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Compound Detail

CHEMBL1116

RALOXIFENE HYDROCHLORIDE
💊 Approved Drug
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💊 Approved Drug
Cl.O=C(c1ccc(OCCN2CCCCC2)cc1)c1c(-c2ccc(O)cc2)sc2cc(O)ccc12
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1116
Name RALOXIFENE HYDROCHLORIDE
Phase Approved
Structure Type MOL
InChI Key BKXVVCILCIUCLG-UHFFFAOYSA-N
Therapeutic ✓ Yes
Parent Compound CHEMBL81
Active Moiety CHEMBL81

Known Names

Evirex Evista Keoxifene hydrochloride LY-156758 LY156758 NSC-706725 Optruma Ostiral Raloxifene hcl Raloxifene hydrochloride Raloxifene teva Razylan
11
Targets
30
Activities
4
Assay Types
4
PK Parameters
20
Publications
12
Known Names
4
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
USAN Stem -ifene
USAN Year 1988

Extended Properties

Molecular Formula C28H28ClNO4S
MW 510.06
Aromatic Rings 4
Heavy Atoms 34
NP-Likeness -0.54

Mechanism of Action

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

Indications

Breast Neoplasms Osteoporosis Osteoporosis, Postmenopausal Prostatic Neoplasms

Drug Warnings

Black Box Warning
vascular toxicity
Country: United States
Black Box Warning
neurotoxicity
Country: United States
Black Box Warning
respiratory toxicity
Country: United States
Black Box Warning
cardiotoxicity
Country: United States
Black Box Warning
gastrointestinal toxicity
Country: United States

Activity Summary

IC50 25 meas. best 9.7
Ki 3 meas. best 10.15
EC50 1 meas. best 10.7
Kd 1 meas. best 4.66

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
MCF7
CHEMBL387
 EC50 10.7 10.7 0.0 1
Estrogen receptor
CHEMBL206
 Ki 10.15 10.15 0.1 1
MCF7
CHEMBL387
 IC50 9.7 9.3167 0.2 3
Estrogen receptor
CHEMBL206
 IC50 9.62 8.748 0.2 5
Estrogen receptor
CHEMBL2093866
 IC50 9.43 8.9 0.4 2
Estrogen receptor
CHEMBL2724
 Ki 9.43 9.43 0.4 1
Estrogen receptor beta
CHEMBL3021
 Ki 8.56 8.56 2.7 1
Estrogen receptor beta
CHEMBL242
 IC50 7.37 6.8067 43.0 3
Plasmodium falciparum
CHEMBL364
 IC50 5.6 5.4143 2511.9 7
Replicase polyprotein 1ab
CHEMBL4523582
 IC50 5.25 5.25 5610.0 1
Ubiquitin-conjugating enzyme E2 N
CHEMBL6089
 IC50 4.85 4.805 14164.0 2
SARS-CoV-2
CHEMBL4303835
 IC50 4.81 4.81 15440.0 2
HLA class I histocompatibility antigen, A alpha chain
CHEMBL2632
 Kd 4.66 4.66 22000.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 157.7 mL.min-1.kg-1 Rattus norvegicus
Cmax 7.5 nM Rattus norvegicus
F 22.0 % Rattus norvegicus
T1/2 1.7 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
MCF7 EC50 = 0.02 nM 10.7 Effective concentration against MCF-7 breast tumor cells using MCF-7 assay. 12825935
Estrogen receptor Ki = 0.07 nM 10.15 Displacement of [3H]estradiol from human ER-alpha expressed in Sf21 cells incuba... 38401456
MCF7 IC50 = 0.2 nM 9.7 Inhibition of 17-beta-estradiol induced MCF-7 cell proliferation 11495597
Estrogen receptor IC50 = 0.24 nM 9.62 Displacement of [3H]estradiol from human ER-alpha expressed in Sf21 cells incuba... 38401456
Estrogen receptor IC50 = 0.37 nM 9.43 Half maximal inhibitory concentration against estrogen-induced proliferation of ... 16250633
Estrogen receptor Ki = 0.37 nM 9.43 Binding affinity for rat estrogen receptor alpha 16250633
MCF7 IC50 = 0.4 nM 9.4 Inhibition of estrogen-induced proliferation in human MCF-7 breast cancer cells 9154963
Estrogen receptor IC50 = 0.72 nM 9.14 Antagonist effect on transcriptional activation in MCF-7 cells expressing estrog... 10673099
MCF7 IC50 = 1.4 nM 8.85 Inhibitory concentration against MCF-7 breast tumor cells using MCF-7 assay. 12825935
Estrogen receptor IC50 = 2.0 nM 8.7 Displacement of [3H]17-beta-estradiol from human Estrogen receptor alpha 10673099
Estrogen receptor IC50 = 2.4 nM 8.62 Inhibitory concentration against estrogen receptor alpha using estrogen response... 12825935
Estrogen receptor beta Ki = 2.74 nM 8.56 Binding affinity for rat estrogen receptor beta 16250633
Estrogen receptor IC50 = 4.32 nM 8.37 Inhibitory concentration against estrogen-induced proliferation of Ishikawa uter... 16250633
Estrogen receptor IC50 = 22.0 nM 7.66 Inhibitory concentration against estrogen receptor alpha using radioligand bindi... 12825935
Estrogen receptor beta IC50 = 43.0 nM 7.37 Displacement of [3H]17-beta-estradiol from human Estrogen receptor beta 10673099
Estrogen receptor beta IC50 = 260.0 nM 6.58 Inhibitory concentration against estrogen receptor 2 using radioligand binding a... 12825935
Estrogen receptor beta IC50 = 341.0 nM 6.47 Inhibitory concentration against estrogen receptor 2 using estrogen response ele... 12825935
Plasmodium falciparum IC50 = 2511.89 nM 5.6 Antiplasmodial activity against Plasmodium falciparum GB4 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 2511.89 nM 5.6 Antiplasmodial activity against Plasmodium falciparum 3D7 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 3162.28 nM 5.5 Antiplasmodial activity against Plasmodium falciparum HB3 after 72 hrs by SYBR g... 19734910

Literature References

PubMed DOI Target Context # Activities
6431104 10.1021/jm00374a021 Rattus norvegicus 32
19734910 10.1038/nchembio.215 Plasmodium falciparum 7
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
16250633 10.1021/jm050723z Estrogen receptor 4
38401456 10.1016/j.bmc.2024.117645 Estrogen receptor 4
10673099 10.1016/s0960-894x(99)00648-4 Estrogen receptor 3
12825935 10.1021/jm030086h MCF7 3
12825935 10.1021/jm030086h Rattus norvegicus 3
9154963 10.1021/jm970167b Estrogen receptor 2
31382118 10.1016/j.ejmech.2019.07.063 A549 2
31382118 10.1016/j.ejmech.2019.07.063 MCF7 2
- 10.6019/CHEMBL4495565 ADMET 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
31382118 10.1016/j.ejmech.2019.07.063 HT-29 2
12825935 10.1021/jm030086h Estrogen receptor beta 2
12825935 10.1021/jm030086h Estrogen receptor 2
- 10.6019/CHEMBL4495565 Vero C1008 2
38401456 10.1016/j.bmc.2024.117645 Steryl-sulfatase 2
12825935 10.1021/jm030086h ADMET 1
11495597 10.1021/jm0101601 Estrogen receptor 1

Data from ChEMBL 36 via Core Engine