Cyclofenil

Modify Date: 2024-01-14 07:17:38

Cyclofenil Structure
Cyclofenil structure
 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

 Use of Cyclofenil


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].

 Names

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

 Cyclofenil Biological Activity

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
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
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

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 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
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