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
PubMed
| Title | Date | PubMed |
|---|---|---|
| N-acetyl-S-farnesyl-l-cysteine suppresses chemokine production by human dermal microvascular endothelial cells. | 2012-09 |
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| Topical N-acetyl-S-farnesyl-L-cysteine inhibits mouse skin inflammation, and unlike dexamethasone, its effects are restricted to the application site. | 2008-03 |
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| Effects of farnesylcysteine analogs on protein carboxyl methylation and signal transduction. | 1991-11-15 |
|
| Methylation and demethylation reactions of guanine nucleotide-binding proteins of retinal rod outer segments. | 1991-04-15 |
Patents
Sample Use Guides
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
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.
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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
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KK6984C8O3
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SUBSTANCE RECORD
