EQUILIN

Investigational

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C18H20O2
Molecular Weight	268.3502
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]3([H])C2=CCC4=C3C=CC(O)=C4

InChI

InChIKey=WKRLQDKEXYKHJB-HFTRVMKXSA-N

InChI=1S/C18H20O2/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,2,6-9H2,1H3/t14-,16+,18+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C18H20O2
Molecular Weight	268.3502
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9927655

Equilin is one of the active components of estrogens used in estrogen replacement therapy. This compound is used as a sulfate conjugate in drug Premarin. Equili is an inhibitor of 17beta-hydroxysteroid dehydrogenase type 1 (17beta-HSD1), a key enzyme responsible for elevated levels of 17beta-estradiol (E2) in breast tumor tissues. Thus equilin reduce the E2 levels in breast tissues and hence the reduce risk of estrogen-dependent breast cancer.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Estradiol 17-beta-dehydrogenase 1 1 Target ID: P14061 Gene ID: 3292.0 Gene Symbol: HSD17B1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/9927655	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
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.	2001 Aug	11566435
Synthesis of ring B unsaturated estriols. Confirming the structure of a diagnostic analyte for Smith-Lemli-Opitz syndrome.	2001 Aug 9	11483057
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	11743748
Molecular mechanisms of estrogen recognition and 17-keto reduction by human 17beta-hydroxysteroid dehydrogenase 1.	2001 Jan 30	11306082
Differential neuroprotective effects of equine estrogens against oxidized low density lipoprotein-induced neuronal cell death.	2001 Jul-Aug	11525901
Synthesis and reactivity of the catechol metabolites from the equine estrogen, 8,9-dehydroestrone.	2001 Jun	11409947
Analytical performance of luminescent immunoassays of different format for serum daidzein analysis.	2001 May	11393242
Metabolism of equilenin in MCF-7 and MDA-MB-231 human breast cancer cells.	2001 May	11368557
Reversed-phase liquid chromatographic method for estrogen determination in equine biological samples.	2001 Sep	11565948
Interaction of endogenous compounds in human and rat urine with P-glycoprotein.	2002	15618676
Protection against gp120-induced neurotoxicity by an array of estrogenic steroids.	2002 Dec 27	12470862
Evaluation of single- and multiple-dose pharmacokinetics of synthetic conjugated estrogens, A (Cenestin) tablets: a slow-release estrogen replacement product.	2002 Mar	11865971
Pharmacokinetics of 17 beta-dihydroequilin sulfate in normal postmenopausal women under steady state conditions.	2002 Mar-Apr	12398033
Equine estrogens induce apolipoprotein E and glial fibrillary acidic protein in mixed glial cultures.	2002 May 3	11959417
Investigations into the biosynthetic pathways for classical and ring B-unsaturated oestrogens in equine placental preparations and allantochorionic tissues.	2002 Nov	12589948
Immature rat uterotrophic assay of 18 chemicals and Hershberger assay of 30 chemicals.	2003 Feb 1	12504345
Conformations of stereoisomeric base adducts to 4-hydroxyequilenin.	2003 Jun	12807352
Catechol estrogen 4-hydroxyequilenin is a substrate and an inhibitor of catechol-O-methyltransferase.	2003 May	12755597
Coordinate regulation of the production and signaling of retinoic acid by estrogen in the human endometrium.	2003 May	12727970
Comparison of the proliferative effects of estradiol and conjugated equine estrogens on human breast cancer cells and impact of continuous combined progestogen addition.	2003 Sep	14567770
Translesion synthesis past equine estrogen-derived 2'-deoxycytidine DNA adducts by human DNA polymerases eta and kappa.	2004 Sep 7	15366941
Mixtures of estrogenic contaminants in bile of fish exposed to wastewater treatment works effluents.	2005 Apr 15	15884336
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.	2005 Aug 12	16078686
Equilenin-derived DNA adducts to cytosine in DNA duplexes: structures and thermodynamics.	2005 Nov 8	16262256
The estrogen metabolite 17beta-dihydroequilenin counteracts interleukin-1alpha induced expression of inflammatory mediators in human endothelial cells in vitro via NF-kappaB pathway.	2006 Jan	16543969
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.	2006 Mar 13	16533397
Translesion synthesis past equine estrogen-derived 2'-deoxyadenosine DNA adducts by human DNA polymerases eta and kappa.	2006 May 16	16681391
Ultrasound-induced destruction of low levels of estrogen hormones in aqueous solutions.	2007 Aug 15	17874799
Ultrasound assisted destruction of estrogen hormones in aqueous solution: effect of power density, power intensity and reactor configuration.	2007 Jul 31	17543445
Effects of estrogens and selective estrogen receptor modulators on vascular reactivity in the perfused mesenteric vascular bed.	2007 Nov	17881618
Free synthetic and natural estrogen hormones in influent and effluent of three municipal wastewater treatment plants.	2007 Sep	17910365
Analysis of steroidal estrogens as pyridine-3-sulfonyl derivatives by liquid chromatography electrospray tandem mass spectrometry.	2008 Apr 1	18162162
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.	2008 Sep	18680315
NMR and computational studies of stereoisomeric equine estrogen-derived DNA cytidine adducts in oligonucleotide duplexes: opposite orientations of diastereomeric forms.	2009 Aug 4	19527068
Molecular clustering of endometrial carcinoma based on estrogen-induced gene expression.	2009 Nov	19755863
Determination of endocrine disrupting compounds using temperature-dependent inclusion chromatography: I. Optimization of separation protocol.	2009 Oct 30	19362314
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.	2009 Oct 30	19356767
Equine estrogen-induced mammary tumors in rats.	2010 Apr 1	20096754
Roles of hCG in Advancing Follicular Growth to Ovulation after Concurrent Injections of PGF(2α) and GnRH in Postpubertal Holstein Heifers Bearing a CL.	2010 Dec 1	21151654
Equine estrogens impair nitric oxide production and endothelial nitric oxide synthase transcription in human endothelial cells compared with the natural 17{beta}-estradiol.	2010 Sep	20606108
Pharmacokinetics of a modified-release estrogen tablet.	2010 Sep-Oct	21043366
Synthesis and biological evaluation of (6- and 7-phenyl) coumarin derivatives as selective nonsteroidal inhibitors of 17β-hydroxysteroid dehydrogenase type 1.	2011 Jan 13	21138273
FDA-approved drugs and other compounds tested as inhibitors of human glutathione transferase P1-1.	2013 Sep 5	23769903
Differing species responsiveness of estrogenic contaminants in fish is conferred by the ligand binding domain of the estrogen receptor.	2014 May 6	24689804

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:47:13 UTC 2023` Edited by `admin` on `Fri Dec 15 16:47:13 UTC 2023`
Record UNII	08O86EX0J4
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

EQUILIN

Common Name

English

EQUILIN [USP-RS]

Common Name

English

NSC-10971

Code

English

EQUILIN [MI]

Common Name

English

EQUILIN [USP MONOGRAPH]

Common Name

English

EQUILIN [MART.]

Common Name

English

3-Hydroxyestra-1,3,5(10),7-tetraen-17-one

Systematic Name

English

Equilin [WHO-DD]

Common Name

English

ESTRA-1,3,5(10),7-TETRAEN-17-ONE, 3-HYDROXY-

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C2293