Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C18H24O2 |
Molecular Weight | 272.382 |
Optical Activity | ( + ) |
Defined Stereocenters | 5 / 5 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
C[C@]12CC[C@H]3[C@@H](CCC4=CC(O)=CC=C34)[C@@H]1CC[C@@H]2O
InChI
InChIKey=VOXZDWNPVJITMN-ZBRFXRBCSA-N
InChI=1S/C18H24O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-17,19-20H,2,4,6-9H2,1H3/t14-,15-,16+,17+,18+/m1/s1
Molecular Formula | C18H24O2 |
Molecular Weight | 272.382 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 5 / 5 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/11250930http://www.drugbank.ca/drugs/DB00783https://pubchem.ncbi.nlm.nih.gov/compound/222757Curator's Comment: description was created based on several sources, including
https://books.google.ru/books?id=68n6f1Nw6EEC&pg=PA64&redir_esc=y#v=onepage&q&f=false | https://www.fda.gov/downloads/AnimalVeterinary/Products/ApprovedAnimalDrugProducts/FOIADrugSummaries/ucm116143.pdf | https://www.fda.gov/downloads/AnimalVeterinary/Products/ApprovedAnimalDrugProducts/FOIADrugSummaries/UCM338208.pdf
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11250930http://www.drugbank.ca/drugs/DB00783https://pubchem.ncbi.nlm.nih.gov/compound/222757
Curator's Comment: description was created based on several sources, including
https://books.google.ru/books?id=68n6f1Nw6EEC&pg=PA64&redir_esc=y#v=onepage&q&f=false | https://www.fda.gov/downloads/AnimalVeterinary/Products/ApprovedAnimalDrugProducts/FOIADrugSummaries/ucm116143.pdf | https://www.fda.gov/downloads/AnimalVeterinary/Products/ApprovedAnimalDrugProducts/FOIADrugSummaries/UCM338208.pdf
Estradiol benzoate is the synthetic benzoate ester of estradiol, a steroid sex hormone vital to the maintenance of fertility and secondary sexual characteristics in females. As the primary, most potent estrogen hormone produced by the ovaries, estradiol binds to and activates specific nuclear receptors. This agent exhibits mild anabolic and metabolic properties, and increases blood coagulability. Although estradiol benzoate is not approved by the FDA for use in humans in the United States, it is approved for veterinary use as a subdermal implant both alone (CELERIN®) and in combination with the anabolic steroid trenbolone acetate (SYNOVEX® Plus).
CNS Activity
Sources: https://books.google.ru/books?id=L4YQ50SbBnsC&pg=PA223&lpg=PA223&dq=estradiol+cross+blood+brain+barrier&source=bl&ots=1XAPNkXVXI&sig=_VCp7qIuyiwBe9cGGJDMvmdR8zg&hl=ru&sa=X&ved=0ahUKEwjjk6vD8r7PAhWCFywKHU3xD8c4ChDoAQg4MAU#v=onepage&q=estradiol%20cross%20blood%20brain%20barrier&f=false, retrieved fromhttps://www.ncbi.nlm.nih.gov/pubmed/25231731
Curator's Comment: Known to be CNS active in rats. Human data not available.
Originator
Sources: https://books.google.ru/books?id=_J2ti4EkYpkC&pg=PA1478&lpg=PA1478&dq=ESTRADIOL+year+introduced&source=bl&ots=N5lzH8ALwu&sig=V9zqvrxhsCojxBpoWmAWSN7AXcc&hl=ru&sa=X&ved=0ahUKEwj975678L7PAhVGXSwKHb5cBkUQ6AEISDAH#v=onepage&q=ESTRADIOL%20year%20introduced&f=false, retrieved from Pharmaceutical Manufacturing Encyclopedia, 3rd Edition : William Andrew Publishing, p.1475http://www.google.ru/patents/US2054271
Curator's Comment: Also in Ravina E., Kubinyi H. (2011). The Evolution of Drug Discovery: From Traditional Medicines to Modern Drugs. John Wiley & Sons. p. 175.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: P08842 Gene ID: 412.0 Gene Symbol: STS Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/11250930 |
|||
Target ID: CHEMBL206 Sources: http://www.drugbank.ca/drugs/DB00783 |
0.0084 nM [EC50] | ||
Target ID: CHEMBL242 Sources: http://www.drugbank.ca/drugs/DB00783 |
1.4 nM [EC50] | ||
Target ID: CHEMBL1871 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16309907 |
19.1 nM [IC50] | ||
Target ID: CHEMBL206 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/222757 |
0.13 nM [Ki] | ||
Target ID: CHEMBL242 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/222757 |
0.09 nM [Kd] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | CLIMARA Approved UseClimara 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 Date1974 |
|||
Preventing | CLIMARA Approved UseClimara 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 Date1974 |
|||
Primary | CLIMARA Approved UseClimara 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 Date1974 |
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Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 serum | Homo sapiens population: UNKNOWN age: ADULT sex: FEMALE food status: UNKNOWN |
|
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 serum | Homo sapiens population: UNKNOWN age: ADULT sex: FEMALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 serum | Homo sapiens population: UNKNOWN age: ADULT sex: FEMALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 serum | Homo sapiens population: UNKNOWN age: ADULT sex: FEMALE food status: UNKNOWN |
|
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 serum | Homo sapiens population: UNKNOWN age: ADULT sex: FEMALE food status: UNKNOWN |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: - |
yes | |||
Sources: https://pubs.acs.org/doi/abs/10.1021/mp900077q Page: - |
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: - |
minor | |||
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minor | |||
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minor | |||
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minor | |||
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minor | |||
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minor | |||
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no | |||
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no | |||
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no | |||
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no | |||
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no | |||
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no | |||
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no | |||
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no | |||
Page: - |
no | |||
Page: - |
yes [Km 7 uM] | |||
Page: - |
yes | |||
Page: - |
yes | |||
Sources: https://www.pnas.org/content/93/18/9776.short Page: - |
yes | |||
Page: - |
yes | |||
Page: - |
yes | |||
Page: - |
yes | |||
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yes | |||
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yes | |||
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yes | |||
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yes | |||
Page: - |
yes | |||
Page: - |
yes | |||
Page: - |
yes | |||
Page: - |
yes |
PubMed
Title | Date | PubMed |
---|---|---|
[The effect of adrenaline and 17beta-estradiol sulfate on transmembrane potentials of guinea pig cardiomyocytes]. | 1996 Dec |
|
Comparison of the ligand binding specificity and transcript tissue distribution of estrogen receptors alpha and beta. | 1997 Mar |
|
Estrogenic and antiestrogenic activities of 16alpha- and 2-hydroxy metabolites of 17beta-estradiol in MCF-7 and T47D human breast cancer cells. | 1998 Dec |
|
Interaction of estrogenic chemicals and phytoestrogens with estrogen receptor beta. | 1998 Oct |
|
Estrogen and aryl hydrocarbon responsiveness of ECC-1 endometrial cancer cells. | 1999 Apr 25 |
|
Lack of mutations in DNA polymerase beta of estradiol-induced hamster kidney tumors: sequence of hamster DNA polymerase beta cDNA. | 1999 Aug |
|
Short-term effects of high-dose 17beta-estradiol in postmenopausal PD patients: a crossover study. | 1999 Jul 13 |
|
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 |
|
Transcriptional activation of c-fos protooncogene by 17beta-estradiol: mechanism of aryl hydrocarbon receptor-mediated inhibition. | 1999 Sep |
|
Involvement of genotoxic effects in the initiation of estrogen-induced cellular transformation: studies using Syrian hamster embryo cells treated with 17beta-estradiol and eight of its metabolites. | 2000 Apr 1 |
|
Changes in serum and tissue zinc levels in sex hormone-induced prostatic carcinogenesis in the noble rat. | 2000 Nov-Dec |
|
Antiestrogenic effects of 2,3,7,8-tetrachlorodibenzo-p-dioxin in mouse uterus: critical role of the aryl hydrocarbon receptor in stromal tissue. | 2000 Oct |
|
NADPH- and hydroperoxide-supported 17beta-estradiol hydroxylation catalyzed by a variant form (432L, 453S) of human cytochrome P450 1B1. | 2000 Sep |
|
Use of salivary biomarkers in biobehavioral research: cotton-based sample collection methods can interfere with salivary immunoassay results. | 2001 Feb |
|
Regulation of progesterone receptors and decidualization in uterine stroma of the estrogen receptor-alpha knockout mouse. | 2001 Jan |
|
Metabolism of estradiol, ethynylestradiol, and moxestrol in rat uterus, vagina, and aorta: influence of sex steroid treatment. | 2001 Jan |
|
Rapid and reversible inhibition of brain aromatase activity. | 2001 Jan |
|
Oestrogen-induced changes in the synaptology of the monkey (Cercopithecus aethiops) arcuate nucleus during gonadotropin feedback. | 2001 Jan |
|
Stimulatory effect of clofibrate and gemfibrozil administration on the formation of fatty acid esters of estradiol by rat liver microsomes. | 2001 Jan |
|
Affinity labeling of rat glutathione S-transferase isozyme 1-1 by 17beta -iodoacetoxy-estradiol-3-sulfate. | 2001 Jan 19 |
|
Hormone binding by protein disulfide isomerase, a high capacity hormone reservoir of the endoplasmic reticulum. | 2001 Jan 5 |
|
The unusual binding properties of the third distinct teleost estrogen receptor subtype ERbetaa are accompanied by highly conserved amino acid changes in the ligand binding domain. | 2004 Jun |
|
Complex actions of estradiol-3-sulfate in late gestation fetal brain. | 2011 Jul |
|
Evaluation of Effects of Topical Estradiol Benzoate Application on Cutaneous Wound Healing in Ovariectomized Female Mice. | 2016 |
|
Changes in Expression of Connexin Isoforms in the Caudal Epididymis of Adult Sprague-Dawley Rats exposed to Estradiol Benzoate or Flutamide at the Neonatal Age. | 2016 Sep |
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21273638
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
Edited
Mon Mar 31 17:51:25 GMT 2025
by
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on
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Record UNII |
4TI98Z838E
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Record Status |
Validated (UNII)
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WHO-VATC |
QG03CA03
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CFR |
21 CFR 522.840
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231706
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25401-1
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2244-2
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admin on Mon Mar 31 17:51:25 GMT 2025 , Edited by admin on Mon Mar 31 17:51:25 GMT 2025
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1013
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admin on Mon Mar 31 17:51:25 GMT 2025 , Edited by admin on Mon Mar 31 17:51:25 GMT 2025
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200-023-8
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admin on Mon Mar 31 17:51:25 GMT 2025 , Edited by admin on Mon Mar 31 17:51:25 GMT 2025
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ESTRADIOL
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admin on Mon Mar 31 17:51:25 GMT 2025 , Edited by admin on Mon Mar 31 17:51:25 GMT 2025
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Estradiol
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admin on Mon Mar 31 17:51:25 GMT 2025 , Edited by admin on Mon Mar 31 17:51:25 GMT 2025
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DB00783
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admin on Mon Mar 31 17:51:25 GMT 2025 , Edited by admin on Mon Mar 31 17:51:25 GMT 2025
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SUB96040
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admin on Mon Mar 31 17:51:25 GMT 2025 , Edited by admin on Mon Mar 31 17:51:25 GMT 2025
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23965
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admin on Mon Mar 31 17:51:25 GMT 2025 , Edited by admin on Mon Mar 31 17:51:25 GMT 2025
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m5028
Created by
admin on Mon Mar 31 17:51:25 GMT 2025 , Edited by admin on Mon Mar 31 17:51:25 GMT 2025
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PRIMARY | Merck Index | ||
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Estradiol (medication)
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admin on Mon Mar 31 17:51:25 GMT 2025 , Edited by admin on Mon Mar 31 17:51:25 GMT 2025
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D004958
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admin on Mon Mar 31 17:51:25 GMT 2025 , Edited by admin on Mon Mar 31 17:51:25 GMT 2025
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20293
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admin on Mon Mar 31 17:51:25 GMT 2025 , Edited by admin on Mon Mar 31 17:51:25 GMT 2025
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DTXSID0020573
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admin on Mon Mar 31 17:51:25 GMT 2025 , Edited by admin on Mon Mar 31 17:51:25 GMT 2025
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406
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admin on Mon Mar 31 17:51:25 GMT 2025 , Edited by admin on Mon Mar 31 17:51:25 GMT 2025
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C478
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admin on Mon Mar 31 17:51:25 GMT 2025 , Edited by admin on Mon Mar 31 17:51:25 GMT 2025
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CHEMBL135
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admin on Mon Mar 31 17:51:25 GMT 2025 , Edited by admin on Mon Mar 31 17:51:25 GMT 2025
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1057
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admin on Mon Mar 31 17:51:25 GMT 2025 , Edited by admin on Mon Mar 31 17:51:25 GMT 2025
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50-28-2
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admin on Mon Mar 31 17:51:25 GMT 2025 , Edited by admin on Mon Mar 31 17:51:25 GMT 2025
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100000091739
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admin on Mon Mar 31 17:51:25 GMT 2025 , Edited by admin on Mon Mar 31 17:51:25 GMT 2025
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9895
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admin on Mon Mar 31 17:51:25 GMT 2025 , Edited by admin on Mon Mar 31 17:51:25 GMT 2025
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4TI98Z838E
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admin on Mon Mar 31 17:51:25 GMT 2025 , Edited by admin on Mon Mar 31 17:51:25 GMT 2025
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16469
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admin on Mon Mar 31 17:51:25 GMT 2025 , Edited by admin on Mon Mar 31 17:51:25 GMT 2025
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1250008
Created by
admin on Mon Mar 31 17:51:25 GMT 2025 , Edited by admin on Mon Mar 31 17:51:25 GMT 2025
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SUB07242MIG
Created by
admin on Mon Mar 31 17:51:25 GMT 2025 , Edited by admin on Mon Mar 31 17:51:25 GMT 2025
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4TI98Z838E
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admin on Mon Mar 31 17:51:25 GMT 2025 , Edited by admin on Mon Mar 31 17:51:25 GMT 2025
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4083
Created by
admin on Mon Mar 31 17:51:25 GMT 2025 , Edited by admin on Mon Mar 31 17:51:25 GMT 2025
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PRIMARY | RxNorm | ||
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SUB21195
Created by
admin on Mon Mar 31 17:51:25 GMT 2025 , Edited by admin on Mon Mar 31 17:51:25 GMT 2025
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3589
Created by
admin on Mon Mar 31 17:51:25 GMT 2025 , Edited by admin on Mon Mar 31 17:51:25 GMT 2025
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5757
Created by
admin on Mon Mar 31 17:51:25 GMT 2025 , Edited by admin on Mon Mar 31 17:51:25 GMT 2025
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Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT | |||
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BINDER->LIGAND |
BINDING
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SALT/SOLVATE -> PARENT |
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TARGET -> INHIBITOR |
BINDING
IC50
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SOLVATE->ANHYDROUS | |||
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METABOLIC ENZYME -> INHIBITOR |
IC50
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (HPLC)
USP
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TARGET -> AGONIST |
BINDING
IC50
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METABOLIC ENZYME -> SUBSTRATE | |||
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METABOLIC ENZYME -> SUBSTRATE | |||
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LABELED -> NON-LABELED |
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SUBSTANCE->BASIS OF STRENGTH |
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METABOLIC ENZYME -> SUBSTRATE | |||
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BINDER->LIGAND |
BINDING
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TARGET -> AGONIST |
Binding Assay
IC50
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TRANSPORTER -> INHIBITOR |
Related Record | Type | Details | ||
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PRODRUG -> METABOLITE ACTIVE | |||
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METABOLITE -> PARENT |
E2 is then extensively metabolized to estrone (E1) (15%), estrone sulfate (E1S) (65%), and other compounds.
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METABOLITE -> PARENT |
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PRODRUG -> METABOLITE ACTIVE |
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PRODRUG -> METABOLITE ACTIVE |
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METABOLITE -> PARENT |
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METABOLITE -> PARENT |
E2 is then extensively metabolized to estrone (E1) (15%), estrone sulfate (E1S) (65%), and other compounds.
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METABOLITE LESS ACTIVE -> PARENT | |||
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PRODRUG -> METABOLITE ACTIVE | |||
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PRODRUG -> METABOLITE ACTIVE | |||
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METABOLITE -> PARENT | |||
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PARENT -> METABOLITE ACTIVE | |||
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PARENT -> METABOLITE |
Metabolite produced by hydrolysis. Estramustine,s primary mechanism of antineoplastic action is inhibition of mitosis.
PLASMA
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METABOLITE -> PARENT |
MAJOR
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METABOLITE -> PARENT | |||
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METABOLITE -> PARENT |
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PRODRUG -> METABOLITE ACTIVE |
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Related Record | Type | Details | ||
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (TLC)
USP
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
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PARENT -> IMPURITY |
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IMPURITY -> PARENT |
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
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Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Tmax | PHARMACOKINETIC |
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ESTRADIOL VALERATE |
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Volume of Distribution | PHARMACOKINETIC |
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Biological Half-life | PHARMACOKINETIC |
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ESTRADIOL VALERATE |
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