Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C20H33NO3S |
Molecular Weight | 367.546 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 2 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(=O)N[C@@H](CSC\C=C(/C)CC\C=C(/C)CCC=C(C)C)C(O)=O
InChI
InChIKey=XTURYZYJYQRJDO-BNAHBJSTSA-N
InChI=1S/C20H33NO3S/c1-15(2)8-6-9-16(3)10-7-11-17(4)12-13-25-14-19(20(23)24)21-18(5)22/h8,10,12,19H,6-7,9,11,13-14H2,1-5H3,(H,21,22)(H,23,24)/b16-10+,17-12+/t19-/m0/s1
N-acetyl-S-farnesyl-L-cysteine (acetyl farnesylcysteine), a modulator of G protein and G-protein coupled receptor signaling, inhibits neutrophil chemotaxis and other inflammatory responses in cell-based assays, is a synthetic substrate for the isoprenylated protein methyltransferase (also known as S-adenosylmethionine-dependent methyltransferase). It was shown, that the topical N-acetyl-S-farnesyl-L-cysteine inhibited mouse skin inflammation and might exert its anti-inflammatory effects through the inhibition of chemokine production by stimulated endothelial cells.
Approval Year
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17882268
in mice: 50 mg of N-acetyl-S-farnesyl-L-cysteine (AFC) was dissolved in CDCl3. For the histology experiments, the AFC was applied 30 minutes after the phorbol ester 12-O-tetradecanoyl-phorbol-13-acetate (TPA), induced edema
Route of Administration:
Topical
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22897577
Curator's Comment: N-acetyl-S-farnesyl-L-cysteine (AFC), dose-dependently inhibits ATP-, ATPγS- and TNFα-induced production of CXCL1, CXCL8 and CCL2 by a human dermal microvascular EC line (HMEC-1) in vitro under conditions that do not affect cell viability. Inhibition of ATPγS- or TNFα-stimulated release of these chemokines was associated with reduced mRNA levels. AFC may exert its anti-inflammatory effects through the inhibition of chemokine production by stimulated endothelial cells.
Unknown
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C068268
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6438381
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KK6984C8O3
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1868830
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DTXSID701021741
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135304-07-3
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m1359
Created by
admin on Fri Dec 15 18:17:47 GMT 2023 , Edited by admin on Fri Dec 15 18:17:47 GMT 2023
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KK6984C8O3
Created by
admin on Fri Dec 15 18:17:47 GMT 2023 , Edited by admin on Fri Dec 15 18:17:47 GMT 2023
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SUBSTANCE RECORD