Afatinib dimaleate
- CAS No.
- 850140-73-7
- Chemical Name:
- Afatinib dimaleate
- Synonyms
- Alfatinib maleate;Afatinib (diMaleate);BAY-2416964;BIBW2992-MA2;Afatinib DimaL;Aftinib maleate;Afatinib DIMELATE;BIBW2992 DiMaleate;Afatinib (maleate);BIBW2993 DiMaleate
- CBNumber:
- CB22630067
- Molecular Formula:
- C28H29ClFN5O7
- Molecular Weight:
- 602.02
- MDL Number:
- MFCD28969755
- MOL File:
- 850140-73-7.mol
- MSDS File:
- SDS
| Melting point | >237oC (dec.) |
|---|---|
| storage temp. | Refrigerator |
| solubility | DMSO (Slightly), Methanol (Slightly) |
| form | Solid |
| color | White to Pale Yellow |
| InChIKey | LIENDGDDWJRJLO-LBXKZPGENA-N |
| SMILES | C(/C(=O)O)=C/C(=O)O.N(C1C=CC(F)=C(Cl)C=1)C1=NC=NC2C=C(O[C@@H]3COCC3)C(NC(=O)/C=C/CN(C)C)=CC1=2 |&1:25,r| |
| NCI Dictionary of Cancer Terms | afatinib dimaleate |
| FDA UNII | V1T5K7RZ0B |
| NCI Drug Dictionary | afatinib dimaleate |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |   GHS07,GHS08 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Warning | |||||||||
| Hazard statements | H362-H319-H302-H372-H361 | |||||||||
| Precautionary statements | P201-P260-P263-P264-P270-P308+P313-P264-P280-P305+P351+P338-P337+P313P-P264-P270-P301+P312-P330-P501-P260-P264-P270-P314-P501-P201-P202-P281-P308+P313-P405-P501 | |||||||||
| HS Code | 29339900 | |||||||||
| NFPA 704 |
|
Afatinib dimaleate price More Price(28)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Cayman Chemical | 21567 | Afatinib (maleate) ≥95% | 850140-73-7 | 250mg | $93 | 2024-03-01 | Buy |
| Cayman Chemical | 21567 | Afatinib (maleate) ≥95% | 850140-73-7 | 500mg | $176 | 2024-03-01 | Buy |
| Cayman Chemical | 21567 | Afatinib (maleate) ≥95% | 850140-73-7 | 1g | $330 | 2024-03-01 | Buy |
| Cayman Chemical | 21567 | Afatinib (maleate) ≥95% | 850140-73-7 | 5g | $1002 | 2024-03-01 | Buy |
| Tocris | 6812 | Afatinibdimaleate ≥98%(HPLC) | 850140-73-7 | 50 | $375 | 2021-12-16 | Buy |
Afatinib dimaleate Chemical Properties,Uses,Production
Description
Afatinib dimaleate (Tovok; BIBW2992; Gilotrif) is a salt form of Afatinib. Afatinib is a second-generation, orally administered, irreversible inhibitor of the ErbB family of tyrosine kinases.
Mechanism of Action
Afatinib (850140-73-7) downregulates ErbB signalling by covalently binding to the kinase domains of epidermal growth factor receptor (EGFR), human epidermal growth factor receptor (HER) 2 and HER4, resulting in irreversible inhibition of tyrosine kinase autophosphorylation; it also inhibits transphosphorylation of HER3. Afatinib is approved as monotherapy for the treatment of EGFR tyrosine kinase inhibitor (TKI)-na?ve adults with locally advanced or metastatic non-small cell lung cancer (NSCLC) with activating EGFR mutations in the EU, and for the first-line treatment of patients with metastatic NSCLC whose tumours have EGFR exon 19 deletions or exon 21 (L858R) substitution mutations as detected by a US FDA-approved test in the US.
Description
Afatinib dimaleate was approved by the U.S. Food and Drug Administration (FDA) in 2013 for the treatment of non-small cell lung cancer (NSCLC). Specifically, it was approved for patients presenting with metastatic NSCLC tumors which contain epidermal growth factor receptor (EGFR) exon deletions or exon 21 mutations. Afatinib dimaleate is a covalent inhibitor of ErbB tyrosine kinases (tyk), which downregulates ErbB signaling by irreversible binding of EGFR tyk binding sites. While no manufacturing route has been disclosed to date, the most scalable published route likely derives from two Boehringer Ingelheim patents.
Uses
Afatinib Dimaleate is a salt of Afatinib {BIBW 2992), an aminocrotonylamino-substituted quinazoline derivative used for treating cancer and diseases of the respiratory tract, lungs, gastrointestinal tract, bile duct, and gallbladder. An anilino-quinazoline that irreversibly inhibits EGFR and HER2 kinase activity.
Definition
ChEBI: Afatinib dimaleate is a maleate salt obtained by combining afatinib with two molar equivalents of maleic acid. Used for the first-line treatment of patients with metastatic non-small cell lung cancer. It has a role as a tyrosine kinase inhibitor and an antineoplastic agent. It contains an afatinib.
General Description
Afatinib dimaleate is the dimaleate form of afatinib. It is a tyrosine kinase inhibitor of epidermal growth factor receptors (ERBB RECEPTORS) and an anti-angiogenic agent. Afatinib dimaleate has anti-tumour activity and is mainly used for the treatment of patients with metastatic non-small cell lung cancer (which has metastasised or spread to other parts of the body), or certain tumours with mutations in the EGFR gene and patients whose disease has worsened after platinum-based chemotherapy. It is also used for the treatment of esophageal squamous cell carcinoma (ESCC) and gastric cancer.
Biological Activity
Afatinib dimaleate is an orally bioavailable and irreversible dual-specific inhibitor of the ErbB family (EGFR and HER2). IC50 are 0.4, 0.5, 10, 14, 1 nM for EGFRL858R, EGFRwt, EGFR L858R/T790M, ErbB2 (HER2) and ErbB4 (HER4), respectively. Afatinib dimaleate is available for cancer (esophageal squamous cell carcinoma (ESCC), non-small cell lung cancer (NSCLC) and gastric cancer) studies.
Side effects
Afatinib dimaleate is similar to afatinib in terms of side effects. Common side effects include: diarrhoea, fever, difficulty urinating, burning or pain, redness, swelling or pain in the skin, discharge or excessive tearing, burning, dryness or itching of the eyes, and skin ulcers. Occasional symptoms of coughing and difficulty breathing. A very small number of patients may have bloody stools, black stools or tarry stools, indigestion, nausea, severe abdominal pain, cramping or burning sensation, and vomiting of a substance that looks like coffee grounds. Please contact your doctor promptly if any serious adverse reactions occur.
Synthesis
Nitroquinazolinone (6), which is commercially available, was first chlorinated with phosphorous oxychloride (POCl3) followed by treatment with commercial 3-chloro-4-fluoroaniline (7) to afford SNAr adduct 8 in 90% yield over two steps. Sulfonylation to afford 9 (86%) and subsequent displacement with (S)-tetrahydrofuran- 3-ol gave 10 in 90% yield. Raney¨CNickel reduction of the nitro group delivered 11 in 97% yield, which set the stage for the final side-chain functionalization. 2-(Diethoxyphosphoryl) acetic acid and N,N0-carbonyldiimidazole (CDI) were pre-mixed and added to aniline 11 to afford 12 in 70% isolated yield. Next, a Horner¨CWadsworth¨CEmmons homologation gave the (E)-olefin 13 in quantitative yield, followed by maleate salt formation (92%) to deliver the final API. The final five steps of this synthesis have been successfully demonstrated on multi-kilogram scale.
storage
Store at -20°C
Afatinib dimaleate Preparation Products And Raw materials
Raw materials
Preparation Products
| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| TAIZHOU YUXIN BIOTECHNOLOGY CO,.LTD | +86-576-88902229;+86-0576-88902229 +8613968687450 | yuxin@yuxchem.com | China | 158 | 58 |
| Shandong Risen-Sun Pharmaceutical Co., Ltd | +86-15552509998 +86-15621883869 | liutf@jewim.com.cn | China | 251 | 58 |
| Shanghai Famo Biotech Co Ltd | +8618550473860 | mayan@famobiotech.com | China | 514 | 58 |
| BEIJING SJAR TECHNOLOGY DEVELOPMENT CO., LTD. | +86-18600796368 +86-18600796368 | sales@sjar-tech.com | China | 123 | 58 |
| S&Y Biochem Co.,Ltd | +8617774091612 | marketing@sybiochem.com | China | 94 | 58 |
| Hebei Yanxi Chemical Co., Ltd. | +86-17531190177; +8617531190177 | peter@yan-xi.com | China | 5873 | 58 |
| Henan Bao Enluo International TradeCo.，LTD | +86-17331933971 +86-17331933971 | deasea125996@gmail.com | China | 2503 | 58 |
| Zibo Hangyu Biotechnology Development Co., Ltd | +86-0533-2185556 +8617865335152 | Mandy@hangyubiotech.com | China | 10977 | 58 |
| Frapp's ChemicalNFTZ Co., Ltd. | +86 (576) 8169-6106 | sales@frappschem.com | China | 885 | 50 |
| Capot Chemical Co.,Ltd. | 571-85586718 +8613336195806 | sales@capotchem.com | China | 29798 | 60 |
Related articles
- BIBW2992 DiMaleate: pharmacokinetic, clinical applications and safety
- BIBW2992 DiMaleate is a well-tolerated medication for certain types of lung cancer, showing bioequivalence and efficacy in cli....
- Nov 20，2023
- BIBW2992 Dimaleate - Pharmacodynamics
- Afatinib dimaleate (Tovok; BIBW2992; Gilotrif) is a salt form of Afatinib. Afatinib is a second-generation, orally administere....
- Dec 13，2019
View Lastest Price from Afatinib dimaleate manufacturers
| Image | Update time | Product | Price | Min. Order | Purity | Supply Ability | Manufacturer | |
|---|---|---|---|---|---|---|---|---|
 |
2024-08-23 | Afatinib DIMELATE
850140-73-7
|
US $2800.00-2600.00 / kg | 0.1kg | 99 | 10 | S&Y Biochem Co.,Ltd | |
 |
2024-08-22 | Afatinib dimaleate
850140-73-7
|
US $0.00 / g | 1g | 99%min | 1000g | WUHAN FORTUNA CHEMICAL CO., LTD | |
 |
2024-08-20 | Afatinib Dimaleate
850140-73-7
|
US $1.00 / g | 1g | More Than 99% | 50kg/Month | BEIJING SJAR TECHNOLOGY DEVELOPMENT CO., LTD. |
-
- Afatinib DIMELATE
850140-73-7
- US $2800.00-2600.00 / kg
- 99
- S&Y Biochem Co.,Ltd
-
- Afatinib dimaleate
850140-73-7
- US $0.00 / g
- 99%min
- WUHAN FORTUNA CHEMICAL CO., LTD
-
- Afatinib Dimaleate
850140-73-7
- US $1.00 / g
- More Than 99%
- BEIJING SJAR TECHNOLOGY DEVELOPMENT CO., LTD.
850140-73-7(Afatinib dimaleate)Related Search:
1of4