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
InChI 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 Y Key:JWBOIMRXGHLCPP-UHFFFAOYSA-N Y
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

• V. P. Komissarenko1, I. S. Chelnakova and A. S. Mikosha (1978). "Effect of o,p-dichlorodiphenyldichloroethane and perthane in vitro on glutathione reductase activity in the adrenals of dogs and guinea pigs". Bulletin of Experimental Biology and Medicine 85 (2): 152–154. doi:10.1007/BF00800110. http://www.springerlink.com/content/wqjmv74186x57wx1.