Polaprezinc

• CAS: 107667-60-7
• Catalog Number: ACM107667607-1
• Category: Main Products
• Molecular Weight: 290.6
• Molecular Formula: C9H13N4O3Zn
• Synonyms: Beta-alanyl-L-histidinato zinc
• IUPAC Name: 3-aminopropanoyl-[(1S)-1-carboxy-2-(1H-imidazol-5-yl)ethyl]azanide;zinc
• Canonical SMILES: C1=C(NC=N1)CC(C(=O)O)[N-]C(=O)CCN.[Zn]
• 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
• InChI Key: GFWBKUDRXMQSFD-FJXQXJEOSA-M
• Boiling Point: 557.6ºC at 760 mmHg
• Melting Point: >300 °C
• Flash Point: 291ºC
• Appearance: white crystalline
• Complexity: 265
• Covalently-Bonded Unit Count: 2
• Defined Atom Stereocenter Count: 1
• EC Number: 600-848-7
• Exact Mass: 289.027907
• Heavy Atom Count: 17
• Hydrogen Bond Acceptor Count: 6
• Hydrogen Bond Donor Count: 3
• Isomeric SMILES: C1=C(NC=N1)C[C@@H](C(=O)O)[N-]C(=O)CCN.[Zn]
• Monoisotopic Mass: 289.027907
• Rotatable Bond Count: 4
• Topological Polar Surface Area: 110 Ų

Case Study

Synthesis and Pharmacological Effects of Polaprezinc

Li, Mingru, et al. Experimental and Therapeutic Medicine, 2021, 22(6), 1-7.

Polaprezinc, the zinc complex of L‑carnosine, is an active ingredient of potent gastric mucosal protectant. Proven clinical uses of polaprezinc include helicobacter pylori eradication, application after ESD, drug-related gastrointestinal mucosal injury, mucosal damage caused by radiotherapy Oral mucositis, radioactive esophagitis, radioactive gastroenteritis, and treatment of ulcerative colitis.
· Synthesis of Polaprezinc
The synthesis of polaprezinc includes two steps: L-carnosine synthesis and L-carnosine-Zn salt complexation. First, b-dihydro-1,3-thiazole-2,4-dione was synthesized from alanine and methyl o-ethylxanthate as raw materials, and then acylated with L-histidine to obtain L-carnosine. L-carnosine is then complexed with zinc acetate to obtain polaprezinc.
· Pharmacological Effects of Polaprezinc
The pharmacological effects of polaprezinc include anti-ulcer effect, anti-Helicobacter pylori (H. pylori) effect, promotion of healing, and anti-liver fibrosis. For example, polaprezinc, an antiulcer drug with enhanced defense factors, was effective in all experimental models, including emergency gastric injury, aspirin hydrochloride gastric injury, histamine hydrochloride gastric injury, and ethanol hydrochloride gastric injury.

Polaprezinc as a Potential Supplement for Fracture Healing

Ko E A, et al. Communications Biology, 2022, 5(1), 462.

Polaprezinc is an orally bioavailable chelate consisting of zinc and L-carnosine. The study employed polaprezinc as a drug repositioning strategy. The results showed that polaprezinc enhanced the differentiation potential of hBMSCs and mBMMs into osteoblasts and osteoclasts, respectively. Polaprezinc treatment upregulated the protein levels of yes-associated protein (YAP), a positive regulator of osteoblast and osteoclast differentiation, in osteoblast and osteoclast precursor cells. This means that Polaprezinc is a potential supplement for fracture healing.
Experimental details with polaprezinc
· Polaprezinc for in vitro osteogenic differentiation: For the purpose of inducing in vitro osteogenesis, human bone marrow mesenchymal stem cells (hBMSCs) were cultured in osteogenic medium composed of DMEM-LG with 10% FBS, 1% antibiotic-antimycotic solution, 10 mM β-glycerophosphate, and 50 μg/mL ascorbic acid. This culture was supplemented with either polaprezinc or ZnSO4, and it was maintained for a period of 5-12 days.
· Polaprezinc for intracellular zinc measurement: Polaprezinc and ZnSO4 were applied to hBMSCs or RAW264.7 cells. Following a 24-hour exposure period, 25 μM of Zinquin was introduced and allowed to incubate for 30 minutes at 37 °C. Fluorescence was measured at an excitation wavelength of 368 nm and emission of 490 nm using a Fluorometer.

Custom Q&A

What is the chemical formula of Polaprezinc?

MF:C9H12N4O3Zn

What is the storage temperature recommended for Polaprezinc?

Refrigerator

What is the melting point of Polaprezinc?

>300°C

What are the synonyms of Polaprezinc?

POLAPREZINC, zinc l-carnosine complex, zinc n-(3-aminopropionyl)histidine, ZINC CARNOSINE, [b-Alanyl-kN-L-histidinato(2-)-kN,kO]-zinc, b-Alanyl-L-histidinato Zinc, Promac, Z 103

What are the uses of Polaprezinc?

Polaprezinc is mentioned as an anti-ulcer agent effective in promoting the healing of gastric ulcers, preventing ulcer relapse, and activating bone formation with inhibitory effects on bone resorption. It is also claimed for the prophylaxis and treatment of alcoholic hepatopathy, viral hepatitis, and other hepatopathies caused by certain drugs, poisons, and radiation.

What are the chemical properties of Polaprezinc?

Polaprezinc is described as a white to pale-yellow crystalline solid.

What is the boiling point of Polaprezinc?

177.5°C

Who is the originator of Polaprezinc?

Hamari Chemicals (Japan)

What is the product category of Polaprezinc?

Polaprezinc falls under the categories of Intermediates & Fine Chemicals and Pharmaceuticals.

How has Polaprezinc been suggested to work in preventing gastric mucosal injury?

Polaprezinc's in vivo antioxidative properties are suggested to be responsible for its protective effect against gastric mucosal injury.