(E/Z)-AG490 ((E/Z)-Tyrphostin AG490) is the racemate of (E)-AG490 and (Z)-AG490. (E)-AG490 is a tyrosine inhibitor that can suppress EGFR, Stat-3 and JAK2/3.

Physicochemical Properties

Molecular Formula	C17H14N2O3
Molecular Weight	294.305
Exact Mass	294.1
CAS #	134036-52-5
Related CAS #	AG490;133550-30-8
PubChem CID	5328779
Appearance	Yellow to brown solid powder
Density	1.337g/cm3
Boiling Point	615.2ºC at 760mmHg
Melting Point	215ºC
Flash Point	325.9ºC
LogP	2.712
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	4
Heavy Atom Count	22
Complexity	460
Defined Atom Stereocenter Count	0
SMILES	C1=CC=C(C=C1)CNC(=O)/C(=C/C2=CC(=C(C=C2)O)O)/C#N
InChi Key	TUCIOBMMDDOEMM-RIYZIHGNSA-N
InChi Code	InChI=1S/C17H14N2O3/c18-10-14(8-13-6-7-15(20)16(21)9-13)17(22)19-11-12-4-2-1-3-5-12/h1-9,20-21H,11H2,(H,19,22)/b14-8+
Chemical Name	(E)-N-benzyl-2-cyano-3-(3,4-dihydroxyphenyl)prop-2-enamide
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

ADME/Pharmacokinetics

Metabolism / Metabolites Tyrphostin B42 has known human metabolites that include Tyrphostin B42, 4-O-glucuronide and Tyrphostin B42, 3-O-glucuronide.

Additional Infomation

Tyrphostin B42 is a monocarboxylic acid amide obtained by formal condensation of the carboxy group of (2E)-2-cyano-3-(3,4-dihydroxyphenyl)prop-2-enoic acid with the amino group of benzylamine. It has a role as an EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor, an antioxidant, a STAT3 inhibitor, an anti-inflammatory agent, an apoptosis inducer and a geroprotector. It is an enamide, a monocarboxylic acid amide, a nitrile, a member of catechols and a secondary carboxamide. Tyrphostin B42 is a member of the tyrphostin family of tyrosine kinase inhibitors that inhibits epidermal growth factor receptor, blocks leukemic cell growth in vitro and in vivo by inducing programmed cell death. Inhibits the constitutive activation of STAT-3 DNA binding and IL-2-induced growth of Mycosis fungoides tumor cells. (NCI)

Solubility Data

Solubility (In Vitro)

DMSO : ~100 mg/mL (~339.79 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.5 mg/mL (8.49 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (8.49 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	3.3978 mL	16.9889 mL	33.9778 mL
	5 mM	0.6796 mL	3.3978 mL	6.7956 mL
	10 mM	0.3398 mL	1.6989 mL	3.3978 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.