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    NCGC00181764-01

    ACTIVE PHARMA INGREDIENTS

    PharmaCompass
    Xls

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    2D Structure
    Also known as: 107667-60-7, Zinc l-carnosine, Beta-alanyl-l-histidinato zinc, Ncgc00181764-01, Dsstox_cid_28541, Dsstox_rid_82813
    Molecular Formula
    C9H13N4O3Zn-
    Molecular Weight
    290.6  g/mol
    InChI Key
    GFWBKUDRXMQSFD-FJXQXJEOSA-M
    Polaprezinc is an orally bioavailable chelate composed of zinc and L-carnosine, with potential gastroprotective, anti-oxidant, anti-ulcer and anti-inflammatory activities. Upon administration, polaprezinc increases the expression of various anti-oxidant enzymes, such as 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) in the gastric mucosa, which protect cells against reactive oxygen species (ROS). In addition, this agent inhibits the activity of the transcription factor nuclear factor-kappaB (NF-kappaB) and reduces the expression of several pro-inflammatory cytokines, such as interleukin (IL) 1beta, IL-6, IL-8, and tumor necrosis factor alpha (TNF-a). Polaprezinc also increases the expression of various growth factors, such as platelet-derived growth factor-B (PDGF-B), vascular endothelial growth factor (VEGF), and nerve growth factor (NGF), and various heat shock proteins (HSPs), including HSP90, HSP70, HSP60, HSP47, HSP27, and HSP10. This protects against damages to, and accelerates healing of the gastric mucosa.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    3-aminopropanoyl-[(1S)-1-carboxy-2-(1H-imidazol-5-yl)ethyl]azanide;zinc
    2.1.2 InChI
    InChI=1S/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);/p-1/t7-;/m0./s1
    2.1.3 InChI Key
    GFWBKUDRXMQSFD-FJXQXJEOSA-M
    2.1.4 Canonical SMILES
    C1=C(NC=N1)CC(C(=O)O)[N-]C(=O)CCN.[Zn]
    2.1.5 Isomeric SMILES
    C1=C(NC=N1)C[C@@H](C(=O)O)[N-]C(=O)CCN.[Zn]
    2.2 Synonyms
    2.2.1 MeSH Synonyms

    1. Ahz-zinc

    2. Beta-alanyl-l-histidinato Zinc

    3. Z 103

    4. Z-103

    5. Zinc Carnosine

    6. Zinc L-carnosine

    7. Zinc L-carnosine Complex

    8. Zinc N-(3-aminopropionyl)histidine

    2.2.2 Depositor-Supplied Synonyms

    1. 107667-60-7

    2. Zinc L-carnosine

    3. Beta-alanyl-l-histidinato Zinc

    4. Ncgc00181764-01

    5. Dsstox_cid_28541

    6. Dsstox_rid_82813

    7. Dsstox_gsid_48615

    8. Chembl3184454

    9. Dtxsid7048615

    10. Tox21_112950

    11. Akos037515832

    12. Db09221

    13. Cas-107667-60-7

    14. E76520

    15. 667p607

    2.3 Create Date
    2011-05-03
    3 Chemical and Physical Properties
    Molecular Weight 290.6 g/mol
    Molecular Formula C9H13N4O3Zn-
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count6
    Rotatable Bond Count4
    Exact Mass289.027907 g/mol
    Monoisotopic Mass289.027907 g/mol
    Topological Polar Surface Area110 Ų
    Heavy Atom Count17
    Formal Charge-1
    Complexity265
    Isotope Atom Count0
    Defined Atom Stereocenter Count1
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2
    4 Drug and Medication Information
    4.1 Drug Indication

    Peptic ulcer disease, dyspepsia.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Used to treat/manage peptic ulcer disease or irritation of the gastrointestinal tract by promoting tissue healing by the elimination of free radicals.

    5.2 MeSH Pharmacological Classification

    Anti-Ulcer Agents

    Various agents with different action mechanisms used to treat or ameliorate PEPTIC ULCER or irritation of the gastrointestinal tract. This has included ANTIBIOTICS to treat HELICOBACTER INFECTIONS; HISTAMINE H2 ANTAGONISTS to reduce GASTRIC ACID secretion; and ANTACIDS for symptomatic relief. (See all compounds classified as Anti-Ulcer Agents.)

    5.3 Absorption, Distribution and Excretion

    Absorption

    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.

    Route of Elimination

    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%.

    5.4 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%.

    5.5 Biological Half-Life

    The half-life of polaprezinc has been studied in rats and found to be approximately 2 hours.

    5.6 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.