Cgp-74588 (HCID 9869737)

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
UNII: 6GOH0N63QD
EC Number: 112-387-4
Nikkaji: J1.690.778B

Properties

Computed structural properties

XLogP: 3
Topological polar surface area: 95.1 Å²
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: 302 · H302-H341-H351-H360-H362
Precautionary statements: 201 · P201-P202-P260-P263-P264-P270-P280-P301+P312-P330-P308+P313-P405-P501
Safety Statements: 24 · 24/25
WGK Germany: 3 · WGK 3
HS Code: 29339900 · 29339900
Storage Class: 6.1 C · 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
Hazard Classifications: 2 Lact.Muta · Carc. 2Lact.Muta. 2Repr. 1B

Safety & regulation

GHS classification

GHS Classification · 4 items

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 · 4 items

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.