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Details

Stereochemistry ABSOLUTE
Molecular Formula C24H32O4
Molecular Weight 384.5085
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ESTRADIOL DIPROPIONATE

SMILES

[H][C@@]12CC[C@H](OC(=O)CC)[C@@]1(C)CC[C@]3([H])C4=C(CC[C@@]23[H])C=C(OC(=O)CC)C=C4

InChI

InChIKey=JQIYNMYZKRGDFK-RUFWAXPRSA-N
InChI=1S/C24H32O4/c1-4-22(25)27-16-7-9-17-15(14-16)6-8-19-18(17)12-13-24(3)20(19)10-11-21(24)28-23(26)5-2/h7,9,14,18-21H,4-6,8,10-13H2,1-3H3/t18-,19-,20+,21+,24+/m1/s1

HIDE SMILES / InChI

Molecular Formula C24H32O4
Molecular Weight 384.5085
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: Description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/020375s027lbl.pdf

Estradiol an aromatized C18 steroid with hydroxyl group at 3-beta- and 17-beta-position. Estradiol-17-beta is the most potent form of mammalian estrogenic steroids. In humans, it is produced primarily by the cyclic ovaries and the placenta. It is also produced by the adipose tissue of men and postmenopausal women. The 17-alpha-isomer of estradiol binds weakly to estrogen receptors (receptors, estrogen) and exhibits little estrogenic activity in estrogen-responsive tissues. Estradiol enters target cells freely (e.g., female organs, breasts, hypothalamus, pituitary) and interacts with a target cell receptor. When the estrogen receptor has bound its ligand it can enter the nucleus of the target cell, and regulate gene transcription which leads to formation of messenger RNA. The mRNA interacts with ribosomes to produce specific proteins that express the effect of estradiol upon the target cell. Estradiol is used for the treatment of urogenital symptoms associated with post-menopausal atrophy of the vagina (such as dryness, burning, pruritus and dyspareunia) and/or the lower urinary tract (urinary urgency and dysuria). Estradiol is marketed under the brand name Climara (among others), indicated for: the treatment of moderate to severe vasomotor symptoms due to menopause, treatment of symptoms of vulvar and vaginal atrophy due to menopause, treatment of hypoestrogenism due to hypogonadism, castration or primary ovarian failure and prevention of postmenopausal osteoporosis.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P08842
Gene ID: 412.0
Gene Symbol: STS
Target Organism: Homo sapiens (Human)
0.0084 nM [EC50]
1.4 nM [EC50]
19.1 nM [IC50]
0.13 nM [Ki]
0.09 nM [Kd]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
CLIMARA

Approved Use

Climara is an estrogen indicated for: •Treatment of Moderate to Severe Vasomotor Symptoms due to Menopause •Treatment of Moderate to Severe Symptoms of Vulvar and Vaginal Atrophy due to Menopause •Treatment of Hypoestrogenism due to Hypogonadism, Castration or Primary Ovarian Failure •Prevention of Postmenopausal Osteoporosis

Launch Date

1974
Preventing
CLIMARA

Approved Use

Climara is an estrogen indicated for: •Treatment of Moderate to Severe Vasomotor Symptoms due to Menopause •Treatment of Moderate to Severe Symptoms of Vulvar and Vaginal Atrophy due to Menopause •Treatment of Hypoestrogenism due to Hypogonadism, Castration or Primary Ovarian Failure •Prevention of Postmenopausal Osteoporosis

Launch Date

1974
Primary
CLIMARA

Approved Use

Climara is an estrogen indicated for: •Treatment of Moderate to Severe Vasomotor Symptoms due to Menopause •Treatment of Moderate to Severe Symptoms of Vulvar and Vaginal Atrophy due to Menopause •Treatment of Hypoestrogenism due to Hypogonadism, Castration or Primary Ovarian Failure •Prevention of Postmenopausal Osteoporosis

Launch Date

1974
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
14.7 pg/mL
0.25 mg 1 times / day steady-state, topical
dose: 0.25 mg
route of administration: Topical
experiment type: STEADY-STATE
co-administered:
ESTRADIOL plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: FEMALE
food status: UNKNOWN
92 pg/mL
0.05 mg 1 times / day multiple, topical
dose: 0.05 mg
route of administration: Topical
experiment type: MULTIPLE
co-administered:
ESTRADIOL plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: FEMALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
236 pg × h/mL
0.25 mg 1 times / day steady-state, topical
dose: 0.25 mg
route of administration: Topical
experiment type: STEADY-STATE
co-administered:
ESTRADIOL plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: FEMALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
10 h
0.25 mg 1 times / day steady-state, topical
dose: 0.25 mg
route of administration: Topical
experiment type: STEADY-STATE
co-administered:
ESTRADIOL plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: FEMALE
food status: UNKNOWN
1.75 h
0.05 mg 1 times / day multiple, topical
dose: 0.05 mg
route of administration: Topical
experiment type: MULTIPLE
co-administered:
ESTRADIOL plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: FEMALE
food status: UNKNOWN
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



Drug as perpetrator​

Drug as perpetrator​

Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
minor
minor
minor
minor
minor
minor
no
no
no
no
no
no
no
no
no
yes [Km 7 uM]
yes
yes
yes
yes
yes
yes
yes
yes
yes
yes
yes
yes
yes
yes
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Sulfation of estrone and 17 beta-estradiol in human liver. Catalysis by thermostable phenol sulfotransferase and by dehydroepiandrosterone sulfotransferase.
1992 May-Jun
[The effect of adrenaline and 17beta-estradiol sulfate on transmembrane potentials of guinea pig cardiomyocytes].
1996 Dec
Estrogenic and antiestrogenic activities of 16alpha- and 2-hydroxy metabolites of 17beta-estradiol in MCF-7 and T47D human breast cancer cells.
1998 Dec
Suppressive effects of estradiol on 2,3,7,8-tetrachlorodibenzo-p-dioxin-mediated transcriptional activation of murine Cyp1a-1 in mouse hepatoma Hepa 1c1c7 cells.
1998 Nov 27
Interaction of estrogenic chemicals and phytoestrogens with estrogen receptor beta.
1998 Oct
Effects of 17beta-estradiol on tachycardia-induced changes of atrial refractoriness and cisapride-induced ventricular arrhythmia.
1999 Apr
Differential regulation of c-fos expression in estrogen-induced hamster renal tumors compared with kidney not due to creation of an estrogen-response element by point mutation in the gene's flanking sequence.
1999 Apr
Estrogenicity of bisphenol A in a human endometrial carcinoma cell line.
1999 Apr 25
Estrogen and aryl hydrocarbon responsiveness of ECC-1 endometrial cancer cells.
1999 Apr 25
Growth stimulation of a rat pituitary cell line MtT/E-2 by environmental estrogens in vitro and in vivo.
1999 Aug
Lack of mutations in DNA polymerase beta of estradiol-induced hamster kidney tumors: sequence of hamster DNA polymerase beta cDNA.
1999 Aug
Amphibians as a model to study endocrine disruptors: II. Estrogenic activity of environmental chemicals in vitro and in vivo.
1999 Jan 12
Estrogen receptor activation via activation function 2 predicts agonism of xenoestrogens in normal and neoplastic cells of the uterine myometrium.
1999 Jul 1
Short-term effects of high-dose 17beta-estradiol in postmenopausal PD patients: a crossover study.
1999 Jul 13
Estrogenic potential of certain pyrethroid compounds in the MCF-7 human breast carcinoma cell line.
1999 Mar
Endometrial cancer after combined hormone replacement therapy.
1999 Mar 15
Sex steroids and odorants modulate gonadotropin-releasing hormone secretion in primary cultures of human olfactory cells.
1999 Nov
Effects of environmental estrogens on tumor necrosis factor alpha-mediated apoptosis in MCF-7 cells.
1999 Nov
Circadian expression of the steroid 15 alpha-hydroxylase (Cyp2a4) and coumarin 7-hydroxylase (Cyp2a5) genes in mouse liver is regulated by the PAR leucine zipper transcription factor DBP.
1999 Oct
Acute activation of Maxi-K channels (hSlo) by estradiol binding to the beta subunit.
1999 Sep 17
Involvement of cyclooxygenase 2 in the protective effect of 17beta-estradiol on hypercholesterolemic rabbit aorta.
2000 Aug 28
The aryl hydrocarbon receptor interacts with estrogen receptor alpha and orphan receptors COUP-TFI and ERRalpha1.
2000 Jan 1
Intrinsic alcohol dehydrogenase and hydroxysteroid dehydrogenase activities of human mitochondrial short-chain L-3-hydroxyacyl-CoA dehydrogenase.
2000 Jan 1
Induction of uterine adenocarcinoma in CD-1 mice by catechol estrogens.
2000 Jan 15
Crosstalk between estrogen receptor alpha and the aryl hydrocarbon receptor in breast cancer cells involves unidirectional activation of proteasomes.
2000 Jul 28
Estradiol enhances the resistance of LDL to oxidation by stabilizing apoB-100 conformation.
2000 Nov 14
Resveratrol acts as a mixed agonist/antagonist for estrogen receptors alpha and beta.
2000 Oct
Effects of arsenite on estrogen receptor-alpha expression and activity in MCF-7 breast cancer cells.
2000 Oct
Constitutive expression of the steroid sulfatase gene supports the growth of MCF-7 human breast cancer cells in vitro and in vivo.
2001 Apr
Vitellogenin-induced pathology in male summer flounder (Paralichthys dentatus).
2001 Feb
Use of salivary biomarkers in biobehavioral research: cotton-based sample collection methods can interfere with salivary immunoassay results.
2001 Feb
Female steroid hormones modulate receptors for nerve growth factor in rat dorsal root ganglia.
2001 Jan
Follicle selection in cattle: role of luteinizing hormone.
2001 Jan
Comparison of histological compositions and apoptosis in canine spontaneous benign prostatic hyperplasia treated with androgen suppressive agents chlormadinone acetate and finasteride.
2001 Jan
Sex steroid hormones enhance immune function in male and female Siberian hamsters.
2001 Jan
Rapid and reversible inhibition of brain aromatase activity.
2001 Jan
Enhanced multispecificity of arabidopsis vacuolar multidrug resistance-associated protein-type ATP-binding cassette transporter, AtMRP2.
2001 Mar 23
Sulfonation of 17beta-estradiol and inhibition of sulfotransferase activity by polychlorobiphenylols and celecoxib in channel catfish, Ictalurus punctatus.
2007 Mar 10
Effects of Exposure to Estradiol Benzoate or Flutamide at the Weaning Age on Expression of Connexins in the Caudal Epididymis of Adult Rat.
2016 Dec
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: Estradiol benzoate is not approved by the FDA for use in humans in the United States.
Unknown
Route of Administration: Unknown
Estradiol-3-sulfate (E2SO4) infused intracerebroventricularly (icv) significantly increased plasma adrenocorticotropic hormone (ACTH) and cortisol concentrations. All minipumps in the treated fetuses were filled with E2SO4 in the vehicle (water) and minipumps in the control fetuses were filled with vehicle only. These minipumps deliver a constant infusion of 5 μL/h; the concentration of E2SO4 in infusates was therefore 8.33 μg/μL. It was concluded, that E2SO4 had complex actions on the fetal brain, which might involve deconjugation by steroid sulfatase. But that the net result of direct E2SO4 icv infusion was more complex than could be accounted for by infusion of E2 alone.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:12:26 GMT 2023
Edited
by admin
on Fri Dec 15 15:12:26 GMT 2023
Record UNII
NIG5418BXB
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ESTRADIOL DIPROPIONATE
JAN   MART.   MI   WHO-DD  
Common Name English
OVOCYCLIN DIPROPIONATE
Brand Name English
PROGYNON-DP
Brand Name English
DIOVOCYLIN
Brand Name English
Estradiol dipropionate [WHO-DD]
Common Name English
ESTRADIOL DIPROPIONATE [JAN]
Common Name English
AGOFOLLIN
Brand Name English
DIMENFORMON DIPROPIONATE
Brand Name English
ESTRADIOL DIPROPIONATE [MI]
Common Name English
DIPROSTRON
Brand Name English
ESTRADIOL DIPROPIONATE [MART.]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C478
Created by admin on Fri Dec 15 15:12:26 GMT 2023 , Edited by admin on Fri Dec 15 15:12:26 GMT 2023
Code System Code Type Description
MERCK INDEX
m5028
Created by admin on Fri Dec 15 15:12:26 GMT 2023 , Edited by admin on Fri Dec 15 15:12:26 GMT 2023
PRIMARY Merck Index
ChEMBL
CHEMBL1697791
Created by admin on Fri Dec 15 15:12:26 GMT 2023 , Edited by admin on Fri Dec 15 15:12:26 GMT 2023
PRIMARY
EPA CompTox
DTXSID8023000
Created by admin on Fri Dec 15 15:12:26 GMT 2023 , Edited by admin on Fri Dec 15 15:12:26 GMT 2023
PRIMARY
MESH
C023482
Created by admin on Fri Dec 15 15:12:26 GMT 2023 , Edited by admin on Fri Dec 15 15:12:26 GMT 2023
PRIMARY
SMS_ID
100000089590
Created by admin on Fri Dec 15 15:12:26 GMT 2023 , Edited by admin on Fri Dec 15 15:12:26 GMT 2023
PRIMARY
EVMPD
SUB22244
Created by admin on Fri Dec 15 15:12:26 GMT 2023 , Edited by admin on Fri Dec 15 15:12:26 GMT 2023
PRIMARY
WIKIPEDIA
Estradiol dipropionate
Created by admin on Fri Dec 15 15:12:26 GMT 2023 , Edited by admin on Fri Dec 15 15:12:26 GMT 2023
PRIMARY
DRUG CENTRAL
1060
Created by admin on Fri Dec 15 15:12:26 GMT 2023 , Edited by admin on Fri Dec 15 15:12:26 GMT 2023
PRIMARY
FDA UNII
NIG5418BXB
Created by admin on Fri Dec 15 15:12:26 GMT 2023 , Edited by admin on Fri Dec 15 15:12:26 GMT 2023
PRIMARY
NCI_THESAURUS
C29770
Created by admin on Fri Dec 15 15:12:26 GMT 2023 , Edited by admin on Fri Dec 15 15:12:26 GMT 2023
PRIMARY
CAS
113-38-2
Created by admin on Fri Dec 15 15:12:26 GMT 2023 , Edited by admin on Fri Dec 15 15:12:26 GMT 2023
PRIMARY
ECHA (EC/EINECS)
204-026-5
Created by admin on Fri Dec 15 15:12:26 GMT 2023 , Edited by admin on Fri Dec 15 15:12:26 GMT 2023
PRIMARY
PUBCHEM
8225
Created by admin on Fri Dec 15 15:12:26 GMT 2023 , Edited by admin on Fri Dec 15 15:12:26 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY