lasofoxifene (CED0009633)

Record Information

Version

1.0

Creation Date

2016-06-03 11:29:24 UTC

Update Date

2026-08-22 08:24:17 UTC

Accession Number

CHEM043963

Identification

Common Name

lasofoxifene

Class

Small Molecule

Description

Lasofoxifene is an organic compound with the formula C28H31NO2 and an average molecular weight of 413.55 g/mol. It belongs to the phenylnaphthalenes, a subclass of naphthalenes within the organic compounds. This substance is associated with healthcare, pharmaceuticals, and veterinary products, specifically as a sex hormone and modulator of the genital system, and is administered via the oral exposure route. The compound interacts with four recorded protein targets. It acts as an agonist, antagonist, negative modulator, inverse agonist, or modulator of the Estrogen receptor (ESR1), Estrogen receptor beta (ESR2), Cannabinoid receptor 2 (CNR2), and Fusion glycoprotein F0.

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Lasofoxifene hydrochloride	MeSH
(-)-cis-5,6,7,8-tetrahydro-6-Phenyl-5-(P-(2-(1-pyrrolidinyl)ethoxy)phenyl)-2-naphthol	MeSH
cis-1R-(4'-Pyrrolidinoethoxyphenyl)-2S-phenyl-6-hydroxy-1,2,3,4-tetrahydronaphthalene, tartrate salt	MeSH
LAS estrogen receptor modulator	MeSH

Chemical Formula

C₂₈H₃₁NO₂

Average Molecular Mass

413.551 g/mol

Monoisotopic Mass

413.235 g/mol

CAS Registry Number

180916-16-9

IUPAC Name

(5R,6S)-6-phenyl-5-{4-[2-(pyrrolidin-1-yl)ethoxy]phenyl}-5,6,7,8-tetrahydronaphthalen-2-ol

Traditional Name

lasofoxifene

SMILES

[H][C@@]1(CCC2=CC(O)=CC=C2[C@@]1([H])C1=CC=C(OCCN2CCCC2)C=C1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C28H31NO2/c30-24-11-15-27-23(20-24)10-14-26(21-6-2-1-3-7-21)28(27)22-8-12-25(13-9-22)31-19-18-29-16-4-5-17-29/h1-3,6-9,11-13,15,20,26,28,30H,4-5,10,14,16-19H2/t26-,28+/m1/s1

InChI Key

GXESHMAMLJKROZ-IAPPQJPRSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylnaphthalenes. Phenylnaphthalenes are compounds containing a phenylnaphthalene skeleton, which consists of a naphthalene bound to a phenyl group.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Phenylnaphthalene
Stilbene
Tetralin
Phenoxy compound
Phenol ether
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
N-alkylpyrrolidine
Pyrrolidine
Tertiary aliphatic amine
Tertiary amine
Ether
Azacycle
Organoheterocyclic compound
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organic oxygen compound
Hydrocarbon derivative
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

naphthols (CHEBI:41282 )
N-alkylpyrrolidine (CHEBI:41282 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.0004 g/L	ALOGPS
logP	6.36	ALOGPS
logP	5.97	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	10.21	ChemAxon
pKa (Strongest Basic)	8.98	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	32.7 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	126.83 m³·mol⁻¹	ChemAxon
Polarizability	47.58 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03di-2021900000-fa2afd3a45e77e79caff	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0002-9142100000-aa9a530d9148928aca60	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0592-9121000000-aa9348b7693d712742d9	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03di-1002900000-e9d0c9bba98fa211160c	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-02t9-3029400000-c4994f82dc45badd2774	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-01b9-8089000000-27271370f02794cae069	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
325	Sex hormones and modulators of the genital system	Healthcare, pharmaceuticals & veterinary products	Not Available
578	Making Cigars	Industrial manufacturing & chemical processing	Not Available

Pathways

1 pathway

Lasofoxifene Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Estrogen receptor	P03372	Humans	Predicted (SEA)	21.4864
Click to view 3D structure	Histamine H3 receptor	Q9Y5N1	Humans	Predicted (SEA)	42.5057
Click to view 3D structure	Sigma non-opioid intracellular receptor 1	Q60492	Cavia porcellus	Predicted (SEA)	82.4423
Click to view 3D structure	Voltage-gated inwardly rectifying potassium channel KCNH2	Q12809	Humans	Predicted (SEA)	376.635
Click to view 3D structure	Sigma intracellular receptor 2	Q5U3Y7	Rattus norvegicus	Predicted (SEA)	45.1525
Click to view 3D structure	Histamine H1 receptor	P35367	Humans	Predicted (SEA)	125.104
Click to view 3D structure	D(3) dopamine receptor	P35462	Humans	Predicted (SEA)	209.57
Click to view 3D structure	Estrogen receptor beta	Q92731	Humans	Predicted (SEA)	27.3251
Click to view 3D structure	D(2) dopamine receptor	P14416	Humans	Predicted (SEA)	291.0
Click to view 3D structure	Sodium-dependent serotonin transporter	P31645	Humans	Predicted (SEA)	152.273
Click to view 3D structure	Sigma non-opioid intracellular receptor 1	Q99720	Humans	Predicted (SEA)	199.45
Click to view 3D structure	Cytochrome P450 2C9	P11712	Humans	Predicted (SEA)	353.747
Click to view 3D structure	Histamine H3 receptor	Q9QYN8	Rattus norvegicus	Predicted (SEA)	33.553
Click to view 3D structure	Amine oxidase [flavin-containing] B	P27338	Humans	Predicted (SEA)	119.499
Click to view 3D structure	Cytochrome P450 3A4	P08684	Humans	Predicted (SEA)	505.553
Click to view 3D structure	Sodium-dependent serotonin transporter	P31652	Rattus norvegicus	Predicted (SEA)	121.6
Click to view 3D structure	Acetylcholinesterase	P22303	Humans	Predicted (SEA)	158.735
Click to view 3D structure	D(1A) dopamine receptor	P21728	Humans	Predicted (SEA)	150.56
Click to view 3D structure	Histamine H1 receptor	P31389	Cavia porcellus	Predicted (SEA)	61.968
Click to view 3D structure	Cytochrome P450 2D6	P10635	Humans	Predicted (SEA)	394.851
Click to view 3D structure	Histamine H4 receptor	Q9H3N8	Humans	Predicted (SEA)	65.4712
Click to view 3D structure	D(2) dopamine receptor	P61169	Rat	Predicted (SEA)	262.352
Click to view 3D structure	Leukotriene A-4 hydrolase	P09960	Humans	Predicted (SEA)	38.5354
Click to view 3D structure	5-hydroxytryptamine receptor 2A	P28223	Humans	Predicted (SEA)	390.959
Click to view 3D structure	Adenosine receptor A2a	P29274	Humans	Predicted (SEA)	122.457