环芬尼

环芬尼用途

Cyclofenil 是一种选择性雌激素受体 (estrogen receptor) 调节剂和排卵诱导剂。Cyclofenil 对 Vero 细胞中的登革热病毒复制具有抑制作用,EC50 为 1.62 μM。 Cyclofenil 具有抗登革热病毒的活性。

环芬尼名称

[ CAS 号 ]:
2624-43-3

[ 中文名 ]:
环芬尼

[ 英文名 ]:
Cyclofenil

[中文别名 ]:

双醋环烷

[英文别名 ]:

ondonid
EINECS 220-089-1
cyclofenil
sexovar
ondogyne
f6066
oginex
h3452
4,4'-Diacetoxybenzhydrylidenecyclohexane
cyclofenyl

环芬尼生物活性

[ 描述 ]:

[ 相关类别 ]:

信号通路 >> 其他 >> 雌激素受体/ERR

信号通路 >> 抗感染 >> 流感病毒

研究领域 >> 内分泌

研究领域 >> 感染

[ 靶点 ]

Estrogen receptor[1]; Dengue virus[1]

[体外研究]

环磷酰胺对登革热病毒(DENV)在哺乳动物细胞中的复制有抑制作用,但对蚊子细胞没有抑制作用[1]。环磷酰胺也能抑制寨卡病毒的复制。添加时间分析表明,环磷酰胺可能干扰登革病毒(DENV)生命周期的两个阶段：翻译RNA合成和组装成熟阶段。环孢芬尼治疗后细胞内感染颗粒的水平较病毒RNA水平下降更为明显,说明细胞的组装成熟期可能是环孢芬尼的主要靶点[1]。

[体内研究]

雌激素受体α(ERα)和β(ERβ)免疫反应细胞(ir)的数量是在正常大鼠动情周期的各个阶段测定的。此外,通过在视前下丘脑前区(POA-AHA)两侧微量注射甲基哌啶吡唑(MPP)或环非尼(Cyclofenil),观察了雌激素受体α(ERα)和雌激素受体β(ERβ)对间期2或动情前期排卵率的影响。POA-AHA中ERα-ir和ERβ-ir细胞的数量在动情周期的各个阶段都有变化。POA-AHA右侧的MPP或环磷酰胺在间期2天降低了排卵率,而在动情前一天,MPP治疗的大鼠和环磷酰胺治疗的大鼠的排卵率都降低了。MPP或环磷酰胺降低了黄体生成素水平(LH)的激增,增加了孕酮和卵泡刺激素(FSH)[2]。

[参考文献]

[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.

环芬尼物理化学性质

[ 密度 ]:
1.2±0.1 g/cm3

[ 沸点 ]:
509.0±30.0 °C at 760 mmHg

[ 熔点 ]:
133-136°C

[ 分子式 ]:
C₂₃H₂₄O₄

[ 分子量 ]:
364.434

[ 闪点 ]:
254.8±23.0 °C

[ 精确质量 ]:
364.167450

[ PSA ]:
52.60000

[ LogP ]:
5.90

[ 外观性状 ]:
solid

[ 蒸汽压 ]:
0.0±1.3 mmHg at 25°C

[ 折射率 ]:
1.573

[ 储存条件 ]:
2-8°C

[ 水溶解性 ]:
DMSO: 10 mg/mL at 60 °C, soluble

环芬尼毒性和生态

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

环芬尼安全信息

[ 个人防护装备 ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ 危害码 (欧洲) ]:
Xi

[ 危险品运输编码 ]:
NONH for all modes of transport

[ WGK德国 ]:
2

[ RTECS号 ]:
GO7550000

环芬尼文献

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...

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环芬尼