Cyclofenil (F-6066; AI3-52271) is a novel and potent gonadal stimulant and inducer of ovulation. It can be used in the treatment of infertility and amenorrhea. It has anti-dengue-virus activity.
Physicochemical Properties
| Molecular Formula | C23H24O4 |
| Molecular Weight | 364.441 |
| Exact Mass | 364.167 |
| Elemental Analysis | C, 75.80; H, 6.64; O, 17.56 |
| CAS # | 2624-43-3 |
| Related CAS # | 5189-40-2 (diphenol);2624-43-3; |
| PubChem CID | 2898 |
| Appearance | White to off-white solid powder |
| Density | 1.2±0.1 g/cm3 |
| Boiling Point | 509.0±30.0 °C at 760 mmHg |
| Melting Point | 133-136°C |
| Flash Point | 254.8±23.0 °C |
| Vapour Pressure | 0.0±1.3 mmHg at 25°C |
| Index of Refraction | 1.573 |
| LogP | 5.9 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 6 |
| Heavy Atom Count | 27 |
| Complexity | 503 |
| Defined Atom Stereocenter Count | 0 |
| SMILES | O(C(C([H])([H])[H])=O)C1C([H])=C([H])C(=C([H])C=1[H])/C(/C1C([H])=C([H])C(=C([H])C=1[H])OC(C([H])([H])[H])=O)=C1\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C\1([H])[H] |
| InChi Key | GVOUFPWUYJWQSK-UHFFFAOYSA-N |
| InChi Code | 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 |
| Chemical Name | 4,4'-(Cyclohexylidenemethylene)diphenol diacetate ester |
| Synonyms | Cyclofenil; H 3452; F 6066; AI3-52271 |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| Targets | Estrogen receptor; Dengue virus |
| ln Vitro |
Dengue virus (DENV) replication in mammalian cells is inhibited by clofenil, but not in mosquito cells[1]. Additionally, clofenil prevents the Zika virus from replicating. Cyclofenil may disrupt the translation-RNA synthesis and assembly-maturation phases of the Dengue virus (DENV) life cycle, according to a time-of-addition experiment. After treatment with clofenil, the amount of intracellular infectious particles dropped more sharply than the amount of viral RNA, suggesting that the assembly-maturation stage may be the primary target of clofenil[1]. |
| ln Vivo | In intact rats, the number of ERα (estrogen receptor) and ERβ (estrogen receptor)-immunoreactive (-ir) cells is counted at each stage of the estrous cycle. Furthermore, the effects of microinjecting methyl-piperidino-pyrazole (MPP) or clofenil on either side of the preoptic-anterior hypothalamic area (POA-AHA) to block ERα and ERβ on the rate of ovulation on diestrus-2 or proestrus day are assessed. In POA-AHA, the quantity of ERα-ir and ERβ-ir cells varied throughout the estrous cycle.On diestrus-2 day, the ovulation rate was decreased in rats treated with MPP on either side and with Cyclofenil on the left side of POA-AHA. On proestrus day, the ovulation rate was decreased in rats treated with MPP on either side. Progesterone and follicle stimulating hormone (FSH) increased while luteinizing hormone (LH) surge was reduced when MPP or clofenil was administered[2]. |
| References |
[1]. An estrogen antagonist, cyclofenil, has anti-dengue-virus activity. Arch Virol. 2019 Jan;164(1):225-234. [2]. Estrogen Receptors Alpha and Beta in POA-AHA Region Regulate Asymmetrically Ovulation. Cell Mol Neurobiol. 2019 Nov;39(8):1139-1149. |
| Additional Infomation |
Cyclofenil is an organic molecular entity. A gonadal stimulant and inducer of ovulation. It is used in the treatment of infertility and amenorrhea, but is thought to be less effective than CLOMIPHENE. |
Solubility Data
| Solubility (In Vitro) | DMSO : 21~100 mg/mL (57.62~274.39 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (6.86 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. Solubility in Formulation 2: 10% DMSO+90% Corn Oil: ≥ 2.5 mg/mL (6.86 mM) (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.7439 mL | 13.7197 mL | 27.4394 mL | |
| 5 mM | 0.5488 mL | 2.7439 mL | 5.4879 mL | |
| 10 mM | 0.2744 mL | 1.3720 mL | 2.7439 mL |