Mitotan
- CAS No.
- 53-19-0
- Chemical Name:
- Mitotan
- Synonyms
- MITOTANE;LYSODREN;Mitotam;O,P'-DDD;2,4'-DDD;Mitotane API;CB-313;Peprin;4′-DDD;p'-DDD
- CBNumber:
- CB0392321
- Molecular Formula:
- C14H10Cl4
- Molecular Weight:
- 320.04
- MOL File:
- 53-19-0.mol
- Modify Date:
- 2024/7/25 20:04:34
| Melting point | 77-78 °C(lit.) |
|---|---|
| Boiling point | 405.59°C (rough estimate) |
| Density | 1.3118 (rough estimate) |
| refractive index | 1.6000 (estimate) |
| storage temp. | Inert atmosphere,Room Temperature |
| solubility | DMSO: soluble20mg/mL, clear |
| form | powder |
| color | white to beige |
| Water Solubility | <0.1 g/100 mL at 24 ºC |
| Merck | 13,6237 / 13,6237 |
| BRN | 2056007 |
| InChI | InChI=1S/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 |
| InChIKey | JWBOIMRXGHLCPP-UHFFFAOYSA-N |
| SMILES | C1(Cl)=CC=CC=C1C(C1=CC=C(Cl)C=C1)C(Cl)Cl |
| CAS DataBase Reference | 53-19-0(CAS DataBase Reference) |
| NIST Chemistry Reference | Mitotane(53-19-0) |
| EPA Substance Registry System | o,p'-DDD (53-19-0) |
Mitotan price More Price(4)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich(India) | SML1885 | Mitotane ≥98% (HPLC) | 53-19-0 | 100MG | ₹5260.95 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | 35485 | 2,4′-DDD PESTANAL?, analytical standard | 53-19-0 | 250MG | ₹7838.65 | 2022-06-14 | Buy |
| TCI Chemicals (India) | M3304 | Mitotane min. 98.0 % | 53-19-0 | 1G | ₹2400 | 2022-05-26 | Buy |
| TCI Chemicals (India) | M3304 | Mitotane min. 98.0 % | 53-19-0 | 5G | ₹8300 | 2022-05-26 | Buy |
Mitotan Chemical Properties,Uses,Production
Description
Mitotane is an inhibitor of steroidogenesis that suppresses the growth of adrenocortical cells. It blocks the expression of several genes that encode proteins involved in steroidogenesis and disrupts mitochondrial respiratory chain activity in human adrenocortical cells. Mitotane has anti-neoplastic actions, alone or in combination with other compounds, and suppresses cortisol synthesis, although it also has significant toxicity in the gastrointestinal tract and nervous system. It is effective against adrenocortical carcinoma and Cushing’s Syndrome in clinical trials.
Chemical Properties
Crystalline Solid
Uses
Mitotane is an inhibitor of steroidogenesis that suppresses the growth of adrenocortical cells. It blocks the expression of several genes that encode proteins involved in steroidogenesis and disrupts mitochondrial respiratory chain activity in human adrenocortical cells. Mitotane has anti-neoplastic actions, alone or in combination with other compounds, and suppresses cortisol synthesis, although it also has significant toxicity in the gastrointestinal tract and nervous system. It is effective against adrenocortical carcinoma and Cushing’s Syndrome in clinical trials.
Indications
Mitotane (Lysodren) produces selective atrophy of the zona fasciculata and zona reticularis, which results in a decrease in the secretion of 17-hydroxycorticosteroids. Direct inhibition of cholesterol side-chain cleavage and 11/18-hydroxylase activities has also been demonstrated.
General Description
Colorless powder.
Air & Water Reactions
Insoluble in water.
Reactivity Profile
Mitotan dehydrohalogenates with strong alkalis. Simple aromatic halogenated organic compounds are very unreactive; halogenated aliphatic compounds are moderately or very reactive. For both subgroups, reactivity generally decreases with increased degree of substitution of halogen for hydrogen atoms. Materials in this group are incompatible with strong oxidizing and reducing agents. Also, they are incompatible with many amines, nitrides, azo/diazo compounds, alkali metals, and epoxides.
Fire Hazard
Flash point data for Mitotan are not available. Mitotan is probably combustible.
Pharmacology
Mitotane, a derivative of the insecticide DDT, quickly lowers the level of corticosteroids, and is metabolized in the blood and urine and used on non-operable metastatic prostate carcinomas. Synonyms of this drug are lysodren and others.
Clinical Use
Mitotane is the drug of choice for the treatment of
primary adrenal carcinoma when surgery or radiation
therapy is not feasible. Its effectiveness
in curtailing adrenal activity is due to an action on
adrenocortical mitochondria to impair cytochrome
P450 steps in steroid biosynthesis. Mitotane requires
metabolic transformation to exert its therapeutic action,
and the differential ability of tumors to metabolize
the drug may determine its clinical effectiveness. It is
advised to measure serum mitotane levels and urinary
free cortisol excretion to ensure adequate therapeutic
concentrations. Mitotane increases circulating cholesterol
by inhibiting cytochrome P450–mediated reactions
and therefore contributes to the cardiovascular
events that are a significant cause of mortality in untreated
Cushing’s syndrome.
Mitotane, being closely related to the organochlorine
insecticides, shares its inductive effects on the liver
microsomal drug-metabolizing enzyme system, and its
use may therefore alter the requirement for concomitantly
administered drugs that are also metabolized by
this pathway.
Side effects
Mitotane is capable of inducing remission of Cushing’s disease, but only after several weeks of therapy and at the price of severe gastrointestinal distress. Moreover, more than half of patients relapse following cessation of therapy. Other side effects include lethargy, mental confusion, skin rashes, and altered hepatic function. Being a lipid-soluble substance, mitotane remains stored in body tissues for extended periods. This may account for the marked patient-to-patient variability in its therapeutic and/or toxic effects.
Purification Methods
Purify Mitotane by recrystallisation from pentane, MeOH or EtOH. It is soluble in isooctane and CCl4. [Haller et al. J Am Chem Soc 67 1600 1945, Beilstein 5 IV 1883.]
Mitotan Preparation Products And Raw materials
| Supplier | Tel | Country | ProdList | Advantage | Inquiry |
|---|---|---|---|---|---|
| TCI Chemicals (India) Pvt. Ltd. | 1800 425 7889 | New Delhi, India | 6778 | 58 | Inquiry |
| Pharmaffiliates Analytics and Synthetics P. Ltd | +91-172-5066494 | Haryana, India | 6773 | 58 | Inquiry |
| CLEARSYNTH LABS LTD. | +91-22-45045900 | Hyderabad, India | 6351 | 58 | Inquiry |
| Pharma Affiliates | 172-5066494 | Haryana, India | 6761 | 58 | Inquiry |
| Shijiazhuang Dingmin Pharmaceutical Sciences Co., Ltd. | +86-0311-67591193 +8613931880626 | China | 252 | 58 | Inquiry |
| Hebei Mojin Biotechnology Co., Ltd | +86 13288715578 +8613288715578 | China | 12495 | 58 | Inquiry |
| Capot Chemical Co.,Ltd. | 571-85586718 +8613336195806 | China | 29798 | 60 | Inquiry |
| Henan Tianfu Chemical Co.,Ltd. | +86-0371-55170693 +86-19937530512 | China | 21663 | 55 | Inquiry |
| ATK CHEMICAL COMPANY LIMITED | +undefined-21-51877795 | China | 32836 | 60 | Inquiry |
| career henan chemical co | +86-0371-86658258 +8613203830695 | China | 29888 | 58 | Inquiry |