CHEBI:91407 - momelotinib

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ChEBI Name momelotinib
ChEBI ID CHEBI:91407
Definition A benzamide obtained by formal condensation of the carboxy group of 4-{2-[4-(morpholin-4-yl)anilino]pyrimidin-4-yl}benzoic acid with the primary amino group of aminoacetonitrile. It is an ATP-competitive JAK1/JAK2 inhibitor with IC50 of 11 nM and 18 nM, respectively. Used for the treatment of patients with intermediate- or high-risk myelofibrosis.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information ChemicalBook:CB22514570, ChemicalBook:CB98229707, eMolecules:31507583, Selleckchem:Cyt387, ZINC000043199890
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Momelotinib, sold under the brand name Ojjaara among others, is an anticancer medication used for the treatment of myelofibrosis. It is a Janus kinase inhibitor and it is taken by mouth. The most common adverse reactions include dizziness, fatigue, bacterial infection, hemorrhage, thrombocytopenia, diarrhea, and nausea. Momelotinib was approved for medical use in the United States in September 2023, and in the European Union in January 2024.
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Formula C23H22N6O2
Net Charge 0
Average Mass 414.469
Monoisotopic Mass 414.18042
InChI InChI=1S/C23H22N6O2/c24-10-12-25-22(30)18-3-1-17(2-4-18)21-9-11-26-23(28-21)27-19-5-7-20(8-6-19)29-13-15-31-16-14-29/h1-9,11H,12-16H2,(H,25,30)(H,26,27,28)
InChIKey ZVHNDZWQTBEVRY-UHFFFAOYSA-N
SMILES O=C(NCC#N)C1=CC=C(C=C1)C2=CC=NC(NC3=CC=C(C=C3)N4CCOCC4)=N2
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor
An EC 2.7.10.* (protein-tyrosine kinase) inhibitor that specifically blocks the action of non-specific protein-tyrosine kinase (EC 2.7.10.2).
apoptosis inducer
Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
anti-anaemic agent
A compound which increases either the number of red cells or the amount of haemoglobin in the blood.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing momelotinib (CHEBI:91407) has role anti-anaemic agent (CHEBI:75835)
momelotinib (CHEBI:91407) has role antineoplastic agent (CHEBI:35610)
momelotinib (CHEBI:91407) has role apoptosis inducer (CHEBI:68495)
momelotinib (CHEBI:91407) has role EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor (CHEBI:76617)
momelotinib (CHEBI:91407) is a aminopyrimidine (CHEBI:38338)
momelotinib (CHEBI:91407) is a benzamides (CHEBI:22702)
momelotinib (CHEBI:91407) is a morpholines (CHEBI:38785)
momelotinib (CHEBI:91407) is a nitrile (CHEBI:18379)
momelotinib (CHEBI:91407) is a secondary amino compound (CHEBI:50995)
momelotinib (CHEBI:91407) is a tertiary amino compound (CHEBI:50996)
IUPAC Name
N-(cyanomethyl)-4-{2-[4-(morpholin-4-yl)anilino]pyrimidin-4-yl}benzamide
INNs Sources
momelotinib WHO MedNet
momélotinib WHO MedNet
momelotinib WHO MedNet
momelotinibum WHO MedNet
Synonyms Sources
CYT 11387 ChEBI
CYT 387 ChEBI
CYT-11387 ChEBI
CYT-387 DrugBank
CYT387 ChemIDplus
GS-0387 LINCS
LM-1149 ChEBI
N-(cyanomethyl)-4-(2-((4-(4-morpholinyl)phenyl)amino)-4-pyrimidinyl)benzamide ChEBI
N-(cyanomethyl)-4-(2-((4-(morpholin-4-yl)phenyl)amino)pyrimidin-4-yl)benzamide ChemIDplus
N-(cyanomethyl)-4-(2-((4-morpholinophenyl)-amino)pyrimidin-4-yl)benzamide ChEBI
N-(cyanomethyl)-4-[2-[4-(4-morpholinyl)anilino]-4-pyrimidinyl]benzamide ChEBI
Brand Name Source
Ojjaara DrugBank
Manual Xrefs Databases
C87 PDBeChem
D10315 KEGG DRUG
DB11763 DrugBank
LSM-1141 LINCS
Momelotinib Wikipedia
View more database links
Registry Number Type Source
1056634-68-4 CAS Registry Number ChemIDplus
Citations
Tefferi A, Pardanani A, Gangat N (2024)
Momelotinib expands the therapeutic armamentarium for myelofibrosis: Impact on hierarchy of treatment choices.
American journal of hematology 99, 300-308 [PubMed:38164985]
[show Abstract]
Oh ST, Verstovsek S, Gupta V, Platzbecker U, Devos T, Kiladjian JJ, McLornan DP, Perkins A, Fox ML, McMullin MF, Mead AJ, Egyed M, Mayer J, Sacha T, Kawashima J, Huang M, Strouse B, Mesa R (2024)
Changes in bone marrow fibrosis during momelotinib or ruxolitinib therapy do not correlate with efficacy outcomes in patients with myelofibrosis.
EJHaem 5, 105-116 [PubMed:38406514]
[show Abstract]
Gupta V, Oh S, Devos T, Dubruille V, Catalano J, Somervaille TCP, Platzbecker U, Giraldo P, Kosugi H, Sacha T, Mayer J, Illes A, Ellis C, Wang Z, Gonzalez Carreras FJ, Strouse B, Mesa R (2024)
Momelotinib vs. ruxolitinib in myelofibrosis patient subgroups by baseline hemoglobin levels in the SIMPLIFY-1 trial.
Leukemia & lymphoma 65, 965-977 [PubMed:38501751]
[show Abstract]
Hudgens S, Verstovsek S, Floden L, Harrison CN, Palmer J, Gupta V, McLornan D, McMullin MF, Kiladjian JJ, Foltz L, Platzbecker U, Fox ML, Mead AJ, Ross DM, Oh ST, Perkins AA, Leahy MF, Deheshi S, Donahue R, Klencke BJ, Mesa RA (2024)
Meaningful Symptomatic Change in Patients With Myelofibrosis From the SIMPLIFY Studies.
Value in health : the journal of the International Society for Pharmacoeconomics and Outcomes Research 27, 607-613 [PubMed:38311180]
[show Abstract]
Gangat N, Begna KH, Al-Kali A, Hogan W, Litzow M, Pardanani A, Tefferi A (2023)
Predictors of anemia response to momelotinib therapy in myelofibrosis and impact on survival.
American journal of hematology 98, 282-289 [PubMed:36349465]
[show Abstract]
Verstovsek S, Mesa R, Gupta V, Lavie D, Dubruille V, Cambier N, Platzbecker U, Hus M, Xicoy B, Oh ST, Kiladjian JJ, Vannucchi AM, Gerds A, Egyed M, Mayer J, Sacha T, Kawashima J, Morris M, Huang M, Harrison C (2023)
Momelotinib long-term safety and survival in myelofibrosis: integrated analysis of phase 3 randomized controlled trials.
Blood advances 7, 3582-3591 [PubMed:37042865]
[show Abstract]
Gangat N, Begna KH, Al-Kali A, Hogan W, Litzow M, Pardanani A, Tefferi A (2023)
Determinants of survival and retrospective comparisons of 183 clinical trial patients with myelofibrosis treated with momelotinib, ruxolitinib, fedratinib or BMS- 911543 JAK2 inhibitor.
Blood cancer journal 13, 3 [PubMed:36599841]
[show Abstract]
Mesa RA, Hudgens S, Floden L, Harrison CN, Palmer J, Gupta V, McLornan DP, McMullin MF, Kiladjian JJ, Foltz L, Platzbecker U, Fox ML, Mead AJ, Ross DM, Oh ST, Perkins A, Leahy MF, Deheshi S, Donahue R, Klencke BJ, Verstovsek S (2023)
Symptomatic benefit of momelotinib in patients with myelofibrosis: Results from the SIMPLIFY phase III studies.
Cancer medicine 12, 10612-10624 [PubMed:37021939]
[show Abstract]
Duminuco A, Chifotides HT, Giallongo S, Giallongo C, Tibullo D, Palumbo GA (2023)
ACVR1: A Novel Therapeutic Target to Treat Anemia in Myelofibrosis.
Cancers 16, 154 [PubMed:38201581]
[show Abstract]
Masarova L (2023)
Momelotinib, the next JAK2 inhibitor?
Clinical advances in hematology & oncology : H&O 21, 195-197 [PubMed:37039727]
Keam SJ (2023)
Momelotinib: First Approval.
Drugs 83, 1709-1715 [PubMed:37989928]
[show Abstract]
Tefferi A, Pardanani A, Gangat N (2023)
Momelotinib (JAK1/JAK2/ACVR1 inhibitor): mechanism of action, clinical trial reports, and therapeutic prospects beyond myelofibrosis.
Haematologica 108, 2919-2932 [PubMed:36861402]
[show Abstract]
Mesa RA, Harrison C, Palmer JM, Gupta V, McLornan DP, McMullin MF, Kiladjian JJ, Foltz L, Platzbecker U, Fox ML, Mead AJ, Ross DM, Oh ST, Perkins AC, Leahy MF, Kawashima J, Ro S, Donahue R, Gorsh B, Deheshi S, Verstovsek S (2023)
Patient-reported Outcomes and Quality of Life in Anemic and Symptomatic Patients With Myelofibrosis: Results From the MOMENTUM Study.
HemaSphere 7, e966 [PubMed:37901848]
[show Abstract]
Kiladjian JJ, Vannucchi AM, Gerds AT, Gupta V, Verstovsek S, Egyed M, Platzbecker U, Mayer J, Grosicki S, Illés Á, Woźny T, Oh ST, McLornan D, Kirgner I, Yoon SS, Harrison CN, Klencke B, Huang M, Kawashima J, Mesa R (2023)
Momelotinib in Myelofibrosis Patients With Thrombocytopenia: Post Hoc Analysis From Three Randomized Phase 3 Trials.
HemaSphere 7, e963 [PubMed:37908862]
[show Abstract]
Palandri F, Masarova L, Verstovsek S, Mesa R, Harrison C, Sajeev G, Gorsh B, Simpson R, Cho S, Wang Z, Ellis C, Conlon S, Signorovitch J (2023)
P1062: INDIRECT TREATMENT COMPARISON OF MOMELOTINIB VS FEDRATINIB SAFETY IN PATIENTS WITH MYELOFIBROSIS
HemaSphere 7, [PubMed Central:PMC10431522]
Verstovsek S, Gerds AT, Vannucchi AM, Al-Ali HK, Lavie D, Kuykendall AT, Grosicki S, Iurlo A, Goh YT, Lazaroiu MC, Egyed M, Fox ML, McLornan D, Perkins A, Yoon SS, Gupta V, Kiladjian JJ, Granacher N, Lee SE, Ocroteala L, Passamonti F, Harrison CN, Klencke BJ, Ro S, Donahue R, Kawashima J, Mesa R, MOMENTUM Study Investigators (2023)
Momelotinib versus danazol in symptomatic patients with anaemia and myelofibrosis (MOMENTUM): results from an international, double-blind, randomised, controlled, phase 3 study.
Lancet (London, England) 401, 269-280 [PubMed:36709073]
[show Abstract]
Gerds AT, Verstovsek S, Vannucchi AM, Al-Ali HK, Lavie D, Kuykendall AT, Grosicki S, Iurlo A, Goh YT, Lazaroiu MC, Egyed M, Fox ML, McLornan D, Perkins A, Yoon SS, Gupta V, Kiladjian JJ, Granacher N, Lee SE, Ocroteala L, Passamonti F, Harrison CN, Oh S, Klencke BJ, Yu J, Donahue R, Kawashima J, Mesa R (2023)
Momelotinib versus danazol in symptomatic patients with anaemia and myelofibrosis previously treated with a JAK inhibitor (MOMENTUM): an updated analysis of an international, double-blind, randomised phase 3 study.
The Lancet. Haematology 10, e735-e746 [PubMed:37517413]
[show Abstract]
Desai J, Patel B, Gite A, Panchal N, Gite S, Argade A, Kumar J, Sachchidanand S, Bandyopadhyay D, Ghoshdastidar K, Patel H, Chatterjee A, Mahapatra J, Sharma M, Giri P, Kumar S, Jain M, Sharma R, Desai R (2022)
Optimisation of momelotinib with improved potency and efficacy as pan-JAK inhibitor.
Bioorganic & medicinal chemistry letters 66, 128728 [PubMed:35413417]
[show Abstract]
Azhar M, Kincaid Z, Kesarwani M, Ahmed A, Wunderlich M, Latif T, Starczynowski D, Azam M (2022)
Momelotinib is a highly potent inhibitor of FLT3-mutant AML.
Blood advances 6, 1186-1192 [PubMed:34768286]
[show Abstract]
Li J, Liang J, Wu L, Xu Y, Xiao C, Yang X, Sun R, Zhao J, Xu J, Liu Q, Zhou B (2022)
CYT387, a JAK-Specific Inhibitor Impedes Osteoclast Activity and Oophorectomy-Induced Osteoporosis via Modulating RANKL and ROS Signaling Pathways.
Frontiers in pharmacology 13, 829862 [PubMed:35345816]
[show Abstract]
Tremblay D, Mesa R (2022)
Momelotinib for the treatment of myelofibrosis with anemia.
Future oncology (London, England) 18, 2559-2571 [PubMed:35603634]
[show Abstract]
Srivastava S, Samarpita S, Ganesan R, Rasool M (2022)
CYT387 Inhibits the Hyperproliferative Potential of Fibroblast-like Synoviocytes via Modulation of IL-6/JAK1/STAT3 Signaling in Rheumatoid Arthritis.
Immunological investigations 51, 1582-1597 [PubMed:34704880]
[show Abstract]
Chifotides HT, Bose P, Verstovsek S (2022)
Momelotinib: an emerging treatment for myelofibrosis patients with anemia.
Journal of hematology & oncology 15, 7 [PubMed:35045875]
[show Abstract]
Mesa R, Harrison C, Oh ST, Gerds AT, Gupta V, Catalano J, Cervantes F, Devos T, Hus M, Kiladjian JJ, Lech-Maranda E, McLornan D, Vannucchi AM, Platzbecker U, Huang M, Strouse B, Klencke B, Verstovsek S (2022)
Overall survival in the SIMPLIFY-1 and SIMPLIFY-2 phase 3 trials of momelotinib in patients with myelofibrosis.
Leukemia 36, 2261-2268 [PubMed:35869266]
[show Abstract]
Mesa R, Oh ST, Gerds AT, Gupta V, Catalano J, Cervantes F, Devos T, Hus M, Kiladjian JJ, Lech-Maranda E, McLornan D, Palmer J, Platzbecker U, Treliński J, Shimoda K, Donahue R, D'Hollander K, Kowalski M, Verstovsek S (2022)
Momelotinib reduces transfusion requirements in patients with myelofibrosis.
Leukemia & lymphoma 63, 1718-1722 [PubMed:35255234]
Cosenza M, Civallero M, Marcheselli L, Sacchi S, Pozzi S (2020)
Citarinostat and Momelotinib co-target HDAC6 and JAK2/STAT3 in lymphoid malignant cell lines: a potential new therapeutic combination.
Apoptosis : an international journal on programmed cell death 25, 370-387 [PubMed:32394008]
[show Abstract]
Xu L, Feng J, Gao G, Tang H (2019)
Momelotinib for the treatment of myelofibrosis.
Expert opinion on pharmacotherapy 20, 1943-1951 [PubMed:31450973]
[show Abstract]
Ng K, Hendifar A, Starodub A, Chaves J, Yang Y, Koh B, Barbie D, Hahn WC, Fuchs CS (2019)
Phase 1 dose-escalation study of momelotinib, a Janus kinase 1/2 inhibitor, combined with gemcitabine and nab-paclitaxel in patients with previously untreated metastatic pancreatic ductal adenocarcinoma.
Investigational new drugs 37, 159-165 [PubMed:30105668]
[show Abstract]
Singer JW, Al-Fayoumi S, Taylor J, Velichko S, O'Mahony A (2019)
Comparative phenotypic profiling of the JAK2 inhibitors ruxolitinib, fedratinib, momelotinib, and pacritinib reveals distinct mechanistic signatures.
PloS one 14, e0222944 [PubMed:31560729]
[show Abstract]
Tefferi A, Barraco D, Lasho TL, Shah S, Begna KH, Al-Kali A, Hogan WJ, Litzow MR, Hanson CA, Ketterling RP, Gangat N, Pardanani A (2018)
Momelotinib therapy for myelofibrosis: a 7-year follow-up.
Blood cancer journal 8, 29 [PubMed:29515114]
[show Abstract]
Barbie DA, Spira A, Kelly K, Humeniuk R, Kawashima J, Kong S, Koczywas M (2018)
Phase 1B Study of Momelotinib Combined With Trametinib in Metastatic, Kirsten Rat Sarcoma Viral Oncogene Homolog-Mutated Non-Small-Cell Lung Cancer After Platinum-Based Chemotherapy Treatment Failure.
Clinical lung cancer 19, e853-e859 [PubMed:30087028]
[show Abstract]
Xin Y, Shao L, Maltzman J, Stefanidis D, Hemenway J, Tarnowski T, Deng W, Silverman JA (2018)
The Relative Bioavailability, Food Effect, and Drug Interaction With Omeprazole of Momelotinib Tablet Formulation in Healthy Subjects.
Clinical pharmacology in drug development 7, 277-286 [PubMed:29024542]
[show Abstract]
Zheng J, Xin Y, Zhang J, Subramanian R, Murray BP, Whitney JA, Warr MR, Ling J, Moorehead L, Kwan E, Hemenway J, Smith BJ, Silverman JA (2018)
Pharmacokinetics and Disposition of Momelotinib Revealed a Disproportionate Human Metabolite-Resolution for Clinical Development.
Drug metabolism and disposition: the biological fate of chemicals 46, 237-247 [PubMed:29311136]
[show Abstract]
Xin Y, Kawashima J, Weng W, Kwan E, Tarnowski T, Silverman JA (2018)
Pharmacokinetics and Safety of Momelotinib in Subjects With Hepatic or Renal Impairment.
Journal of clinical pharmacology 58, 522-532 [PubMed:29283448]
[show Abstract]
Pardanani A, Gotlib J, Roberts AW, Wadleigh M, Sirhan S, Kawashima J, Maltzman JA, Shao L, Gupta V, Tefferi A (2018)
Long-term efficacy and safety of momelotinib, a JAK1 and JAK2 inhibitor, for the treatment of myelofibrosis.
Leukemia 32, 1035-1038 [PubMed:29263442]
Harrison CN, Vannucchi AM, Platzbecker U, Cervantes F, Gupta V, Lavie D, Passamonti F, Winton EF, Dong H, Kawashima J, Maltzman JD, Kiladjian JJ, Verstovsek S (2018)
Momelotinib versus best available therapy in patients with myelofibrosis previously treated with ruxolitinib (SIMPLIFY 2): a randomised, open-label, phase 3 trial.
The Lancet. Haematology 5, e73-e81 [PubMed:29275119]
[show Abstract]
Winton EF, Kota V (2017)
Momelotinib in myelofibrosis: JAK1/2 inhibitor with a role in treating and understanding the anemia.
Future oncology (London, England) 13, 395-407 [PubMed:27785927]
[show Abstract]
Gupta V, Mesa RA, Deininger MW, Rivera CE, Sirhan S, Brachmann CB, Collins H, Kawashima J, Xin Y, Verstovsek S (2017)
A phase 1/2, open-label study evaluating twice-daily administration of momelotinib in myelofibrosis.
Haematologica 102, 94-102 [PubMed:27634203]
[show Abstract]
Mesa RA, Kiladjian JJ, Catalano JV, Devos T, Egyed M, Hellmann A, McLornan D, Shimoda K, Winton EF, Deng W, Dubowy RL, Maltzman JD, Cervantes F, Gotlib J (2017)
SIMPLIFY-1: A Phase III Randomized Trial of Momelotinib Versus Ruxolitinib in Janus Kinase Inhibitor-Naïve Patients With Myelofibrosis.
Journal of clinical oncology : official journal of the American Society of Clinical Oncology 35, 3844-3850 [PubMed:28930494]
[show Abstract]
Lu Z, Hong CC, Jark PC, Assumpção ALFV, Bollig N, Kong G, Pan X (2017)
JAK1/2 Inhibitors AZD1480 and CYT387 Inhibit Canine B-Cell Lymphoma Growth by Increasing Apoptosis and Disrupting Cell Proliferation.
Journal of veterinary internal medicine 31, 1804-1815 [PubMed:28960447]
[show Abstract]
Verstovsek S, Courby S, Griesshammer M, Mesa RA, Brachmann CB, Kawashima J, Maltzman JD, Shao L, Xin Y, Huang D, Bajel A (2017)
A phase 2 study of momelotinib, a potent JAK1 and JAK2 inhibitor, in patients with polycythemia vera or essential thrombocythemia.
Leukemia research 60, 11-17 [PubMed:28622623]
[show Abstract]
Abdelrahman RA, Begna KH, Al-Kali A, Hogan WJ, Litzow MR, Pardanani A, Tefferi A (2015)
Momelotinib treatment-emergent neuropathy: prevalence, risk factors and outcome in 100 patients with myelofibrosis.
British journal of haematology 169, 77-80 [PubMed:25511866]
[show Abstract]
Pardanani A, Abdelrahman RA, Finke C, Lasho TT, Begna KH, Al-Kali A, Hogan WJ, Litzow MR, Hanson CA, Ketterling RP, Tefferi A (2015)
Genetic determinants of response and survival in momelotinib-treated patients with myelofibrosis.
Leukemia 29, 741-744 [PubMed:25322686]
Pardanani A, Laborde RR, Lasho TL, Finke C, Begna K, Al-Kali A, Hogan WJ, Litzow MR, Leontovich A, Kowalski M, Tefferi A (2013)
Safety and efficacy of CYT387, a JAK1 and JAK2 inhibitor, in myelofibrosis.
Leukemia 27, 1322-1327 [PubMed:23459451]
[show Abstract]
Pardanani A, Vannucchi AM, Passamonti F, Cervantes F, Barbui T, Tefferi A (2011)
JAK inhibitor therapy for myelofibrosis: critical assessment of value and limitations.
Leukemia 25, 218-225 [PubMed:21079613]
[show Abstract]
Burns CJ, Bourke DG, Andrau L, Bu X, Charman SA, Donohue AC, Fantino E, Farrugia M, Feutrill JT, Joffe M, Kling MR, Kurek M, Nero TL, Nguyen T, Palmer JT, Phillips I, Shackleford DM, Sikanyika H, Styles M, Su S, Treutlein H, Zeng J, Wilks AF (2009)
Phenylaminopyrimidines as inhibitors of Janus kinases (JAKs).
Bioorganic & medicinal chemistry letters 19, 5887-5892 [PubMed:19762238]
[show Abstract]
Last Modified
16 April 2024