Teriflunomide impurity 3 (4-Amino-N-(4-trifluoromethylphenyl)benzamide) is a selective COX-1 inhibitor (antagonist) with IC50 of 30 µM and low activity against COX-2 (IC50>100 µM).

Physicochemical Properties

Molecular Formula	C14H11F3N2O
Molecular Weight	280.25
Exact Mass	280.082
CAS #	1011244-72-6
PubChem CID	13609518
Appearance	White to yellow solid powder
Density	1.4±0.1 g/cm3
Boiling Point	327.6±42.0 °C at 760 mmHg
Flash Point	151.9±27.9 °C
Vapour Pressure	0.0±0.7 mmHg at 25°C
Index of Refraction	1.602
LogP	2.87
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	2
Heavy Atom Count	20
Complexity	330
Defined Atom Stereocenter Count	0
SMILES	C1=CC(=CC=C1C(=O)NC2=CC=C(C=C2)C(F)(F)F)N
InChi Key	YUWBBWHECQSIKL-UHFFFAOYSA-N
InChi Code	InChI=1S/C14H11F3N2O/c15-14(16,17)10-3-7-12(8-4-10)19-13(20)9-1-5-11(18)6-2-9/h1-8H,18H2,(H,19,20)
Chemical Name	4-amino-N-[4-(trifluoromethyl)phenyl]benzamide
Synonyms	1011244-72-6; 4-Amino-N-(4-trifluoromethylphenyl)benzamide; 824-254-4; 4-AMINO-N-[4-(TRIFLUOROMETHYL)PHENYL]BENZAMIDE; Teriflunomide impurity 3; CHEMBL261598; 4-Amino-N-[4-(trifluoromethyl)phenyl] benzamide; 4-amino-N-(4-(trifluoromethyl)phenyl)benzamide;
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 Note: This product requires protection from light (avoid light exposure) during transportation and storage.
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

Targets	COX-1 (IC50 = 30 μM)
ln Vitro	Compound 11q, or teriflunomide impurity 3, is an amide-bond-reversed compound with trifluoromethyl and amino substituents that exhibited strong COX-1-selective inhibitory activity[1].
References	[1]. Cyclooxygenase-1-selective inhibitors are attractive candidates for analgesics that do not cause gastric damage. design and in vitro/in vivo evaluation of a benzamide-type cyclooxygenase-1 selective inhibitor. J Med Chem. 2008 Apr 24;51(8):2400-11.
Additional Infomation	Although cyclooxygenase-1 (COX-1) inhibition is thought to be a major mechanism of gastric damage by nonsteroidal anti-inflammatory drugs (NSAIDs), some COX-1-selective inhibitors exhibit strong analgesic effects without causing gastric damage. However, it is not clear whether their analgesic effects are attributable to COX-1-inhibitory activity or other bioactivities. Here, we report that N-(5-amino-2-pyridinyl)-4-(trifluoromethyl)benzamide ( 18f, TFAP), which has a structure clearly different from those of currently available COX-1-selective inhibitors, is a potent COX-1-selective inhibitor (COX-1 IC 50 = 0.80 +/- 0.05 microM, COX-2 IC 50 = 210 +/- 10 microM). This compound causes little gastric damage in rats even at an oral dose of 300 mg/kg, though it has an analgesic effect at as low a dose as 10 mg/kg. Our results show that COX-1-selective inhibitors can be analgesic agents without causing gastric damage. [1]

Solubility Data

Solubility (In Vitro)

DMSO: 250 mg/mL (892.06 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.08 mg/mL (7.42 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (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 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	3.5682 mL	17.8412 mL	35.6824 mL
	5 mM	0.7136 mL	3.5682 mL	7.1365 mL
	10 mM	0.3568 mL	1.7841 mL	3.5682 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.