Details of the Drug

General Information of Drug (ID: DMNORK8)

Drug Name

Jakafi

Synonyms

Ruxolitinib phosphate; 1092939-17-7; Ruxolitinib (phosphate); Jakavi; (R)-3-(4-(7H-Pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl)-3-cyclopentylpropanenitrile phosphate; UNII-436LRU32H5; Ruxolitinib phosphate salt; Ruxolitinib phosphate(INCB018424); CHEBI:66917; 436LRU32H5; J-501793; (betaR)-beta-Cyclopentyl-4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazole-1-propanenitrile phosphate; (3R)-3-cyclopentyl-3-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]propanenitrile phosphate; Ruxolitinib phosphate [USAN]; Jaka

Indication

Disease Entry	ICD 11	Status	REF
Essential thrombocythemia	3B63.1Z	Phase 3	[1]
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Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski):
0

Molecular Weight

404.4

Logarithm of the Partition Coefficient

Not Available

Rotatable Bond Count

Hydrogen Bond Donor Count

Hydrogen Bond Acceptor Count

Chemical Identifiers

Formula: C17H21N6O4P
IUPAC Name: (3R)-3-cyclopentyl-3-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile;phosphoric acid
Canonical SMILES: C1CCC(C1)[C@@H](CC#N)N2C=C(C=N2)C3=C4C=CNC4=NC=N3.OP(=O)(O)O
InChI: InChI=1S/C17H18N6.H3O4P/c18-7-5-15(12-3-1-2-4-12)23-10-13(9-22-23)16-14-6-8-19-17(14)21-11-20-16;1-5(2,3)4/h6,8-12,15H,1-5H2,(H,19,20,21);(H3,1,2,3,4)/t15-;/m1./s1
InChIKey: JFMWPOCYMYGEDM-XFULWGLBSA-N

Cross-matching ID

PubChem CID: 25127112
ChEBI ID: CHEBI:66917
CAS Number: 1092939-17-7
TTD ID: D0D8KQ
INTEDE ID: DR1454

Molecular Interaction Atlas of This Drug

Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 3A4 (CYP3A4)_{Main DME}	DE4LYSA	CP3A4_HUMAN	Substrate	[2]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
C-X-C motif chemokine 10 (CXCL10)	OTTLQ6S0	CXL10_HUMAN	Gene/Protein Processing	[3]
C-X-C motif chemokine 11 (CXCL11)	OT353XE3	CXL11_HUMAN	Gene/Protein Processing	[3]
Interferon regulatory factor 7 (IRF7)	OTC1A2PQ	IRF7_HUMAN	Gene/Protein Processing	[3]
Interferon-induced protein with tetratricopeptide repeats 1 (IFIT1)	OTXOQDSG	IFIT1_HUMAN	Gene/Protein Processing	[3]
Mitochondrial brown fat uncoupling protein 1	OT0XMVWH	UCP1_HUMAN	Gene/Protein Processing	[4]
Signal transducer and activator of transcription 1-alpha/beta (STAT1)	OTLMBUZ6	STAT1_HUMAN	Gene/Protein Processing	[3]
Signal transducer and activator of transcription 5B (STAT5B)	OTZVPEBT	STA5B_HUMAN	Post-Translational Modifications	[5]
Tyrosine-protein kinase JAK1 (JAK1)	OT0X3D17	JAK1_HUMAN	Gene/Protein Processing	[6]
Tyrosine-protein kinase JAK2 (JAK2)	OTBIDOOR	JAK2_HUMAN	Gene/Protein Processing	[6]
Vascular endothelial growth factor A, long form	OTIM9MZ3	VEGFA_HUMAN	Gene/Protein Processing	[7]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

References

1	Clinical pipeline report, company report or official report of the Pharmaceutical Research and Manufacturers of America (PhRMA)
2	Ruxolitinib: in the treatment of myelofibrosis. Drugs. 2012 Nov 12;72(16):2117-27.
3	Regulation of inflammatory responses in tumor necrosis factor-activated and rheumatoid arthritis synovial macrophages by JAK inhibitors. Arthritis Rheum. 2012 Dec;64(12):3856-66. doi: 10.1002/art.37691.
4	White-to-brown metabolic conversion of human adipocytes by JAK inhibition. Nat Cell Biol. 2015 Jan;17(1):57-67. doi: 10.1038/ncb3075. Epub 2014 Dec 8.
5	STAT5BN642H is a driver mutation for T cell neoplasia. J Clin Invest. 2018 Jan 2;128(1):387-401. doi: 10.1172/JCI94509. Epub 2017 Dec 4.
6	JAK inhibitors: treatment efficacy and safety profile in patients with psoriasis. J Immunol Res. 2014;2014:283617. doi: 10.1155/2014/283617. Epub 2014 May 5.
7	Differences in gene expression and alterations in cell cycle of acute myeloid leukemia cell lines after treatment with JAK inhibitors. Eur J Pharmacol. 2015 Oct 15;765:188-97. doi: 10.1016/j.ejphar.2015.08.037. Epub 2015 Aug 20.