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Details

Stereochemistry RACEMIC
Molecular Formula C14H10Cl4
Molecular Weight 320.041
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MITOTANE

SMILES

ClC(Cl)C(C1=CC=C(Cl)C=C1)C2=C(Cl)C=CC=C2

InChI

InChIKey=JWBOIMRXGHLCPP-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Molecular Formula C14H10Cl4
Molecular Weight 320.041
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description

Mitotane is an oral chemotherapeutic agent indicated in the treatment of inoperable adrenal cortical carcinoma of both functional and nonfunctional types. Mitotane can best be described as an adrenal cytotoxic agent, although it can cause adrenal inhibition, apparently without cellular destruction. The administration of Mitotane alters the extra-adrenal metabolism of cortisol in man; leading to a reduction in measurable 17-hydroxy corticosteroids, even though plasma levels of corticosteroids do not fall. The drug apparently causes increased formation of 6-B-hydroxyl cortisol. Its biochemical mechanism of action is unknown, although data are available to suggest that the drug modifies the peripheral metabolism of steroids as well as directly suppressing the adrenal cortex. Mitotane is used for treatment of inoperable adrenocortical tumours; Cushing's syndrome

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
38.0 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
LYSODREN

Cmax

ValueDoseCo-administeredAnalytePopulation
11.3 mg/L
1 g 3 times / day multiple, oral
MITOTANE plasma
Homo sapiens
14.3 mg/L
2 g 3 times / day multiple, oral
MITOTANE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
543 mg × day/L
1 g 3 times / day multiple, oral
MITOTANE plasma
Homo sapiens
790 mg × day/L
2 g 3 times / day multiple, oral
MITOTANE plasma
Homo sapiens

Doses

AEs

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as perpetrator​

PubMed

Sample Use Guides

In Vivo Use Guide
Usual Adult Dose for Adrenal Cortical Carcinoma -Initial Dose: 2 to 6 g orally per day in 3 to 4 divided doses -Maintenance Dose: 9 to 10 g orally per day in 3 to 4 divided doses -Maximum Dose: May increase up to 16 g orally per day, if tolerated, in 3 to 4 divided doses; the highest doses used in studies were 18 to 19 g per day.
Route of Administration: Oral
In Vitro Use Guide
Mitotane (10-40uM) inhibited basal and cAMP-induced cortisol secretion in human adrenocortical cancer NCI-H295 cells.
Substance Class Chemical
Record UNII
78E4J5IB5J
Record Status Validated (UNII)
Record Version