Nintedanib

ChemicalBook > CAS DataBase List > Nintedanib

Description Mechanism of action indications Drugbank Description

Product Name: Nintedanib
CAS No.: 656247-17-5
Chemical Name: Nintedanib
Synonyms: Intedanib;Nintedanib (BIBF 1120);INTEDANIB BASE;methyl (3Z)-3-{[(4-{methyl[(4-methylpiperazin-1-yl)acetyl]amino}phenyl)amino](phenyl)methylidene;(3Z)-3-[[4-[methyl-[2-(4-methylpiperazin-1-yl)acetyl]amino]anilino]-phenylmethylidene]-2-oxo-1H-indole-6-carboxylate;methyl (3Z)-2-hydroxy-3-[({4-[N-methyl-2-(4-methylpiperazin-1-yl)acetamido]phenyl}amino)(phenyl)methylidene]-3H-indole-6-carboxylate;100837;Nidanib;NTEDANIB;Vargatef
CBNumber: CB72510401
Molecular Formula: C31H33N5O4
Formula Weight: 539.64
MOL File: 656247-17-5.mol

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Nintedanib Property

Melting point:: >237oC (dec.)
Boiling point:: 742.2±60.0 °C(Predicted)
Density: 1.284±0.06 g/cm3(Predicted)
storage temp.: Refrigerator
solubility: DMSO (Slightly), Methanol (Slightly)
form: Yellow solid.
pka: 11.06±0.20(Predicted)
color: Light Yellow to Light Green
InChIKey: XZXHXSATPCNXJR-ZIADKAODSA-N
SMILES: C(/C1C=CC=CC=1)(=C1\C(NC2=CC(C(=O)OC)=CC=C\12)=O)\NC1C=CC(N(C)C(=O)CN2CCN(C)CC2)=CC=1

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Safety

Hazardous Substances Data: 656247-17-5(Hazardous Substances Data)

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P330Rinse mouth.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Cayman Chemical

Product number: 11022
Product name: BIBF 1120
Purity: ≥95%
Packaging: 10mg
Price: $44
Updated: 2024/03/01

Cayman Chemical

Product number: 11022
Product name: BIBF 1120
Purity: ≥95%
Packaging: 50mg
Price: $109
Updated: 2024/03/01

Cayman Chemical

Product number: 11022
Product name: BIBF 1120
Purity: ≥95%
Packaging: 100mg
Price: $193
Updated: 2024/03/01

Cayman Chemical

Product number: 11022
Product name: BIBF 1120
Packaging: 250mg
Price: $426
Updated: 2024/03/01

Tocris

Product number: 7049
Product name: Nintedanib
Purity: ≥98%(HPLC)
Packaging: 10
Price: $59
Updated: 2021/12/16

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Nintedanib Chemical Properties,Usage,Production

Description

Nintedanib(656247-17-5) is an oral administrated triple tyrosine kinase inhibitors developed by Boehringer Ingelheim, Germany. Its targets include platelet-derived growth factor (PDGF), vascular endothelial growth factor (VEGF) and basic fiber (BFGF), being able to also inhibit the activation of MAPK and Akt. At present, it is mainly used for cancer treatment, such as colorectal cancer, ovarian cancer and multiple myeloma. The study regarding to the respiratory diseases mainly focuses on the clinical treatment of advanced non-small cell lung cancer (NSCLC) and idiopathic pulmonary fibrosis (IPF). In June 2014, Boehringer Ingelheim has announced that the marketing authorization application of Nintedanib for the treatment of Idiopathic Pulmonary Fibrosis (IPF) had been confirmed by the European Medicines Agency (EMA) and been included in the accelerated approval list by the EMA.

Mechanism of action

Nintedanib(656247-17-5) is a small molecule that targets 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). Among them, FGFR, PDGFR, and VEGFR have been implicated in IPF pathogenesis. 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. In addition, nintedanib inhibits the following nRTKs: Lck, Lyn and Src kinases. The contribution of FLT3 and nRTK inhibition to IPF efficacy is unknown.

indications

Nintedanib ( Vargatef ) is an oral triple angiokinase inhibitor which simultaneously inhibits vascular endothelial growth factor receptors (VEGFR), platelet-derived growth factor receptors (PDGFR) and fibroblast growth factor receptors (FGFR) signalling pathways. Growing scientific evidence shows that these three different angiokinase receptors play an important role not only in angiogenesis but also in tumour growth and metastasis.
Nintedanib is currently being investigated in patients with various solid tumours including Phase III studies in advanced NSCLC, colorectal cancer (refractory to standard treatment) and ovarian cancer, and also in Phase II studies in mesothelioma, kidney cancer (renal cell carcinoma) and liver cancer (hepatic cell carcinoma).
In the EU, nintedanib in the treatment of idiopathic pulmonary fibrosis (IPF) has recently received a positive CHMP opinion. The U.S. Food and Drug Administration (FDA) has approved nintedanib capsules under the brand name OFEV for oral use for the treatment of IPF.

Drugbank Description

Nintedanib(656247-17-5) is a drug indicated for the treatment of idiopathic pulmonary fibrosis (IPF) that targets 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). Among them, FGFR, PDGFR, and VEGFR have been implicated in IPF pathogenesis. 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. In addition, nintedanib inhibits the following nRTKs: Lck, Lyn and Src kinases. The contribution of FLT3 and nRTK inhibition to IPF efficacy is unknown. Idiopathic pulmonary fibrosis (IPF) is a progressive and ultimately fatal lung disease characterized by a progressive loss of lung function with worsening dyspnoea and cough. Development is thought to be instigated by repetitive lung injury (such as by cigarette smoke, industrial dusts, gastrooesophageal reflux and viral infection) leading to destruction of epithelial alveolar cells. Subsequent dysregulation of the repair process results in the proliferation/migration of fibroblasts and their differentiation into myofibroblasts, abnormal extracellular matrix deposition and excessive collagen accumulation in the lung interstitium and alveolar space, leading to progressive fibrosis and stiffening of the lungs. Vascular endothelial growth factor (VEGF), fibroblast growth factor (FGF) and platelet-derived growth factor (PDGF) mediate various processes, including fibrogenesis and angiogenesis, and are implicated in the pathogenesis of IPF. By blocking substrate binding and downstream signalling cascades, nintedanib interferes with processes active in fibrosis such as fibroblast proliferation, migration and differentiation, and the secretion of extracellular matrix.
References
https://www.drugbank.ca/drugs/DB09079

Uses

It is an indolinone derivative potently blocking VEGF-, PDGF-, and FGF-receptor kinases; an indolinone as triple angiokinase inhibitors. An antitumor agent.

Uses

BIBF1120 (Vargatef) is a potent inhibitor of VEGFR1/2/3, FGFR1/2/3 and PDGFRα/β with IC50 of 34 nM/13 nM/13 nM, 69 nM/37 nM/108 nM and 59 nM/65 nM, respectively.

Definition

ChEBI: A member of the class of oxindoles that is a kinase inhibitor used (in the form of its ethylsulfonate salt) for the treatment of idiopathic pulmonary fibrosis and cancer.

Biological Activity

nintedanib (bibf 1120) is an indolinone-derived oral active, triple angiokinase inhibitor of vascular endothelial growth factor receptor (vegfr)1-3, fibroblast growth factor receptor (fgfr)1-3 and platelet-derived growth factor receptor (pdgfr)α/β1. it has shown potent antiangiogenic activity at nanomolar (ic50, 20-100 nmol/l) by blocking these receptor-mediated signaling pathways1,2. nintedanib (bibf 1120) is in clinical development for the treatment of idiopathic pulmonary fibrosis as these receptors have been shown to be potentially involved in the pathogenesis of pulmonary fibrosis3,4. as a novel angiogenesis inhibitor, it is also being widely evaluated in different cancer models and has displayed significant anti-tumor activities by inhibiting tumor blood vessel formation5-7.to further evaluate its antitumor effects on multiple tumors, nintedanib is currently entering several

Clinical Use

Tyrosine kinase inhibitor:
Treatment of locally advanced, metastatic or locally recurrent non-small cell lung cancer (NSCLC) of adenocarcinoma tumour histology in combination with docetaxel
Treatment of Idiopathic Pulmonary Fibrosis (IPF)

Side effects

The most common side effects of Nintedanib in clinical studies were gastrointestinal-related side effects, including nausea (31%), vomiting (23%), diarrhoea (76%), abdominal pain (10%) and decreased appetite (10%). Other side effects were hepatic impairment commonly seen as elevated liver enzymes, weight loss (7 per cent), nasopharyngitis (7 per cent), cough (14 per cent), upper respiratory tract infections (14 per cent), headache (12 per cent), fatigue (14 per cent), skin ulcers (16 per cent) and urinary tract infections (12 per cent).
Reported post-marketing adverse events include gastrointestinal perforation, proteinuria and pancreatitis. In several clinical trials, nidanib has also been found to be associated with an increased risk of bleeding, possibly secondary to VEGFR inhibition. Although serious bleeding and arterial thromboembolic events (e.g., myocardial infarction (MI) and stroke) are rare, bleeding events with serious and fatal consequences have been reported in post-marketing surveillance. Therefore, the use of nidazanib has been associated with an increased risk of bleeding, possibly secondary to VEGFR inhibition. Therefore, patients treated with nidazanib and receiving full anticoagulation therapy need to be closely monitored for adverse bleeding events.

target

VEGFR1/2/3

Drug interactions

Potentially hazardous interactions with other drugs
Antibacterials: concentration reduced by rifampicin - avoid.
Antifungals: concentration increased by ketoconazole.
Antipsychotics: increased risk of agranulocytosis with clozapine - avoid.

Metabolism

Nintedanib is metabolised in the liver, initially by hydrolytic cleavage by esterases and then by glucuronidation by uridine diphosphate glucuronosyltransferase enzymes. Only a minor portion is metabolised by cytochrome P450 isoenzymes, mainly CYP3A4. More than 90% of a dose is eliminated by faecal/biliary excretion.

storage

Store at -20°C

References

[1]hilberg, f. et al. bibf 1120: triple angiokinase inhibitor with sustained receptor blockade and good antitumor efficacy. cancer research 68, 4774-4782, doi:10.1158/0008-5472.can-07-6307 (2008).

Nintedanib Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from Nintedanib manufacturers

hebei hongtan Biotechnology Co., Ltd

Product: Nintedanib 656247-17-5
Price: US $60.00/kg
Min. Order: 1kg
Purity: 99%
Supply Ability: 1000
Release date: 2024-03-26

HangZhou RunYan Pharma Technology Co.,LTD.

Product: Nintedanib 656247-17-5
Price: US $0.00/kg
Min. Order: 1kg
Purity: 99% HPLC
Supply Ability: 1000kg
Release date: 2024-09-10

Nanjing Fred Technology Co., Ltd

Product: Nintedanib 656247-17-5
Price: US $0.00-0.00/kg
Min. Order: 1kg
Purity: 99%, Single impurity＜0.1
Supply Ability: 1 ton
Release date: 2023-12-19

656247-17-5, NintedanibRelated Search:

Infigratinib Trametinib Sunitinib Malate Ibrutinib Crizotinib Neratinib LEE011 Alectinib Hydrochloride Nintedanib Ethanesulfonate Salt Olaparib EAI-045 PLX-4720 Alectinib 1,3-DiMethyl 2-[4-(Methoxycarbonyl)-2-nitrophenyl]propanedioate 1-Chloro-4-(trimethoxymethyl)benzene Nintedanib Impurity 76 ALPHA,ALPHA,2,4-TETRACHLOROTOLUENE 1-ACETYL-2-OXO-2,3-DIHYDRO-1H-INDOLE-5-CARBOXYLIC ACID METHYL ESTER

INTEDANIB BASE

Nintedanib (BIBF 1120)

Nintedanib/Intedanib/Vargatef

BIBF 1120; VARGATEF; INTEDANIB;INTEDANIB BASE

Intedanib Vargatef

Nintedanib-016

100837

Nintedanib (Intedanib)

Vargatef (BIBF 1120, Intedanib)

NINTEDANIB; BIBF1120; VARGATEF; BIBF-1120

Nidanib

methyl (3Z)-3-{[(4-{methyl[(4-methylpiperazin-1-yl)acetyl]amino}phenyl)amino](phenyl)methylidene

BIBF1120;VARGATEF;BIBF-1120

(3Z)-3-[[4-[methyl-[2-(4-methylpiperazin-1-yl)acetyl]amino]anilino]-phenylmethylidene]-2-oxo-1H-indole-6-carboxylate

Nintedanib, Free Base, >99%

methyl (3Z)-3-[[4-[methyl-[2-(4-methylpiperazin-1-yl)acetyl]amino]anilino]-phenylmethylidene]-2-oxo-1H-indole-6-carboxylate

NTEDANIB

methyl (3Z)-2-hydroxy-3-[({4-[N-methyl-2-(4-methylpiperazin-1-yl)acetamido]phenyl}amino)(phenyl)methylidene]-3H-indole-6-carboxylate

(3Z)-2,3-dihydro-3-[[[4-[methyl[2-(4-methyl-1-piperazinyl)acetyl]amino]phenyl]amino]phenylmethylene]-2-oxo-1H-Indole-6-carboxylic acid methyl ester

methyl (Z)-3-[[4-[methyl-[2-(4-methylpiperazin-1-yl)acetyl]amino]anilino]-phenylmethylidene]-2-oxo-1H-indole-6-carboxylate

Methyl (Z)-3-[[[4-[N-methyl-2-(4-methylpiperazin-1-yl)acetamido]phenyl]amino](phenyl)methylene]-2-oxoindoline-6-carboxylate

BIBF-1120(Nintedanib,Vargatef)

Intedanib

BIBF 1120; VARGATEF; INTEDANIB

Vargatef

Intedanib (Nintedanib)

1H-Indole-6-carboxylic acid, 2,3-dihydro-3-[[[4-[methyl[2-(4-methyl-1-piperazinyl)acetyl]amino]phenyl]amino]phenylmethylene]-2-oxo-, methyl ester, (3Z)-

Nintedanib whatsapp

methyl (3Z)-3-[[4-[methyl-[2-(4-methylpiperazin-1-yl)acetyl]amino]anilino]-phenylmethylidene]-2-oxo-1H-indole-6-carboxylate Nintedanib (BIBF 1120)

Vargatef (nintedanib)

3-[(4-{Methyl-[2-(4-methyl-piperazin-1-yl)-acetyl]-amino}-phenylamino)-phenyl-methylene]-2-oxo-2,3-dihydro-1H-indole-6-carboxylic acid methyl ester

3-Z-[1-(4-(piperidin-1-yl-methyl)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone

Nidanib ethane sulfonate

Nintedanib USP/EP/BP

Nintedanib (Vargatef

High purity CAS 656247-17-5 Nintedanib in stock

FGFR,PDGFR,Nintedanib,Inhibitor,Platelet-derived growth factor receptor,Fibroblast growth factor receptor,Vascular endothelial growth factor receptor,VEGFR,BIBF1120,BIBF-1120,inhibit

Methyl 2-hydroxy-3- N-[4-[methyl-[2-(4-methyIpiperazin-

Methyl (Z)-3-[[[4-[N-Methyl-2-(4-methyl-1-piperazinyl)acetamido]phenyl]amino](phenyl)methylene]-2-oxoindoline-6-carboxylate

Nidanib alkaloid

656247-17-5

C31H33O4N5

API

Heterocycles

Intermediates & Fine Chemicals

Pharmaceuticals

Amines

Nintedanib

Inhibitors

API

656247-17-5