2,2,o,p-tetrachloroethylidenebisbenzene
1-(2-chlorophenyl)-1-(4-chlorophenyl)-2,2-dichloroethane
CAS: 53-19-0
Molecular Formula: C14H10Cl4
2,2,o,p-tetrachloroethylidenebisbenzene - Names and Identifiers
| Name | 1-(2-chlorophenyl)-1-(4-chlorophenyl)-2,2-dichloroethane |
| Synonyms | Mitotan Mitotane 2,4'-TDE 2,4'-DDD LYSODREN (2,4'-DICHLORODIPHENYL)DICHLOROETHANE 2,2,o,p-tetrachloroethylidenebisbenzene 1-(2-Chlorophenyl)-1-(4-chlorophenyl)-2,2-dichlor 1,1-DICHLORO-2-(O-CHLOROPHENYL)-2-(P-CHLOROPHENYL)ETHANE 1,1-DICHLORO-2-(2-CHLOROPHENYL)-2-(4-CHLOROPHENYL)ETHANE 2-(2-CHLOROPHENYL)-2-(4-CHLOROPHENYL)-1,1-DICHLOROETHANE 1-(2-chlorophenyl)-1-(4-chlorophenyl)-2,2-dichloroethane 2,2-(2-chlorophenyl)-2-(4-chlorophenyl)-1,1-dichloroethane |
| CAS | 53-19-0 |
| EINECS | 200-166-6 |
| InChI | InChI=1/C14H10Cl4/c15-10-7-5-9(6-8-10)13(14(17)18)11-3-1-2-4-12(11)16/h1-8,13-14H |
2,2,o,p-tetrachloroethylidenebisbenzene - Physico-chemical Properties
| Molecular Formula | C14H10Cl4 |
| Molar Mass | 320.04 |
| Density | 1.3118 (rough estimate) |
| Melting Point | 77-78°C(lit.) |
| Boling Point | 405.59°C (rough estimate) |
| Water Solubility | <0.1 g/100 mL at 24 ºC |
| Solubility | DMSO: soluble20mg/mL, clear |
| Appearance | powder |
| Color | white to beige |
| Merck | 13,6237 / 13,6237 |
| BRN | 2056007 |
| Storage Condition | Inert atmosphere,Room Temperature |
| Refractive Index | 1.6000 (estimate) |
| Physical and Chemical Properties | Melting point 76-78°C water-soluble <0.1g/100 mL at 24°C |
| Use | This product is for scientific research only and shall not be used for other purposes. |
| In vitro study | In the mouse TalphaT1 cell line, Mitotane inhibits the expression and secretion of TSH, blocks the response of TSH to TRH, and reduces cell viability, and induces apoptosis. In pituitary TSH-secreting mouse cells, Mitotane does not interfere with thyroid hormone, but directly reduces secretory activity and cell viability. Mitotane induces adrenal cortical necrosis, mitochondrial membrane damage, and irreversible binding to the protein CYP. Mitotane(10-40 μm) inhibited basal and cAMP-induced cortisol secretion but did not cause cell death. Mitotane showed inhibitory effects on basal StAR and P450scc proteins. Mitotane(40 μm) significantly reduced the mRNA levels of StAR, CYP11A1 and cyp21. Mitotane(40 μm) almost completely neutralized the induction of STAR,CYP11A1,CYP17, and CYP21 mRNA by adenosine 8-bromo-cyclic phosphate. In the S phase of H295R cells, the combination of Mitotane and gemcitabine showed antagonism and interfered with gemcitabine-mediated inhibition in the cell cycle. |
| In vivo study | In rats, Mitotane(60 mg/kg) significantly reduced adrenal mitochondrial and microsomal "P-450" and microsomal proteins by 34%,55% and 35%. |
2,2,o,p-tetrachloroethylidenebisbenzene - Risk and Safety
| Hazard Symbols | Xn - Harmful |
| Risk Codes | 40 - Limited evidence of a carcinogenic effect |
| Safety Description | 36/37 - Wear suitable protective clothing and gloves. |
| UN IDs | 3249 |
| WGK Germany | 3 |
| RTECS | KH7880000 |
| HS Code | 2903990002 |
| Hazard Class | 6.1(b) |
| Packing Group | III |
2,2,o,p-tetrachloroethylidenebisbenzene - Reference Information
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| pharmacological action | mitotane structure is similar to insecticide DDT (DDT) and DDD. it can selectively atrophy and necrosis the cells of the adrenal cortex fascicular zone and reticulum zone, but does not affect the globular zone, so aldosterone secretion is not affected. After medication, hydrocortisone and its metabolites in the blood and urine are rapidly reduced, and the levels of adrenal cortex hormones and their metabolites in the body are rapidly reduced. It is suitable for the treatment of inoperable, functional and non-functional adrenal cortical cancer, adrenal tumors, Ku's syndrome caused by adrenal hyperplasia, adrenal cortical hyperplasia, postoperative adjuvant treatment of cortical cancer, and hypercortisolism caused by tumors. About 40% of the oral administration is absorbed by the gastrointestinal tract, and the remaining 60% is excreted in the stool as a prototype. 5~10g per day, the blood drug concentration can reach 10~90 μg/ml, and the metabolite concentration is 30~50 μg/ml. After 6~9 weeks of drug withdrawal, o-chlorane can still be detected in plasma. Mitotane is highly fat-soluble and is mainly stored in fat. Water-soluble metabolites excreted from urine account for about 25% of the dose. |
| use | antineoplastic drugs. Used as an adrenergolytic agent. Anti-tumor drugs are used to treat adrenal cortex cancer. |
| indications | inoperable, functional and non-functional adrenocortical carcinoma, adrenal hyperplasia and hypercortisolism caused by tumors. |
| biological activity | Mitotane (NCI-C04933) is an anti-tumor drug used to treat adrenal cortex cancer. |
| Target | Value |
| production method | is prepared from o-bromochlorobenzene (see 05820) through the following steps. |
| category | toxic substances |
| toxicity classification | poisoning |
| acute toxicity | oral-rat LD50: > 5000 mg/kg; Oral-mouse LD50: > 4000 mg/kg |
| flammability hazard characteristics | thermal decomposition discharges toxic chloride smoke |
| storage and transportation characteristics | warehouse low temperature ventilation and drying |
| fire extinguishing agent | water, carbon dioxide, foam, dry powder |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-10 22:29:15
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