Details of the Drug

General Information of Drug (ID: DM9JPUD)

Drug Name
Droloxifene
Synonyms E-droloxifene; FK-435; K-060; K-060E; RP-60850; K-21.060E; 3-hydroxytamoxifen
Indication
Disease Entry ICD 11 Status REF
Breast cancer 2C60-2C65 Discontinued in Phase 2 [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 1 Molecular Weight (mw) 387.5
Logarithm of the Partition Coefficient (xlogp) 6.8
Rotatable Bond Count (rotbonds) 8
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 3
Chemical Identifiers
Formula
C26H29NO2
IUPAC Name
3-[(E)-1-[4-[2-(dimethylamino)ethoxy]phenyl]-2-phenylbut-1-enyl]phenol
Canonical SMILES
CC/C(=C(/C1=CC=C(C=C1)OCCN(C)C)\\C2=CC(=CC=C2)O)/C3=CC=CC=C3
InChI
InChI=1S/C26H29NO2/c1-4-25(20-9-6-5-7-10-20)26(22-11-8-12-23(28)19-22)21-13-15-24(16-14-21)29-18-17-27(2)3/h5-16,19,28H,4,17-18H2,1-3H3/b26-25+
InChIKey
ZQZFYGIXNQKOAV-OCEACIFDSA-N
Cross-matching ID
PubChem CID
3033767
ChEBI ID
CHEBI:34731
CAS Number
82413-20-5
UNII
0M67U6Z98F
DrugBank ID
DB15641
TTD ID
D0R2JS
VARIDT ID
DR01424

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Estrogen receptor (ESR) TTZAYWL ESR1_HUMAN Modulator [2]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
P-glycoprotein 1 (ABCB1) DTUGYRD MDR1_HUMAN Substrate [3]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Cytochrome P450 1B1 (CYP1B1) OTYXFLSD CP1B1_HUMAN Gene/Protein Processing [4]
Cytochrome P450 3A4 (CYP3A4) OTQGYY83 CP3A4_HUMAN Gene/Protein Processing [4]
Cytochrome P450 3A5 (CYP3A5) OTSXFBXB CP3A5_HUMAN Gene/Protein Processing [4]
Protein kinase C epsilon type (PRKCE) OT7J0P9L KPCE_HUMAN Protein Interaction/Cellular Processes [5]
Sex hormone-binding globulin (SHBG) OTPWU5IW SHBG_HUMAN Protein Interaction/Cellular Processes [6]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Breast cancer
ICD Disease Classification 2C60-2C65
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
P-glycoprotein 1 (ABCB1) DTP P-GP 7.23E-01 -8.20E-02 -3.22E-01
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 Trusted, scientifically sound profiles of drug programs, clinical trials, safety reports, and company deals, written by scientists. Springer. 2015. Adis Insight (drug id 800000847)
2 Droloxifene, a new antiestrogen: its role in metastatic breast cancer. Breast Cancer Res Treat. 1994;31(1):83-94.
3 Human intestinal transporter database: QSAR modeling and virtual profiling of drug uptake, efflux and interactions. Pharm Res. 2013 Apr;30(4):996-1007.
4 Reversible and irreversible inhibition of CYP3A enzymes by tamoxifen and metabolites. Xenobiotica. 2002 Oct;32(10):863-78.
5 Tamoxifen induces selective membrane association of protein kinase C epsilon in MCF-7 human breast cancer cells. Int J Cancer. 1998 Sep 11;77(6):928-32. doi: 10.1002/(sici)1097-0215(19980911)77:6<928::aid-ijc22>3.0.co;2-w.
6 Human sex hormone-binding globulin binding affinities of 125 structurally diverse chemicals and comparison with their binding to androgen receptor, estrogen receptor, and -fetoprotein. Toxicol Sci. 2015 Feb;143(2):333-48. doi: 10.1093/toxsci/kfu231. Epub 2014 Oct 27.