53-19-0
53-19-0
Chemical Structure
Mitotane
Synonym(s): 2,4′-DDD; o,p'-DDD
- CAS No.: 53-19-0
- Formula:C14H10Cl4
- Molecular Weight:320.04
IUPAC Name: 1-chloro-2-(2,2-dichloro-1-(4-chlorophenyl)ethyl)benzene
InChIKey: JWBOIMRXGHLCPP-UHFFFAOYSA-N
SMILES: ClC1=CC=C(C(C2=CC=CC=C2Cl)C(Cl)Cl)C=C1
Biological Activity: Mitotane (2,4′-DDD), an isomer of DDD and derivative of dichlorodiphenyltrichloroethane (DDT), is an antineoplastic agent, can be used to research adrenocortical carcinoma. Mitotane exert its adrenocorticolytic effect at least in part through lipotoxicity induced by intracellular free cholesterol (FC) accumulation. Mitotane can have direct pituitary effects on corticotroph cells. Mitotane can induce CYP3A4 gene expression via steroid and xenobiotic receptor (SXR) activation, and has agent-agent interactions[1][2][3][4].
| Cat. No. | Product Name | Purity | Description | Pricing | |||||||||||||||||||
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Mitotane | 99.95% | Mitotane (2,4′-DDD), an isomer of DDD and derivative of dichlorodiphenyltrichloroethane (DDT), is an antineoplastic agent, can be used to research adrenocortical carcinoma. Mitotane exert its adrenocorticolytic effect at least in part through lipotoxicity induced by intracellular free cholesterol (FC) accumulation. Mitotane can have direct pituitary effects on corticotroph cells. Mitotane can induce CYP3A4 gene expression via steroid and xenobiotic receptor (SXR) activation, and has agent-agent interactions. | ||||||||||||||||||||
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Mitotane (Standard) | 99.99% | Mitotane (Standard) is the analytical standard of Mitotane. This product is intended for research and analytical applications. Mitotane (2,4′-DDD), an isomer of DDD and derivative of dichlorodiphenyltrichloroethane (DDT), is an antineoplastic agent, can be used to research adrenocortical carcinoma. Mitotane exert its adrenocorticolytic effect at least in part through lipotoxicity induced by intracellular free cholesterol (FC) accumulation. Mitotane can have direct pituitary effects on corticotroph cells. Mitotane can induce CYP3A4 gene expression via steroid and xenobiotic receptor (SXR) activation, and has agent-agent interactions. | ||||||||||||||||||||
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Mitotane-13C6 | 98.62% | Mitotane-13C6 is the 13C labeled Mitotane. Mitotane (2,4′-DDD), an isomer of DDD and derivative of dichlorodiphenyltrichloroethane (DDT), is an antineoplastic agent, can be used to research adrenocortical carcinoma. Mitotane exert its adrenocorticolytic effect at least in part through lipotoxicity induced by intracellular free cholesterol (FC) accumulation. Mitotane can have direct pituitary effects on corticotroph cells. Mitotane can induce CYP3A4 gene expression via steroid and xenobiotic receptor (SXR) activation, and has agent-agent interactions. | ||||||||||||||||||||
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Mitotane-d8 | Mitotane-d8 is the deuterium labeled Mitotane. Mitotane (2,4′-DDD), an isomer of DDD and derivative of dichlorodiphenyltrichloroethane (DDT), is an antineoplastic agent, can be used to research adrenocortical carcinoma. Mitotane exert its adrenocorticolytic effect at least in part through lipotoxicity induced by intracellular free cholesterol (FC) accumulation. Mitotane can have direct pituitary effects on corticotroph cells. Mitotane can induce CYP3A4 gene expression via steroid and xenobiotic receptor (SXR) activation, and has agent-agent interactions. | |||||||||||||||||||||
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Mitotane-13C12 | Mitotane-13C12 (2,4′-DDD-13C12) is 13C labeled Mitotane. Mitotane (2,4′-DDD), an isomer of DDD and derivative of dichlorodiphenyltrichloroethane (DDT), is an antineoplastic agent, can be used to research adrenocortical carcinoma. Mitotane exert its adrenocorticolytic effect at least in part through lipotoxicity induced by intracellular free cholesterol (FC) accumulation. Mitotane can have direct pituitary effects on corticotroph cells. Mitotane can induce CYP3A4 gene expression via steroid and xenobiotic receptor (SXR) activation, and has agent-agent interactions. | |||||||||||||||||||||
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Perthane | Perthane is an active compound. | |||||||||||||||||||||
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o,p'-DDE | 99.95% | o,p'-DDE (2,4-Dichlorodiphenyldichloroethylene) is a metabolite and degradation product of the organochlorine pesticide DDT. It accumulates in smallmouth buffalo, channel catfish, and largemouth bass, and in sediments from DDT manufacturing plants around the Huntsville Spring Branch-Indian Creek tributary system, where it is considered a persistent organic pollutant (POP). o,p'-DDE inhibits estrogen binding to the rainbow trout estrogen receptor (rtER) with an IC50 value of 3.2 μM. It induces concentration-dependent estradiol secretion in co-cultures of granulosa and theca cells isolated from porcine follicles. In ovo exposure to o,p'-DDE increases follicular degeneration and reduces testis size in Japanese medaka (O. latipes). | ||||||||||||||||||||
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DDOH | DDOH is an effective metabolite of DTT. DDOH can combine with palmitic acid to form conjugates. | |||||||||||||||||||||
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o,p'-DDT | o,p'-DDT (2,4'-DDT) is a chlorinated organic pesticide with estrogenic activity. o,p'-DDT is persistent in the environment, can accumulate in organisms and disrupt the endocrine system. o,p'-DDT is used in agriculture as a pesticide, especially for controlling insect pests. The use of o,p'-DDT has led to toxic effects in organisms, raising widespread concern about its environmental and health effects. o,p'-DDT has also led to research into its long-term effects in ecosystems. | |||||||||||||||||||||
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p,p'-DDD | 99.37% | p,p'-DDD (4,4’-DDD) is an organochlorine insecticide, a major metabolite of p,p'-DDT. p,p'-DDD is an agonist at estrogen receptor α(ERα) and ERβ. p,p'-DDD increases DNA damage, apoptosis and necrosis in peripheral blood. p,p'-DDD stimulates cell proliferation in SKBR3 cells. p,p'-DDD activates the AP-1 transcription factor. p,p'-DDD decreases sleep times of barbiturates and steroids in rats. | ||||||||||||||||||||
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2,4'-Dichlorobenzophenone | 98.52% | 2,4'-Dichlorobenzophenone is a dichlorinated benzophenone and intermediate in the synthesis of selected fungicides and other agricultural products. | ||||||||||||||||||||
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1-Chloro-4-[2-chloro-1-(4-chlorophenyl)ethyl]benzene | 1-Chloro-4-benzene (1,1-Bis (p-chlorophenyl)-2-chloroethane) (Compound DDMS) is the dechlorination reduction product of DDT (insecticide) and DDD. | |||||||||||||||||||||
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p,p'-DDD-13C12 | p,p'-DDD-13C12 is 13C labeled p,p'-DDD. p,p'-DDD is a major metabolite of p,p'-DDT. p,p'-DDD occurs in the feces and livers of rats, that are given p,p'-DDT by stomach tube, but not of rats injected intraperitoneally with p,p'-DDT. | |||||||||||||||||||||
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References
- [1]. Doghman M, et al. Lack of long-lasting effects of mitotane adjuvant therapy in a mouse xenograft model of adrenocortical carcinoma. Mol Cell Endocrinol. 2013 Dec 5;381(1-2):66-9. [Content Brief]
- [2]. Zatelli MC, et al. Therapeutic concentrations of mitotane (o,p'-DDD) inhibit thyrotroph cell viability and TSH expression and secretion in a mouse cell line model. Endocrinology. 2010 Jun;151(6):2453-61. [Content Brief]
- [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. [Content Brief]
- [4]. Warde KM, et al. Mitotane Targets Lipid Droplets to Induce Lipolysis in Adrenocortical Carcinoma. Endocrinology. 2022 Sep 1;163(9):bqac102. [Content Brief]
