Cgp-74588
Basic information
- CAS
404844-02-6- Standard SMILES
Cc1ccc(NC(=O)c2ccc(CN3CCNCC3)cc2)cc1Nc1nccc(-c2cccnc2)n1- InChIKey
BQQYXPHRXIZMDM-UHFFFAOYSA-N- Molecular formula
- C28H29N7O
- Average molar mass
- 479.6 g/mol
- Monoisotopic mass
- 479.24335855
Overview
N-Demethylated piperazine is a member of benzamides.
Names & identifiers
- Preferred name
- Cgp-74588
- IUPAC
- N-[4-methyl-3-[(4-pyridin-3-ylpyrimidin-2-yl)amino]phenyl]-4-(piperazin-1-ylmethyl)benzamide
- English name
- N-Desmethyl Imatinib
- Molecular formula
- C28H29N7O
- Molecular weight
- 479.58
Names & synonyms
N-Desmethyl Imatinib404844-02-6N-DesmethylimatinibNorimatinibCGP-74588N Desmethyl imatinib6GOH0N63QDCGP 74588STI-50900STI-509-00CGP74588DTXSID80193500
Show more names
N-DesmethyLImatinib Impurity FSTI 509-00no mesylateImatinib Imp.FN-methylimatinibDesMethyl IMatinib
Benzamide, N-(4-methyl-3-((4-(3-pyridinyl)-2-pyrimidinyl)amino)phenyl)-4-(1-piperazinylmethyl)-RefChem:575417DTXCID50115991Imatinib EP Impurity CUNII-6GOH0N63QDN-[4-methyl-3-[(4-pyridin-3-ylpyrimidin-2-yl)amino]phenyl]-4-(piperazin-1-ylmethyl)benzamideMFCD07369291n-desmethyl imatinib;n-{4-methyl-3-((4-pyridin-3-ylpyrimidin-2-yl)amino)phenyl}-4-(piperazin-1-ylmethyl)benzamide
Database identifiers
- CAS
404844-02-6- PubChem CID
- 9869737
- DTXSID
DTXSID80193500- ChEMBL
CHEMBL2386594、CHEMBL3040018- ChEBI
CHEBI:169508
Properties
Computed structural properties
- XLogP
- 3
- Topological polar surface area
- 95.1 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 7
- Heavy atoms
- 36
- Formal charge
- 0
- Complexity
- 679
Physicochemical properties
- Melting point
- 99 · 99-101°C
- Density
- 1.268 · 1.268±0.06 g/cm3(Predicted)
- storage temp.
- -20 °C · -20°C Freezer
- solubility
- 16 mg/ml; · 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 · 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
- FDA UNII
- 6 GOH0N63QD · 6GOH0N63QD
- UNSPSC Code
- 12352205 · 12352205
- NACRES
- 77 · NA.77
- Symbol(GHS)
- 7 · GHS07,GHS08
- Signal word
- Danger
- Hazard statements
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H341 (100%): Suspected of causing genetic defects [Warning Germ cell mutagenicity]
P203, P260, P263, P264, P270, P280, P318, P405, and P501 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesMuta. 2 (100%)
Safety data
- wgk
- WGK 3
- hs_code
- 29339900
- Signal word
- Danger
- Symbol(GHS)
- GHS07,GHS08
- safety_code
- 24/25
- Storage Class
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- Hazard statements
- H302-H341-H351-H360-H362
- Hazard Classifications
- Carc. 2Lact.Muta. 2Repr. 1B
- Precautionary statements
- P201-P202-P260-P263-P264-P270-P280-P301+P312-P330-P308+P313-P405-P501
Chemistry & industry
Pharmacology
Metabolism/MetabolitesN-desmethylimatinib is a known human metabolite of imatinib.
Tissue LocationsKidney
Cellular LocationsExtracellular
Applications
DescriptionN-desmethyl Imatinib is a major active metabolite of imatinib , an anticancer agent that selectively targets tyrosine kinases, including Bcr-ABL, platelet-derived growth factor receptor (PDGFR), and KIT. N-desmethyl Imatinib is formed when imatinib undergoes demethylation by the cytochrome P450 (CYP) isomer CYP3A4. 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.
Usesaminoglycoside antibiotic similar to gentamycin, toxic to bacterial, yeast, higher plant and mammalian cells and to protozoans and helminthes
Usesanti-epileptic
UsesN-Desmethyl Imatinib (Imatinib EP Impurity C) is 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). It is a COVID19-related research product.
Additional notes
DefinitionChEBI: N-Demethylated piperazine is a member of benzamides.
Related reactions
14 records
Compound notes
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