Mitotane

• CAT Number: A000369
• CAS Number: 53-19-0
• Molecular Formula: C14H10Cl4
• Molecular Weight: 320
• Purity: ≥95%
• Storage: -20°C
• 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
• InChIKey: JWBOIMRXGHLCPP-UHFFFAOYSA-N
• SMILES: C1=CC=C(C(=C1)C(C2=CC=C(C=C2)Cl)C(Cl)Cl)Cl

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.

Reference

1: Claps M, Cerri S, Grisanti S, Lazzari B, Ferrari V, Roca E, Perotti P, Terzolo
M, Sigala S, Berruti A. Adding metyrapone to chemotherapy plus mitotane for
Cushing/’s syndrome due to advanced adrenocortical carcinoma. Endocrine. 2017 Oct
10. doi: 10.1007/s12020-017-1428-9. [Epub ahead of print] PubMed PMID: 29019062.

2: Cusato J, De Francia S, Allegra S, Carrella S, Pirro E, Piccione FM, De
Martino F, Ferrero A, Daffara FC, Terzolo M, Berruti A, Di Carlo F, Tampellini M,
D/’Avolio A. Circannual variation of mitotane and its metabolites plasma levels in
patients with adrenocortical carcinoma. J Pharm Pharmacol. 2017
Nov;69(11):1524-1530. doi: 10.1111/jphp.12798. Epub 2017 Aug 15. PubMed PMID:
28809444.

3: Reimondo G, Puglisi S, Zaggia B, Basile V, Saba L, Perotti P, De Francia S,
Volante M, Zatelli MC, Cannavò S, Terzolo M. Effects of mitotane on the
hypothalamic-pituitary-adrenal axis in patients with adrenocortical carcinoma.
Eur J Endocrinol. 2017 Oct;177(4):361-367. doi: 10.1530/EJE-17-0452. Epub 2017
Aug 5. PubMed PMID: 28780517.

4: Reidy-Lagunes DL, Lung B, Untch BR, Raj N, Hrabovsky A, Kelly C, Gerst S, Katz
S, Kampel L, Chou J, Gopalan A, Saltz LB. Complete Responses to Mitotane in
Metastatic Adrenocortical Carcinoma-A New Look at an Old Drug. Oncologist. 2017
Sep;22(9):1102-1106. doi: 10.1634/theoncologist.2016-0459. Epub 2017 May 30.
PubMed PMID: 28559412; PubMed Central PMCID: PMC5599197.

5: Waszut U, Szyszka P, Dworakowska D. Understanding mitotane mode of action. J
Physiol Pharmacol. 2017 Feb;68(1):13-26. PubMed PMID: 28456766.

6: 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. PubMed PMID: 28450646.

7: Feliu C, Cazaubon Y, Guillemin H, Vautier D, Oget O, Millart H, Gozalo C,
Djerada Z. Therapeutic drug monitoring of mitotane: Analytical assay and patient
follow-up. Biomed Chromatogr. 2017 Nov;31(11). doi: 10.1002/bmc.3993. Epub 2017
May 21. PubMed PMID: 28432798.

8: Berruti A, Grisanti S, Pulzer A, Claps M, Daffara F, Loli P, Mannelli M,
Boscaro M, Arvat E, Tiberio G, Hahner S, Zaggia B, Porpiglia F, Volante M,
Fassnacht M, Terzolo M. Long-Term Outcomes of Adjuvant Mitotane Therapy in
Patients With Radically Resected Adrenocortical Carcinoma. J Clin Endocrinol
Metab. 2017 Apr 1;102(4):1358-1365. doi: 10.1210/jc.2016-2894. PubMed PMID:
28324035.

9: Schmouchkovitch A, Herry H, Thuillier P, Kerlan V, Fleuret C, Le Toux G,
Boisramé S. Oral and vulvo-vaginal lichenoid reactions due to mitotane
(Lysodren): A case report. Medicine (Baltimore). 2017 Jan;96(2):e5075. doi:
10.1097/MD.0000000000005075. PubMed PMID: 28079787; PubMed Central PMCID:
PMC5266149.

10: Weigel M, Hahner S, Sherlock M, Agha A, Behan LA, Stewart PM, Arlt W, Beier
D, Frey K, Zopf K, Quinkler M. Immediate versus modified release hydrocortisone
in mitotane-treated patients with adrenocortical cancer. Clin Endocrinol (Oxf).
2017 Apr;86(4):499-505. doi: 10.1111/cen.13302. Epub 2017 Feb 3. PubMed PMID:
28063163.