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
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
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/
|
Solvent |
mg/mL |
mM |
comments |
| 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 |
|
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
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.
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.
