Compound Detail

CHEMBL83

TAMOXIFEN

💊 Approved Drug

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💊 Approved Drug

CC/C(=C(\c1ccccc1)c1ccc(OCCN(C)C)cc1)c1ccccc1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL83
Name	TAMOXIFEN
Phase	Approved
Structure Type	MOL
InChI Key	NKANXQFJJICGDU-QPLCGJKRSA-N
Therapeutic	✓ Yes
Active Moiety	CHEMBL4525767

Known Names

ICI-47699 Mammaton Novaldex NSC-727681 Tamoplex Tamoxifen Tamoxifene Tamoxifeno

111

Targets

475

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Molecular Properties

371.5

MW (Da)

6.00

ALogP

HBA

HBD

12.5

PSA (Å²)

0.45

QED

Ro5 Violations

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	C26H29NO
MW	371.52
Aromatic Rings	3
Heavy Atoms	28
NP-Likeness	-0.40

Indications

Neoplasms Neoplasms Breast Neoplasms Breast Neoplasms Breast Neoplasms Breast Neoplasms, Male Carcinoma, Intraductal, Noninfiltrating Cognitive Dysfunction Coronary Disease Fallopian Tube Neoplasms Hot Flashes Hyperplasia Hypertension Infertility Menopause Muscular Dystrophy, Duchenne Myocardial Ischemia Neoplasm Metastasis Ovarian Neoplasms Ovarian Neoplasms

ATC Classification

L02BA01

tamoxifen

Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS

Level 2: ENDOCRINE THERAPY

Activity Summary

IC50 395 meas. best 8.82

Ki 58 meas. best 9.29

EC50 21 meas. best 9.96

Kd 1 meas. best 9.0

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
MCF7 CHEMBL387	EC50	9.96	8.98	0.1	2
Estrogen receptor beta CHEMBL242	Ki	9.29	9.29	0.5	1
Anti-estrogen binding site (AEBS) CHEMBL612409	Kd	9.0	9.0	1.0	1
Estrogen receptor CHEMBL206	IC50	8.82	6.7348	1.5	33
Emopamil-binding protein-like CHEMBL2311238	Ki	8.55	8.55	2.8	1
3-beta-hydroxysteroid-Delta(8),Delta(7)-isomerase CHEMBL4931	Ki	8.3	8.3	5.0	1
Sigma non-opioid intracellular receptor 1 CHEMBL287	Ki	8.06	7.76	8.7	2
Estrogen receptor CHEMBL2093866	Ki	7.92	7.3933	11.9	3
Anti-estrogen binding site (AEBS) CHEMBL612409	IC50	7.92	7.92	12.0	1
MCF7 CHEMBL387	IC50	7.7	5.1915	20.0	110
Sigma non-opioid intracellular receptor 1 CHEMBL287	IC50	7.68	7.68	21.0	1
Estrogen receptor CHEMBL206	Ki	7.51	7.51	31.2	1
Ishikawa CHEMBL614649	EC50	7.48	7.48	33.0	1
MDA-MB-435 CHEMBL614697	IC50	7.3	7.15	50.0	2
Estrogen-related receptor gamma CHEMBL4245	IC50	7.21	7.21	62.2	1
Estrogen receptor beta CHEMBL242	IC50	7.1	6.5375	79.7	12
MDA-MB-231 CHEMBL400	IC50	7.1	4.7917	80.0	41
ATP-dependent translocase ABCB1 CHEMBL4302	Ki	7.0	7.0	100.0	1
Zaire ebolavirus CHEMBL4513181	IC50	7.0	7.0	100.0	1
Progesterone receptor CHEMBL208	IC50	6.89	6.89	128.8	1
Ishikawa CHEMBL614649	IC50	6.77	5.1867	170.0	9
Cytochrome P450 3A4 CHEMBL340	Ki	6.7	6.7	200.0	1
Steroid hormone receptor ERR1 CHEMBL3429	IC50	6.7	6.7	200.0	1
5-hydroxytryptamine receptor 2C CHEMBL225	Ki	6.62	6.62	241.0	1
Estrogen receptor CHEMBL2093866	IC50	6.55	5.9989	280.0	9
D(3) dopamine receptor CHEMBL234	Ki	6.44	6.44	364.0	1
Unchecked CHEMBL612545	Ki	6.42	5.842	381.0	5
5-hydroxytryptamine receptor 2C CHEMBL225	IC50	6.34	6.34	460.0	1
Unchecked CHEMBL612545	IC50	6.3	5.2263	503.0	16
EL4 CHEMBL614293	IC50	6.27	6.27	535.0	1
Muscarinic acetylcholine receptor M3 CHEMBL245	Ki	6.2	6.2	630.0	1
Muscarinic acetylcholine receptor M4 CHEMBL1821	Ki	6.17	6.17	672.0	1
Muscarinic acetylcholine receptor M1 CHEMBL216	Ki	6.17	6.17	681.0	1
Alpha-2A adrenergic receptor CHEMBL1867	Ki	6.14	6.14	726.0	1
Voltage-gated inwardly rectifying potassium channel KCNH2 CHEMBL240	Ki	6.1	6.1	792.2	1
Cytochrome P450 2B6 CHEMBL4729	Ki	6.05	6.05	900.0	1
Thromboxane-A synthase CHEMBL1835	IC50	6.04	6.04	916.0	1
Voltage-gated inwardly rectifying potassium channel KCNH2 CHEMBL240	IC50	6.01	5.905	967.0	2
Protein kinase C (PKC) CHEMBL2093867	IC50	6.0	5.35	1000.0	2
T47D CHEMBL614361	IC50	6.0	5.0843	1000.0	7
5-hydroxytryptamine receptor 6 CHEMBL3371	Ki	5.98	5.945	1041.0	2
D(3) dopamine receptor CHEMBL234	IC50	5.97	5.97	1072.0	1
Tyrosine-protein kinase Fyn CHEMBL1841	IC50	5.92	5.92	1195.0	1
Sodium-dependent serotonin transporter CHEMBL228	Ki	5.91	5.91	1240.0	1
Substance-K receptor CHEMBL2327	Ki	5.91	5.91	1223.0	1
5-hydroxytryptamine receptor 2B CHEMBL1833	Ki	5.88	5.88	1326.0	1
5-hydroxytryptamine receptor 2A CHEMBL224	Ki	5.86	5.86	1372.0	1
Sodium-dependent noradrenaline transporter CHEMBL222	Ki	5.84	5.84	1459.0	1
Sodium-dependent noradrenaline transporter CHEMBL222	IC50	5.83	5.83	1472.0	1
Sodium-dependent dopamine transporter CHEMBL238	Ki	5.83	5.83	1462.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	-	-	Mus musculus
CL	-	-	Homo sapiens
CL	-	-	Homo sapiens
CL	12.0	mL.min-1.kg-1	Homo sapiens
CL	33.0	mL.min-1.kg-1	Rattus norvegicus
CL	95.0	mL.min-1.kg-1	Rattus norvegicus
Cmax	296.0	nM	Homo sapiens
F	69.0	%	Rattus norvegicus
KA	2.1e-07	M	-
t1/2	-	-	Homo sapiens
T1/2	0.1483	hr	Mus musculus
T1/2	1.0	hr	Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
MCF7	EC50	=	0.11	nM	9.96	Effective dose for [3H]- estradiol against proliferation of MCF-7 cells	2769681
Estrogen receptor beta	Ki	=	0.51	nM	9.29	Displacement of [3H]estradiol from ERbeta after 4 hrs by scintillation counting	22582136
Anti-estrogen binding site (AEBS)	Kd	=	1.0	nM	9.0	Binding affinity towards antiestrogen binding site AEBS	12620065
Estrogen receptor	IC50	=	1.5	nM	8.82	Inhibition of estrogen receptor-alpha (unknown origin) by ELISA	30731397
Emopamil-binding protein-like	Ki	=	2.8	nM	8.55	Binding affinity to emopamil binding protein (unknown origin)	23199475
3-beta-hydroxysteroid-Delta(8),Delta(7)-isomerase	Ki	=	5.0	nM	8.3	Affinity for human EMP expressed in ERG2 deficient strain of Saccharomyces cerev...	16033255
Estrogen receptor	IC50	=	8.0	nM	8.1	Displacement of [3H]-E2 from human ER-alpha incubated for 16 to 20 hrs by liquid...	26896706
Estrogen receptor	IC50	=	8.4	nM	8.08	Displacement of radioligand from Estrogen receptor alpha	11965371
Sigma non-opioid intracellular receptor 1	Ki	=	8.714	nM	8.06	DRUGMATRIX: Sigma1 radioligand binding (ligand: [3H] Haloperidol)	-
MCF7	EC50	=	10.0	nM	8.0	Effective concentration against MCF-7 breast tumor cells using MCF-7 assay.	12825935
Estrogen receptor	Ki	=	11.9	nM	7.92	Inhibition of estradiol binding to estrogen receptor in Human Breast cancer cyto...	9216828
Anti-estrogen binding site (AEBS)	IC50	=	12.0	nM	7.92	Displacement of [3H]tamoxifen from antiestrogen binding site (AEBS)	2909731
MCF7	IC50	=	20.0	nM	7.7	Cytotoxicity against human MCF7 cells assessed as inhibition of cell growth meas...	33479633
Sigma non-opioid intracellular receptor 1	IC50	=	21.0	nM	7.68	DRUGMATRIX: Sigma1 radioligand binding (ligand: [3H] Haloperidol)	-
Estrogen receptor	IC50	=	24.55	nM	7.61	Binding affinity to ERalpha receptor (unknown origin)	26407012
MCF7	IC50	=	27.0	nM	7.57	Cytotoxicity against human MCF7 cells after 48 hrs by SRB assay	22472045
MCF7	IC50	=	30.0	nM	7.52	Antiproliferative activity against human MCF7 cells assessed as inhibition of ce...	33257172
Estrogen receptor	Ki	=	31.19	nM	7.51	Displacement of [2,4,6,7-3H]estradiol from human ERalpha expressed in HeLa cells...	20621492
Ishikawa	EC50	=	33.0	nM	7.48	Concentration of compound required to induce 50 % of the maximum stimulation of ...	8201587
Estrogen receptor	Ki	=	34.4	nM	7.46	Apparent inhibition constant for estrogen receptor in Human uterine cytosol in 3...	9216828

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL3885861	Rattus norvegicus	1418
-	10.6019/CHEMBL3885881	Rattus norvegicus	841
32898794	10.1016/j.ejmech.2020.112775	Unchecked	25
-	10.6019/CHEMBL4295262	Unchecked	24
6431104	10.1021/jm00374a021	Rattus norvegicus	18
16472241	10.2174/1570163043334794	Hepatotoxicity	18
2995668	10.1021/jm00148a022	Estrogen receptor	14
22194678	10.1371/journal.pcbi.1002310	Hepatotoxicity	14
9216828	10.1021/jm970095o	Estrogen receptor	13
18024584	10.1073/pnas.0709695104	H4	12
15646539	10.1016/s0399-8320(04)95062-2	Unchecked	11
21777996	10.1016/j.ejmech.2011.07.005	Albumin	9
3950918	10.1021/jm00153a013	MCF7	8
31884407	10.1016/j.ejmech.2019.111986	MCF7	8
3806590	10.1021/jm00384a022	MCF7	8
25740159	10.1016/j.bmcl.2015.02.013	No relevant target	8
9003514	10.1021/jm9606352	Rattus norvegicus	8
3950918	10.1021/jm00153a013	Rattus norvegicus	8
27128175	10.1016/j.ejmech.2016.03.090	HeLa	8
15646539	10.1016/s0399-8320(04)95062-2	NON-PROTEIN TARGET	8

Data from ChEMBL 36 via Core Engine