Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C18H22O2 |
Molecular Weight | 270.3668 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
C[C@@]12CC[C@]3([H])c4ccc(cc4CC[C@@]3([H])[C@]2([H])CCC1=O)O
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 | 270.3668 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=83dd22a0-7c59-11e6-84ff-424c58303031https://www.ncbi.nlm.nih.gov/pubmed/27960570 | https://www.accessdata.fda.gov/cdrh_docs/pdf/K970915.pdfhttp://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/ja00536a023Curator's Comment:: https://books.google.ru/books?id=Thtz7On_lhEC&pg=PA356&lpg=PA356&dq=DL-ESTRONE retrieved from The Hormones V1: Physiology, Chemistry and Applications
By Gregory Pincus, Thimann Kenneth Vivian Pincus Gregory, p.356
Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=83dd22a0-7c59-11e6-84ff-424c58303031https://www.ncbi.nlm.nih.gov/pubmed/27960570 | https://www.accessdata.fda.gov/cdrh_docs/pdf/K970915.pdfhttp://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/ja00536a023
Curator's Comment:: https://books.google.ru/books?id=Thtz7On_lhEC&pg=PA356&lpg=PA356&dq=DL-ESTRONE retrieved from The Hormones V1: Physiology, Chemistry and Applications
By Gregory Pincus, Thimann Kenneth Vivian Pincus Gregory, p.356
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. Estrogens enter the cells of responsive tissues (e.g. female organs, breasts, hypothalamus, pituitary) where they interact with estrogen receptors. Hormone-bound estrogen receptors dimerize, translocate to the nucleus of cells and bind to estrogen response elements (ERE) of genes. Binding to ERE alters the transcription rate of affected genes. Estrogens increase the hepatic synthesis of sex hormone binding globulin (SHBG), thyroid-binding globulin (TBG), and other serum proteins and suppress follicle-stimulating hormone (FSH) release from the anterior pituitary. Estrone dl-Form is a derivative of estrone. As early as 1935 extensive research programs directed toward the total synthesis of the female
sex hormone estrone were well under way. These studies have since been continued with increasing interest in laboratories all over the world. In
1942 Bachmann, Kushner and Stevenson succeeded in synthesizing a stereoisomer of the hormone,''estrone a." Using essentially the same
synthetic scheme as Bachmann, et al., Anner and
Miescher were able to isolate additional stereoisomers including dl-estrone (Estrone, (+-)-Isomer) . Six of the eight possible racemic forms, estrone, a-f, have now
been reported. Dl-Estrone (Estrone, (+-)-Isomer) is less active than Estrone.
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: https://www.ncbi.nlm.nih.gov/pubmed/22469359http://pubs.acs.org/doi/abs/10.1021/ja01159a529?journalCode=jacsat
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 |
|||
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 |
|||
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. |
|||
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. |
|||
Primary | THEELIN Approved UseFor management of Menopausal and postmenopausal disorders |
|||
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 |
---|---|---|---|
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 |
---|---|---|
Estrone, but not 17 beta-estradiol, attenuates kainate-induced seizures and toxicity in male mice. | 2001 |
|
Effects of testosterone precursor supplementation on intensive weight training. | 2001 Apr |
|
High metabolization of catecholestrogens by type 1 estrogen sulfotransferase (hEST1). | 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 |
|
19-Oxygenation of C19-steroids with an A, B-ring enone structure, competitive inhibitors of estrogen biosynthesis, with human placental aromatase. | 2001 Apr |
|
Serum concentrations of 17beta-estradiol and estrone after multiple-dose administration of percutaneous estradiol gel in symptomatic menopausal women. | 2001 Apr |
|
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 |
|
Oral, water-soluble combined estrogen/calcium preparation for postmenopausal therapy. | 2001 Apr 20 |
|
Cholesterol sulfate: a new adhesive molecule for platelets. | 2001 Apr 24 |
|
Acid dissociation constant, a potential physicochemical factor in the inhibition of the enzyme estrone sulfatase (ES). | 2001 Apr 9 |
|
Estrogenic activity of estradiol and its metabolites in the ER-CALUX assay with human T47D breast cells. | 2001 Feb |
|
4-hydroxy-2',4',6'-trichlorobiphenyl and 4-hydroxy-2',3',4',5'-tetrachlorobiphenyl are estrogenic in rainbow trout. | 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 |
|
Dietary oleoyl-estrone delays the growth rate of young rats. | 2001 Feb |
|
Hormone contents in peripheral tissues after correct and off-label use of growth promoting hormones in cattle: effect of the implant preparations Filaplix-H, Raglo, Synovex-H and Synovex Plus. | 2001 Jan |
|
Molecular mechanisms of estrogen recognition and 17-keto reduction by human 17beta-hydroxysteroid dehydrogenase 1. | 2001 Jan 30 |
|
Characteristics of cystic breast disease with special regard to breast cancer development. | 2001 Jan-Feb |
|
The selective estrogen enzyme modulator (SEEM) in breast cancer. | 2001 Jan-Mar |
|
Molecular basis of perinatal changes in UDP-glucuronosyltransferase activity in maternal rat liver. | 2001 Jul |
|
Menopausal experiences and bone density of Mayan women in Yucatan, Mexico. | 2001 Jul-Aug |
|
Oral gavage of oleoyl-oestrone has a stronger effect on body weight in male Zucker obese rats than in female. | 2001 Jun |
|
Synthesis and reactivity of the catechol metabolites from the equine estrogen, 8,9-dehydroestrone. | 2001 Jun |
|
Association of genetic polymorphisms in UGT1A1 with breast cancer and plasma hormone levels. | 2001 Jun |
|
The effect of aromatase inhibition on sex steroids, gonadotropins, and markers of bone turnover in older men. | 2001 Jun |
|
Regulation of leptin and leptin receptor in baboon pregnancy: effects of advancing gestation and fetectomy. | 2001 Jun |
|
Fecal analysis of ovarian cycles in female black-handed spider monkeys (Ateles geoffroyi). | 2001 Jun |
|
Serum levels of C-reactive protein are associated with obesity, weight gain, and hormone replacement therapy in healthy postmenopausal women. | 2001 Jun 1 |
|
Identification of a new subfamily of sulphotransferases: cloning and characterization of canine SULT1D1. | 2001 Jun 15 |
|
[Effects of exposure to low-level benzene and its analogues on reproductive hormone secretion in female workers]. | 2001 Mar |
|
Circulating plasma leptin and IGF-1 levels in girls with premature adrenarche: potential implications of a preliminary study. | 2001 Mar |
|
Daily oral oleoyl-estrone gavage induces a dose-dependent loss of fat in Wistar rats. | 2001 Mar |
|
Effect of soymilk consumption on serum estrogen and androgen concentrations in Japanese men. | 2001 Mar |
|
Repellent activity of estrogenic compounds toward zoospores of the phytopathogenic fungus Aphanomyces cochlioides. | 2001 Mar-Apr |
|
Urinary excretion pattern of catecholestrogens in preovulatory LH surge during the 4-day estrous cycle of rats. | 2001 May |
|
In vitro generation of peroxynitrite by 2- and 4-hydroxyestrogens in the presence of nitric oxide. | 2001 May |
|
Streamlined beta-galactosidase assay for analysis of recombinant yeast response to estrogens. | 2001 May |
|
Influence of neoadjuvant anastrozole (Arimidex) on intratumoral estrogen levels and proliferation markers in patients with locally advanced breast cancer. | 2001 May |
|
Assessment of oestrogenic potency of chemicals used as growth promoter by in-vitro methods. | 2001 May |
|
Effects of transdermal testosterone on bone and muscle in older men with low bioavailable testosterone levels. | 2001 May |
|
Dexamethasone blocks antioestrogen- and oxidant-induced death of pituitary tumour cells. | 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 |
|
Immature ovaries and polycystic kidneys in the congenital polycystic kidney mouse may be due to abnormal sex steroid metabolism. | 2001 May 15 |
|
A polymorphism in CYP17 and endometrial cancer risk. | 2001 May 15 |
|
Human oestrogenic 17beta-hydroxysteroid dehydrogenase specificity: enzyme regulation through an NADPH-dependent substrate inhibition towards the highly specific oestrone reduction. | 2001 May 15 |
|
Serum hormones and the alcohol-breast cancer association in postmenopausal women. | 2001 May 2 |
|
Genotoxicity of the steroidal oestrogens oestrone and oestradiol: possible mechanism of uterine and mammary cancer development. | 2001 May-Jun |
|
Markedly elevated levels of estrone sulfate after long-term oral, but not transdermal, administration of estradiol in postmenopausal women. | 2001 May-Jun |
Sample Use Guides
In Vivo Use Guide
Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=83dd22a0-7c59-11e6-84ff-424c58303031
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
5 pellets 3 times a day until symptoms are relieved
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27169275
Study was designed to discover filovirus entry inhibitors in a drug library of commercial medicines. One thousand and six hundred drugs were screened using the ZEBOV-GP/HIV model, a pseudovirus formed by an HIV-core packed with the Zaire Ebola virus glycoprotein. Was identified 12 gonadal hormone drugs with inhibitory activities in ZEBOV-GP/HIV entry at final concentration of 10 μmol x L(-1). One of them with moderate activity was estrone IC50: 6.87 ± 0.03 μmol-L1
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Jun 26 14:07:28 UTC 2021
by
admin
on
Sat Jun 26 14:07:28 UTC 2021
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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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LOINC |
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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LOINC |
2257-4
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LOINC |
6776-9
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35208-8
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LOINC |
2261-6
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WHO-ATC |
G03CC04
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LOINC |
14160-6
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LOINC |
34298-0
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2260-8
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LOINC |
2262-4
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LOINC |
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
Created by
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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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C484
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SUB07251MIG
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3188
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200-164-5
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2818
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3324
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D004970
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5870
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1255001
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407
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4103
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M5033
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PRIMARY | Merck Index | ||
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DB00655
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53-16-7
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Related Record | Type | Details | ||
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TRANSPORTER -> INHIBITOR |
Related Record | Type | Details | ||
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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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METABOLITE -> PARENT |
IN-VITRO
Scientific Literature
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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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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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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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Related Record | Type | Details | ||
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ACTIVE MOIETY |