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Compound Detail

CHEMBL786

TAMOXIFEN CITRATE
💊 Approved Drug
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💊 Approved Drug
CC/C(=C(\c1ccccc1)c1ccc(OCCN(C)C)cc1)c1ccccc1.O=C(O)CC(O)(CC(=O)O)C(=O)O

Basic Information

ChEMBL ID CHEMBL786
Name TAMOXIFEN CITRATE
Phase Approved
Structure Type MOL
InChI Key FQZYTYWMLGAPFJ-OQKDUQJOSA-N
Therapeutic ✓ Yes
Parent Compound CHEMBL83
Active Moiety CHEMBL4525767

Known Names

Emblon Fentamox 10 Fentamox 20 I.C.I.46474 CITRATE ICI 46,474 ICI-46474 Kentadex Kessar Kessar 10 Kessar 20 Noltam Nolvadex +17 more
11
Targets
28
Activities
1
Assay Types
0
PK Parameters
20
Publications
29
Known Names
20
Indications
1
Mechanisms

Molecular Properties

371.5
MW (Da)
6.00
ALogP
2
HBA
0
HBD
12.5
PSA (Ų)
0.45
QED
1
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1977
Availability Prescription
Chirality Achiral

Routes of Administration

Oral

Flags

Black Box Warning Prodrug
USAN Year 1976

Extended Properties

Molecular Formula C32H37NO8
MW 563.65
Aromatic Rings 3
Heavy Atoms 28
NP-Likeness -0.40

Mechanism of Action

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

Indications

Breast Neoplasms Breast Neoplasms Bipolar Disorder Carcinoma, Intraductal, Noninfiltrating Carcinoma, Ovarian Epithelial Endometrial Neoplasms Endometrial Neoplasms Endometrial Neoplasms Fallopian Tube Neoplasms Inflammatory Breast Neoplasms Liver Neoplasms Peritoneal Neoplasms Breast Neoplasms, Male Central Nervous System Neoplasms Desmoid Tumors Hereditary Breast and Ovarian Cancer Syndrome Melanoma Neoplasms Paraganglioma Urinary Bladder Neoplasms

Drug Warnings

Black Box Warning
carcinogenicity
Country: United States
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
immune system toxicity
Country: United States

Activity Summary

IC50 28 meas. best 8.3

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Estrogen receptor beta
CHEMBL242
IC50 8.3 8.3 5.0 1
MCF7
CHEMBL387
IC50 6.1 5.236 796.0 5
Estrogen receptor
CHEMBL206
IC50 5.77 5.77 1700.0 1
Plasmodium falciparum
CHEMBL364
IC50 5.1 4.9714 7943.3 7
SARS-CoV-2
CHEMBL4303835
IC50 5.05 4.76 8980.0 2
MDA-MB-231
CHEMBL400
IC50 4.97 4.88 10710.0 4
DU-145
CHEMBL613508
IC50 4.95 4.885 11200.0 2
PC-3
CHEMBL390
IC50 4.93 4.93 11700.0 1
Ishikawa
CHEMBL614649
IC50 4.9 4.9 12500.0 1
Unchecked
CHEMBL612545
IC50 4.65 4.65 22300.0 1
HEK293
CHEMBL614818
IC50 4.56 4.54 27300.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Estrogen receptor beta IC50 = 5.0 nM 8.3 Antagonist activity at human full-length ERbeta expressed in non-human mammalian... 31099568
MCF7 IC50 = 796.0 nM 6.1 Inhibition of 17-beta estradiol-induced cell proliferation in human MCF7 cells i... 28882502
Estrogen receptor IC50 = 1700.0 nM 5.77 Antagonist activity at human full-length ERalpha expressed in non-human mammalia... 31099568
MCF7 IC50 = 6200.0 nM 5.21 Anticancer activity against human MCF7 cells assessed as cell growth inhibition ... 30772606
Plasmodium falciparum IC50 = 7943.28 nM 5.1 Antiplasmodial activity against Plasmodium falciparum W2 after 72 hrs by SYBR gr... 19734910
SARS-CoV-2 IC50 = 8980.0 nM 5.05 IC50 determination at MOI 0.01 using CellTiter- Glo (CTG) assay, performed 3 day... -
MCF7 IC50 = 9530.0 nM 5.02 Cytotoxicity against human MCF7 cells assessed as reduction in cell viability in... 32947093
Plasmodium falciparum IC50 = 10000.0 nM 5.0 Antiplasmodial activity against Plasmodium falciparum 7G8 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 10000.0 nM 5.0 Antiplasmodial activity against Plasmodium falciparum D10 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 10000.0 nM 5.0 Antiplasmodial activity against Plasmodium falciparum Dd2 after 72 hrs by SYBR g... 19734910
MCF7 IC50 = 10200.0 nM 4.99 Cytotoxicity against human MCF7 cells after 18 hrs by MTT assay 19932024
MDA-MB-231 IC50 = 10710.0 nM 4.97 Cytotoxicity against human MDA-MB-231 cells assessed as reduction in cell viabil... 32947093
DU-145 IC50 = 11200.0 nM 4.95 Anticancer activity against human DU-145 cells assessed as cell growth inhibitio... 30772606
PC-3 IC50 = 11700.0 nM 4.93 Anticancer activity against human PC-3 cells assessed as cell growth inhibition ... 30772606
MDA-MB-231 IC50 = 12300.0 nM 4.91 Cytotoxicity against human MDA-MB-231 cells after 18 hrs by MTT assay 19932024
Ishikawa IC50 = 12500.0 nM 4.9 Cytotoxicity against human Ishikawa cells after 18 hrs by MTT assay 19932024
Plasmodium falciparum IC50 = 12589.25 nM 4.9 Antiplasmodial activity against Plasmodium falciparum 3D7 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 12589.25 nM 4.9 Antiplasmodial activity against Plasmodium falciparum GB4 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 12589.25 nM 4.9 Antiplasmodial activity against Plasmodium falciparum HB3 after 72 hrs by SYBR g... 19734910
MDA-MB-231 IC50 = 12800.0 nM 4.89 Anticancer activity against human MDA-MB-231 cells assessed as cell growth inhib... 30772606

Literature References

Data from ChEMBL 36 via Core Engine