zinc (2S)-2-(3-aminopropanoylazanidyl)-3-(1H-imidazol-5-yl)propanoate
Grundinformationen
- CAS
107667-60-7- Standard-SMILES
NCCC(=O)[N-][C@@H](Cc1cnc[nH]1)C(=O)[O-].[Zn+2]- InChIKey
IGXZLYMCFZHNKW-FJXQXJEOSA-L- Summenformel
- C9H12N4O3Zn
- Durchschnittliche Molmasse
- 289,6 g/mol
- Monoisotopische Masse
- 288,020082
Überblick
Polaprezinc is a chelated form of zinc and L-carnosine. It is a zinc-related medicine approved for the first time in Japan, which has been clinically used to treat gastric ulcers. It was determined that polaprezinc may be effective in pressure ulcer treatment. A study in 2013 showed that CO-administration of polaprezinc may be effective against small intestine mucosal injury associated with long-term aspirin therapy.
Namen und Bezeichner
- Bevorzugter Name
- zinc (2S)-2-(3-aminopropanoylazanidyl)-3-(1H-imidazol-5-yl)propanoate
- IUPAC
- zinc (2S)-2-(3-aminopropanoylazanidyl)-3-(1H-imidazol-5-yl)propanoate
- Englischer Name
- Polaprezinc
- Summenformel
- C9H12N4O3Zn
- Molmasse
- 289.61
Namen und Synonyme
ZINC CARNOSINEZinc L-CarnosinePromacZ 103D01611POLAPREZINCPepZinGI(R)Promac (tn)PolyprezineZn Carnosine
Datenbank-Bezeichner
- CAS
107667-60-7- PubChem CID
- 73291726
Eigenschaften
Berechnete Struktureigenschaften
- Polarare Oberfläche (TPSA)
- 113 Ų
- H-Brücken-Donoren
- 2
- H-Brücken-Akzeptoren
- 6
- Frei drehbare Bindungen
- 5
- Schwere Atome
- 17
- Formalladung
- 0
- Komplexität
- 259
Physikochemische Eigenschaften
- Schmelzpunkt
- 300 °C · >300°C
- Siedepunkt
- 177.5 °C · 177.5°C
- storage temp.
- Refrigerator
- Löslichkeit
- Aqueous Acid (Slightly)
- Aggregatzustand
- Solid
- Farbe
- White to Off-White
- InChI
- InChI=1/C9H14N4O3.Zn/c10-2-1-8(14)13-7(9(15)16)3-6-4-11-5-12-6;/h4-5,7H,1-3,10H2,(H3,11,12,13,14,15,16);/q;+2/p-2/t7-;/s3
- InChIKey
- IGXZLYMCFZHNKW-WMASNCOMNA-L
- SMILES
- [C@@H]1(C(=O)O[Zn]N1C(=O)CCN)CC1NC=NC=1 |&1:0,r|
- CAS Datenbank
- 107667 · 107667-60-7(CAS DataBase Reference)
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
Sicherheitsdaten
- wgk
- WGK 3
- Toxizität
- LD50 in male, female mice, rats (mg/kg): 220, 165, 405, 422 i.p.; 758, 874, >5000, >5000 s.c.; 1269, 1331, 8441, 7375 orally (Matsuda)
- Speicherklasse
- 11 - Combustible Solids
Chemie und Industrie
Pharmakologische Informationen
Protein BindingIt has been observed that a diet heavy in proteins accelerates the absorption of zinc, implying that amino acids with low molecular weight may carry zinc into the circulatory system via complexation.
PharmacodynamicsUsed to treat/manage peptic ulcer disease or irritation of the gastrointestinal tract by promoting tissue healing by the elimination of free radicals.
Mechanism of Action
Polaprezinc increases the expression of various antioxidant enzymes, including superoxide dismutase 1 (SOD-1), SOD-2, heme oxygenase-1 (HO-1), glutathione S-transferase (GST), glutathione peroxidase (GSH-px), peroxidredoxin-1 (PRDX1; PRXI) and PRXD5 (PRXV). This process occurs in the gastric mucosa, defending mucosal cells against reactive oxygen species. This drug inhibits the activity of the transcription factor nuclear factor-kappaB (NF-kB) and decreases the expression of various inflammatory cytokines, including interleukin (IL) 1beta, IL-6, IL-8, and tumor necrosis factor alpha (TNF-a). Polaprezinc also promotes the expression of numerous growth factors, including as platelet-derived growth factor-B (PDGF-B), vascular endothelial growth factor (VEGF), and nerve growth factor (NGF), in addition to various heat shock proteins (HSPs), including HSP90, HSP70, HSP60, HSP47, HSP27, and HSP10. This process promotes tissue growth and protects against damage the gastric mucosa.
Biological Half-LifeThe half-life of polaprezinc has been studied in rats and found to be approximately 2 hours.
Metabolism/Metabolites
Excretion rates of polaprezinc after a single administration using 14C-labeled drug to rats are 4.1% in urine, 13.3% in feces, and 38.8% in exhalation, and those using 65Zn-labeled L-CAZ are 0.3% in urine and 85.0% in feces. The absorption rate of zinc is estimated to be about 11%.
Absorption, Distribution and Excretion
Intestinal absorption of L-CAZ was studied in rats by Sano et al. using 14C- and 65Zn-labeled compounds. They suggested that L-CAZ dissociates to its components, L-carnosine and zinc, during intestinal absorption.
Intestinal absorption of the drug was examined using 14C- and 65Zn-labeled compounds. Polaprezinc metabolizes into its components, L-carnosine and zinc, during intestinal absorption. It was found that the excretion rates after one administration using 14C-labeled L-CAZ to rats were 4.1% in urine, 13.3% in feces, and 38.8% in exhalation. The study using 65Zn-labeled Paleprozinc were 0.3% in urine and 85.0% in the feces. The absorption rate of zinc is estimated to be approximately 11%.
Anwendungen
BeschreibungPolaprezinc, a complex of zinc ion and L-carnosine, is an antiulcer agent launched in Japan. It is effective in promoting the healing of gastric ulcers in addition to preventing ulcer relapse. In rat studies, polaprezinc reduces the incidence of stomach lesions induced by ethanol. No effect was seen on ultrastructural damage or on cell proliferation and it appears that polaprezinc combines the cytoprotective effect of zinc with the ulcer healing properties of Lcarnosine. The in vivo antioxidative properties of polaprezinc has been suggested to be responsible for its protective effect against gastric mucosal injury. Recent studies revealed that polaprezinc is an activator of bone formetion and has inhibitory effect of bone resorption. This agent is thus able to prevent the deterioration of bone metabolism indicating its potential usefulness in the treatment of osteoporosis. Polaprezinc has also been claimed for the prophylaxis and treatment of alcoholic hepatopathy, viral hepatitis or other hepatopathies caused by certain drugs, poisons and radiation.
VerwendenA novel anti-gastric ulcer agent
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