Mitotane

Mitotane
Systematic (IUPAC) name
(RS)-1-chloro-2-[2,2-dichloro-1-(4-chlorophenyl)-ethyl]-benzene
Clinical data
AHFS/Drugs.com monograph
MedlinePlus a608050
Licence data US FDA:link
Pregnancy cat. C
Legal status ℞ Prescription only
Routes Oral
Pharmacokinetic data
Bioavailability 40%
Protein binding 6%
Half-life 18 to 159 days
Identifiers
CAS number 53-19-0
ATC code L01XX23
PubChem CID 4211
DrugBank APRD00494
ChemSpider 4066 Y
UNII 78E4J5IB5J Y
KEGG D00420 Y
ChEMBL CHEMBL1670 Y
Chemical data
Formula C14H10Cl4 
Mol. mass 320.04 g/mol
SMILES eMolecules & PubChem
 Y(what is this?)  (verify)

Mitotane, or o,p'-DDD, is an antineoplastic medication used in the treatment of adrenocortical carcinoma.[1] It is an isomer of DDD and is a derivative of DDT.[2] Its main use is in those patients who have persistent disease despite surgical resection, those who are not surgical candidates, or those who have metastatic disease.

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. 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 (2007). "Adjuvant mitotane treatment for adrenocortical carcinoma". N Engl J Med. 356 (23): 2372–2380. doi:10.1056/NEJMoa063360. PMID 17554118. 
  4. ^ Schteinberg DE, Motazedi A, NoonanRA, Thompson NW (1982). "Treatment of Adrenal Carcinomas". Arch.Surg. 117: 1142–1149. 
  5. ^ Canine Cushing’s Syndrome: Diagnosis and Treatment

External links