Mitotane

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Mitotane
Clinical data
Trade namesLysodren
Other names1,1-(Dichlorodiphenyl)-2,2-dichloroethane; o,p'-DDD
AHFS/Drugs.comMonograph
MedlinePlusa608050
License data
Routes of
administration		By mouth
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability40%
Protein binding6%
Elimination half-life18–159 days
Identifiers
  • (RS)-1-chloro-2-[2,2-dichloro-1-(4-chlorophenyl)-ethyl]-benzene
JSmol)
ChiralityRacemic mixture
Melting point76 to 78 °C (169 to 172 °F)
  • Clc1ccccc1C(c2ccc(Cl)cc2)C(Cl)Cl
  • 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 checkY
  • Key:JWBOIMRXGHLCPP-UHFFFAOYSA-N checkY
  (verify)

Mitotane, sold under the brand name Lysodren, is a

derivative of the early insecticide DDT and an isomer of p,p'-DDDTooltip dichlorodiphenyldichloroethane (4,4'-dichlorodiphenyldichloroethane) and is also known as 2,4'-(dichlorodiphenyl)-2,2-dichloroethane (o,p'-DDD).[7]

Medical uses

Mitotane has been produced by Bristol Myers Squibb but it is marketed as an orphan drug for adrenocortical carcinoma due to the small number of patients in need of it. 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. In a 2007 retrospective study of 177 patients from 1985 to 2005 showed a significant increase in the recurrence-free interval after radical surgery followed by mitotane when compared to surgery alone.[8] The drug is also sometimes used in the treatment of Cushing's syndrome.[5]

Side effects

The use of mitotane is unfortunately limited by side effects,[9] which, 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%).[10]

Pharmacology

Pharmacodynamics

Mitotane is an inhibitor of the

cytotoxic effects on the adrenal cortex, via an unknown mechanism, and thereby induces permanent adrenal atrophy similarly to DDD.[11][12]

Chemistry

Analogues of mitotane include aminoglutethimide, amphenone B, and metyrapone.

History

Mitotane was introduced in 1960 for the treatment of adrenocortical carcinoma.[5]

Society and culture

Generic names

Mitotane is the

INNTooltip International Nonproprietary Name, USANTooltip United States Adopted Name, BANTooltip British Approved Name, and JANTooltip Japanese Accepted Name.[6][13]

Brand names

Mitotane is sold under the brand name Lysodren.[6]

Veterinary use

Mitotane is also used to treat

pituitary-dependent Cushing's syndrome) in dogs. The medication is used in the controlled destruction of adrenal tissue, leading to a decrease in cortisol production.[14]

References

  1. FDA
    . Retrieved 22 Oct 2023.
  2. ^ "Product monograph brand safety updates". Health Canada. 7 July 2016. Retrieved 3 April 2024.
  3. ^
    ISBN 978-1-4557-1126-0
    .
  4. PMID 15898346
    .
  5. ^
    ISBN 978-1-60327-449-4
    .
  6. ^
    ISBN 978-1-4757-2085-3
    .
  7. ^ "Mitotane". PubChem. U.S. National Library of Medicine.
  8. PMID 17554118
    .
  9. ^
    ISBN 978-1-84184-951-5
    .
  10. PMID 7115060
    .
  11. ISBN 978-1-61705-019-0
    .
  12. ISBN 978-1-4613-1001-3
    .
  13. ISBN 978-3-88763-075-1
    .
  14. ^ Nichols R. "Canine Cushing's Syndrome: Diagnosis and Treatment Part 1: Typical, Atypical, and Pseudo-Cushing's Disease" (PDF). Archived from the original (PDF) on 2007-10-21.

Further reading

  • Komissarenko VP, Chelnakova IS, Mikosha AS (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.
    S2CID 23181221
    .

External links
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