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Polaprezinc

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Chemistry

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Also known as: Polaprezinc, 107667-60-7, Polaprezinc [inn], Beta-alanyl-l-histidinato zinc, Z 103, Carnosine zinc

Molecular Formula

C₉H₁₁N₄O₃Zn-

Molecular Weight

288.6 g/mol

InChI Key

IUWLTSZHVYHOHY-FJXQXJEOSA-L

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

Polaprezinc

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

zinc;(2S)-2-(3-azanidylpropanoylazanidyl)-3-(1H-imidazol-5-yl)propanoate

2.1.2 InChI

InChI=1S/C9H13N4O3.Zn/c10-2-1-8(14)13-7(9(15)16)3-6-4-11-5-12-6;/h4-5,7,10H,1-3H2,(H3,11,12,13,14,15,16);/q-1;+2/p-2/t7-;/m0./s1

2.1.3 InChI Key

IUWLTSZHVYHOHY-FJXQXJEOSA-L

2.1.4 Canonical SMILES

C1=C(NC=N1)CC(C(=O)[O-])[N-]C(=O)CC[NH-].[Zn+2]

2.1.5 Isomeric SMILES

C1=C(NC=N1)C[C@@H](C(=O)[O-])[N-]C(=O)CC[NH-].[Zn+2]

2.2 Synonyms

2.2.1 MeSH Synonyms

1. Ahz-zinc

2. Beta-alanyl-l-histidinato Zinc

3. Polaprezinc

4. Z 103

5. Z-103

6. Zinc Carnosine

7. Zinc L-carnosine Complex

8. Zinc N-(3-aminopropionyl)histidine

2.2.2 Depositor-Supplied Synonyms

1. Polaprezinc

2. 107667-60-7

3. Polaprezinc [inn]

4. Beta-alanyl-l-histidinato Zinc

5. Z 103

6. Carnosine Zinc

7. (s)-2-(3-aminopropanamido)-3-(1h-imidazol-5-yl)propanoic Acid Zinc Complex

8. 0wa1b15a1z

9. Promac (antiulcer Agent)

10. Unii-0wa1b15a1z

11. Ccris 3974

12. Hy-b0729

13. N(alpha)-(3-aminopropionyl)histidinato(2-)n1,n2,o(alpha))-zinc

14. Cs-7571

15. Zinc, (beta-alanyl-kappan-l-histidinato(2-)-kappan,kappao)-

16. Zinc, (n-beta-alanyl-l-histidinato(2-)-n,n(sup N),o(sup Alpha))-

17. (s)-2-(3-aminopropanamido)-3-(1h-imidazol-5-yl)propanoicacidzinccomplex

18. Zinc, (n-beta-alanyl-l-histidinato(2-)-n,n(n),n3,o(alpha))-, (t-4)-

19. Catena-poly(zinc-mu-(beta-alanyl-l-histidinato(2(-))-n,n(sup N),o:n(sup Tau)))

20. Catena-poly(zinc-mu-(beta-alanyl-l-histidinato(2-)-n,n(sup N),o:n(sup Tau)))

2.3 Create Date

2010-03-29

3 Chemical and Physical Properties

Molecular Formula	C₉H₁₁N₄O₃Zn-
Molecular Weight	288.6 g/mol
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	2
Exact Mass	287.012257 g/mol
Monoisotopic Mass	287.012257 g/mol
Topological Polar Surface Area	87.9 Å²
Heavy Atom Count	17
Formal Charge	-1
Complexity	265
Isotope Atom Count	0
Defined Atom Stereocenter Count	1
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

4 Pharmacology and Biochemistry

4.1 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.)

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