Prezatide

Identification

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Name
Prezatide
Accession Number
DB11296
Type
Small Molecule
Groups
Experimental
Description

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.

Structure
Thumb
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
Product Ingredients
IngredientUNIICASInChI Key
Prezatide monoacetate8AA809EUS972957-37-0MGNUTAFMLGJBGV-ACMTZBLWSA-N
International/Other Brands
Kollaren
Categories
UNII
39TG2H631E
CAS number
49557-75-7
Weight
Average: 340.384
Monoisotopic: 340.185903277
Chemical Formula
C14H24N6O4
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

Pharmacology

Indication

Commonly used in cosmetic products for the skin and hair 6.

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.

Route of elimination
Not Available
Half life

Prezatide is rapidly eliminated within minutes 5.

Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
  1. 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. [PubMed:3169264]
  2. 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. [PubMed:11045606]
  3. 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. [PubMed:1522753]
  4. 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. [PubMed:8227353]
  5. 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. [PubMed:9187381]
  6. 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. [PubMed:26236730]
  7. 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. [PubMed:19071668]
  8. 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. [PubMed:22666519]
  9. 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. [PubMed:17689198]
  10. 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. [PubMed:7498545]
External Links
PubChem Compound
73587
PubChem Substance
347827962
ChemSpider
66263
BindingDB
50350478
ChEBI
75430
ChEMBL
CHEMBL1814493
FDA label
Download (406 KB)
MSDS
Download (32.1 KB)

Clinical Trials

Clinical Trials
Not Available

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
PropertyValueSource
Water Solubility3.14 mg/mLALOGPS
logP-3ALOGPS
logP-5.1ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)3.46ChemAxon
pKa (Strongest Basic)10.2ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area176.22 Å2ChemAxon
Rotatable Bond Count11ChemAxon
Refractivity84.91 m3·mol-1ChemAxon
Polarizability34.52 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

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 / N-acyl-alpha-amino acid / N-acyl-alpha amino acid or derivatives / Alpha-amino acid or derivatives / Imidazolyl carboxylic acid derivative / Medium-chain fatty acid / Amino fatty acid / Heterocyclic fatty acid / Fatty acyl / Fatty acid
show 25 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
tripeptide (CHEBI:75430)

Drug created on December 03, 2015 09:52 / Updated on June 04, 2019 07:18