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SML1457

Sigma-Aldrich

Lonafarnib

≥98% (HPLC)

Synonym(s):

4-[2-[4-[(11R)-3,10-Dibromo-8-chloro-6,11-dihydro-5Hbenzo[5,6]cyclohepta[1,2-b]pyridin-11-yl]-1-piperidinyl]-2-oxoethyl]-1-piperidinecarboxamide, SCH-66336, SCH66336

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About This Item

Empirical Formula (Hill Notation):
C27H31Br2ClN4O2
CAS Number:
193275-84-2
Molecular Weight:
638.82
MDL number:
MFCD06795138
UNSPSC Code:
12352200
PubChem Substance ID:
329825894
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 5 mg/mL, clear (warmed)

storage temp.

−20°C

SMILES string

O=C(N)N(CC1)CCC1CC(N2CCC([C@H]3C(N=CC(Br)=C4)=C4CCC5=C3C(Br)=CC(Cl)=C5)CC2)=O

InChI

1S/C27H31Br2ClN4O2/c28-20-12-19-2-1-18-13-21(30)14-22(29)24(18)25(26(19)32-15-20)17-5-9-33(10-6-17)23(35)11-16-3-7-34(8-4-16)27(31)36/h12-17,25H,1-11H2,(H2,31,36)/t25-/m1/s1

InChI key

DHMTURDWPRKSOA-RUZDIDTESA-N

Gene Information

human ... FNTA(2339) , FNTB(2342)

General description

Lonafarnib (SCH66336) is a farnesyl transferase inhibitor (FTI). K- and N-Ras are substrates of farnesyl transferase.

Biochem/physiol Actions

Lonafarnib is a potent inhibitor of farnesyltransferase, an enzyme responsible for a post-translational modification of proteins (including Ras) that gives a protein sufficient hydrophobicity to translocate to the plasma membrane. Farnesylation regulates signaling cascades controlling cell survival, proliferation and differentiation, so variety of possible uses is not surprising a post-translational modification of proteins (including Ras) that gives a protein sufficient hydrophobicity to translocate to the plasma membrane. Lonafarnib has been studies for possible treatment of progeria, various cancers, and hepatitis D.
Lonafarnib prevents the post-translational lipid modification of H-Ras and other farnesylated proteins. Lonafarnib treatment results in microtubule bundling, increased microtubule acetylation and stabilization and suppression of microtubule dynamics.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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The synergistic combination of the farnesyl transferase inhibitor lonafarnib and paclitaxel enhances tubulin acetylation and requires a functional tubulin deacetylase.
Marcus AI, et al.
Cancer Research, 65(9), 3883-3893 (2005)
The farnesyl transferase inhibitor (FTI) SCH66336 (lonafarnib) inhibits Rheb farnesylation and mTOR signaling Role in FTI enhancement of taxane and tamoxifen anti-tumor activity.
Basso A D, et al.
The Journal of Biological Chemistry, 280(35), 31101-31108 (2005)
Oren Yakovian et al.
iScience, 25(11), 105282-105282 (2022-10-29)
NRas is a key mediator of the mitogenic pathway in normal cells and in cancer cells. Its dynamics and nanoscale organization at the plasma membrane (PM) facilitate its signaling. Here, we used two-color photoactivated localization microscopy to resolve the organization
Woo-Jin Lim et al.
Cells, 10(9) (2021-09-29)
Retrospective observational studies have reported that statins improve clinical outcomes in patients previously treated with programmed cell death protein 1 (PD-1)-targeting monoclonal antibodies for malignant pleural mesothelioma (MPM) and advanced non-small cell lung cancer (NSCLC). In multiple mouse cancer models
Charlotte Bach et al.
Antiviral research, 209, 105477-105477 (2022-12-14)
Chronic hepatitis D is the most aggressive form of chronic viral hepatitis. It is caused by super-infection of hepatitis B virus (HBV)-infected hepatocytes with hepatitis D virus (HDV). While the recent conditional approval of bulevirtide for HDV treatment offers a
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