Endoxifen

Endoxifen
Clinical data
Trade names	Zonalta
Other names	4-Hydroxy-N-desmethyltamoxifen; Desmethylhydroxytamoxifen
Routes of; administration	By mouth
Identifiers
	IUPAC name 4-[1-[4-[2-(methylamino)ethoxy]phenyl]-2-phenylbut-1-enyl]phenol;
CAS Number	112093-28-4 ; 114828-90-9 (E-isomer); 1032008-74-4 (hydrochloride);
PubChem CID	130621;
UNII	46AF8680RC;
ChEMBL	ChEMBL1949791;
PDB ligand	9XY (PDBe, RCSB PDB);
CompTox Dashboard (EPA)	DTXSID80149880 ;
ECHA InfoCard	100.208.548
Chemical and physical data
Formula	C25H27NO2
Molar mass	373.496 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCC(=C(C1=CC=C(C=C1)O)C2=CC=C(C=C2)OCCNC)C3=CC=CC=C3;
	InChI InChI=1S/C25H27NO2/c1-3-24(19-7-5-4-6-8-19)25(20-9-13-22(27)14-10-20)21-11-15-23(16-12-21)28-18-17-26-2/h4-16,26-27H,3,17-18H2,1-2H3; Key:MHJBZVSGOZTKRH-UHFFFAOYSA-N;

Endoxifen, also known as 4-hydroxy-N-desmethyltamoxifen, is a nonsteroidal selective estrogen receptor modulator (SERM) of the triphenylethylene group as well as a protein kinase C (PKC) inhibitor. It is under development for the treatment of estrogen receptor-positive breast cancer and for the treatment of mania in bipolar disorder. It is taken by mouth.

Endoxifen is an active metabolite of tamoxifen and has been found to be effective in patients that have failed previous hormonal therapies (tamoxifen, aromatase inhibitors, and fulvestrant). The prodrug tamoxifen is metabolized by the CYP2D6 enzyme to produce endoxifen and afimoxifene (4-hydroxytamoxifen).

Currently, endoxifen is approved by Drugs Controller General of India for the acute treatment of manic episode with or without mixed features of Bipolar I disorder. It is manufactured and sold by Intas Pharmaceuticals under the brand name Zonalta.

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