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Mitotane


Mitotane
Systematic (IUPAC) name
1-chloro-2-[2,2-dichloro-1-(4-chlorophenyl)-ethyl]-benzene
Identifiers
CAS number	53-19-0
ATC code	L01XX23
PubChem	4211
DrugBank	APRD00494
Chemical data
Formula	C₁₄H₁₀Cl₄
Mol. mass	320.04 g/mol
Pharmacokinetic data
Bioavailability	40%
Protein binding	6%
Metabolism	?
Half life	18 to 159 days
Excretion	?
Therapeutic considerations
Pregnancy cat.	C
Legal status	presciption required
Routes	oral (500mg tablets)

Mitotane, or o,p'-DDD, is a medication used in the treatment of the rare disease adrenocortical carcinoma. It is an isomere chemically to DDT and is a derivative of DDD.^[1]

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It has been produced by Bristol Myers Squibb SpA but it is marketed as an orphan drug due to the small number of patients in need of it. Its administration occurs in cases where the tumour cannot be surgically omitted. A 2007 study of 177 patients shows a significant increase in the recurrence-free interval after radical surgery followed by Mitotane when compared to surgery alone.^[2]

Mitotane alternates steroides peripheral metabolism, represses directly the adrenal cortex and alternates cortisone metabolism leading to hypocortisolism. Side effects as reported by Schteinberg et al. include anorexia and nausea (88%), diarrhea (38%), vomiting (23%), decreased memory and ability to concentrate (50%), rash (23%), gynecomastia (50%), arthralgia (19%), and leukopenia (7%).^[3]

Its trade name is Lysodren.

Veterinary use

Mitotane is also used to treat pituitary-dependent Cushing's syndrome in canines. The medication is used in the controlled destruction of adrenal tissue, leading to a decrease in cortisol production.^[4]

References

^ Information from PubChem
^ Terzolo M, Angeli A, Fassnacht M, Daffara F, Tauchmanova L, Conton PA, Rossetto R, Buci L, Sperone P, Grossrubatscher E, Reimondo G, Bollito E, Papotti M, Saeger W, Hahner S, Koschker AC, Arvat E, Ambrosi B, Loli P, Lombardi G, Mannelli M, Bruzzi P, Mantero F, Allolio B, Dogliotti L, Berruti A.. "Adjuvant mitotane treatment for adrenocortical carcinoma". N Engl J Med. 2007 Jun 7;356(23):2372-80..
^ Schteinberg DE, Motazedi A, NoonanRA, Thompson NW. "Treatment of Adrenal Carcinomas". Arch.Surg. (1982) 117:1142-9.
^ Canine Cushing’s Syndrome: Diagnosis and Treatment

v • d • e Chemotherapeutic agents/Antineoplastic agents (L01)
Alkylating and alkylating-like agents	Nitrogen mustards: (Chlorambucil, Chlormethine, Cyclophosphamide, Ifosfamide, Melphalan). Nitrosoureas:(Carmustine, Fotemustine, Lomustine, Streptozocin). Platinum (alkylating-like): (Carboplatin, Cisplatin, Oxaliplatin, BBR3464). Busulfan, Dacarbazine, Procarbazine, Temozolomide, ThioTEPA, Uramustine
Antimetabolites	Folic acid: (Aminopterin, Methotrexate, Pemetrexed, Raltitrexed). Purine:(Cladribine, Clofarabine, Fludarabine, Mercaptopurine, Pentostatin, Thioguanine). Pyrimidine:(Capecitabine, Cytarabine, Fluorouracil, Floxuridine, Gemcitabine)
Spindle poison/mitotic inhibitor	Taxane: (Docetaxel, Paclitaxel). Vinca: (Vinblastine, Vincristine, Vindesine, Vinorelbine).
Cytotoxic/antitumor antibiotics	Anthracycline family: (Daunorubicin, Doxorubicin, Epirubicin, Idarubicin, Mitoxantrone, Valrubicin) - streptomyces (Actinomycin, Bleomycin, Mitomycin, Plicamycin) - Hydroxyurea
Topoisomerase inhibitors	Camptotheca: (Camptothecin, Topotecan, Irinotecan), Podophyllum:(Etoposide, Teniposide)
CI monoclonal antibodies	Receptor tyrosine kinase (Cetuximab, Panitumumab, Trastuzumab) - CD20 (Rituximab, Tositumomab) - other (Alemtuzumab, Bevacizumab, Gemtuzumab)
Photosensitizers	Aminolevulinic acid, Methyl aminolevulinate, Porfimer sodium, Verteporfin
Tyrosine kinase inhibitors	Dasatinib, Erlotinib, Gefitinib, Imatinib, Lapatinib, Nilotinib, Sorafenib, Sunitinib
Other	retinoids (Alitretinoin, Tretinoin) - Altretamine, Amsacrine, Anagrelide, Arsenic trioxide, Asparaginase (Pegaspargase), Bexarotene, Bortezomib, Denileukin diftitox, Estramustine, Ixabepilone, Masoprocol, Mitotane

Categories: Chemotherapeutic agents | Orphan drugs

This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Mitotane". A list of authors is available in Wikipedia.