Compound Detail

CHEMBL135

ESTRADIOL

💊 Approved Drug

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💊 Approved Drug

C[C@]12CC[C@@H]3c4ccc(O)cc4CC[C@H]3[C@@H]1CC[C@@H]2O

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL135
Name	ESTRADIOL
Phase	Approved
Structure Type	MOL
InChI Key	VOXZDWNPVJITMN-ZBRFXRBCSA-N
Therapeutic	✓ Yes

Known Names

17 .beta.-estradiol 17-.beta.-oestradiol 17-beta-oestradiol 17.beta.-estradiol 17beta-estradiol Adgyn estro Aerodiol Alora Aquagen Bedol Climara Dermestril 100 +18 more

Targets

397

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

272.4

MW (Da)

3.61

ALogP

HBA

HBD

40.5

PSA (Å²)

0.76

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	1975
Availability	Prescription
Chirality	Single Enantiomer

Routes of Administration

Oral Topical

Flags

Black Box Warning Natural Product

USAN Stem

estr-

Extended Properties

Molecular Formula	C18H24O2
MW	272.39
Aromatic Rings	1
Heavy Atoms	20
NP-Likeness	2.24

Mechanism of Action

Mechanism	Action Type	Target	Direct	Efficacy
Estrogen receptor alpha agonist	AGONIST	Estrogen receptor	✓	✓

Indications

Atrophic Vaginitis Atrophic Vaginitis Atrophy Breast Neoplasms Breast Neoplasms Breast Neoplasms Dyspareunia Hypogonadism Menopause Osteoporosis Osteoporosis, Postmenopausal Primary Ovarian Insufficiency Primary Ovarian Insufficiency Amenorrhea Anorexia Nervosa Bone Diseases, Metabolic Coronary Disease Dysmenorrhea Endometriosis Heart Diseases

ATC Classification

G03CA03

estradiol

Level 1: GENITO URINARY SYSTEM AND SEX HORMONES

Level 2: SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM

Drug Warnings

Black Box Warning

neurotoxicity

Country: United States

Black Box Warning

cardiotoxicity

Country: United States

Black Box Warning

vascular toxicity

Country: United States

Black Box Warning

carcinogenicity

Country: United States

Black Box Warning

respiratory toxicity

Country: United States

Activity Summary

IC50 180 meas. best 11.0

EC50 142 meas. best 11.0

Ki 43 meas. best 10.82

Kd 32 meas. best 9.7

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
MCF7 CHEMBL387	EC50	11.0	10.2375	0.0	4
Estrogen receptor beta CHEMBL242	EC50	11.0	9.3596	0.0	50
Ishikawa CHEMBL614649	EC50	11.0	11.0	0.0	1
Estrogen receptor CHEMBL2093866	IC50	11.0	9.1575	0.0	8
Estrogen receptor CHEMBL2093866	EC50	11.0	9.6525	0.0	8
Estrogen receptor CHEMBL206	EC50	11.0	9.3964	0.0	53
Estrogen receptor beta CHEMBL242	Ki	10.82	9.618	0.0	10
Unchecked CHEMBL612545	EC50	10.71	10.1233	0.0	3
Estrogen receptor beta CHEMBL242	IC50	10.34	8.6832	0.0	57
SK-BR-3 CHEMBL613834	IC50	10.0	10.0	0.1	1
Estrogen receptor CHEMBL206	IC50	9.97	8.6499	0.1	68
Estrogen receptor CHEMBL2093866	Ki	9.95	9.778	0.1	5
Estrogen receptor beta CHEMBL3021	EC50	9.85	9.85	0.1	1
Estrogen receptor CHEMBL206	Ki	9.8	9.0714	0.2	14
Estrogen receptor CHEMBL206	Kd	9.7	9.357	0.2	10
G-protein coupled estrogen receptor 1 CHEMBL5872	EC50	9.52	9.52	0.3	2
MCF7 CHEMBL387	IC50	9.49	6.9875	0.3	4
Estrogen receptor CHEMBL2094114	IC50	9.45	9.095	0.4	2
Estrogen receptor CHEMBL2093866	Kd	9.37	9.2244	0.4	9
Estrogen receptor beta CHEMBL242	Kd	9.3	9.0656	0.5	9
Unchecked CHEMBL612545	Kd	9.3	9.3	0.5	1
HeLa CHEMBL399	EC50	9.15	9.15	0.7	1
Sex hormone-binding globulin CHEMBL3305	Kd	8.83	8.83	1.5	1
Estrogen receptor beta CHEMBL3021	IC50	8.77	8.735	1.7	2
Estrogen receptor CHEMBL2724	IC50	8.72	8.71	1.9	2
Estrogen receptor CHEMBL3065	IC50	8.66	8.66	2.2	1
Estrogen receptor beta CHEMBL2995	IC50	8.64	8.64	2.3	1
Unchecked CHEMBL612545	IC50	8.64	8.64	2.3	2
G-protein coupled estrogen receptor 1 CHEMBL5872	Ki	8.57	8.35	2.7	3
Steroid hormone receptor ERR2 CHEMBL3751	IC50	8.49	8.275	3.2	2
Steroid hormone receptor ERR1 CHEMBL3429	IC50	8.44	8.33	3.6	2
Steroid hormone receptor ERR2 CHEMBL3751	EC50	8.34	8.34	4.6	1
Aldehyde oxidase CHEMBL3257	IC50	8.3	7.7	5.0	2
Estrogen receptor CHEMBL2094114	EC50	8.24	8.24	5.7	1
Steroid hormone receptor ERR1 CHEMBL3429	EC50	8.23	8.23	5.9	1
Androgen receptor CHEMBL1871	IC50	7.72	7.6733	19.1	3
Sex hormone-binding globulin CHEMBL3305	IC50	7.3	7.3	50.0	1
Androgen receptor CHEMBL3072	Ki	6.63	6.63	235.0	1
Androgen receptor CHEMBL3072	IC50	6.45	6.42	353.0	2
Aldehyde oxidase CHEMBL3257	Ki	6.06	5.71	870.0	2
Solute carrier family 22 member 3 CHEMBL1770033	IC50	5.96	5.96	1100.0	1
Sulfotransferase 1A1 CHEMBL1743291	Kd	5.92	5.78	1200.0	2
Cytochrome P450 1B1 CHEMBL4878	Ki	5.72	5.72	1900.0	1
Hepatocyte CHEMBL613690	EC50	5.72	5.72	1900.0	1
Solute carrier family 22 member 3 CHEMBL2073673	IC50	5.54	5.54	2880.0	1
Aldehyde oxidase 1 CHEMBL1641355	Ki	5.52	5.52	3000.0	1
Cytochrome P450 2B6 CHEMBL4729	EC50	5.39	5.39	4100.0	1
Progesterone receptor CHEMBL1909044	Ki	5.37	5.37	4247.0	1
Solute carrier organic anion transporter family member 1A1 CHEMBL1781859	Ki	5.33	5.33	4700.0	1
Sodium-dependent serotonin transporter CHEMBL228	Ki	5.24	5.24	5714.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	0.236	ng.hr.mL-1	Homo sapiens
AUC	0.732	ng.hr.mL-1	Homo sapiens
AUC	0.504	ng.hr.mL-1	Homo sapiens
AUC	28.0	ng.hr.mL-1	Canis lupus familiaris
Cavg	9.8	pg/mL	Homo sapiens
Cavg	30.5	pg/mL	Homo sapiens
Cavg	21.0	pg/mL	Homo sapiens
Cavg	34.0	pg/mL	Homo sapiens
Cavg	72.0	pg/mL	Homo sapiens
Cavg	57.0	pg/mL	Homo sapiens
Cavg	104.0	pg/mL	Homo sapiens
Cavg	89.0	pg/mL	Homo sapiens
CL	30.0	mL.min-1.kg-1	Homo sapiens
Cmax	0.05397	nM	Homo sapiens
Cmax	0.1891	nM	Homo sapiens
Cmax	0.1043	nM	Homo sapiens
Cmax	0.1689	nM	Homo sapiens
Cmax	0.3634	nM	Homo sapiens
Cmax	0.3047	nM	Homo sapiens
Cmax	0.5323	nM	Homo sapiens
Cmax	0.4883	nM	Homo sapiens
Cmax	0.232	nM	Homo sapiens
Cmax	0.2041	nM	Homo sapiens
Cmax	279.01	nM	Canis lupus familiaris
Cmin(80hr)	41.0	pg/mL	Homo sapiens
Cmin(84hr)	30.0	pg/mL	Homo sapiens
Cmin(84hr)	60.0	pg/mL	Homo sapiens
Cmin(84hr)	85.0	pg/mL	Homo sapiens
Cmin(84hr)	90.0	pg/mL	Homo sapiens
Css-12w	8.0	pg/mL	Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
MCF7	EC50	=	0.01	nM	11.0	Effective concentration against MCF-7 breast tumor cells using MCF-7 assay.	12825935
Ishikawa	EC50	=	0.01	nM	11.0	Concentration of compound required to induce 50 % of the maximum stimulation of ...	8201587
Estrogen receptor	IC50	=	0.01	nM	11.0	In vitro inhibition of estrogen-stimulated MCF-7 cell proliferation	10098655
Estrogen receptor beta	EC50	=	0.01	nM	11.0	Activation of human ERbeta expressed in human U2-OS cells by luciferase reporter...	23043242
Estrogen receptor	EC50	=	0.01	nM	11.0	Effect on ERalpha in MCF7 cell line transfected with ER responsive luciferase re...	16219463
Estrogen receptor	EC50	=	0.01	nM	11.0	Percent agonistic activity for estrogen-induced pS2 expression in MCF-7 cells	12749898
Estrogen receptor beta	Ki	=	0.015	nM	10.82	Inhibition Assay: The method employed was adapted from the scientific literature...	-
Estrogen receptor beta	Ki	=	0.015	nM	10.82	Binding Assay: The method employed was adapted from the scientific literature an...	-
Estrogen receptor beta	Ki	=	0.015	nM	10.82	Binding Assay: The method employed was adapted from the scientific literature an...	-
Estrogen receptor beta	Ki	=	0.015	nM	10.82	Inhibition Assay: The method employed was adapted from the scientific literature...	-
Estrogen receptor beta	Ki	=	0.015	nM	10.82	In Vitro Assay: The method employed was adapted from the scientific literature a...	-
Estrogen receptor	EC50	=	0.018	nM	10.74	Transcriptional potency (EC50) at Human estrogen receptor alpha	11708925
Estrogen receptor	EC50	=	0.019	nM	10.72	Transcriptional activation of estrogen receptor alpha in U2OS cell using estroge...	16162002
Unchecked	EC50	=	0.0196	nM	10.71	Estrogenic activity at estrogen receptor in human MCF7:D5L cells co-expressing E...	22464681
Estrogen receptor	EC50	=	0.02	nM	10.7	Activation of estrogen response element in HeLa cells stably transfected with hu...	11906280
MCF7	EC50	=	0.02	nM	10.7	Effective dose for [3H]- estradiol against proliferation of MCF-7 cells	2769681
Estrogen receptor beta	EC50	=	0.02	nM	10.7	Activation of human ERbeta assessed as induction of transcriptional activation i...	30967304
Estrogen receptor beta	EC50	=	0.022	nM	10.66	Agonist activity at full length ERbeta (unknown origin) after 24 hrs by cell bas...	30144697
Estrogen receptor beta	EC50	=	0.022	nM	10.66	Agonist activity at full length human ERbeta receptor assessed as transcriptiona...	32912438
Estrogen receptor beta	EC50	=	0.022	nM	10.66	Agonist activity at estrogen receptor beta (unknown origin) after 22 hrs by cell...	29741891

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL3885881	Rattus norvegicus	459
-	10.6019/CHEMBL4689842	HEK-293T	346
-	10.6019/CHEMBL4689842	Fibroblast	345
-	10.6019/CHEMBL4689842	U2OS	345
17571867	10.1021/jm070242a	Mus musculus	27
15771445	10.1021/jm040842z	Estrogen receptor	18
16472241	10.2174/1570163043334794	Hepatotoxicity	18
19004530	10.1016/j.ejmech.2008.09.036	Mus musculus	15
22194678	10.1371/journal.pcbi.1002310	Hepatotoxicity	14
3746826	10.1021/jm00159a044	Estrogen receptor	14
19386502	10.1016/j.bmc.2009.03.057	Mus musculus	12
15646539	10.1016/s0399-8320(04)95062-2	Unchecked	11
30109010	10.1039/C8MD00109J	Rattus norvegicus	10
22464681	10.1016/j.bmc.2012.03.012	Unchecked	10
2995668	10.1021/jm00148a022	Estrogen receptor	9
30109010	10.1039/C8MD00109J	I-kappa-B kinase	9
15646539	10.1016/s0399-8320(04)95062-2	NON-PROTEIN TARGET	8
9216828	10.1021/jm970095o	Estrogen receptor	8
26795112	10.1016/j.bmc.2015.12.045	Unchecked	8
12467635	10.1016/s0960-894x(02)00847-8	Rattus norvegicus	7

Data from ChEMBL 36 via Core Engine