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
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 |
|||
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: - |
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no | |||
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yes [Km 7 uM] | |||
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yes | |||
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yes | |||
Sources: https://www.pnas.org/content/93/18/9776.short Page: - |
yes | |||
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yes | |||
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yes | |||
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yes | |||
Page: - |
yes |
PubMed
Title | Date | PubMed |
---|---|---|
Sulfation of estrone and 17 beta-estradiol in human liver. Catalysis by thermostable phenol sulfotransferase and by dehydroepiandrosterone sulfotransferase. | 1992 May-Jun |
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[The effect of adrenaline and 17beta-estradiol sulfate on transmembrane potentials of guinea pig cardiomyocytes]. | 1996 Dec |
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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 |
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Rapid inhibition of rat brain mitochondrial proton F0F1-ATPase activity by estrogens: comparison with Na+, K+ -ATPase of porcine cortex. | 1999 Feb 26 |
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Amphibians as a model to study endocrine disruptors: II. Estrogenic activity of environmental chemicals in vitro and in vivo. | 1999 Jan 12 |
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Endometrial cancer after combined hormone replacement therapy. | 1999 Mar 15 |
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Steroid feedback on gonadotropin release and pituitary gonadotropin subunit mRNA in mice lacking a functional estrogen receptor alpha. | 1999 Oct |
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Acute activation of Maxi-K channels (hSlo) by estradiol binding to the beta subunit. | 1999 Sep 17 |
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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 |
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Involvement of cyclooxygenase 2 in the protective effect of 17beta-estradiol on hypercholesterolemic rabbit aorta. | 2000 Aug 28 |
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High concentrations of bisphenol A induce cell growth and prolactin secretion in an estrogen-responsive pituitary tumor cell line. | 2000 Feb 1 |
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The pregnane X receptor: a promiscuous xenobiotic receptor that has diverged during evolution. | 2000 Jan |
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Atheroprotective effect of estriol and estrone sulfate on human vascular smooth muscle cells. | 2000 Jan-Feb |
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Estradiol acts as a germ cell survival factor in the human testis in vitro. | 2000 May |
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Female sex steroids: effects upon microglial cell activation. | 2000 Nov 1 |
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Differential effects of xenoestrogens on coactivator recruitment by estrogen receptor (ER) alpha and ERbeta. | 2000 Nov 17 |
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Changes in serum and tissue zinc levels in sex hormone-induced prostatic carcinogenesis in the noble rat. | 2000 Nov-Dec |
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Resveratrol acts as a mixed agonist/antagonist for estrogen receptors alpha and beta. | 2000 Oct |
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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 |
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NADPH- and hydroperoxide-supported 17beta-estradiol hydroxylation catalyzed by a variant form (432L, 453S) of human cytochrome P450 1B1. | 2000 Sep |
|
Constitutive expression of the steroid sulfatase gene supports the growth of MCF-7 human breast cancer cells in vitro and in vivo. | 2001 Apr |
|
Use of salivary biomarkers in biobehavioral research: cotton-based sample collection methods can interfere with salivary immunoassay results. | 2001 Feb |
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Effects of follicle-stimulating hormone with and without luteinizing hormone on serum hormone concentrations, follicle growth, and intrafollicular estradiol and aromatase activity in gonadotropin-releasing hormone-immunized heifers. | 2001 Jan |
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Regulation of progesterone receptors and decidualization in uterine stroma of the estrogen receptor-alpha knockout mouse. | 2001 Jan |
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Pregnancy stimulates secretion of adrenocorticotropin and nitric oxide from peripheral bovine lymphocytes. | 2001 Jan |
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Metabolism of estradiol, ethynylestradiol, and moxestrol in rat uterus, vagina, and aorta: influence of sex steroid treatment. | 2001 Jan |
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Sex steroid hormones enhance immune function in male and female Siberian hamsters. | 2001 Jan |
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Rapid and reversible inhibition of brain aromatase activity. | 2001 Jan |
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Oestrogen-induced changes in the synaptology of the monkey (Cercopithecus aethiops) arcuate nucleus during gonadotropin feedback. | 2001 Jan |
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Stimulatory effect of clofibrate and gemfibrozil administration on the formation of fatty acid esters of estradiol by rat liver microsomes. | 2001 Jan |
|
Influence of gender and sex hormones on nicotine acute pharmacological effects in mice. | 2001 Jan |
|
Heat-shock factor-1, steroid hormones, and regulation of heat-shock protein expression in the heart. | 2001 Jan |
|
Evaluation of an EIA method for measuring serum levels of the estrogen metabolite 2-hydroxyestrone in adults. | 2001 Jan |
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Effects of heterocyclic amines with mammary gland carcinogenic potential on estrogenic response of uterus in ovariectomized rats. | 2001 Jan 10 |
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Estrogen decreases osteoclast formation by down-regulating receptor activator of NF-kappa B ligand (RANKL)-induced JNK activation. | 2001 Mar 23 |
|
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 |
|
Evaluation of Effects of Topical Estradiol Benzoate Application on Cutaneous Wound Healing in Ovariectomized Female Mice. | 2016 |
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.
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13736-4
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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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LOINC |
55858-5
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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LOINC |
83096-8
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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LOINC |
2242-6
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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LOINC |
2244-2
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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Code System | Code | Type | Description | ||
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1013
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 | |||
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200-023-8
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 | |||
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ESTRADIOL
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 | |||
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Estradiol
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 | |||
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DB00783
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 | |||
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SUB96040
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 | |||
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23965
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 | |||
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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)
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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D004958
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 | |||
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20293
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 | |||
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DTXSID0020573
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 | |||
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406
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 | |||
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C478
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 | |||
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CHEMBL135
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 | |||
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1057
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 | |||
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50-28-2
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 | |||
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100000091739
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 | |||
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9895
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 | |||
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4TI98Z838E
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 | |||
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16469
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 | |||
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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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PRIMARY | |||
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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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PRIMARY | |||
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4TI98Z838E
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 | |||
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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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PRIMARY | |||
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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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PRIMARY | |||
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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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PRIMARY |
ACTIVE MOIETY
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METABOLITE (PARENT)
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METABOLITE (PARENT)
METABOLITE (PARENT)
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METABOLITE LESS ACTIVE (PARENT)
PARENT (METABOLITE ACTIVE)
PARENT (METABOLITE)
PRODRUG (METABOLITE ACTIVE)
PRODRUG (METABOLITE ACTIVE)
PRODRUG (METABOLITE ACTIVE)
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PRODRUG (METABOLITE ACTIVE)
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