CYCLOFENIL

Details

Stereochemistry	ACHIRAL
Molecular Formula	C23H24O4
Molecular Weight	364.4343
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(=O)OC1=CC=C(C=C1)C(=C2CCCCC2)C3=CC=C(OC(C)=O)C=C3

InChI

InChIKey=GVOUFPWUYJWQSK-UHFFFAOYSA-N

InChI=1S/C23H24O4/c1-16(24)26-21-12-8-19(9-13-21)23(18-6-4-3-5-7-18)20-10-14-22(15-11-20)27-17(2)25/h8-15H,3-7H2,1-2H3

HIDE SMILES / InChI

Description
Sources: http://www.ncbi.nlm.nih.gov/pubmed/7097643
Curator's Comment: description was created based on several sources, including, http://www.ncbi.nlm.nih.gov/pubmed/7097643

Cyclofenil is a anti-estrogen drug developed for the treatment of female infertility and for induction of ovulation. Cyclofenil exerts its action by binding to estrogen receptor beta and demonstrates agonism or antagonism depending on tissues type. The drug was withdrawn from the market due to high risk of hepatotoxicity.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Estrogen receptor beta 110 Target ID: Q92731\|\|\|O75584 Gene ID: 2100.0 Gene Symbol: ESR2 Target Organism: Homo sapiens (Human) Sources: http://www.ncbi.nlm.nih.gov/pubmed/16610793	Antagonist 2778		9.4 nM [Kd]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Ovulation disorder 1 Sources: http://www.ncbi.nlm.nih.gov/pubmed/7097643	Curative		Withdrawn	SEXOVID Approved Use Unknown

PubMed

Title	Date	PubMed
[Comparative clinical studies on clomiphen, cyclofenil and epimestrol (author's transl)].	1977 Jun	885325
Follicular stimulation and ovarian cancer.	1989 Sep 16	2508904
Efficacy of clomiphene citrate and cyclofenil for infertile women with normal ovulatory cycles.	2001 Aug	11476800
Mass spectrometric analysis of cyclofenil and its metabolites in human urine.	2002	11921260
Exploration of the bicyclo[3.3.1]nonane system as a template for the development of new ligands for the estrogen receptor.	2003 Dec 15	14643352
The inhibitory effects of flavonoids and antiestrogens on the Glut1 glucose transporter in human erythrocytes.	2003 Dec 15	14642735
Infertility and subfertility.	2004 Jun	15652117
Design and synthesis of functionalized cyclopentadienyl tricarbonylmetal complexes for technetium-94m PET imaging of estrogen receptors.	2005 Mar-Apr	15769078
Fluorine-substituted cyclofenil derivatives as estrogen receptor ligands: synthesis and structure-affinity relationship study of potential positron emission tomography agents for imaging estrogen receptors in breast cancer.	2006 Apr 20	16610793
Elemental isomerism: a boron-nitrogen surrogate for a carbon-carbon double bond increases the chemical diversity of estrogen receptor ligands.	2007 Jun	17584613
Synthesis and biodistribution of fluorine-18-labeled fluorocyclofenils for imaging the estrogen receptor.	2007 May	17499727
Synthesis of new carbon-11 labeled cyclofenil derivatives for PET imaging of breast cancer estrogen receptors.	2008 Apr	18155914
Fluorimetric determination of cyclofenil using photochemical derivatization.	2008 Feb 15	18371802
Synthesis and identification of hydroxylated metabolites of the anti-estrogenic agent cyclofenil.	2008 Jul	18576435
Nonclassical SNAPFL analogue as a Cy5 resonance energy transfer partner.	2008 Nov 6	18841988
Terameprocol, a methylated derivative of nordihydroguaiaretic acid, inhibits production of prostaglandins and several key inflammatory cytokines and chemokines.	2009 Jan 8	19133137
Characterization of the pharmacophore properties of novel selective estrogen receptor downregulators (SERDs).	2010 Apr 22	20334372
Monitoring a coordinated exchange process in a four-component biological interaction system: development of a time-resolved terbium-based one-donor/three-acceptor multicolor FRET system.	2010 Apr 7	20230029
Photocontrol of protein activity in cultured cells and zebrafish with one- and two-photon illumination.	2010 Mar 22	20187057
Design, synthesis, and evaluation of cyclofenil derivatives for potential SPECT imaging agents.	2010 May	20195693

Patents

Sample Use Guides

In Vivo Use Guide

600 mg/daily

Route of Administration: Oral

In Vitro Use Guide

Unknown

Name

Type

Language

CYCLOFENIL

Official Name

English

ICI-48213

Code

English

NSC-86464

Code

English

Cyclofenil [WHO-DD]

Common Name

English

ICI 48213

Code

English

F 6066

Code

English

F-6066

Code

English

SEXOVID

Brand Name

English

CYCLOFENIL [MART.]

Common Name

English

cyclofenil [INN]

Common Name

English

CYCLOFENIL [JAN]

Common Name

English

CYCLOFENIL [MI]

Common Name

English

4,4'-(CYCLOHEXYLIDENEMETHYLENE)DIPHENOL DIACETATE ESTER

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C481