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Ruxolitinib

Ruxolitinib structure

CAS No:
941678-49-5
Formula:
C17H18N6
Chemical Name:
Ruxolitinib
Synonyms:
1H-Pyrazole-1-propanenitrile,β-cyclopentyl-4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-,(βR)-;(βR)-β-Cyclopentyl-4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazole-1-propanenitrile;Ruxolitinib;INCB 018424;(3R)-3-Cyclopentyl-3-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]propanenitrile;INC 424;(R)-3-[4-(7H-Pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]-3-cyclopentylpropanenitrile;1138325-12-8
Categories:
Pharmaceutical Intermediates > Bulk Drug Intermediates

Description

Ruxolitinib is a potent and selective JAK1/2 inhibitor with IC50s of 3.3 nM and 2.8 nM in cell-free assays, and has 130-fold selectivity for JAK1/2 over JAK3.

Ruxolitinib Basic Attributes

Molecular Weight：

306.371

Exact Mass：

306.36

EC Number：

1312995-182-4

HScode：

29335990

Characteristics

PSA：

83.2

XLogP3：

2.1

Density：

1.4

Flash Point：

312.2±30.1 °C

Refractive Index：

1.747

Water Solubility：

soluble in aqueous buffers across a pH of 1-8;In water, 100.8 mg/L at 25 deg C (est)

Storage Conditions：

Conditions for safe storage, including any incompatibilities: Keep container tightly sealed in cool, well-ventilated area. Keep away from direct sunlight and sources of ignition. Recommended storage temperature: Store at -20 deg C.

Vapor Pressure：

1.27X10-10 mm Hg at 25 deg C (est)

Safety Information

Stability/Shelf Life：

Stable under recommended storage conditions.

Ruxolitinib Use and Manufacturing

Methods of Manufacturing

(R)-3-cyclopentyl-3-(4-(7H-pyrrolo[2, 3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl)propionitrile 14.6 g of (R)-3-(4-(7H-pyrrolo[2, 3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl)-3-cyclopentylpropionamide was added to a mixed solvent of 480 mL of dichloromethane and 40 mL of NMP, and then 28 mL of phosphorus oxychloride was added dropwise thereto. The reaction was performed at room temperature, the temperature during this process was kept not higher than 30 C., and the reaction was carried out for 3 hours. After the reaction was completed, to the reaction solution was added 600 mL of purified water, and then a saturated sodium bicarbonate solution was added dropwise until the pH of the mixture solution was 7. The mixture solution was layered, and the organic phase was concentrated under reduced pressure to obtain (R)-3-cyclopentyl-3-(4-(7H-pyrrolo[2, 3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl)propionitrile (10.6 g, 77.3%). 1H-NMR (500 MHz, DMSO-d6): delta=12.13 (bs, 1H), 8.84 (d, J=0.4 Hz, 1H), 8.69 (s, 1H), 8.37 (s, 1H), 7.63 (dd, J=2.3, 3.5 Hz, 1H), 7.01 (dd, J=1.4, 3.4 Hz, 1H), 4.56 (td, J=19.5, 4.6 Hz, 1H), 3.26 (dd, J=17.3, 9.9 Hz, 1H), 3.17 (dd, J=17.4, 4.3 Hz, 1H), 2.43 (m, 1H), 1.83 (m, 1H), 1.64'1.09 (m, 7H); MS (ES): 307.17 (M+H+).

Uses

Janus-associated kinases (JAKs) are cytoplasmic tyrosine kinases that are required for activating the signaling of certain cytokines and growth factor receptors. A JAK2 gene fusion mutation, JAK2V617F, that causes unchecked activation of various growth factors and cytokines, has been linked to myeloproliferative neoplasms (MPNs), including polycythemia vera, essential thrombocythemia, and primary myelofibrosis. Ruxolitinib is a potent ATP mimetic that inhibits both JAK1 and JAK2 with IC50 values of 2.7 and 4.5 nM, respectively and is relatively less selective for JAK3 (IC50 = 322 nM). It can block interleukin-6 (IL-6) signaling (IC50 = 281 nM) and proliferation of JAK2V617F+ Ba/F3 cells (IC50 = 127 nM). In primary cultures, ruxolitinib preferentially suppresses erythroid progenitor colony formation from JAK2V617F+ polycythemia vera patients (IC50 = 67 nM) versus healthy donors (IC50 > 400 nM). In a mouse model of JAK2V617F+ MPN, 90 mg/kg ruxolitinib reduced splenomegaly, decreased circulating levels of IL-6 and TNF-α, eliminated neoplastic cells, and prolonged survival of the treated animals.[Cayman Chemical]

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