CAS 2624-43-3|Cyclofenil

Introduction：Basic information about CAS 2624-43-3|Cyclofenil, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Cyclofenil BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
5. Safety Information
6. Articles28
7. Synonyms

Common Name	Cyclofenil
CAS Number	2624-43-3	Molecular Weight	364.434
Density	1.2±0.1 g/cm3	Boiling Point	509.0±30.0 °C at 760 mmHg
Molecular Formula	C₂₃H₂₄O₄	Melting Point	133-136°C
MSDS	USA	Flash Point	254.8±23.0 °C

Names

Name	Cyclofenil,4,4'-(Cyclohexylidenemethylene)bisphenol1,1'-diacetate
Synonym	More Synonyms

Cyclofenil BiologicalActivity

Description	Cyclofenil is a selective estrogen receptor modulator and an ovulation-inducing agent. Cyclofenil shows an inhibitory effect on dengue virus replication in Vero cells with an EC50 of 1.62 μM. Cyclofenil has anti-dengue-virus activity[1][2].
Related Catalog	Signaling Pathways >>Others >>Estrogen Receptor/ERRSignaling Pathways >>Anti-infection >>Influenza VirusResearch Areas >>EndocrinologyResearch Areas >>Infection
Target	Estrogen receptor[1]; Dengue virus[1]
In Vitro	Cyclofenil shows an inhibitory effect on dengue virus (DENV) replication in mammalian cells but not in mosquito cells[1]. Cyclofenil also inhibits the replication of Zika virus. A time-of-addition assay suggested that Cyclofenil may interfere with two stages of the Dengue virus (DENV) life cycle: the translation-RNA synthesis and assembly-maturation stages. The level of intracellular infectious particles decreased more drastically after treatment with Cyclofenil than the viral RNA level do, indicating that the assembly-maturation stage might be the main target of Cyclofenil[1].
In Vivo	The number of estrogen receptors α (ERα) and β (ERβ)-immunoreactive (-ir) cells is determined of each stage of the estrous cycle in intact rats. Additionally, the effects of blocking ERα and ERβ on ovulation rate on diestrus-2 or proestrus day through the microinjection of methyl-piperidino-pyrazole (MPP) or Cyclofenil in either side of preoptic-anterior hypothalamic area (POA-AHA) are evaluated. The number of ERα-ir and ERβ-ir cells in POA-AHA varied in each phase of estrous cycle. Either MPP or Cyclofenil in the right side of POA-AHA on diestrus-2 day reduced the ovulation rate, while at proestrus day it was decreased in rats treated in either side with MPP, and in those treated with Cyclofenil in the left side. MPP or Cyclofenil produced a decrease in the surge of luteinizing hormone levels (LH) and an increase in progesterone and follicle stimulating hormone (FSH)[2].
References	[1]. Tohma D, et al. An estrogen antagonist, cyclofenil, has anti-dengue-virus activity. Arch Virol. 2019 Jan;164(1):225-234. [2]. Arrieta-Cruz I, et al. Estrogen Receptors Alpha and Beta in POA-AHA Region Regulate Asymmetrically Ovulation. Cell Mol Neurobiol. 2019 Nov;39(8):1139-1149.

Chemical & Physical Properties

Density	1.2±0.1 g/cm3
Boiling Point	509.0±30.0 °C at 760 mmHg
Melting Point	133-136°C
Molecular Formula	C₂₃H₂₄O₄
Molecular Weight	364.434
Flash Point	254.8±23.0 °C
Exact Mass	364.167450
PSA	52.60000
LogP	5.90
Appearance of Characters	solid
Vapour Pressure	0.0±1.3 mmHg at 25°C
Index of Refraction	1.573
InChIKey	GVOUFPWUYJWQSK-UHFFFAOYSA-N
SMILES	CC(=O)Oc1ccc(C(=C2CCCCC2)c2ccc(OC(C)=O)cc2)cc1
Storage condition	2-8°C
Water Solubility	DMSO: 10 mg/mL at 60 °C, soluble

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: GO7550000

CHEMICAL NAME :: p-Cresol, alpha-cyclohexylidene-alpha-(p-hydroxyphenyl)-, diacetate

CAS REGISTRY NUMBER :: 2624-43-3

LAST UPDATED :: 199707

DATA ITEMS CITED :: 30

MOLECULAR FORMULA :: C23-H24-O4

MOLECULAR WEIGHT :: 364.47

WISWESSER LINE NOTATION :: L6YTJ AUYR DQ&R DQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >12 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,313,1982

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1700 mg/kg

TOXIC EFFECTS :: Behavioral - altered sleep time (including change in righting reflex) Behavioral - somnolence (general depressed activity) Skin and Appendages - hair

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 4,821,1970

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >12 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,313,1982

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >12500 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - anorexia (human) Gastrointestinal - hypermotility, diarrhea

REFERENCE :: APTOA6 Acta Pharmacologica et Toxicologica. (Copenhagen, Denmark) V.1-59, 1945-86. For publisher information, see PHTOEH Volume(issue)/page/year: 23,365,1966

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1080 mg/kg

TOXIC EFFECTS :: Behavioral - altered sleep time (including change in righting reflex) Behavioral - somnolence (general depressed activity) Skin and Appendages - hair

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 4,821,1970

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >12 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,313,1982 ** OTHER MULTIPLE DOSE TOXICITY DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 9375 mg/kg/15W-I

TOXIC EFFECTS :: Nutritional and Gross Metabolic - weight loss or decreased weight gain Related to Chronic Data - changes in ovarian weight Related to Chronic Data - changes in prostate weight

REFERENCE :: APTOA6 Acta Pharmacologica et Toxicologica. (Copenhagen, Denmark) V.1-59, 1945-86. For publisher information, see PHTOEH Volume(issue)/page/year: 23,365,1966

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 3750 mg/kg/30D-I

TOXIC EFFECTS :: Liver - other changes Related to Chronic Data - changes in ovarian weight

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 6,1599,1972 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 1577 mg/kg

SEX/DURATION :: male 46 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count) Reproductive - Paternal Effects - testes, epididymis, sperm duct

REFERENCE :: ASUPAZ Acta Societatis Medicorum Upsaliensis. (Uppsala, Sweden) V.55-76, 1950-71. For publisher information, see UJMSAP. Volume(issue)/page/year: 73,199,1968

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 24 mg/kg

SEX/DURATION :: female 1-6 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Specific Developmental Abnormalities - musculoskeletal system

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 4,635,1970

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 48 mg/kg

SEX/DURATION :: female 9-14 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain) Reproductive - Effects on Newborn - physical

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 4,635,1970

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 32 mg/kg

SEX/DURATION :: female 3-4 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetal death

REFERENCE :: APTOA6 Acta Pharmacologica et Toxicologica. (Copenhagen, Denmark) V.1-59, 1945-86. For publisher information, see PHTOEH Volume(issue)/page/year: 25,65,1967

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 96 mg/kg

SEX/DURATION :: female 9-14 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - urogenital system

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 4,635,1970

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 80 mg/kg

SEX/DURATION :: female 3-4 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - abortion

REFERENCE :: APTSAI Acta Pharmacologica et Toxicologica, Supplementun. (Munksgaard International Pub., POB 2148, DK-1016 Copenhagen K, Denmark) No.1- 1947- Volume(issue)/page/year: 26(1),1,1968

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 175 mg/kg

SEX/DURATION :: male 7 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Paternal Effects - testes, epididymis, sperm duct Reproductive - Paternal Effects - prostate, seminal vesicle, Cowper's gland, accessory glands

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 4,835,1970

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 375 mg/kg

SEX/DURATION :: female 75 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Maternal Effects - ovaries, fallopian tubes

REFERENCE :: APTOA6 Acta Pharmacologica et Toxicologica. (Copenhagen, Denmark) V.1-59, 1945-86. For publisher information, see PHTOEH Volume(issue)/page/year: 23,365,1966

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 500 ug/kg

SEX/DURATION :: female 1 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Maternal Effects - uterus, cervix, vagina Reproductive - Maternal Effects - other effects

REFERENCE :: JRPFA4 Journal of Reproduction and Fertility. (Biochemical Soc. Book Depot, POB 32, Commerce Way, Colchester, Essex CO2 8HP, UK) V.1- 1960- Volume(issue)/page/year: 65,355,1982

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 300 mg/kg

SEX/DURATION :: female 30 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Fertility - female fertility index (e.g. # females pregnant per # sperm positive females; # females pregnant per # females mated)

REFERENCE :: APTOA6 Acta Pharmacologica et Toxicologica. (Copenhagen, Denmark) V.1-59, 1945-86. For publisher information, see PHTOEH Volume(issue)/page/year: 23,365,1966

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 300 mg/kg

SEX/DURATION :: male 30 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Fertility - male fertility index (e.g. # males impregnating females per # males exposed to fertile nonpregnant females)

REFERENCE :: APTOA6 Acta Pharmacologica et Toxicologica. (Copenhagen, Denmark) V.1-59, 1945-86. For publisher information, see PHTOEH Volume(issue)/page/year: 23,365,1966

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Parenteral

DOSE :: 150 mg/kg

SEX/DURATION :: female 3 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Maternal Effects - uterus, cervix, vagina

REFERENCE :: BIREBV Biology of Reproduction. (Soc. for the Study of Reproduction, 309 W. Clark St., Champaign, IL 61820) V.1- 1969- Volume(issue)/page/year: 1,397,1969

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 48 mg/kg

SEX/DURATION :: female 1-6 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth) Reproductive - Effects on Embryo or Fetus - fetal death

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 4,645,1970

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 32 mg/kg

SEX/DURATION :: female 1-2 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - female fertility index (e.g. # females pregnant per # sperm positive females; # females pregnant per # females mated)

REFERENCE :: APTOA6 Acta Pharmacologica et Toxicologica. (Copenhagen, Denmark) V.1-59, 1945-86. For publisher information, see PHTOEH Volume(issue)/page/year: 25,65,1967

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 20 mg/kg

SEX/DURATION :: female 3-4 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - abortion

REFERENCE :: APTSAI Acta Pharmacologica et Toxicologica, Supplementun. (Munksgaard International Pub., POB 2148, DK-1016 Copenhagen K, Denmark) No.1- 1947- Volume(issue)/page/year: 26(1),1,1968

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 6400 ug/kg

SEX/DURATION :: female 5 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Maternal Effects - uterus, cervix, vagina

REFERENCE :: APTOA6 Acta Pharmacologica et Toxicologica. (Copenhagen, Denmark) V.1-59, 1945-86. For publisher information, see PHTOEH Volume(issue)/page/year: 23,365,1966

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 4500 ug/kg

SEX/DURATION :: female 3 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Maternal Effects - uterus, cervix, vagina

REFERENCE :: ACENA7 Acta Endocrinologica (Copenhagen). (Periodica, Skolegade 12 E, DK-2500 Valby, Denmark) V.1- 1948- Volume(issue)/page/year: 63,283,1970

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 15 mg/kg

SEX/DURATION :: female 2-5 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - female fertility index (e.g. # females pregnant per # sperm positive females; # females pregnant per # females mated) Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea)

REFERENCE :: ACENA7 Acta Endocrinologica (Copenhagen). (Periodica, Skolegade 12 E, DK-2500 Valby, Denmark) V.1- 1948- Volume(issue)/page/year: 63,283,1970

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 900 mg/kg

SEX/DURATION :: female 1-9 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth)

REFERENCE :: CCPTAY Contraception. (Geron-X, Inc., POB 1108, Los Altos, CA 94022) V.1- 1970- Volume(issue)/page/year: 3,347,1971

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 1800 mg/kg

SEX/DURATION :: female 1-9 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea)

REFERENCE :: CCPTAY Contraception. (Geron-X, Inc., POB 1108, Los Altos, CA 94022) V.1- 1970- Volume(issue)/page/year: 3,347,1971

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 700 mg/kg

SEX/DURATION :: female 7 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Maternal Effects - uterus, cervix, vagina

REFERENCE :: CCPTAY Contraception. (Geron-X, Inc., POB 1108, Los Altos, CA 94022) V.1- 1970- Volume(issue)/page/year: 3,347,1971 *** REVIEWS *** TOXICOLOGY REVIEW CLECAP Clinical Endocrinology (Oxford). (Blackwell Scientific Pub. Ltd., POB 88, Oxford, UK) V.1- 1972- Volume(issue)/page/year: 4,551,1975

Safety Information

Personal Protective Equipment	Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
Hazard Codes	Xi
RIDADR	NONH for all modes of transport
WGK Germany	2
RTECS	GO7550000

Articles28

A misguided 'pill in the pocket' approach with flecainide leading to cardiac arrest.

BMJ Case Rep. 2012 , doi:10.1136/bcr-2012-006868, (2012)

Exploration of the bicyclo[3.3.1]nonane system as a template for the development of new ligands for the estrogen receptor.

Bioorg. Med. Chem. Lett. 13(24) , 4485-8, (2003)

Three novel structural motifs based on a bicyclo [3.3.1]nonane template were examined as new ligands for estrogen receptor (ER). Type III compounds emerged as the most promising leads for developing h...

Synthesis of new carbon-11 labeled cyclofenil derivatives for PET imaging of breast cancer estrogen receptors.

Appl. Radiat. Isot. 66(4) , 523-9, (2008)

Carbon-11 labeled cyclofenil derivatives, [(11)C]methyl-2-{4-[bis(4-hydroxyphenyl)methylene]cyclohexyl}acetate ([(11)C]16a), [(11)C]methyl-4-[bis(4-hydroxyphenyl)methylene]cyclohexanecarboxylate ([(11...

Synonyms

ondonid

p-Cresol, α-cyclohexylidene-α- (p-hydroxyphenyl)-, diacetate

EINECS 220-089-1

(Cyclohexylidenemethylene)di-4,1-phenylene diacetate

cyclofenil

4-[[4-(Acetyloxy)phenyl]cyclohexylidenemethyl]phenol Acetate

sexovar

Phenol, 4,4'-(cyclohexylidenemethylene)bis-, diacetate

Phenol, 4-((4-(acetyloxy)phenyl)cyclohexylidenemethyl)-, acetate (9CI)

ondogyne

a-Cyclohexylidene-a-(p-hydroxyphenyl)-p-cresol Diacetate

Phenol, 4-[[4- (acetyloxy)phenyl]cyclohexylidenemethyl]-, acetate

f6066

oginex

h3452

4,4'-Diacetoxybenzhydrylidenecyclohexane

cyclofenyl

MFCD00190153

(cyclohexylidenemethanediyl)dibenzene-4,1-diyl diacetate

Bis(p-acetoxyphenyl)cyclohexylidenemethane

sexadieno

fertodur

Recommended......