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
Structure for Prezatide copper (DB14683)
- 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.
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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
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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 copper acetate A3LEI4P1NB 130120-57-9 LUNQZVCDZKODKF-PFVVTREHSA-J - Active Moieties
Name Kind UNII CAS InChI Key Prezatide complex 39TG2H631E 49557-75-7 MVORZMQFXBLMHM-QWRGUYRKSA-N Cupric cation complex 8CBV67279L 15158-11-9 JPVYNHNXODAKFH-UHFFFAOYSA-N - Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Dermaheal Skin Delight Mask Pack Plus Patch 0.22 mg/22g Topical YBK Investment, INC 2013-10-21 Not applicable US 
Elcure Pepta Hair Shampoo 0.1 g/100mL Topical Elcure Co., Ltd. 2016-03-30 2017-04-20 US Elcure Pepta Hair Essence Liquid 0.1 g/100mL Topical Elcure Co., Ltd. 2016-03-30 2017-04-20 US NEWSTEM Rx FRACTIONAL REPAIR Energy Ampoule Liquid 0.01 g/100g Topical Yj Lab Co., Ltd. 2022-01-02 Not applicable US Pepta Hair Shampoo 0.1 g/100mL Topical Elcure Co., Ltd. 2016-03-30 2016-04-01 US Pepta Hair Essence Liquid 0.1 g/100mL Topical Elcure Co., Ltd. 2016-03-30 2016-04-01 US Skin Delight Mask Pack Patch 0.22 mg/22g Topical YBK Investment, INC 2013-10-21 2013-10-29 US Skin Delight Mask Pack Plus Patch 0.22 mg/22g Topical YBK Investment, INC 2013-10-21 Not applicable US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Cosmeceutical Mask Pack Prezatide 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) Patch Topical YBK Investment, INC 2013-10-21 2013-10-29 US Cosmeceutical Mask Pack Prezatide 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) Patch Topical YBK Investment, INC 2013-10-21 Not applicable US Dermaheal Cosmeceutical Mask Pack Plus Prezatide 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) Patch Topical YBK Investment, INC 2013-10-21 Not applicable US Pepplus Special Skin Care Lifting Program Prezatide copper (0.002 g/100mL) + Basic Fibroblast Growth Factor (0.001 g/100mL) + Green tea leaf (1.28 g/100mL) Kit Topical Picobio Co., Ltd. 2021-11-02 Not applicable US Special Skin Care Lifting Program Prezatide copper (0.002 g/100mL) + Basic Fibroblast Growth Factor (0.001 g/100mL) + Green tea leaf (1.28 g/100mL) Kit Topical Picobio Co., Ltd. 2019-05-15 Not applicable US - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Cosmeceutical Mask Pack Prezatide 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) Patch Topical YBK Investment, INC 2013-10-21 2013-10-29 US Cosmeceutical Mask Pack Prezatide 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) Patch Topical YBK Investment, INC 2013-10-21 Not applicable US Dermaheal Cosmeceutical Mask Pack Plus Prezatide 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) Patch Topical YBK Investment, INC 2013-10-21 Not applicable US Dermaheal Skin Delight Mask Pack Plus Prezatide copper (0.22 mg/22g) Patch Topical YBK Investment, INC 2013-10-21 Not applicable US Elcure Pepta Hair Prezatide copper (0.1 g/100mL) Shampoo Topical Elcure Co., Ltd. 2016-03-30 2017-04-20 US Elcure Pepta Hair Essence Prezatide copper (0.1 g/100mL) Liquid Topical Elcure Co., Ltd. 2016-03-30 2017-04-20 US NEWSTEM Rx FRACTIONAL REPAIR Energy Ampoule Prezatide copper (0.01 g/100g) Liquid Topical Yj Lab Co., Ltd. 2022-01-02 Not applicable US Pepplus Special Skin Care Lifting Program Prezatide copper (0.002 g/100mL) + Basic Fibroblast Growth Factor (0.001 g/100mL) + Green tea leaf (1.28 g/100mL) Kit Topical Picobio Co., Ltd. 2021-11-02 Not applicable US Pepta Hair Prezatide copper (0.1 g/100mL) Shampoo Topical Elcure Co., Ltd. 2016-03-30 2016-04-01 US Pepta Hair Essence Prezatide copper (0.1 g/100mL) Liquid Topical Elcure Co., Ltd. 2016-03-30 2016-04-01 US
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
- 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
- ChemSpider
- 32698045
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Patch Topical Patch Topical 0.22 mg/22g Liquid Topical 0.01 g/100g Shampoo Topical 0.1 g/100mL Liquid Topical 0.1 g/100mL Kit Topical - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Not Available
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 2.08 mg/mL ALOGPS logP -0.94 ALOGPS logP -5.4 Chemaxon logS -2.3 ALOGPS pKa (Strongest Acidic) 3.46 Chemaxon pKa (Strongest Basic) 10.2 Chemaxon Physiological Charge 2 Chemaxon Hydrogen Acceptor Count 7 Chemaxon Hydrogen Donor Count 5 Chemaxon Polar Surface Area 179.05 Å2 Chemaxon Rotatable Bond Count 11 Chemaxon Refractivity 96.31 m3·mol-1 Chemaxon Polarizability 34.21 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes 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
- Not Available
Drug created at September 05, 2018 22:31 / Updated at June 12, 2020 16:53