Acetyl hexapeptide-3

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Acetyl hexapeptide-3

IUPAC name (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
Other names Argireline
Identifiers
CAS number	616204-22-9
ChemSpider	9403386^Y
Jmol-3D images	Image 1 Image 2
SMILES NC([C@H](CCCNC(N)=N)NC([C@H](CCCNC(N)=N)NC([C@H](CCC(N)=O)NC([C@H](CCSC)NC([C@H](CCC(O)=O)NC([C@H](CCC(O)=O)NC(C)=O)=O)=O)=O)=O)=O)=O O=C(N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N)CCC/N=C(\N)N)CCC/N=C(\N)N)CCC(=O)N)CCSC)[C@@H](NC(=O)[C@@H](NC(=O)C)CCC(=O)O)CCC(=O)O
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^Y Key: RJZNPROJTJSYLC-LLINQDLYSA-N^Y InChI=1/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-LLINQDLYBN
Properties
Molecular formula	C₃₄H₆₀N₁₄O₁₂S
Molar mass	888.99 g mol⁻¹
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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

Contents

1 Overview and common uses
2 Cosmetic studies
3 Safety research
4 Chemistry
5 References

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

^ ^a ^b ^c ^d 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
^ 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.

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