N-Acetyl Carnosine
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N-Acetyl Carnosine

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N-Acetyl Carnosine is a naturally-occurring dipeptide used in the treatment of cataracts and in the treatment of UV-induced immunosuppression.

Category
Cosmetic Peptides
Catalog number
BAT-006160
CAS number
56353-15-2
Molecular Formula
C11H16N4O4
Molecular Weight
268.27
N-Acetyl Carnosine
Size Price Stock Quantity
1 g $199 In stock
IUPAC Name
(2S)-2-(3-acetamidopropanoylamino)-3-(1H-imidazol-5-yl)propanoic acid
Synonyms
NAC, N-α-Acetyl-N-β-alanyl-L-histidine; N-Acetylcarnosine
Appearance
White to Off-white Solid
Purity
98%
Density
1.343±0.06 g/cm3(Predicted)
Melting Point
253-260°C
Boiling Point
775.9±60.0 °C(Predicted)
Sequence
Ac-bAla-His-OH
Storage
Store at -20°C
Solubility
Soluble in methanol, water
InChI
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
InChI Key
BKAYIFDRRZZKNF-VIFPVBQESA-N
Canonical SMILES
CC(=O)NCCC(=O)NC(CC1=CN=CN1)C(=O)O
1.Effects of N-acetyl-L-carnosine aluminum (CL-1700) on various acute gastric lesions and gastric secretion in rats.
Okabe S, Kunimi H. Jpn J Pharmacol. 1981 Dec;31(6):941-50.
Effects of a newly synthesized compound, N-acetyl-L-carnosine aluminum (CL-1700), on the formation of various types of acute gastric lesions were studied in rats. CL-1700 at 300 or 1,000 mg/kg (p.o.) significantly inhibited Shay ulcers and water-immersion stress- and aspirin-induced erosions in pylorus-ligated rats, and indomethacin- or phenylbutazone-induced erosions. CL-1700 had a weak effect on water-immersion stress-induced erosions in rats with an intact pylorus. CL-1700 at 100 or 300 mg/kg (i.p.) significantly inhibited Shay ulcers and water-immersion stress-induced erosions in rats with an intact pylorus. However, this compound (i.p.) had no effect on aspirin- and indomethacin-induced gastric erosions. CL-1700 at 1,000 mg/kg (i.d.) significantly reduced the gastric acid output in pylorus-ligated rats but at 300 or 1,000 mg/kg (p.o.) increased the volume, pepsin output and raised the pH value. The effects of CL-1700 on experimental gastric lesions were slightly weaker than those of aluminum sucrose sulfate but almost equal to or better than those of cimetidine.
2.Effects of CL-1700 and its constituents on acute or chronic gastric lesions and gastric secretion in rats.
Kunimi H, Okabe S. Jpn J Pharmacol. 1982 Jun;32(3):469-77.
Effects of CL-1700 (N-acetyl-L-carnosine aluminum) and its constituents, L-carnosine, N-acetyl-L-carnosine and Al(OH)3 on acute or chronic gastric lesions in intact rats and on gastric secretion in pylorus-ligated rats were studied. CL-1700 at 600 or 1,000 mg/kg p.o markedly inhibited Shay ulcers or indomethacin-induced erosions, but its constituents at the doses contained in CL-1700 did not. Also, CL-1700 at 300 mg/kg i.p. significantly inhibited water-immersion stress-induced erosions, but its constituents did not. CL-1700 at 600 mg/kg i.p. and Al(OH)3 at 143 mg/kg i.p. significantly inhibited Shay ulcers. CL-1700 at 1,000 mg/kg p.o. almost completely inhibited aspirin- or histamine-induced erosions, but both L-carnosine at 639 mg/kg p.o. and N-acetyl-L-carnosine at 817 mg/kg p.o. also markedly inhibited the formation of erosions. CL-1700 at 1,000 mg/kg p.o. increased the volume and raised the pH value, and the agent at 600 mg/kg i.p. reduced the acid output.
3.Dermal peptide delivery using enhancer molecules and colloidal carrier systems--part I: carnosine.
Goebel AS1, Schmaus G, Neubert RH, Wohlrab J. Skin Pharmacol Physiol. 2012;25(6):281-7. doi: 10.1159/000341085. Epub 2012 Aug 7.
Due to the lipophilic properties of the uppermost skin layer of the stratum corneum (SC), it is highly challenging to attain therapeutic concentrations of active substances; hydrophilic drugs, in particular, penetrate poorly. The purpose of this study was the improvement of the topical bioavailability of the hydrophilic dipeptides L-carnosine and its related compound N-acetyl-L-carnosine. Different strategies were investigated. On the one hand, an enhancer molecule, 1,2-pentylene glycol (PG), was added to a standard preparation, and on the other hand, a microemulsion (ME-PG) system was developed. Both were compared to the standard formulation without an enhancer molecule. For all 3 preparations, the penetration of the peptides in ex vivo human skin was investigated. This allows statements to be made regarding dermal penetration, localization and distribution of the active substances in each skin layer as well as the influence of vehicle variations, in this case, the addition of PG or the incorporation of N-acetyl-L-carnosine in an ME-PG system.
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