Prezatide copper

Identification

Generic Name
Prezatide copper
DrugBank Accession Number
DB14683
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: 402.921
Monoisotopic: 402.107128
Chemical Formula
C14H23CuN6O4
Synonyms
  • CG-copper peptide
  • Copper tripeptide-1
  • GHK complex with copper
  • GHK copper

Pharmacology

Indication

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

Reduce drug development failure rates
Build, train, & validate machine-learning models
with evidence-based and structured datasets.
See how
Build, train, & validate predictive machine-learning models with structured datasets.
See how
Contraindications & Blackbox Warnings
Prevent Adverse Drug Events Today
Tap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.
Learn more
Avoid life-threatening adverse drug events with our Clinical API
Learn more
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

Adverse Effects
Improve decision support & research outcomes
With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!
See the data
Improve decision support & research outcomes with our structured adverse effects data.
See a data sample
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 regions
Our datasets provide approved product information including:
dosage, form, labeller, route of administration, and marketing period.
Access now
Access drug product information from over 10 global regions.
Access now
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 EndRegionImage
Dermaheal Skin Delight Mask Pack PlusPatch0.22 mg/22gTopicalYBK Investment, INC2013-10-21Not applicableUS flag
Elcure Pepta HairShampoo0.1 g/100mLTopicalElcure Co., Ltd.2016-03-302017-04-20US flag
Elcure Pepta Hair EssenceLiquid0.1 g/100mLTopicalElcure Co., Ltd.2016-03-302017-04-20US flag
NEWSTEM Rx FRACTIONAL REPAIR Energy AmpouleLiquid0.01 g/100gTopicalYj Lab Co., Ltd.2022-01-02Not applicableUS flag
Pepta HairShampoo0.1 g/100mLTopicalElcure Co., Ltd.2016-03-302016-04-01US flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
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 flag
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 flag
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 flag
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.2021-11-02Not applicableUS flag
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 flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
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 flag
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 flag
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 flag
Dermaheal Skin Delight Mask Pack PlusPrezatide copper (0.22 mg/22g)PatchTopicalYBK Investment, INC2013-10-21Not applicableUS flag
Elcure Pepta HairPrezatide copper (0.1 g/100mL)ShampooTopicalElcure Co., Ltd.2016-03-302017-04-20US flag

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
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-amino acid amide / Alpha-amino acid or derivatives / Alpha-oligopeptide / Amine / Amino acid / Amino acid or derivatives / Amino fatty acid / Aromatic heteromonocyclic compound / Azacycle / Azole
show 32 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
6BJQ43T1I9
CAS number
89030-95-5
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

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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
ChemSpider
32698045

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
PatchTopical
PatchTopical0.22 mg/22g
LiquidTopical0.01 g/100g
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
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-188.647098
predicted
DarkChem Lite v0.1.0
[M+H]+188.001098
predicted
DarkChem Lite v0.1.0
[M+Na]+187.827698
predicted
DarkChem Lite v0.1.0

Drug created at September 05, 2018 22:31 / Updated at June 12, 2020 16:53