Mitotane | CAS#53-19-0 | anti-adrenocorticoid

Mitotane
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 100640

CAS#: 53-19-0

Description: Mitotane is a synthetic derivative of the insecticide dichlorodiphenyl trichloroethane (DDT) with anti-adrenocorticoid properties. Following its metabolism in the adrenal cortex to a reactive acyl chloride intermediate, mitotane covalently binds to adrenal proteins, specifically inhibiting adrenal cortical hormone production.

Chemical Structure

Mitotane

CAS# 53-19-0

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 100640
Name: Mitotane
CAS#: 53-19-0
Chemical Formula: C14H10Cl4
Exact Mass: 317.95
Molecular Weight: 320.034
Elemental Analysis: C, 52.54; H, 3.15; Cl, 44.31

Price and Availability

Size	Price	Availability
1g	USD 250	2 weeks
5g	USD 550	2 weeks
25g	USD 950	2 weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: CB313; CB-313; CB 313; WR13045; WR-13045; WR 13045; DDD, Chloditan; Chlodithane; Khloditan; Mytotan; brand name: Lysodren. Lisodren.

IUPAC/Chemical Name: 1-chloro-2-(2,2-dichloro-1-(4-chlorophenyl)ethyl)benzene

InChi Key: JWBOIMRXGHLCPP-UHFFFAOYSA-N

InChi Code: 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

SMILES Code: ClC1=CC=C(C(C2=CC=CC=C2Cl)C(Cl)Cl)C=C1

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >5 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

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Product Data:

Product Data

Instruction:

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Biological target:	Mitotane (2,4’-DDD), an isomer of DDD and derivative of dichlorodiphenyltrichloroethane (DDT), is an antineoplastic agent.
In vitro activity:	Cell viability was measured by quantifying propidium iodide-positive cells following mitotane treatment and pharmacological inhibitors of lipolysis. Decreased lipid droplets were associated with increased lipolysis in H295R and in MUC-1 at toxic mitotane concentrations. Pharmacological inhibition of lipolysis attenuated mitotane-induced toxicity in both models. Reference: Endocrinology. 2022 Sep 1;163(9):bqac102. https://pubmed.ncbi.nlm.nih.gov/35797592/
In vivo activity:	These results revealed that treatment of CD1 mice with MTT (mitotane) induces a decrease in early antral follicles with a subsequent increase in the secondary follicles, measured by the increased levels of anti-Mullerian Hormone (P < 0.05) and decreased levels of FSH receptor (P < 0.05). Reference: J Endocrinol. 2017 Jul;234(1):29-39. https://pubmed.ncbi.nlm.nih.gov/28450646/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMF	30.0	93.74
	DMSO	64.7	202.06
	DMSO:PBS (pH 7.2) (1:2)	0.3	1.03
	Ethanol	42.0	131.24

Preparing Stock Solutions

The following data is based on the product molecular weight 320.03 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:	1. Warde KM, Lim YJ, Ribes Martinez E, Beuschlein F, O'Shea P, Hantel C, Dennedy MC. Mitotane Targets Lipid Droplets to Induce Lipolysis in Adrenocortical Carcinoma. Endocrinology. 2022 Sep 1;163(9):bqac102. doi: 10.1210/endocr/bqac102. PMID: 35797592; PMCID: PMC9342684. 2. Sbiera S, Leich E, Liebisch G, Sbiera I, Schirbel A, Wiemer L, Matysik S, Eckhardt C, Gardill F, Gehl A, Kendl S, Weigand I, Bala M, Ronchi CL, Deutschbein T, Schmitz G, Rosenwald A, Allolio B, Fassnacht M, Kroiss M. Mitotane Inhibits Sterol-O-Acyl Transferase 1 Triggering Lipid-Mediated Endoplasmic Reticulum Stress and Apoptosis in Adrenocortical Carcinoma Cells. Endocrinology. 2015 Nov;156(11):3895-908. doi: 10.1210/en.2015-1367. Epub 2015 Aug 25. PMID: 26305886. 3. Innocenti F, Cerquetti L, Pezzilli S, Bucci B, Toscano V, Canipari R, Stigliano A. Effect of mitotane on mouse ovarian follicle development and fertility. J Endocrinol. 2017 Jul;234(1):29-39. doi: 10.1530/JOE-17-0203. Epub 2017 Apr 27. PMID: 28450646.
In vitro protocol:	1. Warde KM, Lim YJ, Ribes Martinez E, Beuschlein F, O'Shea P, Hantel C, Dennedy MC. Mitotane Targets Lipid Droplets to Induce Lipolysis in Adrenocortical Carcinoma. Endocrinology. 2022 Sep 1;163(9):bqac102. doi: 10.1210/endocr/bqac102. PMID: 35797592; PMCID: PMC9342684. 2. Sbiera S, Leich E, Liebisch G, Sbiera I, Schirbel A, Wiemer L, Matysik S, Eckhardt C, Gardill F, Gehl A, Kendl S, Weigand I, Bala M, Ronchi CL, Deutschbein T, Schmitz G, Rosenwald A, Allolio B, Fassnacht M, Kroiss M. Mitotane Inhibits Sterol-O-Acyl Transferase 1 Triggering Lipid-Mediated Endoplasmic Reticulum Stress and Apoptosis in Adrenocortical Carcinoma Cells. Endocrinology. 2015 Nov;156(11):3895-908. doi: 10.1210/en.2015-1367. Epub 2015 Aug 25. PMID: 26305886.
In vivo protocol:	1. Innocenti F, Cerquetti L, Pezzilli S, Bucci B, Toscano V, Canipari R, Stigliano A. Effect of mitotane on mouse ovarian follicle development and fertility. J Endocrinol. 2017 Jul;234(1):29-39. doi: 10.1530/JOE-17-0203. Epub 2017 Apr 27. PMID: 28450646.

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1: Terzolo M, Zaggia B, Allasino B, De Francia S. Practical treatment using mitotane for adrenocortical carcinoma. Curr Opin Endocrinol Diabetes Obes. 2014 Jun;21(3):159-65. doi: 10.1097/MED.0000000000000056. Review. PubMed PMID: 24732405.

2: Tripto-Shkolnik L, Blumenfeld Z, Bronshtein M, Salmon A, Jaffe A. Pregnancy in a patient with adrenal carcinoma treated with mitotane: a case report and review of literature. J Clin Endocrinol Metab. 2013 Feb;98(2):443-7. doi: 10.1210/jc.2012-2839. Epub 2012 Dec 28. Review. PubMed PMID: 23275528.

3: Menaa F, Menaa B. Development of mitotane lipid nanocarriers and enantiomers: two-in-one solution to efficiently treat adreno-cortical carcinoma. Curr Med Chem. 2012;19(34):5854-62. Review. PubMed PMID: 22934807.

4: Terzolo M, Ardito A, Zaggia B, Laino F, Germano A, De Francia S, Daffara F, Berruti A. Management of adjuvant mitotane therapy following resection of adrenal cancer. Endocrine. 2012 Dec;42(3):521-5. doi: 10.1007/s12020-012-9719-7. Epub 2012 Jun 17. Review. PubMed PMID: 22706605.

5: De Francia S, Ardito A, Daffara F, Zaggia B, Germano A, Berruti A, Di Carlo F. Mitotane treatment for adrenocortical carcinoma: an overview. Minerva Endocrinol. 2012 Mar;37(1):9-23. Review. PubMed PMID: 22382612.

6: Kroiss M, Quinkler M, Lutz WK, Allolio B, Fassnacht M. Drug interactions with mitotane by induction of CYP3A4 metabolism in the clinical management of adrenocortical carcinoma. Clin Endocrinol (Oxf). 2011 Nov;75(5):585-91. doi: 10.1111/j.1365-2265.2011.04214.x. Review. PubMed PMID: 21883349.

7: Sane T. [Mitotane in the treatment of adrenal carcinoma]. Duodecim. 2010;126(17):2040-6. Review. Finnish. PubMed PMID: 21053521.

8: Veytsman I, Nieman L, Fojo T. Management of endocrine manifestations and the use of mitotane as a chemotherapeutic agent for adrenocortical carcinoma. J Clin Oncol. 2009 Sep 20;27(27):4619-29. doi: 10.1200/JCO.2008.17.2775. Epub 2009 Aug 10. Review. PubMed PMID: 19667279; PubMed Central PMCID: PMC2754909.

9: Reine NJ. Medical management of pituitary-dependent hyperadrenocorticism: mitotane versus trilostane. Clin Tech Small Anim Pract. 2007 Feb;22(1):18-25. Review. PubMed PMID: 17542193.

10: Hahner S, Fassnacht M. Mitotane for adrenocortical carcinoma treatment. Curr Opin Investig Drugs. 2005 Apr;6(4):386-94. Review. PubMed PMID: 15898346.

11: Peterson ME, Kintzer PP. Medical treatment of pituitary-dependent hyperadrenocorticism. Mitotane. Vet Clin North Am Small Anim Pract. 1997 Mar;27(2):255-72. Review. PubMed PMID: 9076906.

12: Parma A, D'Agnolo B. [Adrenocortical carcinoma and its treatment with mitotane. Description of a case]. Minerva Med. 1991 Dec;82(12):883-8. Review. Italian. PubMed PMID: 1780099.

13: Touitou Y, Bogdan A, Legrand JC, Desgrez P. [Metabolism of o,p'-DDD (mitotane) in human and animals. Actual notions and practical deductions (author's transl)]. Ann Endocrinol (Paris). 1977;38(1):13-25. Review. French. PubMed PMID: 324349.

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