Halofuginone CAS#: 55837-20-2

Halofuginone CAS#: 55837-20-2; ChemWhat Code: 1369431

Identification	Physical Data	Spectra
Route of Synthesis (ROS)	Safety and Hazards	Other Data

Identification

Patent Information
Patent ID	Title	Publication Date
WO2007/120606	METHODS FOR MODULATING FORMATION AND PROGRESSION OF CELLULITE	2007
EP1109559	INHIBITION OF PATHOGENIC PROCESSES RELATED TO TISSUE TRAUMA	2005
US4665100	Process for formulating a synthetic drug for use in animal feed, and resulting formulation	1987

Physical Data

Appearance	White or off-white powder
Solubility	DMSO : 9 mg/mL (21.70 mM; Need ultrasonic and warming)
Boiling Point	595.8 °C at 760 mmHg
Density	1.73 g/cm³

Melting Point, °C

144 – 147

160

Spectra

Description (NMR Spectroscopy)	Nucleus (NMR Spectroscopy)	Solvents (NMR Spectroscopy)	Frequency (NMR Spectroscopy), MHz
Chemical shifts	1H	dimethylsulfoxide-d6	500
Chemical shifts	13C	dimethylsulfoxide-d6	125
Chemical shifts	13C	chloroform-d1	125
Chemical shifts	1H	chloroform-d1	500

Description (IR Spectroscopy)	Solvent (IR Spectroscopy)
Bands	neat (no solvent, solid phase)

Route of Synthesis (ROS)

Conditions

Yield

With potassium carbonate In water pH=10

Experimental Procedure
The salt (-)-32HBr was basified topH 10 with 0.1Maq. K2CO3 and extracted with DCM (5 5 mL). Thecombined organic layers were washed with brine (25 mL), driedover MgSO4, filtered, and concentrated in vacuo (without heating) to afford (-)-3 (14 mg, 93percent) as a white solid. Mp 143e145 C;{lit.,9 Mp 160 C (decomp.)}; [a]D20 5.4 (c 0.50, EtOH); {lit.,9[a]D2010 (c 0.5, DMF)}; IR (neat): 3128, 2926, 2852, 1722, 1674,1607, 1448, 1382, 1309, 1223, 1106, 1075, 1043, 900 cm1; HRMS(ESI): calcd. for [C16H1779Br35ClN3O3 H] 414.0220, found 414.0212;1H NMR ((CD3)2SO, 500 MHz): d 1.16e1.42 (m, 2H), 1.52e1.61 (m,1H), 1.84e1.95 (m, 1H), 2.32e2.40 (m, 1H), 2.45 (dd, J 15.5, 9.0 Hz,1H), 2.64 (td, J 9.0, 4.0 Hz, 1H), 2.75e2.84 (m, 1H), 2.93e3.03 (m,2H), 4.76 (d, J 6.0 Hz, 1H), 4.94e5.06 (m, 2H), 8.16 (s, 1H), 8.22 (s,1H), 8.24 (s, 1H) ppm (OH not visible by 1H NMR spectroscopy); 13CNMR ((CD3)2SO, 125 MHz): d 26.3 (CH2), 34.7 (CH2), 44.1 (CH2), 46.0(CH2), 55.3 (CH2), 60.5 (CH), 71.2 (CH), 122.2 (C), 127.4 (CH), 128.8(C), 132.2 (C), 132.8 (CH), 147.8 (C), 150.2 (CH), 159.1 (C), 203.9 (C)ppm.

93%

Safety and Hazards

Pictogram(s)
Signal	Danger
GHS Hazard Statements	H300: Fatal if swallowed [Danger Acute toxicity, oral] H301: Toxic if swallowed [Danger Acute toxicity, oral] H310: Fatal in contact with skin [Danger Acute toxicity, dermal] H315: Causes skin irritation [Warning Skin corrosion/irritation] H317: May cause an allergic skin reaction [Warning Sensitization, Skin] H318: Causes serious eye damage [Danger Serious eye damage/eye irritation] H330: Fatal if inhaled [Danger Acute toxicity, inhalation] H361: Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity] H372: Causes damage to organs through prolonged or repeated exposure [Danger Specific target organ toxicity, repeated exposure] H400: Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard] H410: Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard] Information may vary between notifications depending on impurities, additives, and other factors.
Precautionary Statement Codes	P201, P202, P260, P261, P262, P264, P270, P271, P272, P273, P280, P281, P284, P301+P310, P302+P350, P302+P352, P304+P340, P305+P351+P338, P308+P313, P310, P314, P320, P321, P322, P330, P332+P313, P333+P313, P361, P362, P363, P391, P403+P233, P405, and P501 (The corresponding statement to each P-code can be found at the GHS Classification page.) For more detailed information, please visit ECHA C&L website

Other Data

Transportation	Not dangerous goods
	Under the room temperature and away from light
HS Code	294200
Storage	Keep container tightly sealed in cool, well-ventilated area. Keep away from direct sunlight and sources of ignition. Recommended storage temperature: -20°C 3 years 4°C 2 years
Shelf Life	1 year
Market Price	USD 2300/kg

Use Pattern

Halofuginone CAS#: 55837-20-2 is usually used as a pharmaceutical

angioplasty

atherectomy

atherosclerosis

bypass surgical procedure

drug-eluting stent

Halofuginone CAS#: 55837-20-2 is a less-toxic form of Febrifugine, which is isolated from the plant Dichroa febrifuga. Halofuginone inhibits prolyl-tRNA synthetase in an ATP-dependent manner with a Ki of 18.3 nM. Halofuginone attenuates osteoarthritis (OA) by inhibition of TGF-β activity.

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Product Name	Halofuginone
IUPAC Name	7-bromo-6-chloro-3-[3-[(2S,3R)-3-hydroxypiperidin-2-yl]-2-oxopropyl]quinazolin-4-one
Molecular Structure
CAS Registry Number	55837-20-2
Synonyms	7-bromo-6-chlorofebrifugine; halofuginone; halofunginone; Stenorol; 7-bromo-6-chloro-3-[3-[(2S,3R)-3-hydroxypiperidin-2-yl]-2-oxopropyl]quinazolin-4-one; Tempostatin; RU 19110
Molecular Formula	C₁₆H₁₇BrClN₃O₃
Molecular Weight	414.686
InChI	InChI=1S/C16H17BrClN3O3/c17-11-6-13-10(5-12(11)18)16(24)21(8-20-13)7-9(22)4-14-15(23)2-1-3-19-14/h5-6,8,14-15,19,23H,1-4,7H2/t14-,15+/m0/s1
InChI Key	LVASCWIMLIKXLA-LSDHHAIUSA-N
Canonical SMILES	C1CC(C(NC1)CC(=O)CN2C=NC3=CC(=C(C=C3C2=O)Cl)Br)O
Isomeric SMILES	C1C[C@H]([C@@H](NC1)CC(=O)CN2C=NC3=CC(=C(C=C3C2=O)Cl)Br)O