Afatinib dimaleate
Description Mechanism of Action- Product Name
- 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
- Formula Weight
- 602.02
- MOL File
- 850140-73-7.mol
Afatinib dimaleate Property
- Melting point:
- >237oC (dec.)
- storage temp.
- Refrigerator
- solubility
- DMSO (Slightly), Methanol (Slightly)
- form
- Solid
- color
- White to Pale Yellow
- InChI
- InChI=1/C24H25ClFN5O3.C4H4O4/c1-31(2)8-3-4-23(32)30-21-11-17-20(12-22(21)34-16-7-9-33-13-16)27-14-28-24(17)29-15-5-6-19(26)18(25)10-15;5-3(6)1-2-4(7)8/h3-6,10-12,14,16H,7-9,13H2,1-2H3,(H,30,32)(H,27,28,29);1-2H,(H,5,6)(H,7,8)/b4-3+;2-1-/t16-;/s3
- 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|
Safety
- HS Code
- 29339900
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H302Harmful if swallowed
H319Causes serious eye irritation
H361Suspected of damaging fertility or the unborn child
H362May cause harm to breast-fed children
H372Causes damage to organs through prolonged or repeated exposure
- Precautionary statements
-
P201Obtain special instructions before use.
P202Do not handle until all safety precautions have been read and understood.
P260Do not breathe dust/fume/gas/mist/vapours/spray.
P263Avoid contact during pregnancy/while nursing.
P264Wash hands thoroughly after handling.
P264Wash skin thouroughly after handling.
P270Do not eat, drink or smoke when using this product.
P280Wear protective gloves/protective clothing/eye protection/face protection.
P281Use personal protective equipment as required.
P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P308+P313IF exposed or concerned: Get medical advice/attention.
P314Get medical advice/attention if you feel unwell.
P330Rinse mouth.
P405Store locked up.
P501Dispose of contents/container to..…
N-Bromosuccinimide Price
- Product number
- 21567
- Product name
- Afatinib (maleate)
- Purity
- ≥95%
- Packaging
- 250mg
- Price
- $93
- Updated
- 2024/03/01
- Product number
- 21567
- Product name
- Afatinib (maleate)
- Purity
- ≥95%
- Packaging
- 500mg
- Price
- $176
- Updated
- 2024/03/01
- Product number
- 21567
- Product name
- Afatinib (maleate)
- Purity
- ≥95%
- Packaging
- 1g
- Price
- $330
- Updated
- 2024/03/01
- Product number
- 21567
- Product name
- Afatinib (maleate)
- Purity
- ≥95%
- Packaging
- 5g
- Price
- $1002
- Updated
- 2024/03/01
- Product number
- 6812
- Product name
- Afatinibdimaleate
- Purity
- ≥98%(HPLC)
- Packaging
- 50
- Price
- $375
- Updated
- 2021/12/16
Afatinib dimaleate Chemical Properties,Usage,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
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View Lastest Price from Afatinib dimaleate manufacturers
- Product
- Afatinib dimaleate 850140-73-7
- Price
- US $0.00-0.00/kg
- Min. Order
- 1kg
- Purity
- 99%，single impurity＜0.1
- Supply Ability
- 1 ton
- Release date
- 2023-12-20
- Product
- BIBW2992 DiMaleate 850140-73-7
- Price
- US $0.00-0.00/g
- Min. Order
- 10g
- Purity
- 99% HPLC
- Supply Ability
- 10000
- Release date
- 2024-09-21
- Product
- Afatinib dimaleate 850140-73-7
- Price
- US $0.00/g
- Min. Order
- 1g
- Purity
- 99%min
- Supply Ability
- 1000g
- Release date
- 2021-09-17