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Compound Detail

CHEMBL81

RALOXIFENE
💊 Approved Drug
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💊 Approved Drug
O=C(c1ccc(OCCN2CCCCC2)cc1)c1c(-c2ccc(O)cc2)sc2cc(O)ccc12

Basic Information

ChEMBL ID CHEMBL81
Name RALOXIFENE
Phase Approved
Structure Type MOL
InChI Key GZUITABIAKMVPG-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Eviden J22.982B Keoxifene LY-139481 NSC-747974 Raloxifene Raloxifeno Raloxiphene Raxeto
63
Targets
238
Activities
4
Assay Types
30
PK Parameters
20
Publications
9
Known Names
13
Indications
1
Mechanisms

Molecular Properties

473.6
MW (Da)
6.08
ALogP
6
HBA
2
HBD
70.0
PSA (Ų)
0.32
QED
1
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1997
Availability Prescription
Chirality Achiral

Routes of Administration

Oral

Flags

Black Box Warning Natural Product
USAN Stem -ifene
USAN Year 1988

Extended Properties

Molecular Formula C28H27NO4S
MW 473.59
Aromatic Rings 4
Heavy Atoms 34
NP-Likeness -0.54

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Estrogen receptor modulator MODULATOR Estrogen receptor

Indications

Bone Diseases, Metabolic Breast Neoplasms Cognitive Dysfunction Osteoporosis Osteoporosis, Postmenopausal Polycystic Ovary Syndrome Psychotic Disorders Schizophrenia Alzheimer Disease Endometrial Neoplasms Menopause Severe Acute Respiratory Syndrome Prostatic Neoplasms

ATC Classification

G03XC01
raloxifene
Level 1: GENITO URINARY SYSTEM AND SEX HORMONES
Level 2: SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM

Activity Summary

IC50 172 meas. best 9.74
Ki 54 meas. best 10.52
EC50 11 meas. best 10.4
Kd 1 meas. best 6.15

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Estrogen receptor
CHEMBL206
Ki 10.52 9.5375 0.0 8
Ishikawa
CHEMBL614649
EC50 10.4 7.55 0.0 2
Estrogen receptor
CHEMBL206
IC50 9.74 8.5375 0.2 32
MCF7
CHEMBL387
IC50 9.7 6.5847 0.2 17
Estrogen receptor
CHEMBL2093866
IC50 9.7 8.6492 0.2 12
Estrogen receptor
CHEMBL206
EC50 9.18 8.1667 0.7 3
Estrogen receptor
CHEMBL2724
IC50 9.15 8.65 0.7 2
Aldehyde oxidase
CHEMBL3257
Ki 9.06 8.9883 0.9 6
Ishikawa
CHEMBL614649
IC50 9.03 5.775 0.9 4
3-beta-hydroxysteroid-Delta(8),Delta(7)-isomerase
CHEMBL4931
Ki 9.0 9.0 1.0 1
Estrogen receptor beta
CHEMBL242
IC50 8.8 7.4542 1.6 24
Estrogen receptor
CHEMBL2094114
IC50 8.73 8.73 1.9 1
Unchecked
CHEMBL612545
IC50 8.62 6.202 2.4 10
Estrogen receptor beta
CHEMBL242
Ki 8.56 8.215 2.7 6
Aldehyde oxidase
CHEMBL3257
IC50 8.52 8.0525 3.0 4
U2OS
CHEMBL615023
IC50 8.51 8.51 3.1 1
Estrogen receptor beta
CHEMBL3021
IC50 8.47 7.4 3.4 2
Sigma non-opioid intracellular receptor 1
CHEMBL287
Ki 7.42 6.98 38.0 2
C-8 sterol isomerase ERG2
CHEMBL3224
Ki 7.18 7.18 66.0 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
Ki 7.16 6.905 69.0 2
MDA-MB-231
CHEMBL400
IC50 7.04 5.1733 92.3 6
Alpha-2C adrenergic receptor
CHEMBL1916
Ki 6.97 6.97 107.0 1
Unchecked
CHEMBL612545
Ki 6.84 6.562 144.0 5
Estrogen receptor beta
CHEMBL242
EC50 6.58 6.58 260.0 1
Sodium-dependent noradrenaline transporter
CHEMBL222
Ki 6.55 6.55 280.0 1
Sodium-dependent noradrenaline transporter
CHEMBL222
IC50 6.55 6.55 282.0 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
IC50 6.45 6.45 355.0 1
D(2) dopamine receptor
CHEMBL217
Ki 6.41 6.41 391.0 1
Acetylcholinesterase
CHEMBL220
IC50 6.4 6.4 400.0 1
5-hydroxytryptamine receptor 2A
CHEMBL224
Ki 6.38 6.38 414.0 1
Alpha-1D adrenergic receptor
CHEMBL223
Ki 6.32 6.32 478.0 1
Mu-type opioid receptor
CHEMBL233
Ki 6.32 6.32 477.0 1
Aldehyde oxidase 1
CHEMBL1641354
IC50 6.3 6.3 500.0 1
Aldehyde oxidase 1
CHEMBL1641357
IC50 6.3 6.3 500.0 1
D(3) dopamine receptor
CHEMBL234
Ki 6.28 6.28 531.0 1
5-hydroxytryptamine receptor 2C
CHEMBL225
Ki 6.21 6.21 617.0 1
Alpha-2A adrenergic receptor
CHEMBL1867
Ki 6.21 6.21 624.0 1
Kappa-type opioid receptor
CHEMBL237
Ki 6.19 6.19 641.0 1
Sigma non-opioid intracellular receptor 1
CHEMBL287
IC50 6.17 6.17 681.0 1
Complement C5
CHEMBL2364163
Kd 6.15 6.15 710.0 1
Alpha-2C adrenergic receptor
CHEMBL1916
IC50 6.13 6.13 738.0 1
5-hydroxytryptamine receptor 6
CHEMBL3371
Ki 6.12 6.12 750.0 1
5-hydroxytryptamine receptor 1B
CHEMBL3459
Ki 6.07 6.07 846.0 1
Alpha-1A adrenergic receptor
CHEMBL319
Ki 6.05 6.05 892.0 1
Alpha-1D adrenergic receptor
CHEMBL223
IC50 6.01 6.01 973.0 1
Aldehyde oxidase 1
CHEMBL1641355
IC50 5.96 5.96 1100.0 1
5-hydroxytryptamine receptor 2C
CHEMBL225
IC50 5.93 5.93 1178.0 1
Mu-type opioid receptor
CHEMBL233
IC50 5.93 5.93 1176.0 1
D(2) dopamine receptor
CHEMBL217
IC50 5.93 5.93 1174.0 1
Adenosine receptor A2a
CHEMBL251
Ki 5.93 5.93 1185.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 157.7 mL.min-1.kg-1 Rattus norvegicus
CL 21.0 mL.min-1.g-1 Homo sapiens
CL 40.0 mL.min-1.g-1 Canis lupus familiaris
CL 58.0 mL.min-1.g-1 Rattus norvegicus
CL 108.0 mL.min-1.g-1 Mus musculus
CL 24.0 mL.min-1.g-1 Homo sapiens
CL 79.0 mL.min-1.g-1 Homo sapiens
CL 346.0 mL.min-1.g-1 Homo sapiens
CL 6.0 mL.min-1.g-1 Homo sapiens
CL 26.0 mL.min-1.g-1 Canis lupus familiaris
CL 178.0 mL.min-1.g-1 Canis lupus familiaris
CL 22.0 mL.min-1.g-1 Canis lupus familiaris
CL 6.0 mL.min-1.g-1 Canis lupus familiaris
CL 11.0 mL.min-1.g-1 Rattus norvegicus
CL 79.0 mL.min-1.g-1 Rattus norvegicus
CL 5.0 mL.min-1.g-1 Rattus norvegicus
CL 6.0 mL.min-1.g-1 Rattus norvegicus
CL 6.0 mL.min-1.g-1 Mus musculus
CL 66.0 mL.min-1.g-1 Mus musculus
CL 34.0 mL.min-1.g-1 Mus musculus
CL 6.0 mL.min-1.g-1 Mus musculus
CL 21.0 mL.min-1.g-1 Homo sapiens
CL 30.0 uL.min-1.(10^6cells)-1 Rattus norvegicus
CL - mL.min-1.kg-1 Homo sapiens
CL 8.9 mL.min-1.g-1 Homo sapiens
CL 14.7 mL.min-1.kg-1 Homo sapiens
CL 20.7 mL.min-1.g-1 Homo sapiens
CL 2180.0 mL.min-1.g-1 Homo sapiens
CL 2224.0 mL.min-1.g-1 Homo sapiens
CL 735.0 mL.min-1.kg-1 Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Estrogen receptor Ki = 0.03 nM 10.52 Antagonistic activity against estrogen receptor alpha in presence of 0.1 nM estr... 16162002
Ishikawa EC50 = 0.04 nM 10.4 Stimulation of alkaline phosphatase activity in Ishikawa human endometrial adeno... 11738564
Estrogen receptor Ki = 0.158 nM 9.8 DRUGMATRIX: Estrogen ERalpha radioligand binding (ligand: [3H] Estradiol) -
Estrogen receptor IC50 = 0.18 nM 9.74 Antagonist activity at FLAG-tagged ERalpha (unknown origin) expressed in HEK293 ... 30940565
MCF7 IC50 = 0.2 nM 9.7 Antiproliferative activity against human MCF7 cells 22405286
Estrogen receptor IC50 = 0.2 nM 9.7 Inhibition of estradiol-stimulated MCF-7 breast adenocarcinoma cell proliferatio... 12749895
Estrogen receptor IC50 = 0.2 nM 9.7 In vitro inhibition of estrogen-stimulated MCF-7 cell proliferation 10098655
Estrogen receptor IC50 = 0.2 nM 9.7 Antagonist effect in breast tissue was assayed by inhibition of estrogen stimula... -
MCF7 IC50 = 0.2 nM 9.7 Inhibition of estrogen-stimulated MCF-7 cell proliferation 9548817
Estrogen receptor IC50 = 0.2 nM 9.7 Antagonism of estrogen action in a mammary tumor cell line was assayed via inhib... 9003514
Estrogen receptor Ki = 0.22 nM 9.66 Ability to displace [3H]17-beta-estradiol from Estrogen receptor alpha by scinti... 11459665
Estrogen receptor IC50 = 0.3 nM 9.52 Antagonist activity at human wild type ERalpha expressed in HEK293T cells co-exp... 20659801
Estrogen receptor IC50 = 0.34 nM 9.47 Inhibition of 17-beta-estradiol (10e-11 M) mediated MCF-7 cell proliferation 10328300
Estrogen receptor Ki = 0.37 nM 9.43 Displacement of [3H]estradiol from ERalpha after 4 hrs by scintillation counting 22582136
Estrogen receptor Ki = 0.38 nM 9.42 Binding affinity to ERalpha ligand binding domain 22582136
Estrogen receptor Ki = 0.4 nM 9.4 Binding affinity for estrogen receptor alpha 12749895
Estrogen receptor Ki = 0.43 nM 9.37 Binding affinity to ERalpha (unknown origin) 26795112
Estrogen receptor IC50 = 0.46 nM 9.34 Antagonist activity at human ERalpha expressed in african green monkey CV1 cells... 16499324
Estrogen receptor IC50 = 0.47 nM 9.33 Displacement of Fluormone ES2 from human recombinant full length untagged-ERalph... 27185013
Estrogen receptor IC50 = 0.553 nM 9.26 DRUGMATRIX: Estrogen ERalpha radioligand binding (ligand: [3H] Estradiol) -

Literature References

Data from ChEMBL 36 via Core Engine