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Tipifarnib

CAT: 0804-HY-10502-03Size: 25 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-10502-03Size:25 mg
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Description
Tipifarnib (IND 58359) binds to and inhibits farnesyltransferase (FTase) with an IC50 of 0.86 nM. Antineoplastic activity and antiparasitic activity[1].
CAS Number
192185-72-1
Product Name Alternative
IND 58359; R115777
UNSPSC
12352005
Hazard Statement
H315, H319, H335
Target
Farnesyl Transferase
Type
Reference compound
Related Pathways
Metabolic Enzyme/Protease
Applications
Cancer-programmed cell death
Field of Research
Cancer; Infection
Assay Protocol
https://www.medchemexpress.com/Tipifarnib.html
Purity
99.89
Solubility
DMSO : 33.33 mg/mL (ultrasonic; warming; heat to 60°C)
Smiles
O=C1N(C2=C(C(C3=CC=CC(Cl)=C3)=C1)C=C(C=C2)[C@@](N)(C4=CN=CN4C)C5=CC=C(C=C5)Cl)C
Molecular Formula
C27H22Cl2N4O
Molecular Weight
489.40
Precautions
H315, H319, H335
References & Citations
[1]Devendra S Puntambekar, et al. Inhibition of farnesyltransferase: a rational approach to treat cancer? J Enzyme Inhib Med Chem. 2007 Apr;22 (2) :127-40.|[2]End DW, et al. Characterization of the antitumor effects of the selective farnesyl protein transferase inhibitor R115777 in vivo and in vitro. Cancer Res. 2001 Jan 1;61 (1) :131-7|[3]Amrita Datta, et al. High-throughput screening identified selective inhibitors of exosome biogenesis and secretion: A drug repurposing strategy for advanced cancer. Sci Rep. 2018 May 25;8 (1) :8161.
Shipping Conditions
Room Temperature
Storage Conditions
-20°C, 3 years; 4°C, 2 years (Powder)
Scientific Category
Reference compound1
Clinical Information
Phase 3

Chemical Information

Tipifarnib

Tipifarnib is a quinolone that is 1-methylquinolin-2-one which carries a 3-chlorophenyl and an amino(4-chlorophenyl)(1-methyl-imidazol-5-yl)methyl groups at the 4 and 6 positions, respectively (the R-isomer). It has a role as an antineoplastic agent, an EC 2.5.1.58 (protein farnesyltransferase) inhibitor and an apoptosis inducer. It is a quinolone, a member of imidazoles, a primary amino compound and a member of monochlorobenzenes.

CAS Number192185-72-1
PubChem CID159324
IUPAC Name6-[(R)-amino-(4-chlorophenyl)-(3-methylimidazol-4-yl)methyl]-4-(3-chlorophenyl)-1-methylquinolin-2-one
Molecular FormulaC27H22Cl2N4O
Molecular Weight489.4
XLogP4.1
Topological Polar Surface Area64.2
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count4
Heavy Atom Count34
Formal Charge0
Complexity785
SMILES
CN1C=NC=C1[C@@](C2=CC=C(C=C2)Cl)(C3=CC4=C(C=C3)N(C(=O)C=C4C5=CC(=CC=C5)Cl)C)N
InChI
InChI=1S/C27H22Cl2N4O/c1-32-16-31-15-25(32)27(30,18-6-9-20(28)10-7-18)19-8-11-24-23(13-19)22(14-26(34)33(24)2)17-4-3-5-21(29)12-17/h3-16H,30H2,1-2H3/t27-/m1/s1
InChIKey
PLHJCIYEEKOWNM-HHHXNRCGSA-N
Chemical Structure
2D Structure
2D structure of Tipifarnib
CAS: 192185-72-1
CID: 159324
Formula: C27H22Cl2N4O
MW: 489.4
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight489.4
XLogP34.1
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count4
Exact Mass488.1170667
Monoisotopic Mass488.1170667
Topological Polar Surface Area64.2 Ų
Heavy Atom Count34
Formal Charge0
Complexity785
Isotope Atom Count0
Defined Atom Stereocenter Count1
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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CatalogName
T6271-01Tipifarnib

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