Details of the Drug

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]
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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)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

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
UNII: E569WG6E60
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]

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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]

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Molecular Interaction Atlas (MIA)

MIA Detail

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.