N-Acetyl-L-farnesylcysteine

Names

[ Name ]:
N-Acetyl-L-farnesylcysteine

[Synonym ]:
L-Cysteine, N-acetyl-S-[(2E,6E)-3,7,11-trimethyl-2,6,10-dodecatrien-1-yl]-
N-Acetyl-S-[(2E,6E)-3,7,11-trimethyl-2,6,10-dodecatrien-1-yl]-L-cysteine
N-Acetylfarnesylcysteine
N-acetyl-S-farnesyl-L-Cysteine
N-acetyl-S-farnesylcysteine
Arazine
N-Acetyl-S-trans,trans-farnesyl-L-cysteine
N-AFC
afc

Biological Activity

[Description]:

Arazine (N-Acetyl-S-farnesyl-L-cysteine) is a cell-permeable modulator of G protein and G-protein coupled receptor signaling. Arazine can be a a substrate for isoprenylcysteine methyltransferase by competing with prenylated G protein or its receptors site[1].

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Inflammation/Immunology

[In Vitro]

Arazine (2 hours) inhibits ATPγS induced CXCL1, CXCL8 and CCL2 production as a dose-dependent manner in HMEC-1 cell[1]. Arazine (10–100 μM;8 hours) significantly affects the HMEC-1 cell viability as measured by trypan blue exclusion in HMEC-1 cell[1].

[In Vivo]

Arazine (AFC) (2,000 μg/20 μl; applied on ear) produces a dose-dependent inhibition of the TPA-induced edema, with the maximal reduction of edema approaching 73%, with a 50% effective dose (ED50) of 55±12 μg/20 μl[1]. Animal Model: TPA-induced ear acute inflammation in mouse[1] Dosage: 2000 μg/20 μl Administration: 2000 μg/20 μl; Applied on ear Result: Inhibited ear edema, as measured by ear weight.

[References]

[1]. Gordon JS, et al. Topical N-acetyl-S-farnesyl-L-cysteine inhibits mouse skin inflammation, and unlike dexamethasone, its effects are restricted to the application site.J Invest Dermatol. 2008 Mar;128(3):643-54. Epub 2007 Sep 20.

[2]. Adhami K, et al. N-acetyl-S-farnesyl-l-cysteine suppresses chemokine production by human dermal microvascular endothelial cells.Exp Dermatol. 2012 Sep;21(9):700-5.

Chemical & Physical Properties

[ Density]:
1.0±0.1 g/cm3

[ Boiling Point ]:
566.1±50.0 °C at 760 mmHg

[ Molecular Formula ]:
C₂₀H₃₃NO₃S

[ Molecular Weight ]:
367.546

[ Flash Point ]:
296.1±30.1 °C

[ Exact Mass ]:
367.218109

[ PSA ]:
91.70000

[ LogP ]:
5.86

[ Vapour Pressure ]:
0.0±3.3 mmHg at 25°C

[ Index of Refraction ]:
1.520

[ Storage condition ]:
-15°C

Safety Information

[ HS Code ]:
2930909090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2930909090

[ Summary ]:
2930909090. other organo-sulphur compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%