Gefitinib
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MedKoo CAT#: 100140

CAS#: 184475-35-2

Description: Gefitinib, also known as ZD1839, is an anilinoquinazoline with antineoplastic activity. Gefitinib inhibits the catalytic activity of numerous tyrosine kinases including the epidermal growth factor receptor (EGFR), which may result in inhibition of tyrosine kinase-dependent tumor growth. Specifically, this agent competes with the binding of ATP to the tyrosine kinase domain of EGFR, thereby inhibiting receptor autophosphorylation and resulting in inhibition of signal transduction. Gefitinib may also induce cell cycle arrest and inhibit angiogenesis. It is marketed by AstraZeneca and Teva.


Price and Availability

Size
Price

2g
USD 90
20g
USD 450
200g
USD 1950
Size
Price

5g
USD 150
50g
USD 750
500g
USD 2950
Size
Price

10g
USD 250
100g
USD 1250
1kg
USD 4950

Gefitinib purity > 98%, is in stock. The same day shipping out after order is received. Note: the estimated shipping out time for order > 10g may be 2 weeks.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 100140
Name: Gefitinib
CAS#: 184475-35-2
Chemical Formula: C22H24ClFN4O3
Exact Mass: 446.1521
Molecular Weight: 446.9
Elemental Analysis: C, 59.13; H, 5.41; Cl, 7.93; F, 4.25; N, 12.54; O, 10.74


Synonym: ZD 1839; ZD1839; ZD-1839; Gefitinib; US brand name: Iressa.

IUPAC/Chemical Name: N-(3-chloro-4-fluorophenyl)-7-methoxy-6-(3-morpholinopropoxy)quinazolin-4-amine

InChi Key: XGALLCVXEZPNRQ-UHFFFAOYSA-N

InChi Code: InChI=1S/C22H24ClFN4O3/c1-29-20-13-19-16(12-21(20)31-8-2-5-28-6-9-30-10-7-28)22(26-14-25-19)27-15-3-4-18(24)17(23)11-15/h3-4,11-14H,2,5-10H2,1H3,(H,25,26,27)

SMILES Code: COC1=CC2=NC=NC(NC3=CC=C(F)C(Cl)=C3)=C2C=C1OCCCN4CCOCC4


Technical Data

Appearance:
white solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Safety Data Sheet (MSDS):

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.

Storage Condition:
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, not in water

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
293490


Additional Information

 
According to http://en.wikipedia.org/wiki/Gefitinib, Gefitinib is the first selective inhibitor of epidermal growth factor receptor's (EGFR) tyrosine kinase domain. Thus gefitinib is an EGFR inhibitor. The target protein (EGFR) is also sometimes referred to as Her1 or ErbB-1 depending on the literature source. EGFR is overexpressed in the cells of certain types of human carcinomas - for example in lung and breast cancers. This leads to inappropriate activation of the anti-apoptotic Ras signalling cascade, eventually leading to uncontrolled cell proliferation. Research on gefitinib-sensitive non-small cell lung cancers has shown that a mutation in the EGFR tyrosine kinase domain is responsible for activating anti-apoptotic pathways.  These mutations tend to confer increased sensitivity to tyrosine kinase inhibitors such as gefitinib and erlotinib. Of the types of non-small cell lung cancer histologies, adenocarcinoma is the type that most often harbors these mutations. These mutations are more commonly seen in Asians, women, and non-smokers (who also tend to more often have adenocarcinoma). Gefitinib inhibits EGFR tyrosine kinase by binding to the adenosine triphosphate (ATP)-binding site of the enzyme. Thus the function of the EGFR tyrosine kinase in activating the Ras signal transduction cascade is inhibited, and malignant cells are inhibited.
 
 
Gefitinib is currently only indicated for the treatment of locally advanced or metastatic non-small cell lung cancer (NSCLC) in patients who have previously received chemotherapy. While gefitinib has yet to be proven to be effective in other cancers, there is potential for its use in the treatment of other cancers where EGFR overexpression is involved.  In 2004, AstraZeneca informed the United States Food and Drug Administration (FDA) that a large randomized study failed to demonstrate a survival advantage for gefitinib in the treatment of non-small cell lung cancer (NSCLC). Whether progression-free survival is prolonged is not clear from this statement. AstraZeneca also withdrew their application to market gefitinib in Europe shortly after this announcement. Erlotinib is another EGFR tyrosine kinase inhibitor that works in the same way as gefitinib. Given the lack of survival advantage for gefitinib and the positive results for erlotinib, erlotinib has replaced gefitinib in the United States (except in patients where gefitinib has had a proven response).
Gefitinib is currently only indicated for the treatment of locally advanced or metastatic non-small cell lung cancer (NSCLC) in patients who have previously received chemotherapy. While gefitinib has yet to be proven to be effective in other cancers, there is potential for its use in the treatment of other cancers where EGFR overexpression is involved.  In 2004, AstraZeneca informed the United States Food and Drug Administration (FDA) that a large randomized study failed to demonstrate a survival advantage for gefitinib in the treatment of non-small cell lung cancer (NSCLC). Whether progression-free survival is prolonged is not clear from this statement. AstraZeneca also withdrew their application to market gefitinib in Europe shortly after this announcement. Erlotinib is another EGFR tyrosine kinase inhibitor that works in the same way as gefitinib. Given the lack of survival advantage for gefitinib and the positive results for erlotinib, erlotinib has replaced gefitinib in the United States (except in patients where gefitinib has had a proven response).


References

1: Marech I, Vacca A, Gnoni A, Silvestris N, Lorusso V. Surgical resection of locally advanced epidermal growth factor receptor (EGFR) mutated lung adenocarcinoma after gefitinib and review of the literature. Tumori. 2013 Sep-Oct;99(5):e241-4. doi: 10.1700/1377.15324. Review. PubMed PMID: 24362878.

2: Chen X, Liu Y, Røe OD, Qian Y, Guo R, Zhu L, Yin Y, Shu Y. Gefitinib or erlotinib as maintenance therapy in patients with advanced stage non-small cell lung cancer: a systematic review. PLoS One. 2013;8(3):e59314. doi: 10.1371/journal.pone.0059314. Epub 2013 Mar 21. Review. PubMed PMID: 23555654; PubMed Central PMCID: PMC3605444.

3: Biaoxue R, Shuanying Y, Wei L, Wei Z, Zongjuan M. Maintenance therapy of gefitinib for non-small-cell lung cancer after first-line chemotherapy regardless of epidermal growth factor receptor mutation: a review in Chinese patients. Curr Med Res Opin. 2012 Oct;28(10):1699-708. doi: 10.1185/03007995.2012.728525. Epub 2012 Oct 2. Review. PubMed PMID: 22978775.

4: Erdem L, Giovannetti E, Leon LG, Honeywell R, Peters GJ. Polymorphisms to predict outcome to the tyrosine kinase inhibitors gefitinib, erlotinib, sorafenib and sunitinib. Curr Top Med Chem. 2012;12(15):1649-59. Review. PubMed PMID: 22978339.

5: Toda N, Fujimoto N, Kato T, Fujii N, Nakanishi G, Nagao T, Tanaka T. Erosive pustular dermatosis of the scalp-like eruption due to gefitinib: case report and review of the literature of alopecia associated with EGFR inhibitors. Dermatology. 2012;225(1):18-21. doi: 10.1159/000341528. Epub 2012 Aug 22. Review. PubMed PMID: 22922680.

6: Koma Y, Matsuoka H, Yoshimatsu H, Suzuki Y. Successful treatment with erlotinib after gefitinib-induced interstitial lung disease: a case report and literature review. Int J Clin Pharmacol Ther. 2012 Oct;50(10):760-4. doi: 10.5414/CP201759. Review. PubMed PMID: 22853866.

7: Wang F, Wang LD, Li B, Sheng ZX. Gefitinib compared with systemic chemotherapy as first-line treatment for chemotherapy-naive patients with advanced non-small cell lung cancer: a meta-analysis of randomised controlled trials. Clin Oncol (R Coll Radiol). 2012 Aug;24(6):396-401. doi: 10.1016/j.clon.2011.09.013. Epub 2011 Oct 22. Review. PubMed PMID: 22019482.

8: D'Incecco A, Cappuzzo F. Gefitinib for non-small-cell lung cancer treatment. Expert Opin Drug Saf. 2011 Nov;10(6):987-96. doi: 10.1517/14740338.2011.617738. Epub 2011 Sep 12. Review. PubMed PMID: 21905963.

9: Costanzo R, Piccirillo MC, Sandomenico C, Carillio G, Montanino A, Daniele G, Giordano P, Bryce J, De Feo G, Di Maio M, Rocco G, Normanno N, Perrone F, Morabito A. Gefitinib in non small cell lung cancer. J Biomed Biotechnol. 2011;2011:815269. doi: 10.1155/2011/815269. Epub 2011 May 23. Review. PubMed PMID: 21660144; PubMed Central PMCID: PMC3110340.

10: Gottschling S, Penzel R, Pelz T, Herpel E, Schnabel PA, Dyckhoff G, Thomas M, Kuhnt T. KRAS-mutation positive, metastatic tonsil carcinoma with cancer stem-like cell features and long-term response to gefitinib: a case report and review of the literature. J Clin Oncol. 2011 Jul 20;29(21):e616-9. doi: 10.1200/JCO.2011.34.5892. Epub 2011 May 9. Review. PubMed PMID: 21555681.