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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

Molecular Formula C20H33NO3S
Molecular Weight 367.546
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 2
Optical Activity UNSPECIFIED

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
Methylation and demethylation reactions of guanine nucleotide-binding proteins of retinal rod outer segments.
1991 Apr 15
Effects of farnesylcysteine analogs on protein carboxyl methylation and signal transduction.
1991 Nov 15
Topical N-acetyl-S-farnesyl-L-cysteine inhibits mouse skin inflammation, and unlike dexamethasone, its effects are restricted to the application site.
2008 Mar
N-acetyl-S-farnesyl-l-cysteine suppresses chemokine production by human dermal microvascular endothelial cells.
2012 Sep
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
Substance Class Chemical
Created
by admin
on Fri Dec 15 18:17:47 GMT 2023
Edited
by admin
on Fri Dec 15 18:17:47 GMT 2023
Record UNII
KK6984C8O3
Record Status Validated (UNII)
Record Version
  • Download
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