Prezatide copper

Identification

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Name
Prezatide copper
Accession Number
DB14683  (DBSALT002419)
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
  • CG-copper peptide
  • Copper tripeptide-1
  • GHK complex with copper
  • GHK copper
Product Ingredients
IngredientUNIICASInChI Key
Prezatide copper acetateA3LEI4P1NB130120-57-9LUNQZVCDZKODKF-PFVVTREHSA-J
Active Moieties
NameKindUNIICASInChI Key
Prezatidecomplex39TG2H631E49557-75-7MVORZMQFXBLMHM-QWRGUYRKSA-N
Cupric cationcomplex8CBV67279L15158-11-9JPVYNHNXODAKFH-UHFFFAOYSA-N
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Dermaheal Skin Delight Mask Pack PlusPatch0.22 mg/22gTopicalYBK Investment, INC2013-10-21Not applicableUs
Elcure Pepta HairShampoo0.1 g/100mLTopicalElcure Co., Ltd.2016-03-302017-04-20Us
Elcure Pepta Hair EssenceLiquid0.1 g/100mLTopicalElcure Co., Ltd.2016-03-302017-04-20Us
Pepta HairShampoo0.1 g/100mLTopicalElcure Co., Ltd.2016-03-302016-04-01Us
Pepta Hair EssenceLiquid0.1 g/100mLTopicalElcure Co., Ltd.2016-03-302016-04-01Us
Skin Delight Mask PackPatch0.22 mg/22gTopicalYBK Investment, INC2013-10-212013-10-29Us
Skin Delight Mask Pack PlusPatch0.22 mg/22gTopicalYBK Investment, INC2013-10-21Not applicableUs
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Cosmeceutical Mask PackPrezatide copper (0.22 mg/22g) + Basic Fibroblast Growth Factor (0.044 mg/22g) + Mecasermin (0.044 mg/22g) + Nepidermin (0.044 mg/22g) + Palmitoyl oligopeptide (0.044 mg/22g) + Thioredoxin (0.044 mg/22g)PatchTopicalYBK Investment, INC2013-10-21Not applicableUs
Cosmeceutical Mask PackPrezatide copper (0.22 mg/22g) + Basic Fibroblast Growth Factor (0.044 mg/22g) + Mecasermin (0.044 mg/22g) + Nepidermin (0.044 mg/22g) + Palmitoyl oligopeptide (0.044 mg/22g) + Thioredoxin (0.044 mg/22g)PatchTopicalYBK Investment, INC2013-10-212013-10-29Us
Dermaheal Cosmeceutical Mask Pack PlusPrezatide copper (0.22 mg/22g) + Basic Fibroblast Growth Factor (0.044 mg/22g) + Mecasermin (0.044 mg/22g) + Nepidermin (0.044 mg/22g) + Palmitoyl oligopeptide (0.044 mg/22g) + Thioredoxin (0.044 mg/22g)PatchTopicalYBK Investment, INC2013-10-21Not applicableUs
Pepplus Special Skin Care Lifting ProgramPrezatide copper (0.002 g/100mL) + Basic Fibroblast Growth Factor (0.001 g/100mL) + Green tea leaf (1.28 g/100mL)KitTopicalPicobio Co., Ltd.2019-05-15Not applicableUs
Special Skin Care Lifting ProgramPrezatide copper (0.002 g/100mL) + Basic Fibroblast Growth Factor (0.001 g/100mL) + Green tea leaf (1.28 g/100mL)KitTopicalPicobio Co., Ltd.2019-05-15Not applicableUs
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Cosmeceutical Mask PackPrezatide copper (0.22 mg/22g) + Basic Fibroblast Growth Factor (0.044 mg/22g) + Mecasermin (0.044 mg/22g) + Nepidermin (0.044 mg/22g) + Palmitoyl oligopeptide (0.044 mg/22g) + Thioredoxin (0.044 mg/22g)PatchTopicalYBK Investment, INC2013-10-212013-10-29Us
Cosmeceutical Mask PackPrezatide copper (0.22 mg/22g) + Basic Fibroblast Growth Factor (0.044 mg/22g) + Mecasermin (0.044 mg/22g) + Nepidermin (0.044 mg/22g) + Palmitoyl oligopeptide (0.044 mg/22g) + Thioredoxin (0.044 mg/22g)PatchTopicalYBK Investment, INC2013-10-21Not applicableUs
Dermaheal Cosmeceutical Mask Pack PlusPrezatide copper (0.22 mg/22g) + Basic Fibroblast Growth Factor (0.044 mg/22g) + Mecasermin (0.044 mg/22g) + Nepidermin (0.044 mg/22g) + Palmitoyl oligopeptide (0.044 mg/22g) + Thioredoxin (0.044 mg/22g)PatchTopicalYBK Investment, INC2013-10-21Not applicableUs
Dermaheal Skin Delight Mask Pack PlusPrezatide copper (0.22 mg/22g)PatchTopicalYBK Investment, INC2013-10-21Not applicableUs
Elcure Pepta HairPrezatide copper (0.1 g/100mL)ShampooTopicalElcure Co., Ltd.2016-03-302017-04-20Us
Elcure Pepta Hair EssencePrezatide copper (0.1 g/100mL)LiquidTopicalElcure Co., Ltd.2016-03-302017-04-20Us
Pepplus Special Skin Care Lifting ProgramPrezatide copper (0.002 g/100mL) + Basic Fibroblast Growth Factor (0.001 g/100mL) + Green tea leaf (1.28 g/100mL)KitTopicalPicobio Co., Ltd.2019-05-15Not applicableUs
Pepta HairPrezatide copper (0.1 g/100mL)ShampooTopicalElcure Co., Ltd.2016-03-302016-04-01Us
Pepta Hair EssencePrezatide copper (0.1 g/100mL)LiquidTopicalElcure Co., Ltd.2016-03-302016-04-01Us
Skin Delight Mask PackPrezatide copper (0.22 mg/22g)PatchTopicalYBK Investment, INC2013-10-212013-10-29Us
Categories
Not Available
UNII
6BJQ43T1I9
CAS number
89030-95-5
Weight
Average: 402.921
Monoisotopic: 402.107128
Chemical Formula
C14H23CuN6O4
InChI Key
NZWIFMYRRCMYMN-ACMTZBLWSA-M
InChI
InChI=1S/C14H24N6O4.Cu/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);/q;+2/p-1/t10-,11-;/m0./s1
IUPAC Name
copper(2+) (2S)-6-amino-2-[(2S)-2-(2-aminoacetamido)-3-(1H-imidazol-5-yl)propanamido]hexanoate
SMILES
[Cu++].NCCCC[C@H](NC(=O)[C@H](CC1=CN=CN1)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

Additional Data Available
Adverse Effects

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Additional Data Available
Contraindications

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Additional Data Available
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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
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

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
ChemSpider
32698045

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
PatchTopical
PatchTopical0.22 mg/22g
ShampooTopical0.1 g/100mL
LiquidTopical0.1 g/100mL
KitTopical
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility2.08 mg/mLALOGPS
logP-0.94ALOGPS
logP-5.4ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)3.46ChemAxon
pKa (Strongest Basic)10.2ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area179.05 Å2ChemAxon
Rotatable Bond Count11ChemAxon
Refractivity96.31 m3·mol-1ChemAxon
Polarizability34.21 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Oligopeptides
Alternative Parents
Histidine and derivatives / N-acyl-L-alpha-amino acids / Alpha amino acid amides / Imidazolyl carboxylic acids and derivatives / Medium-chain fatty acids / Amino fatty acids / Fatty amides / Heteroaromatic compounds / Secondary carboxylic acid amides / Amino acids
show 11 more
Substituents
Alpha-oligopeptide / Histidine or derivatives / N-acyl-alpha amino acid or derivatives / N-acyl-alpha-amino acid / N-acyl-l-alpha-amino acid / Alpha-amino acid amide / N-substituted-alpha-amino acid / Alpha-amino acid or derivatives / Medium-chain fatty acid / Imidazolyl carboxylic acid derivative
show 32 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available

Drug created on September 05, 2018 16:31 / Updated on September 02, 2019 22:05