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Mitotane
Systematic (IUPAC) name
(RS)-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 C 14H10Cl4  
Mol. mass 320.04 g/mol
Pharmacokinetic data
Bioavailability 40%
Protein binding 6%
Metabolism  ?
Half life 18 to 159 days
Excretion  ?
Therapeutic considerations
Licence data

US FDA:link

Pregnancy cat. C
Legal status Prescription only
Routes Oral
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Mitotane, or o,p'-DDD, is a medication used in the treatment of the rare disease adrenocortical carcinoma.[1] It is an isomer of DDD and is a derivative of DDT.[2]

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.[3]

Mitotane alters steroid peripheral metabolism, directly suppresses the adrenal cortex and alters 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%).[4]

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.[5]

References

  1. ^ Hahner S, Fassnacht M (April 2005). "Mitotane for adrenocortical carcinoma treatment". Current opinion in investigational drugs (London, England : 2000) 6 (4): 386–94. PMID 15898346.  
  2. ^ Information from PubChem
  3. ^ 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..  
  4. ^ Schteinberg DE, Motazedi A, NoonanRA, Thompson NW. "Treatment of Adrenal Carcinomas". Arch.Surg. (1982) 117:1142-9.  
  5. ^ Canine Cushing’s Syndrome: Diagnosis and Treatment

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