Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C18H22O2 |
Molecular Weight | 270.3661 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12CCC(=O)[C@@]1(C)CC[C@]3([H])C4=C(CC[C@@]23[H])C=C(O)C=C4
InChI
InChIKey=DNXHEGUUPJUMQT-CBZIJGRNSA-N
InChI=1S/C18H22O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-16,19H,2,4,6-9H2,1H3/t14-,15-,16+,18+/m1/s1
Molecular Formula | C18H22O2 |
Molecular Weight | 270.3661 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: http://www.drugfuture.com/chemdata/estrone.html | http://pubs.acs.org/doi/abs/10.1021/ja01159a529?journalCode=jacsat | http://pubs.acs.org/doi/abs/10.1021/ja00536a023https://www.ncbi.nlm.nih.gov/pubmed/27960570 | https://www.accessdata.fda.gov/cdrh_docs/pdf/K970915.pdfhttps://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=83dd22a0-7c59-11e6-84ff-424c58303031Curator's Comment: description was created based on several sources, including
http://www.drugbank.ca/drugs/DB00655
https://www.ncbi.nlm.nih.gov/pubmed/2011412
https://www.ncbi.nlm.nih.gov/pubmed/17943537
Sources: http://www.drugfuture.com/chemdata/estrone.html | http://pubs.acs.org/doi/abs/10.1021/ja01159a529?journalCode=jacsat | http://pubs.acs.org/doi/abs/10.1021/ja00536a023https://www.ncbi.nlm.nih.gov/pubmed/27960570 | https://www.accessdata.fda.gov/cdrh_docs/pdf/K970915.pdfhttps://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=83dd22a0-7c59-11e6-84ff-424c58303031
Curator's Comment: description was created based on several sources, including
http://www.drugbank.ca/drugs/DB00655
https://www.ncbi.nlm.nih.gov/pubmed/2011412
https://www.ncbi.nlm.nih.gov/pubmed/17943537
Estrone, one of the major mammalian estrogens, is an aromatized C18 steroid with a 3-hydroxyl group and a 17-ketone. It is produced in vivo from androstenedione or from testosterone via estradiol. It is produced primarily in the ovaries, placenta, and in peripheral tissues (especially adipose tissue) through conversion of adrostenedione. Estrone may be further metabolized to 16-alpha-hydroxyestrone, which may be reduced to estriol by estradiol dehydrogenase. It’s used as hameopatic in management of premenopausal and postmenopausal symptoms. In 1929, Butenandt isolated estrone from the urine of pregnant women. Estrone is known to be a carcinogen for human females as well as a cause of breast tenderness or pain, nausea, headache, hypertension, and leg cramps in the context of non-endogenous exposure. In men, estrone has been known to cause anorexia, nausea, vomiting, and erectile dysfunction. Estrone is relevant to health and disease states because of its conversion to estrone sulfate, a long-lived derivative. Estrone sulfate acts as a reservoir that can be converted as needed to the more active estradiol.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11105986
Curator's Comment: Estrone sulfate crossed the blood brain barrier in rats.
Originator
Sources: http://pubs.acs.org/doi/abs/10.1021/ja01159a529?journalCode=jacsathttps://www.ncbi.nlm.nih.gov/pubmed/22469359
Curator's Comment: Estrone is one of the hormones responsible for sexual development and function in females.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL206 |
7.0 nM [EC50] | ||
Target ID: CHEMBL206 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2011412 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Diagnostic | Unknown Approved UseUnknown |
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Diagnostic | Unknown Approved UseUnknown |
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Diagnostic | Unknown Approved UseUnknown |
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Diagnostic | Unknown Approved UseUnknown |
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Diagnostic | Unknown Approved UseUnknown |
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Diagnostic | Unknown Approved UseUnknown |
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Diagnostic | Unknown Approved UseUnknown |
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Diagnostic | Unknown Approved UseUnknown |
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Diagnostic | Unknown Approved UseUnknown |
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Primary | Estragyn Approved UseEstragyn Vaginal Cream is prescribed in the treatment of menopausal and post menopausal symptoms.
Estragyn Vaginal Cream should be prescribed with an appropriate dosage of a progestin for women with intact uteri to prevent endometrial hyperplasia/carcinoma. |
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Primary | Estragyn Approved UseEstragyn Vaginal Cream is prescribed in the treatment of menopausal and post menopausal symptoms.
Estragyn Vaginal Cream should be prescribed with an appropriate dosage of a progestin for women with intact uteri to prevent endometrial hyperplasia/carcinoma. |
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Primary | THEELIN Approved UseFor management of Menopausal and postmenopausal disorders |
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Palliative | Unknown Approved UseUnknown |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
733 pg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/908445/ |
0.5 mg single, vaginal dose: 0.5 mg route of administration: Vaginal experiment type: SINGLE co-administered: |
ESTRONE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
550 pg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/908445/ |
0.5 mg single, vaginal dose: 0.5 mg route of administration: Vaginal experiment type: SINGLE co-administered: |
ESTRONE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/908445/ |
0.5 mg single, vaginal dose: 0.5 mg route of administration: Vaginal experiment type: SINGLE co-administered: |
ESTRONE plasma | Homo sapiens population: UNHEALTHY 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 |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/15290871/ |
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
major | ||||
no | ||||
weak | ||||
weak | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes | weak (co-administration study) Comment: Coadministration with ketoconazole (CYP3A4 inhibitor) resulted in estrone expsoure increase of ~1.4 foold Sources: https://pubmed.ncbi.nlm.nih.gov/9625734/ |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
Reproducibility of plasma and urinary sex hormone levels in premenopausal women over a one-year period. | 1999 Dec |
|
Molecular cloning and characterization of a new multispecific organic anion transporter from rat brain. | 1999 May 7 |
|
15-ketodihydro-PGF2 alpha, progesterone and cortisol profiles in heifers after induction of parturition by injection of dexamethasone. | 2001 |
|
Home monitoring with the ClearPlan Easy Fertility Monitor for fertility awareness. | 2001 |
|
Futile cycling of estrone sulfate and estrone in the recirculating perfused rat liver preparation. | 2001 Apr |
|
Constitutive expression of the steroid sulfatase gene supports the growth of MCF-7 human breast cancer cells in vitro and in vivo. | 2001 Apr |
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Effects of testosterone precursor supplementation on intensive weight training. | 2001 Apr |
|
Aromatase inhibition reduces specifically one display of the ring dove courtship behavior. | 2001 Apr |
|
Effects of oral and transdermal estrogen replacement therapy on markers of coagulation, fibrinolysis, inflammation and serum lipids and lipoproteins in postmenopausal women. | 2001 Apr |
|
Comparative study on reduction of bone loss and lipid metabolism abnormality in ovariectomized rats by soy isoflavones, daidzin, genistin, and glycitin. | 2001 Apr |
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Serum concentrations of 17beta-estradiol and estrone after multiple-dose administration of percutaneous estradiol gel in symptomatic menopausal women. | 2001 Apr |
|
Measurement of urinary and fecal steroid metabolites during the ovarian cycle in captive and wild Japanese macaques, Macaca fuscata. | 2001 Apr |
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Up-regulation of steroid sulphatase activity in HL60 promyelocytic cells by retinoids and 1alpha,25-dihydroxyvitamin D3. | 2001 Apr 15 |
|
Do urinary estrogen metabolites reflect the differences in breast cancer risk between Singapore Chinese and United States African-American and white women? | 2001 Apr 15 |
|
Structural and functional consequences of inactivation of human glutathione S-transferase P1-1 mediated by the catechol metabolite of equine estrogens, 4-hydroxyequilenin. | 2001 Apr 17 |
|
Oral, water-soluble combined estrogen/calcium preparation for postmenopausal therapy. | 2001 Apr 20 |
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Identification of an amino acid residue in multidrug resistance protein 1 critical for conferring resistance to anthracyclines. | 2001 Apr 20 |
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Cholesterol sulfate: a new adhesive molecule for platelets. | 2001 Apr 24 |
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Equine estrogen metabolite 4-hydroxyequilenin induces DNA damage in the rat mammary tissues: formation of single-strand breaks, apurinic sites, stable adducts, and oxidized bases. | 2001 Dec |
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Estrogenic activity of estradiol and its metabolites in the ER-CALUX assay with human T47D breast cells. | 2001 Feb |
|
Estrogenic potency of chemicals detected in sewage treatment plant effluents as determined by in vivo assays with Japanese medaka (Oryzias latipes). | 2001 Feb |
|
Plasma beta-endorphin levels in obese and non-obese patients with polycystic ovary disease. | 2001 Feb |
|
Inhibition of postmenopausal atherosclerosis progression: a comparison of the effects of conjugated equine estrogens and soy phytoestrogens. | 2001 Jan |
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Sleep in menopause: differential effects of two forms of hormone replacement therapy. | 2001 Jan-Feb |
|
The selective estrogen enzyme modulator (SEEM) in breast cancer. | 2001 Jan-Mar |
|
Regulation of leptin and leptin receptor in baboon pregnancy: effects of advancing gestation and fetectomy. | 2001 Jun |
|
Increased prostacyclin synthesis by atherosclerotic arteries from estrogen-treated monkeys. | 2001 Jun 15 |
|
Effect of soymilk consumption on serum estrogen and androgen concentrations in Japanese men. | 2001 Mar |
|
Can variability in the hormonal status of elderly women assist in the decision to administer estrogens? | 2001 Mar |
|
Endogenous sex hormone levels in postmenopausal women with Alzheimer's disease. | 2001 Mar |
|
Determination of steroid sex hormones and related synthetic compounds considered as endocrine disrupters in water by fully automated on-line solid-phase extraction-liquid chromatography-diode array detection. | 2001 Mar 16 |
|
Metabolism of equilenin in MCF-7 and MDA-MB-231 human breast cancer cells. | 2001 May |
|
Actions of the soy phytoestrogen genistein in models of human chronic disease: potential involvement of transforming growth factor beta. | 2001 May |
|
Streamlined beta-galactosidase assay for analysis of recombinant yeast response to estrogens. | 2001 May |
|
Pharmacologic, but not dietary, genistein supports endometriosis in a rat model. | 2001 May |
|
2,3,7,8-Tetrachlorodibenzo-p-dioxin and diindolylmethanes differentially induce cytochrome P450 1A1, 1B1, and 19 in H295R human adrenocortical carcinoma cells. | 2001 May |
|
Influence of culture system and medium enrichment on sulfotransferase and sulfatase expression in male rat hepatocyte cultures. | 2001 May 1 |
|
A polymorphism in CYP17 and endometrial cancer risk. | 2001 May 15 |
|
Genotoxicity of the steroidal oestrogens oestrone and oestradiol: possible mechanism of uterine and mammary cancer development. | 2001 May-Jun |
|
Endocrinology of gynaecomastia. | 2001 Nov |
|
Tibolone: a compound with tissue specific inhibitory effects on sulfatase. | 2001 Oct 25 |
|
Induction of puberty in the hypogonadal girl--practices and attitudes of pediatric endocrinologists in Europe. | 2002 |
|
A randomized isoflavone intervention among premenopausal women. | 2002 Feb |
|
The bovine placenta; a source and target of steroid hormones: observations during the second half of gestation. | 2002 Jul |
|
A naturally occurring mutation in MRP1 results in a selective decrease in organic anion transport and in increased doxorubicin resistance. | 2002 Jun |
|
Nonsteroidal compounds designed to mimic potent steroid sulfatase inhibitors. | 2002 Mar |
|
Characterization of iodothyronine sulfatase activities in human and rat liver and placenta. | 2002 Mar |
|
Involvement of rat organic anion transporter 3 (rOAT3) in cephaloridine-induced nephrotoxicity: in comparison with rOAT1. | 2002 Mar 8 |
|
Interaction of human organic anion transporters with various cephalosporin antibiotics. | 2002 Mar 8 |
|
Endometrial thickness and uterine diameter not affected by ultralow doses of 17beta-estradiol in elderly women. | 2002 May |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.rxwiki.com/estrone
Curator's Comment: Vaginal route is possible: The recommended dose is 2.0 to 4.0 g intravaginally per day, adjusted to the lowest amount that controls symptoms http://www.rxlist.com/estragyn-drug.htm
Estrone is available in the following doses:
Estrone 2 Mg/ml Intramuscular Solution
Estrone 5 Mg/ml Intramuscular Solution
Estrone Compounding Powder
Forms of Medication
Estrone is available in the following forms:
Injectable Solution
Injectable Suspension
Vaginal Suppository
Route of Administration:
Intramuscular
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11039493
At 1.0 x 10(-8) M, estrone promoted growth of MTW9/PL cells established from the carcinogen-induced hormone-responsive MT-W9A rat mammary tumor of a Wistar-Furth (W/Fu) rat.
Substance Class |
Chemical
Created
by
admin
on
Edited
Thu Jul 06 21:34:07 UTC 2023
by
admin
on
Thu Jul 06 21:34:07 UTC 2023
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Record UNII |
2DI9HA706A
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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LOINC |
25403-7
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LOINC |
2258-2
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LIVERTOX |
376
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LOINC |
13739-8
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WHO-ATC |
G03CA07
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LOINC |
22663-9
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34297-2
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LOINC |
34299-8
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LOINC |
31177-9
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CFR |
21 CFR 862.1430
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LOINC |
27998-4
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2257-4
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6776-9
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35208-8
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2261-6
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WHO-ATC |
G03CC04
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LOINC |
14160-6
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34298-0
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2260-8
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2262-4
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2259-0
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WHO-VATC |
QG03CA07
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CFR |
21 CFR 862.1280
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WHO-VATC |
QG03CC04
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Code System | Code | Type | Description | ||
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ESTRONE
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53-16-7
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2DI9HA706A
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CHEMBL1405
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2DI9HA706A
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C484
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SUB07251MIG
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9699
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3188
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100000082364
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200-164-5
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2818
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Estrone (medication)
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3324
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D004970
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5870
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407
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4103
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M5033
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DB00655
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1255001
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DTXSID4022367
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TRANSPORTER -> INHIBITOR |
Related Record | Type | Details | ||
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METABOLITE -> PARENT |
IN-VIVO
URINE
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METABOLITE LESS ACTIVE -> PARENT |
IN-VITRO
Scientific Literature
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PARENT -> METABOLITE |
E2 is then extensively metabolized to estrone (E1) (15%), estrone sulfate (E1S) (65%), and other compounds.
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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CHROMATOGRAPHIC PURITY (TLC)
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ACTIVE MOIETY |