General Information of Drug (ID: DMOKCVI)

Drug Name
ARZOXIFENE
Synonyms
Arzoxifene; 182133-25-1; UNII-E569WG6E60; LY 353381; E569WG6E60; 2-(4-methoxyphenyl)-3-[4-(2-piperidin-1-ylethoxy)phenoxy]-1-benzothiophen-6-ol; 2-(4-methoxyphenyl)-3-(4-(2-(piperidin-1-yl)ethoxy)phenoxy)benzo[b]thiophen-6-ol; Arzoxifene [INN]; LY-353381; SCHEMBL285277; CHEMBL226267; BDBM19442; DTXSID10171255; ZINC1544683; AC1L4522; AN-538; AKOS030631785; SB19713; KB-05502; FT-0751607; 124708-EP2295426A1; 124708-EP2295427A1; 124708-EP2292592A1; 124708-EP2292576A2; Benzo(b)thiophene-6-ol, 2-(4-methoxyphenyl)-3-(4-(2-(1-piperidinyl)
Indication
Disease Entry ICD 11 Status REF
Breast cancer 2C60-2C65 Approved [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 1 Molecular Weight (mw) 475.6
Logarithm of the Partition Coefficient (xlogp) 6.6
Rotatable Bond Count (rotbonds) 8
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 6
Chemical Identifiers
Formula
C28H29NO4S
IUPAC Name
2-(4-methoxyphenyl)-3-[4-(2-piperidin-1-ylethoxy)phenoxy]-1-benzothiophen-6-ol
Canonical SMILES
COC1=CC=C(C=C1)C2=C(C3=C(S2)C=C(C=C3)O)OC4=CC=C(C=C4)OCCN5CCCCC5
InChI
InChI=1S/C28H29NO4S/c1-31-22-8-5-20(6-9-22)28-27(25-14-7-21(30)19-26(25)34-28)33-24-12-10-23(11-13-24)32-18-17-29-15-3-2-4-16-29/h5-14,19,30H,2-4,15-18H2,1H3
InChIKey
MCGDSOGUHLTADD-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
179337
CAS Number
182133-25-1
DrugBank ID
DB06249
TTD ID
D06LOQ

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Estrogen receptor (ESR) TTZAYWL ESR1_HUMAN Inhibitor [2]
Estrogen receptor beta (ESR2) TTOM3J0 ESR2_HUMAN Inhibitor [2]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Cathepsin D (CTSD) OTQZ36F3 CATD_HUMAN Gene/Protein Processing [3]
Estrogen receptor (ESR1) OTKLU61J ESR1_HUMAN Gene/Protein Processing [4]
G1/S-specific cyclin-D1 (CCND1) OT8HPTKJ CCND1_HUMAN Drug Response [5]
NAD(P)H dehydrogenase 1 (NQO1) OTZGGIVK NQO1_HUMAN Gene/Protein Processing [6]
Plasma serine protease inhibitor (SERPINA5) OTTZXPGD IPSP_HUMAN Gene/Protein Processing [3]
Progesterone receptor (PGR) OT0FZ3QE PRGR_HUMAN Gene/Protein Processing [3]
Trefoil factor 1 (TFF1) OTCYQH4F TFF1_HUMAN Gene/Protein Processing [3]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 Clinical pipeline report, company report or official report of Lilly.
2 Benzothiophene selective estrogen receptor modulators with modulated oxidative activity and receptor affinity. J Med Chem. 2007 May 31;50(11):2682-92.
3 The effect of the new SERM arzoxifene on growth and gene expression in MCF-7 breast cancer cells. Mol Cell Endocrinol. 2004 Apr 30;219(1-2):27-36. doi: 10.1016/j.mce.2004.02.003.
4 Structure-activity relationships for a family of benzothiophene selective estrogen receptor modulators including raloxifene and arzoxifene. ChemMedChem. 2007 Oct;2(10):1520-6. doi: 10.1002/cmdc.200700104.
5 Resistance to antiestrogen arzoxifene is mediated by overexpression of cyclin D1. Mol Endocrinol. 2009 Sep;23(9):1335-45. doi: 10.1210/me.2008-0268. Epub 2009 May 28.
6 Structural modulation of reactivity/activity in design of improved benzothiophene selective estrogen receptor modulators: induction of chemopreventive mechanisms. Mol Cancer Ther. 2007 Sep;6(9):2418-28.