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941678-49-5,MFCD12031592
Catalog No.:AA0034XX

941678-49-5 | (R)-3-(4-(7H-Pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl)-3-cyclopentylpropanenitrile (Synonyms:Ruxolitinib)

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1mg
98%
in stock  
$11.00   $8.00
- +
5mg
98%
in stock  
$25.00   $18.00
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100mg
98%
in stock  
$53.00   $37.00
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250mg
98%
in stock  
$107.00   $75.00
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5g
98%
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$1,537.00   $1,076.00
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA0034XX
Chemical Name:
(R)-3-(4-(7H-Pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl)-3-cyclopentylpropanenitrile (Synonyms:Ruxolitinib)
CAS Number:
941678-49-5
Molecular Formula:
C17H18N6
Molecular Weight:
306.3650
MDL Number:
MFCD12031592
SMILES:
N#CC[C@@H](n1ncc(c1)c1[nH]cnc2c1ccn2)C1CCCC1
Properties
Properties
 
Form:
Solid  
MP:
84-89°C  
Storage:
Inert atmosphere;-20 ℃;  

Computed Properties
 
Complexity:
453  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
1  
Heavy Atom Count:
23  
Hydrogen Bond Acceptor Count:
4  
Hydrogen Bond Donor Count:
1  
Rotatable Bond Count:
4  
XLogP3:
2.1  

Downstream Synthesis Route

[1]Patent:US2008/312259,2008,A1.Locationinpatent:Page/Pagecolumn6

[2]Patent:WO2013/23119,2013,A1.Locationinpatent:Page/Pagecolumn33

[1]Patent:US2010/190981,2010,A1.Locationinpatent:Page/Pagecolumn80

[2]Patent:US2008/312259,2008,A1.Locationinpatent:Page/Pagecolumn6

[3]Patent:WO2013/23119,2013,A1.Locationinpatent:Page/Pagecolumn33

[4]Patent:WO2016/35014,2016,A1.Locationinpatent:Page/Pagecolumn29

[5]Patent:WO2016/24232,2016,A1.Locationinpatent:Paragraph00676

[6]Patent:WO2016/24230,2016,A1.Locationinpatent:Paragraph00651

[7]Patent:EP2574168,2016,B1.Locationinpatent:Paragraph0151-0153

[8]Patent:CN107759623,2018,A.Locationinpatent:Paragraph0118;0119

[1]Patent:US2008/312259,2008,A1.Locationinpatent:Page/Pagecolumn6

[2]Patent:WO2013/23119,2013,A1.Locationinpatent:Page/Pagecolumn33

[1]Patent:US2019/23712,2019,A1.Locationinpatent:Paragraph0278-0280

[2]OrganicLetters,2009,vol.11,p.1999-2002

[3]Patent:WO2016/24232,2016,A1.Locationinpatent:Paragraph00675

[4]Patent:WO2016/24230,2016,A1.Locationinpatent:Paragraph00650

[5]Patent:WO2013/23119,2013,A1.Locationinpatent:Page/Pagecolumn32;33

[6]Patent:WO2016/26975,2016,A1.Locationinpatent:Page/Pagecolumn12;14

[7]Patent:EP2349260,2016,B1.Locationinpatent:Paragraph0110;0113

[1]OrganicLetters,2009,vol.11,p.1999-2002

[2]Patent:US2010/190981,2010,A1.Locationinpatent:Page/Pagecolumn65-66

Literature

Title: Momelotinib versus best available therapy in patients with myelofibrosis previously treated with ruxolitinib (SIMPLIFY 2): a randomised, open-label, phase 3 trial.

Journal: The Lancet. Haematology 20180201

Title: Impairment of human neural crest cell migration by prolonged exposure to interferon-beta.

Journal: Archives of toxicology 20170101

Title: Differences in gene expression and alterations in cell cycle of acute myeloid leukemia cell lines after treatment with JAK inhibitors.

Journal: European journal of pharmacology 20151015

Title: White-to-brown metabolic conversion of human adipocytes by JAK inhibition.

Journal: Nature cell biology 20150101

Title: Structure-activity relationship of 3,5-diaryl-2-aminopyridine ALK2 inhibitors reveals unaltered binding affinity for fibrodysplasia ossificans progressiva causing mutants.

Journal: Journal of medicinal chemistry 20141009

Title: The novel Janus kinase inhibitor ruxolitinib confers protection against carbon tetrachloride-induced hepatotoxicity via multiple mechanisms.

Journal: Chemico-biological interactions 20140905

Title: Alopecia areata is driven by cytotoxic T lymphocytes and is reversed by JAK inhibition.

Journal: Nature medicine 20140901

Title: The evaluation of p,p'-DDT exposure on cell adhesion of hepatocellular carcinoma.

Journal: Toxicology 20140801

Title: Discovery and development of Janus kinase (JAK) inhibitors for inflammatory diseases.

Journal: Journal of medicinal chemistry 20140626

Title: Ruxolitinib and tofacitinib are potent and selective inhibitors of HIV-1 replication and virus reactivation in vitro.

Journal: Antimicrobial agents and chemotherapy 20140401

Title: JAK inhibitors: treatment efficacy and safety profile in patients with psoriasis.

Journal: Journal of immunology research 20140101

Title: Identification of potent Yes1 kinase inhibitors using a library screening approach.

Journal: Bioorganic & medicinal chemistry letters 20130801

Title: Myelofibrosis: an update on current pharmacotherapy and future directions.

Journal: Expert opinion on pharmacotherapy 20130501

Title: Regulation of inflammatory responses in tumor necrosis factor-activated and rheumatoid arthritis synovial macrophages by JAK inhibitors.

Journal: Arthritis and rheumatism 20121201

Title: Discovery of potent and selective pyrazolopyrimidine janus kinase 2 inhibitors.

Journal: Journal of medicinal chemistry 20121126

Title: Ruxolitinib: in the treatment of myelofibrosis.

Journal: Drugs 20121112

Title: Ruxolitinib, an oral JAK1 and JAK2 inhibitor, in myelofibrosis.

Journal: Expert opinion on pharmacotherapy 20121101

Title: Targeting JAK1/2 and mTOR in murine xenograft models of Ph-like acute lymphoblastic leukemia.

Journal: Blood 20121025

Title: Preliminary clinical activity of a topical JAK1/2 inhibitor in the treatment of psoriasis.

Journal: Journal of the American Academy of Dermatology 20121001

Title: Role of additional novel therapies in myeloproliferative neoplasms.

Journal: Hematology/oncology clinics of North America 20121001

Title: Current outlook on molecular pathogenesis and treatment of myeloproliferative neoplasms.

Journal: Molecular diagnosis & therapy 20121001

Title: Advances in the management of myelofibrosis.

Journal: Cancer control : journal of the Moffitt Cancer Center 20121001

Title: [Novel therapeutic options in the treatment of BCR/ABL-negative myeloproliferative neoplasms].

Journal: Deutsche medizinische Wochenschrift (1946) 20121001

Title: Therapeutic effects of ruxolitinib in patients with myelofibrosis without clinically significant splenomegaly.

Journal: Blood 20120927

Title: Inhibition of JAKs in macrophages increases lipopolysaccharide-induced cytokine production by blocking IL-10-mediated feedback.

Journal: Journal of immunology (Baltimore, Md. : 1950) 20120915

Title: Ruxolitinib inhibits transforming JAK2 fusion proteins in vitro and induces complete cytogenetic remission in t(8;9)(p22;p24)/PCM1-JAK2-positive chronic eosinophilic leukemia.

Journal: Blood 20120816

Title: Long-term outcomes of 107 patients with myelofibrosis receiving JAK1/JAK2 inhibitor ruxolitinib: survival advantage in comparison to matched historical controls.

Journal: Blood 20120809

Title: How I treat polycythemia vera.

Journal: Blood 20120712

Title: Ruxolitinib for myelofibrosis therapy: current context, pros and cons.

Journal: Leukemia 20120701

Title: Identification of imidazo-pyrrolopyridines as novel and potent JAK1 inhibitors.

Journal: Journal of medicinal chemistry 20120628

Title: U.S. Food and Drug Administration approval: ruxolitinib for the treatment of patients with intermediate and high-risk myelofibrosis.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20120615

Title: The effect of CYP3A4 inhibition or induction on the pharmacokinetics and pharmacodynamics of orally administered ruxolitinib (INCB018424 phosphate) in healthy volunteers.

Journal: Journal of clinical pharmacology 20120601

Title: Ruxolitinib: the first FDA approved therapy for the treatment of myelofibrosis.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20120601

Title: Phase 2 study of the JAK kinase inhibitor ruxolitinib in patients with refractory leukemias, including postmyeloproliferative neoplasm acute myeloid leukemia.

Journal: Blood 20120517

Title: Ruxolitinib (Jakafi) for myelofibrosis.

Journal: The Medical letter on drugs and therapeutics 20120402

Title: Kinase domain mutations confer resistance to novel inhibitors targeting JAK2V617F in myeloproliferative neoplasms.

Journal: Leukemia 20120401

Title: Breakthroughs in myeloproliferative neoplasms.

Journal: Hematology (Amsterdam, Netherlands) 20120401

Title: JAK2 inhibitors and their impact in myeloproliferative neoplasms.

Journal: Hematology (Amsterdam, Netherlands) 20120401

Title: JAK inhibitors for myeloproliferative neoplasms: clarifying facts from myths.

Journal: Blood 20120322

Title: New generation small-molecule inhibitors in myeloproliferative neoplasms.

Journal: Current opinion in hematology 20120301

Title: Management of myeloproliferative neoplasms: from academic guidelines to clinical practice.

Journal: Current hematologic malignancy reports 20120301

Title: JAK inhibition with ruxolitinib versus best available therapy for myelofibrosis.

Journal: The New England journal of medicine 20120301

Title: A double-blind, placebo-controlled trial of ruxolitinib for myelofibrosis.

Journal: The New England journal of medicine 20120301

Title: Ruxolitinib.

Journal: Nature reviews. Drug discovery 20120201

Title: Ruxolitinib: the first agent approved for myelofibrosis.

Journal: Clinical advances in hematology & oncology : H&O 20120201

Title: Incyte comes of age with JAK inhibitor approval.

Journal: Nature biotechnology 20120109

Title: STAT3 is activated by JAK2 independent of key oncogenic driver mutations in non-small cell lung carcinoma.

Journal: PloS one 20120101

Title: Serious adverse events during ruxolitinib treatment discontinuation in patients with myelofibrosis.

Journal: Mayo Clinic proceedings 20111201

Title: Ruxolitinib for the treatment of myelofibrosis.

Journal: Drugs of today (Barcelona, Spain : 1998) 20111101

Title: Comprehensive analysis of kinase inhibitor selectivity.

Journal: Nature biotechnology 20111030

Title: Long-term outcome of treatment with ruxolitinib in myelofibrosis.

Journal: The New England journal of medicine 20111013

Title: Ruxolitinib: a new JAK1/2 inhibitor that offers promising options for treatment of myelofibrosis.

Journal: Future oncology (London, England) 20110901

Title: A potential role of ruxolitinib in leukemia.

Journal: Expert opinion on investigational drugs 20110801

Title: Targeting myeloproliferative neoplasms with JAK inhibitors.

Journal: Current opinion in hematology 20110301

Title: JAK inhibitor therapy for myelofibrosis: critical assessment of value and limitations.

Journal: Leukemia 20110201

Title: JAK inhibition in myelofibrosis.

Journal: The New England journal of medicine 20101216

Title: Diamino-1,2,4-triazole derivatives are selective inhibitors of TYK2 and JAK1 over JAK2 and JAK3.

Journal: Bioorganic & medicinal chemistry letters 20101215

Title: Activation state-dependent binding of small molecule kinase inhibitors: structural insights from biochemistry.

Journal: Chemistry & biology 20101124

Title: Metabolism, excretion, and pharmacokinetics of [14C]INCB018424, a selective Janus tyrosine kinase 1/2 inhibitor, in humans.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20101101

Title: Ruxolitinib, a selective JAK1 and JAK2 inhibitor for the treatment of myeloproliferative neoplasms and psoriasis.

Journal: IDrugs : the investigational drugs journal 20100601

Title: Preclinical characterization of the selective JAK1/2 inhibitor INCB018424: therapeutic implications for the treatment of myeloproliferative neoplasms.

Journal: Blood 20100415

Title: Enantioselective synthesis of Janus kinase inhibitor INCB018424 via an organocatalytic aza-Michael reaction.

Journal: Organic letters 20090507

Title: Novel strategies for patients with chronic myeloproliferative disorders.

Journal: Current opinion in hematology 20090301

Title: Therapeutic potential of JAK2 inhibitors.

Journal: Hematology. American Society of Hematology. Education Program 20090101

Title: Quintas-Cardama A, et al. Preclinical characterization of the selective JAK1/2 inhibitor INCB018424: therapeutic implications for the treatment of myeloproliferative neoplasms. Blood, 2010, 115(15), 3109-3117.

Title: Verstovsek S, et al. A double-blind, placebo-controlled trial of ruxolitinib for myelofibrosis. N Engl J Med, 2012, 366(9), 799-807.

Title: Tavallai M, et al. Rationally Repurposing Ruxolitinib (Jakafi (®)) as a Solid Tumor Therapeutic.Front Oncol. 2016 Jun 13;6:142.

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Tags:941678-49-5 Molecular Formula|941678-49-5 MDL|941678-49-5 SMILES|941678-49-5 (R)-3-(4-(7H-Pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl)-3-cyclopentylpropanenitrile (Synonyms:Ruxolitinib)