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474-86-2,MFCD00046223
Catalog No.:AA00JNZM

474-86-2 | Equilin

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  • Technical Information
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA00JNZM
Chemical Name:
Equilin
CAS Number:
474-86-2
Molecular Formula:
C18H20O2
Molecular Weight:
268.3502
MDL Number:
MFCD00046223
SMILES:
Oc1ccc2c(c1)CC=C1[C@@H]2CC[C@]2([C@H]1CCC2=O)C
NSC Number:
10971
Properties
Properties
 
Form:
Solid  
MP:
233-235°C  
Storage:
2-8℃;  

Computed Properties
 
Complexity:
466  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
3  
Heavy Atom Count:
20  
Hydrogen Bond Acceptor Count:
2  
Hydrogen Bond Donor Count:
1  
XLogP3:
2.9  

Literature

Title: An in vitro approach for prioritization and evaluation of chemical effects on glucocorticoid receptor mediated adipogenesis.

Journal: Toxicology and applied pharmacology 20180915

Title: Identifying environmental chemicals as agonists of the androgen receptor by using a quantitative high-throughput screening platform.

Journal: Toxicology 20170615

Title: Gene expression analyses of vitellogenin, choriogenin and estrogen receptor subtypes in the livers of male medaka (Oryzias latipes) exposed to equine estrogens.

Journal: Journal of applied toxicology : JAT 20161101

Title: Endocrine-disrupting potentials of equine estrogens equilin, equilenin, and their metabolites, in the medaka Oryzias latipes: in silico and DNA microarray studies.

Journal: Journal of applied toxicology : JAT 20150901

Title: Differing species responsiveness of estrogenic contaminants in fish is conferred by the ligand binding domain of the estrogen receptor.

Journal: Environmental science & technology 20140506

Title: FDA-approved drugs and other compounds tested as inhibitors of human glutathione transferase P1-1.

Journal: Chemico-biological interactions 20130905

Title: Ozonation of a mixture of estrogens and progestins in aqueous solution: interpretation of experimental results by computational methods.

Journal: Chemosphere 20121101

Title: Photochemical induced changes of in vitro estrogenic activity of steroid hormones.

Journal: Water research 20121015

Title: Comparison of multiple API techniques for the simultaneous detection of microconstituents in water by on-line SPE-LC-MS/MS.

Journal: Journal of mass spectrometry : JMS 20121001

Title: Tartrazine and sunset yellow are xenoestrogens in a new screening assay to identify modulators of human oestrogen receptor transcriptional activity.

Journal: Toxicology 20120816

Title: Evaluation of relative importance of ultrasound reactor parameters for the removal of estrogen hormones in water.

Journal: Ultrasonics sonochemistry 20120701

Title: Biomimetic oxidation of aromatic xenobiotics: synthesis of the phenolic metabolites from the anti-HIV drug efavirenz.

Journal: Organic & biomolecular chemistry 20120621

Title: Modelling defined mixtures of environmental oestrogens found in domestic animal and sewage treatment effluents using an in vitro oestrogen-mediated transcriptional activation assay (T47D-KBluc).

Journal: International journal of andrology 20120601

Title: Oxidative DNA damage following microsome/Cu(II)-mediated activation of the estrogens, 17β-estradiol, equilenin, and equilin: role of reactive oxygen species.

Journal: Chemical research in toxicology 20120220

Title: Application of density functional theory (DFT) to study the properties and degradation of natural estrogen hormones with chemical oxidizers.

Journal: The Science of the total environment 20120215

Title: Occurrence of estrogen hormones in biosolids, animal manure and mushroom compost.

Journal: Environmental monitoring and assessment 20120101

Title: Hydroxybenzothiazoles as new nonsteroidal inhibitors of 17β-hydroxysteroid dehydrogenase type 1 (17β-HSD1).

Journal: PloS one 20120101

Title: Selective determination of estrogenic compounds in water by microextraction by packed sorbents and a molecularly imprinted polymer coupled with large volume injection-in-port-derivatization gas chromatography-mass spectrometry.

Journal: Analytica chimica acta 20111003

Title: Investigation of the temperature stability of premarin intravenous using liquid chromatography-mass spectrometry.

Journal: Journal of pharmaceutical and biomedical analysis 20110715

Title: Cellular and molecular actions displayed by estrone on vascular endothelium.

Journal: Molecular and cellular endocrinology 20110606

Title: A randomized, multiple-dose parallel study to compare the pharmacokinetic parameters of synthetic conjugated estrogens, A, administered as oral tablet or vaginal cream.

Journal: Menopause (New York, N.Y.) 20110401

Title: Synthesis and biological evaluation of (6- and 7-phenyl) coumarin derivatives as selective nonsteroidal inhibitors of 17β-hydroxysteroid dehydrogenase type 1.

Journal: Journal of medicinal chemistry 20110113

Title: Estrogens and selective estrogen receptor modulators regulate gene and protein expression in the mesenteric arteries.

Journal: Vascular pharmacology 20110101

Title: Drug discovery for Duchenne muscular dystrophy via utrophin promoter activation screening.

Journal: PloS one 20110101

Title: Effects of Erxian decoction, a Chinese medicinal formulation, on serum lipid profile in a rat model of menopause.

Journal: Chinese medicine 20110101

Title: Raloxifene and desmethylarzoxifene block estrogen-induced malignant transformation of human breast epithelial cells.

Journal: PloS one 20110101

Title: A component of Premarin(®) enhances multiple cognitive functions and influences nicotinic receptor expression.

Journal: Hormones and behavior 20101101

Title: Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.

Journal: Bioorganic & medicinal chemistry letters 20101101

Title: Equine estrogens impair nitric oxide production and endothelial nitric oxide synthase transcription in human endothelial cells compared with the natural 17{beta}-estradiol.

Journal: Hypertension (Dallas, Tex. : 1979) 20100901

Title: Equine estrogen-induced mammary tumors in rats.

Journal: Toxicology letters 20100401

Title: Influence of alkalinity and salinity on the sonochemical degradation of estrogen hormones in aqueous solution.

Journal: Environmental science & technology 20100215

Title: DNA-Destabilizing Agents as an Alternative Approach for Targeting DNA: Mechanisms of Action and Cellular Consequences.

Journal: Journal of nucleic acids 20100101

Title: Pharmacokinetics of a modified-release estrogen tablet.

Journal: The Journal of reproductive medicine 20100101

Title: Roles of hCG in Advancing Follicular Growth to Ovulation after Concurrent Injections of PGF(2α) and GnRH in Postpubertal Holstein Heifers Bearing a CL.

Journal: Veterinary medicine international 20100101

Title: Potent and selective steroidal inhibitors of 17beta-hydroxysteroid dehydrogenase type 7, an enzyme that catalyzes the reduction of the key hormones estrone and dihydrotestosterone.

Journal: Journal of medicinal chemistry 20091210

Title: Molecular clustering of endometrial carcinoma based on estrogen-induced gene expression.

Journal: Cancer biology & therapy 20091101

Title: Determination of endocrine disrupting compounds using temperature-dependent inclusion chromatography: II. Fast screening of free steroids and related low-molecular-mass compounds fraction in the environmental samples derived from surface waters, treated and untreated sewage waters as well as activated sludge material.

Journal: Journal of chromatography. A 20091030

Title: Determination of endocrine disrupting compounds using temperature-dependent inclusion chromatography: I. Optimization of separation protocol.

Journal: Journal of chromatography. A 20091030

Title: NMR and computational studies of stereoisomeric equine estrogen-derived DNA cytidine adducts in oligonucleotide duplexes: opposite orientations of diastereomeric forms.

Journal: Biochemistry 20090804

Title: Structure activity relationships and differential interactions and functional activity of various equine estrogens mediated via estrogen receptors (ERs) ERalpha and ERbeta.

Journal: Endocrinology 20081001

Title: Determination of absolute configurations of 4-hydroxyequilenin-cytosine and -adenine adducts by optical rotatory dispersion, electronic circular dichroism, density functional theory calculations, and mass spectrometry.

Journal: Chemical research in toxicology 20080901

Title: Proliferation of the superficial epithelium of ovaries in senile female rats following oral administration of conjugated equine estrogens.

Journal: Clinics (Sao Paulo, Brazil) 20080601

Title: Analysis of steroidal estrogens as pyridine-3-sulfonyl derivatives by liquid chromatography electrospray tandem mass spectrometry.

Journal: Analytical biochemistry 20080401

Title: Steady-state pharmacokinetics of conjugated equine estrogens in healthy, postmenopausal women.

Journal: The Journal of reproductive medicine 20080201

Title: Effects of estrogens and selective estrogen receptor modulators on vascular reactivity in the perfused mesenteric vascular bed.

Journal: American journal of physiology. Regulatory, integrative and comparative physiology 20071101

Title: Free synthetic and natural estrogen hormones in influent and effluent of three municipal wastewater treatment plants.

Journal: Water environment research : a research publication of the Water Environment Federation 20070901

Title: Mechanism of translesion synthesis past an equine estrogen-DNA adduct by Y-family DNA polymerases.

Journal: Journal of molecular biology 20070831

Title: Ultrasound-induced destruction of low levels of estrogen hormones in aqueous solutions.

Journal: Environmental science & technology 20070815

Title: Ultrasound assisted destruction of estrogen hormones in aqueous solution: effect of power density, power intensity and reactor configuration.

Journal: Journal of hazardous materials 20070731

Title: Effects of the components of hormone therapy on matrix metalloproteinases in breast-cancer cells: an in vitro study.

Journal: Fertility and sterility 20070401

Title: 4-hydroxyequilenin-adenine lesions in DNA duplexes: stereochemistry, damage site, and structure.

Journal: Biochemistry 20070109

Title: Translesion synthesis past equine estrogen-derived 2'-deoxyadenosine DNA adducts by human DNA polymerases eta and kappa.

Journal: Biochemistry 20060516

Title: Microsphere-based protease assays and screening application for lethal factor and factor Xa.

Journal: Cytometry. Part A : the journal of the International Society for Analytical Cytology 20060501

Title: Active site analysis of 17beta-hydroxysteroid dehydrogenase type 1 enzyme complexes with SPROUT.

Journal: Molecular and cellular endocrinology 20060327

Title: Select estrogens within the complex formulation of conjugated equine estrogens (Premarin) are protective against neurodegenerative insults: implications for a composition of estrogen therapy to promote neuronal function and prevent Alzheimer's disease.

Journal: BMC neuroscience 20060101

Title: The estrogen metabolite 17beta-dihydroequilenin counteracts interleukin-1alpha induced expression of inflammatory mediators in human endothelial cells in vitro via NF-kappaB pathway.

Journal: Thrombosis and haemostasis 20060101

Title: Equilenin-derived DNA adducts to cytosine in DNA duplexes: structures and thermodynamics.

Journal: Biochemistry 20051108

Title: Separation and detection of the isomeric equine conjugated estrogens, equilin sulfate and delta8,9-dehydroestrone sulfate, by liquid chromatography--electrospray-mass spectrometry using carbon-coated zirconia and porous graphitic carbon stationary phases.

Journal: Journal of chromatography. A 20050812

Title: Mixtures of estrogenic contaminants in bile of fish exposed to wastewater treatment works effluents.

Journal: Environmental science & technology 20050415

Title: Ultrafiltration tandem mass spectrometry of estrogens for characterization of structure and affinity for human estrogen receptors.

Journal: Journal of the American Society for Mass Spectrometry 20050201

Title: [Menopause in 2004: 'hormone replacement therapy' is not what it used to be anymore].

Journal: La Revue de medecine interne 20041101

Title: Translesion synthesis past equine estrogen-derived 2'-deoxycytidine DNA adducts by human DNA polymerases eta and kappa.

Journal: Biochemistry 20040907

Title: Targeting oestrogen to kill the cancer but not the patient.

Journal: British journal of cancer 20040308

Title: B-ring unsaturated estrogens: biological evaluation of 17alpha-Dihydroequilein and novel B-Nor-6-thiaequilenins as tissue selective estrogens.

Journal: Bioorganic & medicinal chemistry letters 20031215

Title: Comparison of the proliferative effects of estradiol and conjugated equine estrogens on human breast cancer cells and impact of continuous combined progestogen addition.

Journal: Climacteric : the journal of the International Menopause Society 20030901

Title: Equine estrogens differentially prevent neuronal cell death induced by glutamate.

Journal: Journal of the Society for Gynecologic Investigation 20030701

Title: Conformations of stereoisomeric base adducts to 4-hydroxyequilenin.

Journal: Chemical research in toxicology 20030601

Title: Effect of halogenated substituents on the metabolism and estrogenic effects of the equine estrogen, equilenin.

Journal: Chemical research in toxicology 20030601

Title: Estrogens and menopause: pharmacology of conjugated equine estrogens and their potential role in the prevention of neurodegenerative diseases such as Alzheimer's.

Journal: The Journal of steroid biochemistry and molecular biology 20030601

Title: Coordinate regulation of the production and signaling of retinoic acid by estrogen in the human endometrium.

Journal: The Journal of clinical endocrinology and metabolism 20030501

Title: Catechol estrogen 4-hydroxyequilenin is a substrate and an inhibitor of catechol-O-methyltransferase.

Journal: Chemical research in toxicology 20030501

Title: Mutagenic events induced by 4-hydroxyequilin in supF shuttle vector plasmid propagated in human cells.

Journal: Carcinogenesis 20030501

Title: Immature rat uterotrophic assay of 18 chemicals and Hershberger assay of 30 chemicals.

Journal: Toxicology 20030201

Title: Potential role of the interaction between equine estrogens, low-density lipoprotein (LDL) and high-density lipoprotein (HDL) in the prevention of coronary heart and neurodegenerative diseases in postmenopausal women.

Journal: Lipids in health and disease 20030101

Title: Equine estrogens differentially inhibit DNA fragmentation induced by glutamate in neuronal cells by modulation of regulatory proteins involved in programmed cell death.

Journal: BMC neuroscience 20030101

Title: Protection against gp120-induced neurotoxicity by an array of estrogenic steroids.

Journal: Brain research 20021227

Title: Investigations into the biosynthetic pathways for classical and ring B-unsaturated oestrogens in equine placental preparations and allantochorionic tissues.

Journal: The Journal of steroid biochemistry and molecular biology 20021101

Title: Equine estrogens induce apolipoprotein E and glial fibrillary acidic protein in mixed glial cultures.

Journal: Neuroscience letters 20020503

Title: Evaluation of single- and multiple-dose pharmacokinetics of synthetic conjugated estrogens, A (Cenestin) tablets: a slow-release estrogen replacement product.

Journal: Journal of clinical pharmacology 20020301

Title: Cytotoxicity of estradiol, equilin, equilenin, and their derivatives on Chinese hamster V79 cells.

Journal: Drug and chemical toxicology 20020201

Title: Comparison of reporter gene assay and immature rat uterotrophic assay of twenty-three chemicals.

Journal: Toxicology 20020115

Title: Pharmacokinetics of 17 beta-dihydroequilin sulfate in normal postmenopausal women under steady state conditions.

Journal: Journal of the Society for Gynecologic Investigation 20020101

Title: Interaction of endogenous compounds in human and rat urine with P-glycoprotein.

Journal: Drug metabolism and pharmacokinetics 20020101

Title: 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.

Journal: Chemical research in toxicology 20011201

Title: Reversed-phase liquid chromatographic method for estrogen determination in equine biological samples.

Journal: Journal of chromatographic science 20010901

Title: Synthesis of ring B unsaturated estriols. Confirming the structure of a diagnostic analyte for Smith-Lemli-Opitz syndrome.

Journal: Organic letters 20010809

Title: Structure-effect relationship in the induction of mitotic phase-specific abnormality of centrosome integrity and multipolar spindles by steroidal estrogens and their derivatives in cultured mammalian cells.

Journal: The Journal of steroid biochemistry and molecular biology 20010801

Title: Synthesis and reactivity of the catechol metabolites from the equine estrogen, 8,9-dehydroestrone.

Journal: Chemical research in toxicology 20010601

Title: Metabolism of equilenin in MCF-7 and MDA-MB-231 human breast cancer cells.

Journal: Chemical research in toxicology 20010501

Title: Analytical performance of luminescent immunoassays of different format for serum daidzein analysis.

Journal: Fresenius' journal of analytical chemistry 20010501

Title: Molecular mechanisms of estrogen recognition and 17-keto reduction by human 17beta-hydroxysteroid dehydrogenase 1.

Journal: Chemico-biological interactions 20010130

Title: Evidence that a metabolite of equine estrogens, 4-hydroxyequilenin, induces cellular transformation in vitro.

Journal: Chemical research in toxicology 20010101

Title: Differential neuroprotective effects of equine estrogens against oxidized low density lipoprotein-induced neuronal cell death.

Journal: Journal of the Society for Gynecologic Investigation 20010101

Title: Comparison of the antioxidant effects of equine estrogens, red wine components, vitamin E, and probucol on low-density lipoprotein oxidation in postmenopausal women.

Journal: Menopause (New York, N.Y.) 20010101

Title: Hormone replacement therapy and risk of heart disease.

Journal: American family physician 19991115

Title: Structure of the ternary complex of human 17beta-hydroxysteroid dehydrogenase type 1 with 3-hydroxyestra-1,3,5,7-tetraen-17-one (equilin) and NADP+.

Journal: Proceedings of the National Academy of Sciences of the United States of America 19990202

Title: Differential biochemical and cellular actions of Premarin estrogens: distinct pharmacology of bazedoxifene-conjugated estrogens combination.

Journal: Molecular endocrinology (Baltimore, Md.)

Title: David K, et al. Some biological properties of equilin. Biochem J. 1935;29(2):371-377.

Title: Brinton RD, et al. Equilin, a principal component of the estrogen replacement therapy premarin, increases the growth of cortical neurons via an NMDA receptor-dependent mechanism. Exp Neurol. 1997;147(2):211-220.

Title: Ito F, et al. Equilin in conjugated equine estrogen increases monocyte-endothelial adhesion via NF-κB signaling. PLoS One. 2019;14(1):e0211462. Published 2019 Jan 30.

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