RXT

(3R)-3-cyclopentyl-3-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]propanenitrile

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is present as a standalone ligand in 5 entries

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Chemical Component Summary
Name	(3R)-3-cyclopentyl-3-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]propanenitrile
Synonyms	Ruxolitinib
Identifiers	(3R)-3-cyclopentyl-3-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile
Formula	C₁₇ H₁₈ N₆
Molecular Weight	306.365
Type	NON-POLYMER
Isomeric SMILES	c1c[nH]c2c1c(ncn2)c3cnn(c3)[C@H](CC#N)C4CCCC4
InChI	InChI=1S/C17H18N6/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/h6,8-12,15H,1-5H2,(H,19,20,21)/t15-/m1/s1
InChIKey	HFNKQEVNSGCOJV-OAHLLOKOSA-N

Chemical Details
Formal Charge	0
Atom Count	41
Chiral Atom Count	1
Bond Count	44
Aromatic Bond Count	15

Drug Info: DrugBank

DrugBank ID	DB08877 ?
Name	Ruxolitinib
Groups	approved
Description	Ruxolitinib, formerly known as INCB018424 or INC424, is an anticancer drug and a Janus kinase (JAK) inhibitor. It is a potent and selective inhibitor of JAK1 and JAK2,[A229698] which are tyrosine kinases involved in cytokine signalling and hematopoiesis.[A7450] Myeloproliferative neoplasms, such as myelofibrosis and polycythemia vera, are often characterized by aberrant activation of the JAK-STAT pathway, leading to abnormal blood cell counts and thrombotic complications. By inhibiting JAK1 and JAK2, ruxolitinib works to block the dysregulated cell signalling pathways and prevents abnormal blood cell proliferation.[A229708] Due to a large number of patients with myeloproliferative neoplasms who have JAK2 mutations, ruxolitinib was the first ATP-competitive inhibitor of JAK1 and JAK2 ever developed.[A229938] Ruxolitinib was first approved for the treatment of adult patients with myelofibrosis by the FDA in 2011, followed by EMA's approval in 2012.[A229708] In 2014, it was approved for the treatment of polycythemia vera in adults who have an inadequate response to or are intolerant of [hydroxyurea] and in 2019, ruxolitinib was approved for use in steroid-refractory acute graft-versus-host disease in adults and children.[L31958] The topical formulation of ruxolitinib is used to treat atopic dermatitis and vitiligo.[L39125] It is being investigated for other inflammatory skin conditions.[A229883] Ruxolitinib has been investigated to treat patients with coronavirus disease 2019 (COVID-19) accompanied by severe systemic hyperinflammation. In phase II clinical trials, ruxolitinib improved chest computed tomography and improved recovery in patients with lymphopenia.[A229713, A229718] However, phase III clinical trials later determined that ruxolitinib was inadequate in meeting its primary endpoint of reducing the number of hospitalized COVID-19 patients who experienced severe complications [L31968] thus the drug was not approved as a treatment for COVID-19.
Synonyms	Ruxolitinib Recilisib sodium Ruxolitinib phosphate
Brand Names	Opzelura Jakafi Jakavi
Indication	Ruxolitinib is indicated for the treatment of the following conditions: - intermediate or high-risk myelofibrosis (MF), including prima1y MF, post-polycythemia vera MF and post-essential thrombocythemia MF in adults.[L31938] It is also used to treat disease-related splenomegaly or symptoms in adult patients with these conditions.[L32073] - polycythemia vera (PV) in adults who have had an inadequate response to or are intolerant of hydroxyurea.[L31938] - steroid-refracto1y acute graft-versus-host disease (GVHD) in adult and pediatric patients 12 years and older.[L31938] - chronic GVHD in patients aged 12 years and older who have failed one or two lines of systemic therapy.[L31938] Topical ruxolitinib is indicated for: - the short-term and non-continuous chronic treatment of mild to moderate atopic dermatitis in non-immunocompromised patients patients 12 years of age and older whose disease is not adequately controlled with topical prescription therapies or when those therapies are not advisable.[L39125] - the treatment of non-segmental vitiligo in adult and pediatric patients 12 years of age and older.[L39125, L46068]
Categories	Agents for Dermatitis, Excluding Corticosteroids Antineoplastic Agents Antineoplastic and Immunomodulating Agents Cancer immunotherapy Cytochrome P-450 CYP2C9 Substrates Cytochrome P-450 CYP2C9 Substrates with a Narrow Therapeutic Index Cytochrome P-450 CYP3A Substrates Cytochrome P-450 CYP3A4 Substrates Cytochrome P-450 CYP3A4 Substrates with a Narrow Therapeutic Index Cytochrome P-450 Substrates Dermatologicals Drugs that are Mainly Renally Excreted Immunosuppressive Agents Immunotherapy Janus Kinase Inhibitor Janus Kinases, antagonists & inhibitors Kinase Inhibitor Myelosuppressive Agents Narrow Therapeutic Index Drugs Protein Kinase Inhibitors Tyrosine Kinase Inhibitors
ATC-Code	D11AH09 L01EJ01
CAS number	941678-49-5

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
Tyrosine-protein kinase JAK2	MGMACLTMTEMEGTSTSSIYQNGDISGNANSMKQIDPVLQVYLYHSLGKS...	unknown	inhibitor
Tyrosine-protein kinase JAK1	MQYLNIKEDCNAMAFCAKMRSSKKTEVNLEAPEPGVEVIFYLSDREPLRL...	unknown	inhibitor
Tyrosine-protein kinase JAK3	MAPPSEETPLIPQRSCSLLSTEAGALHVLLPARGPGPPQRLSFSFGDHLA...	unknown	inhibitor
Non-receptor tyrosine-protein kinase TYK2	MPLRHWGMARGSKPVGDGAQPMAAMGGLKVLLHWAGPGGGEPWVTFSESS...	unknown	inhibitor
Cytochrome P450 3A4	MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...	unknown	substrate
Cytochrome P450 2C9	MDSLVVLVLCLSCLLLLSLWRQSSGRGKLPPGPTPLPVIGNILQIGIKDI...	unknown	substrate
Serum albumin	MKWVTFISLLFLFSSAYSRGVFRRDAHKSEVAHRFKDLGEENFKALVLIA...	unknown	binder
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Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682