Mitotane

Modify Date: 2024-01-05 11:53:19

Mitotane Structure
Mitotane structure
 Common Name Mitotane
CAS Number 53-19-0 Molecular Weight 320.041
Density 1.4±0.1 g/cm3 Boiling Point 398.9±37.0 °C at 760 mmHg
Molecular Formula C14H10Cl4 Melting Point 77-78 °C(lit.)
MSDS Chinese USA Flash Point 194.2±23.9 °C
Symbol GHS08
GHS08		 Signal Word Warning

 Use of Mitotane


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%), gynecomastia (50%), arthralgia (19%), and leukopenia (7%).

 Names

Name 1-chloro-2-[2,2-dichloro-1-(4-chlorophenyl)ethyl]benzene
Synonym More Synonyms

 Mitotane Biological Activity

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%), gynecomastia (50%), arthralgia (19%), and leukopenia (7%).
Related Catalog
References

[1]. Gentilin E, Tagliati F, Terzolo M, Mitotane reduces human and mouse ACTH-secreting pituitary cell viability and function. J Endocrinol. 2013 Jul 29;218(3):275-285.

[2]. Lehmann TP, Wrzesiński T, Jagodziński PP. The effect of mitotane on viability, steroidogenesis and gene expression in NCI H295R adrenocortical cells. Mol Med Rep. 2013 Mar;7(3):893-900.

[3]. Takeshita A, Igarashi-Migitaka J, Koibuchi N, Mitotane induces CYP3A4 expression via activation of the steroid and xenobiotic receptor. J Endocrinol. 2013 Feb 15;216(3):297-305.

[4]. Ederhy S, Cohen A, Dufaitre G, No evidence for relevant QT interval prolongation in mitotane-treated patients with adrenocortical carcinoma. J Endocrinol Invest. 2012 Nov;35(10):911-4.

[5]. Alexandraki KI, Kaltsas GA, le Roux CW, Assessment of serum-free cortisol levels in patients with adrenocortical carcinoma treated with mitotane: a pilot study. Clin Endocrinol (Oxf). 2010 Mar;72(3):305-11.

 Chemical & Physical Properties

Density 1.4±0.1 g/cm3
Boiling Point 398.9±37.0 °C at 760 mmHg
Melting Point 77-78 °C(lit.)
Molecular Formula C14H10Cl4
Molecular Weight 320.041
Flash Point 194.2±23.9 °C
Exact Mass 317.953674
LogP 5.39
Vapour Pressure 0.0±0.9 mmHg at 25°C
Index of Refraction 1.599
Water Solubility <0.1 g/100 mL at 24 ºC

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
KH7880000
CHEMICAL NAME :
Ethane, 2-(o-chlorophenyl)-2-(p-chlorophenyl)-1,1-dichloro-
CAS REGISTRY NUMBER :
53-19-0
BEILSTEIN REFERENCE NO. :
2056007
LAST UPDATED :
199612
DATA ITEMS CITED :
25
MOLECULAR FORMULA :
C14-H10-Cl4
MOLECULAR WEIGHT :
320.04
WISWESSER LINE NOTATION :
GYGYR BG&R DG

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
17 gm/kg/35W
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
800 mg/kg/4D
TOXIC EFFECTS :
Skin and Appendages - dermatitis, other (after systemic exposure)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
11 gm/kg/15W
TOXIC EFFECTS :
Vascular - BP lowering not characterized in autonomic section Blood - normocytic anemia Blood - pigmented or nucleated red blood cells
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
14 gm/kg/22W
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Gastrointestinal - hypermotility, diarrhea Gastrointestinal - nausea or vomiting
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>5 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>4 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - guinea pig
DOSE/DURATION :
>5 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
8400 mg/kg/28D-I
TOXIC EFFECTS :
Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - phosphatases
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
2800 mg/kg/28D-I
TOXIC EFFECTS :
Endocrine - other changes Endocrine - changes in adrenal weight Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - phosphatases
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - guinea pig
DOSE/DURATION :
4200 mg/kg/14D-I
TOXIC EFFECTS :
Endocrine - other changes Related to Chronic Data - death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
10 gm/kg/52W-C
TOXIC EFFECTS :
Tumorigenic - equivocal tumorigenic agent by RTECS criteria Reproductive - Tumorigenic effects - testicular tumors
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
2500 mg/kg/7W-I
TOXIC EFFECTS :
Tumorigenic - equivocal tumorigenic agent by RTECS criteria Blood - lymphoma, including Hodgkin's disease Skin and Appendages - tumors
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
9750 mg/kg/26W-I
TOXIC EFFECTS :
Tumorigenic - equivocal tumorigenic agent by RTECS criteria Lungs, Thorax, or Respiration - tumors Blood - lymphoma, including Hodgkin's disease
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
16 gm/kg
SEX/DURATION :
male 15 week(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count) Reproductive - Paternal Effects - testes, epididymis, sperm duct
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
250 mg/kg
SEX/DURATION :
female 15-19 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - endocrine system Reproductive - Specific Developmental Abnormalities - urogenital system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
900 mg/kg
SEX/DURATION :
female 6-14 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth) Reproductive - Effects on Embryo or Fetus - extra-embryonic structures (e.g., placenta, umbilical cord) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
900 mg/kg
SEX/DURATION :
female 6-14 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - Central Nervous System Reproductive - Specific Developmental Abnormalities - eye/ear Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
900 mg/kg
SEX/DURATION :
female 6-14 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetal death

MUTATION DATA

TYPE OF TEST :
Cytogenetic analysis
TEST SYSTEM :
Rodent - rat Cells - not otherwise specified
DOSE/DURATION :
10 ug/L
REFERENCE :
34LXAP "Insecticide Biochemistry and Physiology," Wilkinson, C.F., ed., New York, Plenum Pub. Corp., 1976 Volume(issue)/page/year: -,555,1976 *** REVIEWS *** IARC Cancer Review:Animal Sufficient Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 53,179,1991 IARC Cancer Review:Human Inadequate Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 53,179,1991 IARC Cancer Review:Group 2B IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 53,179,1991 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X2075 No. of Facilities: 10 (estimated) No. of Industries: 1 No. of Occupations: 1 No. of Employees: 197 (estimated) No. of Female Employees: 59 (estimated)

 Safety Information

Symbol GHS08
GHS08
Signal Word Warning
Hazard Statements H351
Precautionary Statements P280
Personal Protective Equipment dust mask type N95 (US);Eyeshields;Gloves
Hazard Codes Xn:Harmful
Risk Phrases R40
Safety Phrases S36/37
RIDADR 3249
WGK Germany 3
RTECS KH7880000
Packaging Group III
Hazard Class 6.1(b)
HS Code 2903999090

 Synthetic Route

 Customs

HS Code 2903999090
Summary 2903999090 halogenated derivatives of aromatic hydrocarbons VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:5.5% General tariff:30.0%

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 Synonyms

2,4'-Ddd
Khlodithan
1-Chloro-2-[2,2-dichloro-1-(4-chlorophenyl)ethyl]benzene
Opeprim
EINECS 200-166-6
O,P'-DDD
Mitotan
o,p′-DDD
o,p'-Dichlorodiphenyldichloroethane
Mitotane (Lsodren)
o,p'-TDE
Lysodren
Chlodithan
Chloditan
(2,4'-Dichlorodiphenyl)dichloroethane
Benzene, 1-chloro-2-(2,2-dichloro-1-(4-chlorophenyl)ethyl)-
Mitotane
Chlodithane
Benzene, 1-chloro-2-[2,2-dichloro-1-(4-chlorophenyl)ethyl]-
MFCD00000850
DDD, o,p'-
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