Nintedanib esylate
Nintedanib, also known as BIBF1120, is a potent inhibitor of multiple receptor tyrosine kinases (RTKs) and non-receptor tyrosine kinases (nRTKs). Nintedanib inhibits the following RTKs: platelet-derived growth factor receptor (PDGFR) α and β, fibroblast growth factor receptor (FGFR) 1-3, vascular endothelial growth factor receptor (VEGFR) 1-3, and Fms-like tyrosine kinase-3 (FLT3). Nintedanib binds competitively to the adenosine triphosphate (ATP) binding pocket of these receptors and blocks the intracellular signaling which is crucial for the proliferation, migration, and transformation of fibroblasts representing essential mechanisms of the IPF pathology. Nintedanib esylate was approved in 2014 for the treatment of idiopathic pulmonary fibrosis (IPF).
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Chemical Information
| Name | Nintedanib esylate |
|---|---|
| Iupac Chemical Name | Methyl (3Z)-3-(((4-(N-methyl-2-(4-methylpiperazin-1-yl)acetamido)phenyl)amino) (phenyl)methylidene)-2-oxo-2,3-dihydro-1H-indole-6-carboxylate ethanesulfonate |
| Synonyms | BIBF1120; BIBF 1120 BIBF-1120; Nintedanib esylate. Nintedanib ethanesulfonate salt; Intedanib; Brand name OFEV. Vargatef. |
| Molecular Formula | C33H39N5O7S |
| Molecular Weight | 649.763 |
| Smile | O=C(C1=CC(NC/2=O)=C(C=C1)C2=C(NC3=CC=C(N(C)C(CN4CCN(C)CC4)=O)C=C3)/C5=CC=CC=C5)OC.CCS(=O)(O)=O |
| InChiKey | MMMVNAGRWOJNMW-FJBFXRHMSA-N |
| InChi | InChI=1S/C31H33N5O4.C2H6O3S/c1-34-15-17-36(18-16-34)20-27(37)35(2)24-12-10-23(11-13-24)32-29(21-7-5-4-6-8-21)28-25-14-9-22(31(39)40-3)19-26(25)33-30(28)38;1-2-6(3,4)5/h4-14,19,32H,15-18,20H2,1-3H3,(H,33,38);2H2,1H3,(H,3,4,5)/b29-28-; |
| CAS Number | 656247-18-6 |
| Related CAS |
Ordering Information
| Packaging | Price | Availability | Purity | Shipping Time |
|---|---|---|---|---|
| Bulk | Enquiry | Enquiry | Enquiry |
| Formulation | Solid powder |
|---|---|
| Purity | 98% Min. |
| Storage | Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years). |
| Solubility | Soluble in DMSO |
| Handling | |
| Shipping Condition | Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs. |
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| Mechanism | |
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| Clinical study |
1: Scagliotti GV, Gaafar R, Nowak A, Vogelzang NJ, Von Wangenheim U, Morsli N, Velema D, Popat S. P2.01: LUME-MeSO: Phase II/III Study of Nintedanib + Pemetrexed/Cisplatin in Patients With Malignant Pleural Mesothelioma: Track: SCLC, Mesothelioma, Thymoma. J Thorac Oncol. 2016 Oct;11(10S):S216. doi: 10.1016/j.jtho.2016.08.075. Epub 2016 Sep 22. PubMed PMID: 27676538.
2: Kolb M, Richeldi L, Behr J, Maher TM, Tang W, Stowasser S, Hallmann C, du Bois RM. Nintedanib in patients with idiopathic pulmonary fibrosis and preserved lung volume. Thorax. 2016 Sep 26. pii: thoraxjnl-2016-208710. doi: 10.1136/thoraxjnl-2016-208710. [Epub ahead of print] PubMed PMID: 27672117.
3: Chambers DC. Nintedanib for idiopathic pulmonary fibrosis: An Asian perspective. Respirology. 2016 Sep 20. doi: 10.1111/resp.12903. [Epub ahead of print] PubMed PMID: 27651286.
4: Okusaka T, Otsuka T, Ueno H, Mitsunaga S, Sugimoto R, Muro K, Saito I, Tadayasu Y, Inoue K, Loembé AB, Ikeda M. Phase I study of nintedanib in Japanese patients with advanced hepatocellular carcinoma and liver impairment. Cancer Sci. 2016 Sep 14. doi: 10.1111/cas.13077. [Epub ahead of print] PubMed PMID: 27627050.
5: Hughes G, Toellner H, Morris H, Leonard C, Chaudhuri N. Real World Experiences: Pirfenidone and Nintedanib are Effective and Well Tolerated Treatments for Idiopathic Pulmonary Fibrosis. J Clin Med. 2016 Sep 2;5(9). pii: E78. doi: 10.3390/jcm5090078. Review. PubMed PMID: 27598213.
6: Quintela-Fandino M, Lluch A, Manso LM, Calvo I, Cortes J, García-Saenz JA, Gil JM, Martinez-Jañez N, González-Martín A, Adrover E, De Andres R, Viñas G, Llombart Cussac A, Alba E, Guerra J, Bermejo B, Zamora E, Moreno-Anton F, Pernas-Simon S, Carrato A, Lopez A, Escudero MJ, Campo R, Carrasco EM, Palacios J, Mulero F, Colomer R. 18F-fluoromisonidazole PET and activity of neoadjuvant nintedanib in early HER2-negative breast cancer: a window-of-opportunity randomized trial. Clin Cancer Res. 2016 Sep 1. pii: clincanres.0738.2016. [Epub ahead of print] PubMed PMID: 27587436.
7: Hibi M, Kaneda H, Tanizaki J, Sakai K, Togashi Y, Terashima M, De Velasco MA, Fujita Y, Banno E, Nakamura Y, Takeda M, Ito A, Mitsudomi T, Nakagawa K, Okamoto I, Nishio K. FGFR gene alterations in lung squamous cell carcinoma are potential targets for the multikinase inhibitor nintedanib. Cancer Sci. 2016 Sep 1. doi: 10.1111/cas.13071. [Epub ahead of print] PubMed PMID: 27581340.
8: Olin JL, Woods JA, Garner SJ. Delayed Presentation of Hepatocellular Liver Injury After Nintedanib Administration. Am J Ther. 2016 Aug 17. [Epub ahead of print] PubMed PMID: 27574930.
9: Espinosa Bosch M, Asensi Diez R, García Agudo S, Clopes Estela A. Nintedanib in combination with docetaxel for second-line treatment of advanced non-small-cell lung cancer; GENESIS-SEFH drug evaluation report. Farm Hosp. 2016 Jun 1;40(4):316-27. doi: 10.7399/fh.2016.40.4.10455. PubMed PMID: 27571499.
10: Bonella F, Kreuter M, Hagmeyer L, Neurohr C, Keller C, Kohlhaeufl MJ, Müller-Quernheim J, Milger K, Prasse A; German Nintedanib Compassionate Use Consortium. Insights from the German Compassionate Use Program of Nintedanib for the Treatment of Idiopathic Pulmonary Fibrosis. Respiration. 2016;92(2):98-106. doi: 10.1159/000448288. Epub 2016 Aug 20. PubMed PMID: 27544537.
11: Gann CN, Morsli N, Chen X, Barrueco J. Response to 'Dai W et al. Am J Cancer Res 2015;5(10):3270-3275' from the makers of nintedanib. Am J Cancer Res. 2016 Jul 1;6(7):1547-8. eCollection 2016. PubMed PMID: 27508096; PubMed Central PMCID: PMC4969403.
12: Slobbe P, Poot AJ, Haumann R, Schuit RC, Windhorst AD, van Dongen GA. Two anti-angiogenic TKI-PET tracers, [(11)C]axitinib and [(11)C]nintedanib: Radiosynthesis, in vivo metabolism and initial biodistribution studies in rodents. Nucl Med Biol. 2016 Oct;43(10):612-24. doi: 10.1016/j.nucmedbio.2016.07.003. Epub 2016 Jul 14. PubMed PMID: 27497236.
13: Rogliani P, Calzetta L, Cavalli F, Matera MG, Cazzola M. Pirfenidone, nintedanib and N-acetylcysteine for the treatment of idiopathic pulmonary fibrosis: A systematic review and meta-analysis. Pulm Pharmacol Ther. 2016 Oct;40:95-103. doi: 10.1016/j.pupt.2016.07.009. Epub 2016 Jul 29. PubMed PMID: 27481628.
14: Taniguchi H, Xu Z, Azuma A, Inoue Y, Li H, Fujimoto T, Bailes Z, Schlenker-Herceg R, Kim DS. Subgroup analysis of Asian patients in the INPULSIS® trials of nintedanib in idiopathic pulmonary fibrosis. Respirology. 2016 Jul 11. doi: 10.1111/resp.12852. [Epub ahead of print] PubMed PMID: 27399197.
15: Lobo P. Nintedanib data challenge IPF guidelines. Lancet Respir Med. 2016 Aug;4(8):610. doi: 10.1016/S2213-2600(16)30196-5. Epub 2016 Jul 4. PubMed PMID: 27388655.
16: Wuyts WA, Kolb M, Stowasser S, Stansen W, Huggins JT, Raghu G. First Data on Efficacy and Safety of Nintedanib in Patients with Idiopathic Pulmonary Fibrosis and Forced Vital Capacity of ≤50 % of Predicted Value. Lung. 2016 Oct;194(5):739-43. doi: 10.1007/s00408-016-9912-1. Epub 2016 Jul 4. PubMed PMID: 27377558.
17: Englinger B, Lötsch D, Pirker C, Mohr T, van Schoonhoven S, Boidol B, Lardeau CH, Spitzwieser M, Szabó P, Heffeter P, Lang I, Cichna-Markl M, Grasl-Kraupp B, Marian B, Grusch M, Kubicek S, Szakács G, Berger W. Acquired nintedanib resistance in FGFR1-driven small cell lung cancer: role of endothelin-A receptor-activated ABCB1 expression. Oncotarget. 2016 Jun 29. doi: 10.18632/oncotarget.10324. [Epub ahead of print] PubMed PMID: 27367030.
18: Ryerson CJ, Camp PG, Eves ND, Schaeffer M, Syed N, Dhillon S, Jensen D, Maltais F, O'Donnell DE, Raghavan N, Roman M, Stickland MK, Assayag D, Bourbeau J, Dion G, Fell CD, Hambly N, Johannson KA, Kalluri M, Khalil N, Kolb M, Manganas H, Morán-Mendoza O, Provencher S, Ramesh W, Rolf JD, Wilcox PG, Guenette JA. High Oxygen Delivery to Preserve Exercise Capacity in Patients with Idiopathic Pulmonary Fibrosis Treated with Nintedanib. Methodology of the HOPE-IPF Study. Ann Am Thorac Soc. 2016 Sep;13(9):1640-7. doi: 10.1513/AnnalsATS.201604-267OC. PubMed PMID: 27348402.
19: Nintedanib. Aust Prescr. 2016 Apr;39(2):62-3. doi: 10.18773/austprescr.2016.031. Epub 2016 Feb 22. Review. PubMed PMID: 27340326; PubMed Central PMCID: PMC4917623.
20: Raghu G, Wells AU, Nicholson AG, Richeldi L, Flaherty KR, Le Maulf F, Stowasser S, Schlenker-Herceg R, Hansell DM. Effect of Nintedanib in Subgroups of Idiopathic Pulmonary Fibrosis by Diagnostic Criteria. Am J Respir Crit Care Med. 2016 Jun 22. [Epub ahead of print] PubMed PMID: 27331880.
Chemical Structure
