Acetyl hexapeptide-3

Acetyl hexapeptide-3

Names
Other names (6S,9S,12S,15S,18S,21S)-21-Acetamido-1-amino-12-(3-amino-3-oxopropyl)-6-carbamoyl-18-(2-carboxyethyl)-9-(3-guanidinopropyl)-1-imino-15-(2-(methylthio)ethyl)-8,11,14,17,20-pentaoxo-2,7,10,13,16,19-hexaazatetracosan-24-oic acid Argireline
Identifiers
CAS Number	616204-22-9
ChemSpider	9403386
Jmol interactive 3D	Image Image
PubChem	11228338
UNII	L4EL31FWIL
InChI InChI=1S/C34H60N14O12S/c1-17(49)43-20(8-11-25(51)52)29(57)47-22(9-12-26(53)54)31(59)48-23(13-16-61-2)32(60)46-21(7-10-24(35)50)30(58)45-19(6-4-15-42-34(39)40)28(56)44-18(27(36)55)5-3-14-41-33(37)38/h18-23H,3-16H2,1-2H3,(H2,35,50)(H2,36,55)(H,43,49)(H,44,56)(H,45,58)(H,46,60)(H,47,57)(H,48,59)(H,51,52)(H,53,54)(H4,37,38,41)(H4,39,40,42)/t18-,19-,20-,21-,22-,23-/m0/s1 Key: RJZNPROJTJSYLC-LLINQDLYSA-N
SMILES CSCC[C@H]([nH]:c(:[o])[C@H](CCc(:[o]):[oH])[nH]:c(:[o])[C@H](CCc(:[o]):[oH])[nH]:c(C):[o])c(:[o]):[nH][C@@H](CCc(:[nH2]):[o])c(:[o]):[nH][C@@H](CCC[nH]:c(:[nH]):[nH2])c(:[o]):[nH][C@@H](CCC[nH]:c(:[nH]):[nH2])c(:[nH2]):[o] CSCC[C@H](NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(C)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCNC(N)=N)C(N)=O
Properties
Chemical formula	C34H60N14O12S
Molar mass	889.00 g·mol^−1
Related compounds
Related compounds	Gusperimus Stearamidopropyl dimethylamine
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Acetyl hexapeptide-3 is a synthetic anti-wrinkle cosmetics ingredient. It is a peptide which is a fragment of SNAP-25, a substrate of Botulinum toxin (Botox). Acetyl hexapeptide-3 is marketed as Argireline by the Barcelona-based research laboratory Lipotec.^[1]

Overview and common uses

Argireline is used in attempts to decrease the visible effects of aging by reducing the deep wrinkles and lines that occur around the forehead and eyes.^[1][2]

Chemically, when applied as a solution to specific areas of the face, Argireline inhibits the reactions that cause muscles to move or contract^[1] – for example when forming facial expressions such as smiling or frowning.

Cosmetic studies

Both in vitro (outside a living organism) and in vivo (using a living organism) tests have been carried out on Argireline, but double-blind clinical trials results have not been published.

Safety research

Argireline has been developed relatively recently and therefore reports on its long-term use have not yet been produced.

Chemistry

Argireline is the hexapeptide with the sequence Ac-Glu-Glu-Met-Gln-Arg-Arg-NH₂.^[1]

References

1. Blanes-Mira, C; et al. (October 2002). "A synthetic hexapeptide (Argireline) with antiwrinkle activity". Int J Cosmet Sci 24 (5): 303–10. doi:10.1046/j.1467-2494.2002.00153.x. PMID 18498523.
2. Ruiz, MA; Clares, B; Morales, ME; Cazalla, S; Gallardo, V (2007). "Preparation and stability of cosmetic formulations with an anti-aging peptide.". Journal of cosmetic science 58 (2): 157–71. PMID 17520155.