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Mitotane

Mitotane structure

CAS No:
53-19-0
Formula:
C14H10Cl4
Chemical Name:
Mitotane
Synonyms:
Benzene,1-chloro-2-[2,2-dichloro-1-(4-chlorophenyl)ethyl]-;Ethane,1,1-dichloro-2-(o-chlorophenyl)-2-(p-chlorophenyl)-;1-Chloro-2-[2,2-dichloro-1-(4-chlorophenyl)ethyl]benzene;1-(2-Chlorophenyl)-1-(4-chlorophenyl)-2,2-dichloroethane;o,p′-DDD;Mitotane;o,p′-TDE;1,1-Dichloro-2-(o-chlorophenyl)-2-(p-chlorophenyl)ethane;Chlodithane;1-(o-Chlorophenyl)-1-(p-chlorophenyl)-2,2-dichloroethane;2-(p-Chlorophenyl)-2-(o-chlorophenyl)-1,1-dichloroethane;o,p′-Dichlorodiphenyldichloroethane;Chloditan;2,4′-Dichlorodiphenyldichloroethane;Lysodren;Mitotan;CB 313;NSC 38721;2-(2-Chlorophenyl)-2-(4-chlorophenyl)-1,1-dichloroethane;Opeprim;1-(2′-Chlorophenyl)-1-(4′-chlorophenyl)-2,2-dichloroethane;1-Chloro-4-[2,2-dichloro-1-(2-chlorophenyl)ethyl]benzene;102976-59-0
Categories:
Active Pharmaceutical Ingredients > Antineoplastic Agents

Description

Mitotane(2,4′-DDD), an isomer of DDD and derivative of DDT, is an antineoplastic medication used in the treatment of adrenocortical carcinoma.IC50 value: Target: Mitotane alters steroid peripheral metabolism, directly suppresses the adrenal cortex and alters cortisone metabolism leading to hypocortisolism. Side effects as reported by Schteinberg et al. include anorexia and nausea (88%), diarrhea (38%), vomiting (23%), decreased memory and ability to concentrate (50%), rash (23%), gynecom

Mitotane Basic Attributes

Molecular Weight：

320.04

Exact Mass：

320.04

EC Number：

200-166-6

HScode：

2903999090

Characteristics

PSA：

XLogP3：

6.2

Appearance：

white to beige

Density：

1.4±0.1 g/cm3

Melting Point：

76-78 °C

Boiling Point：

398.9°C at 760 mmHg

Flash Point：

194.2±23.9 °C

Refractive Index：

1.599

Water Solubility：

H2O: <0.1 g/100 mL at 24 ºC;DMSO: soluble 20mg/mL, clear

Storage Conditions：

APPROX 4°C

Vapor Pressure：

1.94X10-6 mm Hg at 25 deg C

Toxicity：

Oral-rat LD50: > 5000 mg/kg; Oral-Mouse LD50: > 4000 mg/kg

Flammability characteristics：

Thermal decomposition to emit toxic chloride fumes

Safety Information

Packing level：

Ⅲ

Hazard category：

6.1(b)

Transport codes：

3249

wgk germany：

hazard class code：

safety instructions：

36/37

RTECS Number：

KH7880000

Marks：

Storage features：

The warehouse is low-temperature, ventilated and dry

Precautionary statement(s)：

P280

Hazard Statements：

H351

Toxicity

Toxicity class：

moderately toxic

Mitotane Use and Manufacturing

Methods of Manufacturing

It is prepared from o-bromochlorobenzene (see 05820) through the following steps.

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.

Computed Properties

Molecular Weight:320.0
XLogP3:6.2
Rotatable Bond Count:3
Exact Mass:319.950711
Monoisotopic Mass:317.953661
Heavy Atom Count:18
Complexity:248
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Material

Chlorobenzene

Sulfuric acid

2-Chlorobenzaldehyde

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CAS No.: 53-19-0

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CAS No.: 53-19-0

Grade: Pharmaceutical Grade

Content: 99%

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