References
[1]. Babizhayev MA, et al. N-Acetylcarnosine, a natural histidine-containing dipeptide, as a potent ophthalmic drug in treatment of human cataracts. Peptides. 2001 Jun;22(6):979-94.
[2]. Dubois VD, et al. N-acetylcarnosine (NAC) drops for age-related cataract. Cochrane Database Syst Rev. 2017 Feb 28;2:CD009493.
[3]. Babizhayev MA, et al. Potentiation of intraocular absorption and drug metabolism of N-acetylcarnosine lubricant eye drops: drug interaction with sight threatening lipid peroxides in the treatment for age-related eye diseases. Drug Metabol Drug Interact. 2009;24(2-4):275-323.
Additional Infomation
N-acetylcarnosine is a dipeptide, an N-acetyl derivative of carnosine. It functions as a metabolite and is functionally related to carnosine.
N-Acetylcarnosine is a synthetic derivative of the naturally occurring dipeptide carnosine, composed of beta-alanine and histidine. It is used in the treatment of cataracts and UV-induced immunosuppression. In ophthalmology, the compound is used in eye drop formulations for the prevention and treatment of cataracts, oxidative stress-related eye disorders, and age-related vision decline. The compound is also known as N-acetyl-L-carnosine or NAC. It acts as an antioxidant, scavenging free radicals and protecting cells from oxidative damage. N-Acetylcarnosine is available as a dietary supplement and as an ingredient in ophthalmic products in some countries.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C11H16N4O4
Molecular Weight
268.2691
Exact Mass
268.117
CAS #
56353-15-2
PubChem CID
9903482
Appearance
Typically exists as solid at room temperature
Density
1.3±0.1 g/cm3
Boiling Point
775.9±60.0 °C at 760 mmHg
Melting Point
253 - 260ºC
Flash Point
423.0±32.9 °C
Vapour Pressure
0.0±2.8 mmHg at 25°C
Index of Refraction
1.563
LogP
-2.56
Hydrogen Bond Donor Count
4
Hydrogen Bond Acceptor Count
5
Rotatable Bond Count
7
Heavy Atom Count
19
Complexity
348
Defined Atom Stereocenter Count
1
SMILES
[C@H](C(=O)O)(NC(=O)CCNC(=O)C)CC1N=CNC=1
InChi Key
BKAYIFDRRZZKNF-VIFPVBQESA-N
InChi Code
InChI=1S/C11H16N4O4/c1-7(16)13-3-2-10(17)15-9(11(18)19)4-8-5-12-6-14-8/h5-6,9H,2-4H2,1H3,(H,12,14)(H,13,16)(H,15,17)(H,18,19)/t9-/m0/s1
Chemical Name
(2S)-2-(3-acetamidopropanoylamino)-3-(1H-imidazol-5-yl)propanoic acid
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: Please store this product in a sealed and protected environment, avoid exposure to moisture.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
H2O : ~250 mg/mL (~931.90 mM)
Solubility (In Vivo)
Solubility in Formulation 1: 100 mg/mL (372.76 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with sonication.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 3.7276 mL 18.6379 mL 37.2759 mL
5 mM 0.7455 mL 3.7276 mL 7.4552 mL
10 mM 0.3728 mL 1.8638 mL 3.7276 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
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