Prezatide
Identification
- Generic Name
- Prezatide
- DrugBank Accession Number
- DB11296
- Background
Prezatide is a tripeptide consisting of glycine, histidine, and lysine which readily forms a complex with copper ions 6. Prezatide is used in cosmetic products for the skin and hair. It is known to aid wound healing and its potential applications in chronic obstructive pulmonary disease and metastatic colon cancer are currently being investigated.
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 340.384
Monoisotopic: 340.185903277 - Chemical Formula
- C14H24N6O4
- Synonyms
- GHK
- Gly-His-Lys
- Glycyl-L-histidyl-L-lysine
- Glycylhistidyllysine
- Growth-modulating peptide (human)
- Liver cell growth factor
- Tripeptide-1
- External IDs
- NSC-379527
Pharmacology
- Indication
Commonly used in cosmetic products for the skin and hair 6.
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- Pharmacodynamics
Prezatide in complex with copper improve skin elasticity, density, and firmness, reduces fine lines and wrinkles, reduces photodamage, increases keratinocyte proliferation 6. Prezatide also displays anti-oxidant and angiogenic effects and appears to modulate tissue remodeling in injury.
- Mechanism of action
Prezatide in complex with copper increases the synthesis and deposition of type I collagen and glycosaminoglycan 1 3. It also increases the expression of matrix metalloproteinase-2 as well as tissue inhibitor of matrix metalloproteinases-1 and -2, suggesting that it plays a role in the modulation of tissue remodeling 2. It is thought that prezatide's antioxidant activity is due to its ability to supply copper for superoxide dismutase and its anti inflammatory ability due to the blockage the of iron (Fe2+) release during injury 8. Prezatide also increases angiogenesis to injury sites. The precise mechanisms of these effects are unknown. It is also unknown whether prezatide's effects are due to the action of the tripeptide itself or its ability to localize and transport copper 9. Prezatide is known to be bound by heparin and heparin sulfate 10
- Absorption
Prezatide both free and in complex with copper can pass through the stratum corneum 7. Its absorption is pH dependent with the highest absorption occurring at physiological pH.
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
Prezatide is broken down to histidyl-lysine which is likely further degraded to other metabolites of proteolysis 5.
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- Route of elimination
Not Available
- Half-life
Prezatide is rapidly eliminated within minutes 5.
- Clearance
Not Available
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Products
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- Product Ingredients
Ingredient UNII CAS InChI Key Prezatide monoacetate 8AA809EUS9 72957-37-0 MGNUTAFMLGJBGV-ACMTZBLWSA-N - International/Other Brands
- Kollaren
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as peptides. These are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another.
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- Carboxylic acids and derivatives
- Sub Class
- Amino acids, peptides, and analogues
- Direct Parent
- Peptides
- Alternative Parents
- N-acyl-alpha amino acids / Imidazolyl carboxylic acids and derivatives / Medium-chain fatty acids / Amino fatty acids / Heterocyclic fatty acids / Heteroaromatic compounds / Amino acids / Propargyl-type 1,3-dipolar organic compounds / Azacyclic compounds / Carboximidic acids show 7 more
- Substituents
- Alpha peptide / Alpha-amino acid or derivatives / Amine / Amino acid / Amino acid or derivatives / Amino fatty acid / Aromatic heteromonocyclic compound / Azacycle / Azole / Carbonyl group show 25 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- tripeptide (CHEBI:75430)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 39TG2H631E
- CAS number
- 49557-75-7
- InChI Key
- MVORZMQFXBLMHM-QWRGUYRKSA-N
- InChI
- InChI=1S/C14H24N6O4/c15-4-2-1-3-10(14(23)24)20-13(22)11(19-12(21)6-16)5-9-7-17-8-18-9/h7-8,10-11H,1-6,15-16H2,(H,17,18)(H,19,21)(H,20,22)(H,23,24)/t10-,11-/m0/s1
- IUPAC Name
- (2S)-6-amino-2-[(2S)-2-(2-aminoacetamido)-3-(1H-imidazol-4-yl)propanamido]hexanoic acid
- SMILES
- NCCCC[C@H](NC(=O)[C@H](CC1=CNC=N1)NC(=O)CN)C(O)=O
References
- General References
- Maquart FX, Pickart L, Laurent M, Gillery P, Monboisse JC, Borel JP: Stimulation of collagen synthesis in fibroblast cultures by the tripeptide-copper complex glycyl-L-histidyl-L-lysine-Cu2+. FEBS Lett. 1988 Oct 10;238(2):343-6. [Article]
- Simeon A, Emonard H, Hornebeck W, Maquart FX: The tripeptide-copper complex glycyl-L-histidyl-L-lysine-Cu2+ stimulates matrix metalloproteinase-2 expression by fibroblast cultures. Life Sci. 2000 Sep 22;67(18):2257-65. [Article]
- Wegrowski Y, Maquart FX, Borel JP: Stimulation of sulfated glycosaminoglycan synthesis by the tripeptide-copper complex glycyl-L-histidyl-L-lysine-Cu2+. Life Sci. 1992;51(13):1049-56. [Article]
- Maquart FX, Bellon G, Chaqour B, Wegrowski J, Patt LM, Trachy RE, Monboisse JC, Chastang F, Birembaut P, Gillery P, et al.: In vivo stimulation of connective tissue accumulation by the tripeptide-copper complex glycyl-L-histidyl-L-lysine-Cu2+ in rat experimental wounds. J Clin Invest. 1993 Nov;92(5):2368-76. [Article]
- Endo T, Miyagi M, Ujiie A: Simultaneous determination of glycyl-L-histidyl-L-lysine and its metabolite, L-histidyl-L-lysine, in rat plasma by high-performance liquid chromatography with post-column derivatization. J Chromatogr B Biomed Sci Appl. 1997 Apr 25;692(1):37-42. [Article]
- Pickart L, Vasquez-Soltero JM, Margolina A: GHK Peptide as a Natural Modulator of Multiple Cellular Pathways in Skin Regeneration. Biomed Res Int. 2015;2015:648108. doi: 10.1155/2015/648108. Epub 2015 Jul 7. [Article]
- Mazurowska L, Mojski M: ESI-MS study of the mechanism of glycyl-l-histidyl-l-lysine-Cu(II) complex transport through model membrane of stratum corneum. Talanta. 2007 Apr 30;72(2):650-4. doi: 10.1016/j.talanta.2006.11.034. Epub 2006 Dec 22. [Article]
- Pickart L, Vasquez-Soltero JM, Margolina A: The human tripeptide GHK-Cu in prevention of oxidative stress and degenerative conditions of aging: implications for cognitive health. Oxid Med Cell Longev. 2012;2012:324832. doi: 10.1155/2012/324832. Epub 2012 May 10. [Article]
- Borkow G, Gabbay J, Zatcoff RC: Could chronic wounds not heal due to too low local copper levels? Med Hypotheses. 2008;70(3):610-3. Epub 2007 Aug 6. [Article]
- Rabenstein DL, Robert JM, Hari S: Binding of the growth factor glycyl-L-histidyl-L-lysine by heparin. FEBS Lett. 1995 Dec 4;376(3):216-20. [Article]
- External Links
- PubChem Compound
- 73587
- PubChem Substance
- 347827962
- ChemSpider
- 66263
- BindingDB
- 50350478
- 1368533
- ChEBI
- 75430
- ChEMBL
- CHEMBL1814493
- ZINC
- ZINC000013507674
- FDA label
- Download (406 KB)
- MSDS
- Download (32.1 KB)
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 3.14 mg/mL ALOGPS logP -3 ALOGPS logP -5.1 Chemaxon logS -2 ALOGPS pKa (Strongest Acidic) 3.46 Chemaxon pKa (Strongest Basic) 10.2 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 7 Chemaxon Hydrogen Donor Count 6 Chemaxon Polar Surface Area 176.22 Å2 Chemaxon Rotatable Bond Count 11 Chemaxon Refractivity 84.91 m3·mol-1 Chemaxon Polarizability 34.52 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-00lr-9521000000-775a68f040c2f4d3f1bf Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-006x-0149000000-6b60ce7d8971edfc78bb Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-000i-0096000000-e9ea700c59ad9140bff1 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-08i9-1691000000-1583ddf35a442b70a473 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0w29-0960000000-714da9f4986f44e44e26 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0gx9-7950000000-6a2e7123a1be89277260 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0k97-7900000000-7cb3ae350d5b61b0855d Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 190.371898 predictedDarkChem Lite v0.1.0 [M-H]- 178.42491 predictedDeepCCS 1.0 (2019) [M+H]+ 191.653098 predictedDarkChem Lite v0.1.0 [M+H]+ 180.78291 predictedDeepCCS 1.0 (2019) [M+Na]+ 191.508498 predictedDarkChem Lite v0.1.0 [M+Na]+ 187.92291 predictedDeepCCS 1.0 (2019)
Drug created at December 03, 2015 16:52 / Updated at June 12, 2020 16:53