| Identification | Back Directory | [Name]
N-Desmethyl Imatinib | [CAS]
404844-02-6 | [Synonyms]
CGP-74588
STI 509-00
Norimatinib
DesMethyl IMatinib
Imatinib Impurity F
DesMethyl IMatinib-d8
Imatinib EP Impurity C
iMatinib related substance A
IMatinib N-DesMethyl IMpurity
Imatinib metabolite N-Desmethyl Imatinib
N-{4-Methyl-3-[(4-pyridin-3-ylpyrimidin-2-yl)amino]phenyl}-4-(piperazin-1-ylmethyl)benzamide
N-[4-Methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]phenyl]-4-(1-piperazinylmethyl)-benzamide | [EINECS(EC#)]
1592732-453-0 | [Molecular Formula]
C28H29N7O | [MDL Number]
MFCD07369291 | [MOL File]
404844-02-6.mol | [Molecular Weight]
479.585 |
| Chemical Properties | Back Directory | [Appearance]
Off-White to Pale-Yellow Solid | [Melting point ]
99-101°C | [density ]
1.268±0.06 g/cm3(Predicted) | [storage temp. ]
-20°C Freezer | [solubility ]
DMF: 16 mg/ml; DMF:PBS (pH 7.2) (1:4): 0.20 mg/ml; DMSO: 14 mg/ml; Ethanol: 0.20 mg/ml | [form ]
A lyophilized solid | [pka]
13.28±0.70(Predicted) | [color ]
Light yellow to yellow | [biological source]
synthetic | [InChIKey]
BQQYXPHRXIZMDM-UHFFFAOYSA-N | [SMILES]
C(NC1=CC=C(C)C(NC2=NC=CC(C3=CC=CN=C3)=N2)=C1)(=O)C1=CC=C(CN2CCNCC2)C=C1 |
| Hazard Information | Back Directory | [Chemical Properties]
Off-White to Pale-Yellow Solid | [Uses]
A metabolite of Gleevec, a tyrosine kinase inhibitor which is highly specific for BCR-ABL, the enzyme associated with chronic myelogenous leukemia (CML) and certain forms of acute lymphoblastic leukemia (ALL) | [Uses]
aminoglycoside antibiotic similar to gentamycin, toxic to bacterial, yeast, higher plant and mammalian cells and to protozoans and helminthes | [Uses]
anti-epileptic | [Description]
N-desmethyl Imatinib is a major active metabolite of imatinib (Item No. 13139), an anticancer agent that selectively targets tyrosine kinases, including Bcr-ABL, platelet-derived growth factor receptor (PDGFR), and KIT.1,2 N-desmethyl Imatinib is formed when imatinib undergoes demethylation by the cytochrome P450 (CYP) isomer CYP3A4.3 N-desmethyl Imatinib has the same in vitro potency at Bcr-ABL kinase as imatinib (IC50 = 38 nM for both) but is only present in plasma at 10-15% of the levels of imatinib, indicating the majority of the anticancer activity can be attributed to the parent compound. | [Definition]
ChEBI: N-Demethylated piperazine is a member of benzamides. | [References]
[1] DRUKER B J. Translation of the Philadelphia chromosome into therapy for CML.[J]. Blood, 2008: 4808-4817. DOI: 10.1182/blood-2008-07-077958
[2] MüLLER B A. Imatinib and its successors–how modern chemistry has changed drug development.[J]. Current pharmaceutical design, 2009, 15 2: 120-133. DOI: 10.2174/138161209787002933
[3] OBACH R S. Pharmacologically active drug metabolites: impact on drug discovery and pharmacotherapy.[J]. Pharmacological Reviews, 2013, 65 2: 578-640. DOI: 10.1124/pr.111.005439 |
| Safety Data | Back Directory | [Safety Statements ]
24/25 | [WGK Germany ]
WGK 3 | [HS Code ]
29339900 | [Storage Class]
6.1C - Combustible acute toxic Cat.3
toxic compounds or compounds which causing chronic effects | [Hazard Classifications]
Carc. 2
Lact.
Muta. 2
Repr. 1B |
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