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53-19-0,MFCD00000850
Catalog No.:AA00ILLB

53-19-0 | Benzene, 1-chloro-2-[2,2-dichloro-1-(4-chlorophenyl)ethyl]-

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  • Technical Information
  • Properties
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA00ILLB
Chemical Name:
Benzene, 1-chloro-2-[2,2-dichloro-1-(4-chlorophenyl)ethyl]-
CAS Number:
53-19-0
Molecular Formula:
C14H10Cl4
Molecular Weight:
320.0412
MDL Number:
MFCD00000850
SMILES:
ClC(C(c1ccccc1Cl)c1ccc(cc1)Cl)Cl
Properties
Properties
 
BP:
398.9°C at 760 mmHg  
Form:
Solid  
MP:
77-78 °C(lit.)  
Refractive Index:
1.6000 (estimate)  
Solubility:
DMSO: soluble20mg/mL, clear  
Storage:
Inert atmosphere;Room Temperature;  

Computed Properties
 
Complexity:
248  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
18  
Rotatable Bond Count:
3  
Undefined Atom Stereocenter Count:
1  
XLogP3:
6.2  

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Title: Interferon-β is a potent inhibitor of cell growth and cortisol production in vitro and sensitizes human adrenocortical carcinoma cells to mitotane.

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Title: Influence of the CYP2B6 polymorphism on the pharmacokinetics of mitotane.

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Title: Mitotane alters mitochondrial respiratory chain activity by inducing cytochrome c oxidase defect in human adrenocortical cells.

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Title: Mitotane induces CYP3A4 expression via activation of the steroid and xenobiotic receptor.

Journal: The Journal of endocrinology 20130301

Title: The effect of mitotane on viability, steroidogenesis and gene expression in NCI‑H295R adrenocortical cells.

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Title: Simultaneous analysis of mitotane and its main metabolites in human blood and urine samples by SPE-HPLC technique.

Journal: Biomedical chromatography : BMC 20121101

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Title: The organochlorine o,p'-DDT plays a role in coactivator-mediated MAPK crosstalk in MCF-7 breast cancer cells.

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Title: Effects of mitotane on gene expression in the adrenocortical cell line NCI-H295R: a microarray study.

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Title: Mitotane exhibits dual effects on steroidogenic enzymes gene transcription under basal and cAMP-stimulating microenvironments in NCI-H295 cells.

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Title: Structural requirements for mitotane activity: development of analogs for treatment of adrenal cancer.

Journal: Anticancer research 20120701

Title: Ribonucleotide reductase large subunit (RRM1) gene expression may predict efficacy of adjuvant mitotane in adrenocortical cancer.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20120615

Title: Combination chemotherapy in advanced adrenocortical carcinoma.

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Title: [German adrenocortical carcinoma registry. Surgical therapy results and follow-up treatment].

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Title: Mitotane treatment for adrenocortical carcinoma: an overview.

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Title: High-dose mitotane strategy in adrenocortical carcinoma: prospective analysis of plasma mitotane measurement during the first 3 months of follow-up.

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Title: Preclinical investigation of nanoparticle albumin-bound paclitaxel as a potential treatment for adrenocortical cancer.

Journal: Annals of surgery 20120101

Title: Assessment of salivary free cortisol levels by liquid chromatography with tandem mass spectrometry (LC-MS/MS) in patients treated with mitotane.

Journal: Hormones (Athens, Greece) 20120101

Title: Metronomic therapy concepts in the management of adrenocortical carcinoma.

Journal: Hormones & cancer 20111201

Title: Therapeutic management of advanced adrenocortical carcinoma: what do we know in 2011?

Journal: Hormones & cancer 20111201

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Journal: Hormones & cancer 20111201

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Title: Drug interactions with mitotane by induction of CYP3A4 metabolism in the clinical management of adrenocortical carcinoma.

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Journal: Ugeskrift for laeger 20110912

Title: Mitotane, metyrapone, and ketoconazole combination therapy as an alternative to rescue adrenalectomy for severe ACTH-dependent Cushing's syndrome.

Journal: The Journal of clinical endocrinology and metabolism 20110901

Title: A simple HPLC method for plasma level monitoring of mitotane and its two main metabolites in adrenocortical cancer patients.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20110801

Title: Enhancement of dissolution rate of mitotane and warfarin prepared by using microemulsion systems.

Journal: Colloids and surfaces. B, Biointerfaces 20110701

Title: Plasma concentrations of o,p'DDD, o,p'DDA, and o,p'DDE as predictors of tumor response to mitotane in adrenocortical carcinoma: results of a retrospective ENS@T multicenter study.

Journal: The Journal of clinical endocrinology and metabolism 20110601

Title: Thyroid effects and anticancer treatment.

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Title: Surgical resection of a virilizing adrenal mass with extensive tumor thrombus.

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Title: A comparison of factors that influence survival in dogs with adrenal-dependent hyperadrenocorticism treated with mitotane or trilostane.

Journal: Journal of veterinary internal medicine 20110101

Title: Pregnancy in a patient with adrenocortical carcinoma during treatment with Mitotane - a case report.

Journal: Endokrynologia Polska 20110101

Title: Normal adrenal function in an infant following a pregnancy complicated by maternal adrenal cortical carcinoma and mitotane exposure.

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Title: High (18)F-FDG uptake by the remaining adrenal gland four months after surgery and initiation of mitotane treatment in two patients with adrenocortical carcinoma.

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Title: Mitotane serum level analysis; good agreement between two different assays.

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Title: Mitotane sensitizes adrenocortical cancer cells to ionizing radiations by involvement of the cyclin B1/CDK complex in G2 arrest and mismatch repair enzymes modulation.

Journal: International journal of oncology 20100801

Title: Successful therapy of Cushing's disease caused by an extrapituitary parasellar adenoma.

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Title: Therapeutic concentrations of mitotane (o,p'-DDD) inhibit thyrotroph cell viability and TSH expression and secretion in a mouse cell line model.

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Title: Development of microemulsion of mitotane for improvement of oral bioavailability.

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Title: Assessment of serum-free cortisol levels in patients with adrenocortical carcinoma treated with mitotane: a pilot study.

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Journal: The Journal of clinical endocrinology and metabolism 20100201

Title: Recurrence of adrenal cortical carcinoma following resection: surgery alone can achieve results equal to surgery plus mitotane.

Journal: Annals of surgical oncology 20100101

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Title: Metastatic virilizing adrenocortical carcinoma: a rare case of cure with surgery and mitotane therapy.

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Title: Effects of o,p'-DDE, heptachlor, and 17beta-estradiol on vitellogenin gene expression and the growth hormone/insulin-like growth factor-I axis in the tilapia, Oreochromis mossambicus.

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Journal: Endocrine-related cancer 20081201

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Title: Mitotane increases the radiotherapy inhibitory effect and induces G2-arrest in combined treatment on both H295R and SW13 adrenocortical cell lines.

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Title: A novel pretreatment approach for fast determination of organochlorine pesticides in biotic samples.

Journal: Journal of environmental science and health. Part. B, Pesticides, food contaminants, and agricultural wastes 20080501

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Title: Modulation of proteomic profile in H295R adrenocortical cell line induced by mitotane.

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Title: A young woman with a severe bilateral pneumonia as the presenting sign of an adrenal carcinoma.

Journal: The Netherlands journal of medicine 20080301

Title: Pharmacokinetics of the adrenocorticolytic compounds 3-methylsulphonyl-DDE and o,p'-DDD (mitotane) in Minipigs.

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Title: [Adrenocortical carcinoma. Diagnostic work-up and treatment].

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Title: Successful treatment of adrenocortical carcinoma with pulmonary metastasis in a child: report of a case.

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Title: Comparison of non-selective adrenocorticolysis with mitotane or trilostane for the treatment of dogs with pituitary-dependent hyperadrenocorticism.

Journal: The Veterinary record 20071215

Title: Response to mitotane predicts outcome in patients with recurrent adrenal cortical carcinoma.

Journal: Surgery 20071201

Title: DDT- and DDE-induced disruption of ovarian steroidogenesis in prepubertal porcine ovarian follicles: a possible interaction with the main steroidogenic enzymes and estrogen receptor beta.

Journal: Journal of physiology and pharmacology : an official journal of the Polish Physiological Society 20071201

Title: Comparative CYP-dependent binding of the adrenocortical toxicants 3-methylsulfonyl-DDE and o,p'-DDD in Y-1 adrenal cells.

Journal: Archives of toxicology 20071101

Title: Pharmacological management of Cushing's syndrome: an update.

Journal: Arquivos brasileiros de endocrinologia e metabologia 20071101

Title: Adjuvant mitotane in adrenocortical carcinoma.

Journal: The New England journal of medicine 20070920

Title: Adjuvant mitotane in adrenocortical carcinoma.

Journal: The New England journal of medicine 20070920

Title: Adjuvant mitotane in adrenocortical carcinoma.

Journal: The New England journal of medicine 20070920

Title: Adjuvant mitotane in adrenocortical carcinoma.

Journal: The New England journal of medicine 20070920

Title: Tailored hormonal therapy in secretory adrenocortical cancer.

Journal: Annals of oncology : official journal of the European Society for Medical Oncology 20070701

Title: Adjuvant mitotane treatment for adrenocortical carcinoma.

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Title: Adjuvant mitotane therapy of adrenal cancer - use and controversy.

Journal: The New England journal of medicine 20070607

Title: The unique case of adrenocortical malignant and functioning oncocytic tumour.

Journal: Experimental and clinical endocrinology & diabetes : official journal, German Society of Endocrinology [and] German Diabetes Association 20070601

Title: [Cushing syndrome].

Journal: Revue de l'infirmiere 20070401

Title: Attenuation of the glucocorticoid response during Ad5IL-12 adenovirus vector treatment enhances natural killer cell-mediated killing of MHC class I-negative LNCaP prostate tumors.

Journal: Cancer research 20070301

Title: Adrenocortical cancer: pathophysiology and clinical management.

Journal: Endocrine-related cancer 20070301

Title: Hyperadrenocorticism: treating dogs.

Journal: Compendium (Yardley, PA) 20070301

Title: Adrenocortical carcinoma.

Journal: The Netherlands journal of medicine 20070201

Title: Long QT syndrome under mitotane therapy.

Journal: Journal of endocrinological investigation 20070201

Title: Medical management of pituitary-dependent hyperadrenocorticism: mitotane versus trilostane.

Journal: Clinical techniques in small animal practice 20070201

Title: Cortisol as a possible marker of metastatic adrenocortical carcinoma: a case report with 3-year follow-up.

Journal: Anticancer research 20070101

Title: Effect of o,p'-DDD and Li+ on apoptotic DNA fragmentation in conventionally normal and tumour tissues of human adrenal cortex.

Journal: Ukrains'kyi biokhimichnyi zhurnal (1999 ) 20070101

Title: Efficacy of adjuvant radiotherapy of the tumor bed on local recurrence of adrenocortical carcinoma.

Journal: The Journal of clinical endocrinology and metabolism 20061101

Title: Effect of mitotane on pituitary corticotrophs in clinically normal dogs.

Journal: American journal of veterinary research 20060801

Title: Dendritic cells as potential adjuvant for immunotherapy in adrenocortical carcinoma.

Journal: Clinical endocrinology 20060801

Title: Mitotane associated with cisplatin, etoposide, and doxorubicin in advanced childhood adrenocortical carcinoma: mitotane monitoring and tumor regression.

Journal: Journal of pediatric hematology/oncology 20060801

Title: Clinical and biological features in the prognosis of adrenocortical cancer: poor outcome of cortisol-secreting tumors in a series of 202 consecutive patients.

Journal: The Journal of clinical endocrinology and metabolism 20060701

Title: A new simple HPLC method for measuring mitotane and its two principal metabolites Tests in animals and mitotane-treated patients.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20060606

Title: Mitotane has an estrogenic effect on sex hormone-binding globulin and corticosteroid-binding globulin in humans.

Journal: The Journal of clinical endocrinology and metabolism 20060601

Title: Long-term disease free survival in a patient with metastatic adreno-cortical carcinoma after complete pathological response to chemotherapy plus mitotane.

Journal: Journal of endocrinological investigation 20060601

Title: [Deoxycorticosterone-producing adrenal tumor].

Journal: Nihon rinsho. Japanese journal of clinical medicine 20060528

Title: [Selective hypoaldosteronism].

Journal: Nihon rinsho. Japanese journal of clinical medicine 20060528

Title: [Virilizing adrenocortical tumor].

Journal: Nihon rinsho. Japanese journal of clinical medicine 20060528

Title: [Feminizing adrenocortical tumor].

Journal: Nihon rinsho. Japanese journal of clinical medicine 20060528

Title: [Adrenocortical carcinoma].

Journal: Nihon rinsho. Japanese journal of clinical medicine 20060528

Title: Microsphere-based protease assays and screening application for lethal factor and factor Xa.

Journal: Cytometry. Part A : the journal of the International Society for Analytical Cytology 20060501

Title: Rapid effects of pesticides on human granulosa-lutein cells.

Journal: Reproduction (Cambridge, England) 20060201

Title: Adrenocortical carcinoma.

Journal: Current opinion in oncology 20060101

Title: Acute hepatopathy associated with mitotane administration in a dog.

Journal: Journal of the American Animal Hospital Association 20060101

Title: [Normalisation of contralateral adrenal function after long-term mitotane therapy in a girl after surgical treatment of adrenocortical carcinoma].

Journal: Endokrynologia, diabetologia i choroby przemiany materii wieku rozwojowego : organ Polskiego Towarzystwa Endokrynologow Dzieciecych 20060101

Title: A case of adrenal gland dependent hyperadrenocorticism with mitotane therapy in a Yorkshire terrier dog.

Journal: Journal of veterinary science 20051201

Title: Biology, clinical characteristics, and management of adrenocortical tumors in children.

Journal: Pediatric blood & cancer 20050901

Title: Etoposide, doxorubicin and cisplatin plus mitotane in the treatment of advanced adrenocortical carcinoma: a large prospective phase II trial.

Journal: Endocrine-related cancer 20050901

Title: Clinical features and immunoexpression of p53, MIB-1 and proliferating cell nuclear antigen in adrenal neoplasms.

Journal: The Journal of urology 20050601

Title: Corticosterone- and aldosterone-secreting adrenocortical tumor in a dog.

Journal: Journal of the American Veterinary Medical Association 20050515

Title: [A long term survival of the patient treated due to advanced adrenocortical carcinoma].

Journal: Polskie Archiwum Medycyny Wewnetrznej 20050501

Title: Mitotane for adrenocortical carcinoma treatment.

Journal: Current opinion in investigational drugs (London, England : 2000) 20050401

Title: [Recurrent operations on the adrenal glands].

Journal: Der Chirurg; Zeitschrift fur alle Gebiete der operativen Medizen 20050301

Title: [Practical use of o,p'DDD in adrenocortical carcinoma].

Journal: Bulletin du cancer 20050301

Title: A six month mitotane course induced sustained correction of hypercortisolism in a young woman with PPNAD and Carney complex.

Journal: Journal of endocrinological investigation 20050101

Title: A comparison of the survival times of dogs treated with mitotane or trilostane for pituitary-dependent hyperadrenocorticism.

Journal: Journal of veterinary internal medicine 20050101

Title: Clinical role of determination of plasma mitotane and its metabolites levels in patients with adrenal cancer: results of a long-term follow-up.

Journal: Journal of experimental therapeutics & oncology 20050101

Title: [Chloditane therapy of adrenocortical cancer].

Journal: Likars'ka sprava 20041201

Title: Adrenal steroid hormone concentrations in dogs with hair cycle arrest (Alopecia X) before and during treatment with melatonin and mitotane.

Journal: Veterinary dermatology 20041001

Title: Oncocytic adrenocortical carcinoma.

Journal: Urology 20040801

Title: [Thyroid metastases of an adrenocortical carcinoma 41 years after the diagnosis of the primary tumor].

Journal: Annales de pathologie 20040601

Title: [Diagnosis and treatment for adrenocortical carcinoma].

Journal: Gan to kagaku ryoho. Cancer & chemotherapy 20040301

Title: [Histoculture drug response assay guided concurrent chemoradiotherapy for lung metastasis from adrenocortical carcinoma--a case report].

Journal: Gan to kagaku ryoho. Cancer & chemotherapy 20040301

Title: [Adrenocortical carcinoma and its treatment].

Journal: Postepy higieny i medycyny doswiadczalnej (Online) 20040226

Title: Recombinant human estrogen, androgen and progesterone receptors for detection of potential endocrine disruptors.

Journal: Analytical and bioanalytical chemistry 20040201

Title: [Analysis of postoperative recurrence of malignant tumors of adrenal glands].

Journal: Klinichna khirurhiia 20040201

Title: Effect of single and repeated in vitro exposure of ovarian follicles to o,p'-DDT and p,p'-DDT and their metabolites.

Journal: Polish journal of pharmacology 20040101

Title: Toxicity of o,p'-DDE to medaka d-rR strain after a one-time embryonic exposure by in ovo nanoinjection: an early through juvenile life cycle assessment.

Journal: Chemosphere 20031201

Title: [Features of clinical presentation of malignant adrenocortical tumor cortex metabolism over time].

Journal: Likars'ka sprava 20031201

Title: Short-term exposure of Chinook salmon (Oncoryhnchus tshawytscha) to o,p-DDE or DMSO during early life-history stages causes long-term humoral immunosuppression.

Journal: Environmental health perspectives 20031001

Title: Study of 202 natural, synthetic, and environmental chemicals for binding to the androgen receptor.

Journal: Chemical research in toxicology 20031001

Title: Differential mechanisms for regulation of the stress response across latitudinal gradients.

Journal: American journal of physiology. Regulatory, integrative and comparative physiology 20030901

Title: The organochlorine o,p'-DDD disrupts the adrenal steroidogenic signaling pathway in rainbow trout (Oncorhynchus mykiss).

Journal: Toxicology and applied pharmacology 20030801

Title: Pigmentary retinopathy, macular oedema, and abnormal ERG with mitotane treatment.

Journal: The British journal of ophthalmology 20030401

Title: Irreversible binding of o,p'-DDD in interrenal cells of Atlantic cod (Gadus morhua).

Journal: Chemosphere 20030301

Title: In ovo exposure to o,p -DDE affects sexual development but not sexual differentiation in Japanese medaka (Oryzias latipes).

Journal: Environmental health perspectives 20030101

Title: [Surgical strategy in the treatment of adrenal cortex cancer. Expanded and repeated interventions].

Journal: Annali italiani di chirurgia 20030101

Title: Medical treatment of hyperadrenocorticism in the dog.

Journal: Australian veterinary journal 20030101

Title: Investigation of the role of aldosterone in hypertension associated with spontaneous pituitary-dependent hyperadrenocorticism in dogs.

Journal: The Journal of small animal practice 20021101

Title: Long-term (15 years) outcome in an infant with metastatic adrenocortical carcinoma.

Journal: The Journal of clinical endocrinology and metabolism 20021001

Title: Development of a fish reporter gene system for the assessment of estrogenic compounds and sewage treatment plant effluents.

Journal: Environmental toxicology and chemistry 20020901

Title: Loss of capacity to elevate plasma cortisol in rainbow trout (Oncorhynchus mykiss) treated with a single injection of o,p'-dichlorodiphenyldichloroethane.

Journal: Environmental toxicology and chemistry 20020801

Title: A phase II trial of combination chemotherapy and surgical resection for the treatment of metastatic adrenocortical carcinoma: continuous infusion doxorubicin, vincristine, and etoposide with daily mitotane as a P-glycoprotein antagonist.

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Title: [Changes in metabolism of sialoglycoproteins of the rat stomach during long-term immobilization stress and glucocorticoid hormone deficiency].

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Title: Decreased cortisol secretion by adrenal glands perfused with the P-glycoprotein inhibitor valspodar and mitotane or doxorubicin.

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Title: Expression of P-glycoprotein in relation to clinical manifestation, treatment and prognosis of adrenocortical cancer.

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Title: Possible mechanism and treatment of o,p'DDD-induced hypercholesterolaemia.

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Title: Neuropsychologic and neurologic side effects of mitotane and reversibility of symptoms.

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Title: Reversible mental deterioration and neurological disturbances with o,p'-DDD therapy.

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Title: Mitotane enhances cytotoxicity of chemotherapy in cell lines expressing a multidrug resistance gene (mdr-1/P-glycoprotein) which is also expressed by adrenocortical carcinomas.

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Title: Primary hypogonadism associated with o,p' DDD (mitotane) therapy.

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Title: 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.

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Tags:53-19-0 Molecular Formula|53-19-0 MDL|53-19-0 SMILES|53-19-0 Benzene, 1-chloro-2-[2,2-dichloro-1-(4-chlorophenyl)ethyl]-