SMB00950
O-Desmethyl gefitinib
≥95%, research grade
Synonym(s):
4-[(3-Chloro-4-fluorophenyl)amino]-6-[3-(4-morpholinyl)propoxy]-7-quinazolinol, O-Desmethylgefitinib
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About This Item
Empirical Formula (Hill Notation):
C21H22ClFN4O3
CAS Number:
Molecular Weight:
432.88
UNSPSC Code:
12352205
NACRES:
NA.77
biological source
synthetic
Quality Level
Assay
≥95%
form
solid
technique(s)
HPLC: suitable
color
light yellow to yellow
storage temp.
−20°C
SMILES string
Fc1c(cc(cc1)Nc2ncnc3c2cc(c(c3)O)OCCCN4CCOCC4)Cl
InChI
1S/C21H22ClFN4O3/c22-16-10-14(2-3-17(16)23)26-21-15-11-20(19(28)12-18(15)24-13-25-21)30-7-1-4-27-5-8-29-9-6-27/h2-3,10-13,28H,1,4-9H2,(H,24,25,26)
InChI key
IFMMYZUUCFPEHR-UHFFFAOYSA-N
General description
O-Desmethyl Gefitinib, a key metabolite of the anticancer drug gefitinib, belongs to the quinazoline family and is present in human plasma. Its formation is facilitated by the cytochrome P450 isoform CYP2D6. This compound exhibits significant activity as an inhibitor of tyrosine residue phosphorylation in EGFR, with an IC50 of 36 nM in subcellular assays. While its effectiveness is comparable to that of gefitinib, O-Desmethyl Gefitinib shows slightly reduced activity in whole-cell assays, with an IC50 of 760, in contrast to gefitinib′s 49 nM. Studies conducted in LoVo tumor mouse xenograft models have revealed that the tumor concentration of O-Desmethyl Gefitinib is notably lower than that of gefitinib, without causing a substantial reduction in tumor growth. Remarkably, increased plasma concentrations of O-Desmethyl Gefitinib in individuals homozygous for CYP2D6 do not lead to an increase in adverse effects. O-Desmethyl Gefitinib holds promise for biochemical and biomedical research, providing potential insights into drug development and cancer treatment.
Application
O-Desmethyl Gefitinib finds application in metabolomics and drug discovery research, particularly in the investigation of cancer and tumor management.
Biochem/physiol Actions
O-Desmethyl gefitinib is generated by the removal of a methyl group from gefitinib during the body′s metabolic processing of this compound within the body.
Features and Benefits
- High quality compound suitable for multiple research applications
- Compatible with a wide variety of chromatographic and spectrometry techniques
Other Notes
For additional information on our range of Biochemicals, please complete this form.
This product is intended for research purposes only, and it is not meant for human consumption.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
Target Organs
Respiratory system
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Regulatory Information
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Hiroyuki Kobayashi et al.
Medical oncology (Northwood, London, England), 33(6), 57-57 (2016-05-08)
We investigated the effects of polymorphisms in CYP2D6, ABCB1, and ABCG2 and the side effects induced by gefitinib on the pharmacokinetics of O-desmethyl gefitinib, the active metabolite of gefitinib. On day 14 after beginning therapy with gefitinib, plasma concentrations of
Minimal contribution of desmethyl-gefitinib, the major human plasma metabolite of gefitinib, to epidermal growth factor receptor (EGFR)-mediated tumour growth inhibition
McKillop et al.
Xenobiotica, 36, 29-39 (2006)
Ping Fang et al.
Drug design, development and therapy, 11, 1283-1290 (2017-05-04)
Cytochrome P450 2D6 (CYP2D6), a member of the CYP450 enzyme super family, is a polymorphic enzyme that metabolizes ~25% of therapeutic drugs. CYP2D6 exhibits significant genetic polymorphisms which might cause adverse effects and therapeutic failures of some drugs. The purpose
Metabolic disposition of gefitinib, an epidermal growth factor receptor tyrosine kinase inhibitor, in rat, dog and man
McKillop et al.
Xenobiotica,
34, 917-934 (2004)
Can Zhao et al.
Biomedical chromatography : BMC, 33(11), e4638-e4638 (2019-07-02)
Monitoring gefitinib and its metabolites may help to explore the underlying mechanisms of gefitinib resistance. The concentration of gefitinib and its metabolites in tumor tissues could influence its anticancer activities more than that in the plasma. In the present study
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