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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
Structure of ACETYL FARNESYLCYSTEINE

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

HIDE SMILES / InChI
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

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: O60725
Gene ID: 23463.0
Gene Symbol: ICMT
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Effects of farnesylcysteine analogs on protein carboxyl methylation and signal transduction.
1991 Nov 15
Patents

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.
Unknown
Name Type Language
ACETYL FARNESYLCYSTEINE
INCI  
INCI  
Official Name English
N-ACETYL-S-FARNESYLCYSTEINE
Systematic Name English
N-ACETYL-L-FARNESYLCYSTEINE [MI]
Common Name English
L-CYSTEINE, N-ACETYL-S-((2E,6E)-3,7,11-TRIMETHYL-2,6,10-DODECATRIEN-1-YL)-
Systematic Name English
AFC
Common Name English
L-CYSTEINE, N-ACETYL-S-(3,7,11-TRIMETHYL-2,6,10-DODECATRIENYL)-, (E,E)-
Common Name English
N-ACETYL-S-FARNESYL-L-CYSTEINE
Systematic Name English
N-ACETYL-L-FARNESYLCYSTEINE
MI  
Common Name English
N-ACETYL-S-TRANS,TRANS-FARNESYL-L-CYSTEINE
Common Name English
ACETYLFARNESYLCYSTEINE
Systematic Name English
ARAZINE
Common Name English
L-CYSTEINE, N-ACETYL-S-((2E,6E)-3,7,11-TRIMETHYL-2,6,10-DODECATRIENYL)-
Systematic Name English
ACETYL FARNESYLCYSTEINE [INCI]
Common Name English
Code System Code Type Description
MESH
C068268
Created by admin on Fri Dec 15 18:17:47 GMT 2023 , Edited by admin on Fri Dec 15 18:17:47 GMT 2023
PRIMARY
PUBCHEM
6438381
Created by admin on Fri Dec 15 18:17:47 GMT 2023 , Edited by admin on Fri Dec 15 18:17:47 GMT 2023
PRIMARY
FDA UNII
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
PRIMARY
RXCUI
1868830
Created by admin on Fri Dec 15 18:17:47 GMT 2023 , Edited by admin on Fri Dec 15 18:17:47 GMT 2023
PRIMARY
EPA CompTox
DTXSID701021741
Created by admin on Fri Dec 15 18:17:47 GMT 2023 , Edited by admin on Fri Dec 15 18:17:47 GMT 2023
PRIMARY
CAS
135304-07-3
Created by admin on Fri Dec 15 18:17:47 GMT 2023 , Edited by admin on Fri Dec 15 18:17:47 GMT 2023
PRIMARY
MERCK INDEX
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
PRIMARY Merck Index
DAILYMED
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
PRIMARY