Details of the Drug

General Information of Drug (ID: DMGDOS2)

Drug Name
(Z)-endoxifen
Synonyms
Endoxifen; Z-Endoxifen; 4-Hydroxy-N-desmethyltamoxifen; (E/Z)-Endoxifen; Endoxifen Z-Isomer; UNII-46AF8680RC; N-Desmethyl-4-hydroxytamoxifen; 110025-28-0; 4-Hydroxy-N-desmethyl-tamoxifen; CHEBI:80555; 46AF8680RC; 4OHNDtam; W-200834; N-Desmethyl-4-hydroxy Tamoxifen (approx. 1:1 E/Z Mixture); (Z)-4-Hydroxy-N-desmethyl Tamoxifen (contains up to 10% E isomer); 4-hydroxy-N-desmethyltamoxifen, (Z)-isomer; (Z)-Endoxifen; Endoxifen(E/Z=1:1); 4-hydroxy-N-desmethyl tamoxifen; SCHEMBL10107920; CHEMBL1093458; GTPL10203; EX-A645
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski):
0		 Molecular Weight 373.5
Logarithm of the Partition Coefficient Not Available
Rotatable Bond Count 8
Hydrogen Bond Donor Count 2
Hydrogen Bond Acceptor Count 3
Chemical Identifiers
Formula
C25H27NO2
IUPAC Name
4-[(Z)-1-[4-[2-(methylamino)ethoxy]phenyl]-2-phenylbut-1-enyl]phenol
Canonical 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/b25-24-
InChIKey
MHJBZVSGOZTKRH-IZHYLOQSSA-N
Cross-matching ID
PubChem CID
10090750
ChEBI ID
CHEBI:80555
CAS Number
112093-28-4
VARIDT ID
DR01627

Molecular Interaction Atlas of This Drug


Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
P-glycoprotein 1 (ABCB1) DTUGYRD MDR1_HUMAN Substrate [1]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Aromatase (CYP19A1) OTZ6XF74 CP19A_HUMAN Regulation of Drug Effects [2]
Cytochrome P450 1A1 (CYP1A1) OTE4EFH8 CP1A1_HUMAN Gene/Protein Processing [2]
Cytochrome P450 1A2 (CYP1A2) OTLLBX48 CP1A2_HUMAN Regulation of Drug Effects [2]
Cytochrome P450 2B6 (CYP2B6) OTOYO4S7 CP2B6_HUMAN Regulation of Drug Effects [2]
Cytochrome P450 2C8 (CYP2C8) OTHCWT42 CP2C8_HUMAN Gene/Protein Processing [2]
Cytochrome P450 2C9 (CYP2C9) OTGLBN29 CP2C9_HUMAN Gene/Protein Processing [2]
Cytochrome P450 2D6 (CYP2D6) OTZJC802 CP2D6_HUMAN Regulation of Drug Effects [2]
Cytochrome P450 3A4 (CYP3A4) OTQGYY83 CP3A4_HUMAN Regulation of Drug Effects [2]
Cytochrome P450 3A5 (CYP3A5) OTSXFBXB CP3A5_HUMAN Regulation of Drug Effects [2]
Estrogen receptor (ESR1) OTKLU61J ESR1_HUMAN Gene/Protein Processing [3]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 P-glycoprotein (ABCB1) transports the primary active tamoxifen metabolites endoxifen and 4-hydroxytamoxifen and restricts their brain penetration. J Pharmacol Exp Ther. 2011 Jun;337(3):710-7.
2 The formation of estrogen-like tamoxifen metabolites and their influence on enzyme activity and gene expression of ADME genes. Arch Toxicol. 2018 Mar;92(3):1099-1112.
3 The tamoxifen metabolite, endoxifen, is a potent antiestrogen that targets estrogen receptor alpha for degradation in breast cancer cells. Cancer Res. 2009 Mar 1;69(5):1722-7. doi: 10.1158/0008-5472.CAN-08-3933. Epub 2009 Feb 24.