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

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 of the ternary complex of human 17beta-hydroxysteroid dehydrogenase type 1 with 3-hydroxyestra-1,3,5,7-tetraen-17-one (equilin) and NADP+.	1999 Feb 2	9927655
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
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
Cytotoxicity of estradiol, equilin, equilenin, and their derivatives on Chinese hamster V79 cells.	2002 Feb	11850971
Comparison of reporter gene assay and immature rat uterotrophic assay of twenty-three chemicals.	2002 Jan 15	11750080
Evaluation of single- and multiple-dose pharmacokinetics of synthetic conjugated estrogens, A (Cenestin) tablets: a slow-release estrogen replacement product.	2002 Mar	11865971
Investigations into the biosynthetic pathways for classical and ring B-unsaturated oestrogens in equine placental preparations and allantochorionic tissues.	2002 Nov	12589948
Equine estrogens differentially inhibit DNA fragmentation induced by glutamate in neuronal cells by modulation of regulatory proteins involved in programmed cell death.	2003 Dec 23	14693041
Conformations of stereoisomeric base adducts to 4-hydroxyequilenin.	2003 Jun	12807352
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.	2003 Jun 20	12848896
Mutagenic events induced by 4-hydroxyequilin in supF shuttle vector plasmid propagated in human cells.	2003 May	12771036
Catechol estrogen 4-hydroxyequilenin is a substrate and an inhibitor of catechol-O-methyltransferase.	2003 May	12755597
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
Ultrafiltration tandem mass spectrometry of estrogens for characterization of structure and affinity for human estrogen receptors.	2005 Feb	15694777
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
Active site analysis of 17beta-hydroxysteroid dehydrogenase type 1 enzyme complexes with SPROUT.	2006 Mar 27	16412556
Translesion synthesis past equine estrogen-derived 2'-deoxyadenosine DNA adducts by human DNA polymerases eta and kappa.	2006 May 16	16681391
Mechanism of translesion synthesis past an equine estrogen-DNA adduct by Y-family DNA polymerases.	2007 Aug 31	17603077
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
Steady-state pharmacokinetics of conjugated equine estrogens in healthy, postmenopausal women.	2008 Feb	18357800
Proliferation of the superficial epithelium of ovaries in senile female rats following oral administration of conjugated equine estrogens.	2008 Jun	18568250
Structure activity relationships and differential interactions and functional activity of various equine estrogens mediated via estrogen receptors (ERs) ERalpha and ERbeta.	2008 Oct	18599548
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
Differential biochemical and cellular actions of Premarin estrogens: distinct pharmacology of bazedoxifene-conjugated estrogens combination.	2009 Jan	19036900
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
Influence of alkalinity and salinity on the sonochemical degradation of estrogen hormones in aqueous solution.	2010 Feb 15	20092297
DNA-Destabilizing Agents as an Alternative Approach for Targeting DNA: Mechanisms of Action and Cellular Consequences.	2010 Jul 25	20725618
Drug discovery for Duchenne muscular dystrophy via utrophin promoter activation screening.	2011	22028826
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
Tartrazine and sunset yellow are xenoestrogens in a new screening assay to identify modulators of human oestrogen receptor transcriptional activity.	2012 Aug 16	22562034
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

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